Enterprise Sales Series

Enterprise SaaS Sales

How SaaS founders break into enterprise sales. Long sales cycles, procurement hurdles, and the strategies that close six-figure deals.

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Yosef Peterseil, Blings

Enterprise Sales: How Blings Landed McDonald’s as Their First Customer

Yosef Peterseil is the co-founder and COO of Blings, a personalized video platform for enterprise brands. In 2019, Yosef and his friend Yonatan saw a problem that wouldn't go away. Yonatan had worked at a company trying to create personalized videos for customers, but there was no technical way to do it at scale. So they decided to build a solution—a new video format called MP5 that renders personalized videos in real-time on the user's device. But finding customers proved brutal. They interviewed dozens of customer success managers before realizing their target ICP had no budget. After pivoting to marketing where the money actually was, Yosef got lucky—someone sent him the McDonald's CMO's phone number. A few persistent texts and follow-up calls later, he had a meeting. Before the call, they scrambled to put together a custom video for the brand. The CMO loved it. But closing even the proof-of-concept took nearly nine months—all while they were bootstrapping with zero revenue and couldn't afford a real lawyer. Then came more setbacks. They tried events but had no system to follow up. 70 hard-earned leads went cold. They also hired salespeople twice, but even talented reps couldn't close deals since there was no playbook. But they kept at it. Blings now serves companies like McDonald's, Mercedes, Meta, and Rocket Mortgage. They hit $1M ARR in 2023 and have been growing since then with a team of just 19 people.

Bassem Hamdy, Briq

Enterprise Sales: How to Close Deals in 9 Days, Not 9 Months

Bassem Hamdy is the co-founder and CEO of Briq, an AI orchestration platform for the construction and manufacturing industries. In 2018, after spending nearly two decades in construction tech—including a stint at Procore where he helped scale the company from $10 million to $100 million ARR—Bassem set out to build what he called the "construction data cloud." The idea was to aggregate all project data through APIs, creating a Carfax-like record for physical assets. It seemed like a perfect fit given his experience. There was just one problem. The software systems used in construction were 30 to 40 years old, and none of them had APIs. His entire concept was technically impossible. Bassem was ready to give up and go back to corporate life when a chance meeting with an engineer introduced him to robotic process automation. These bots could log into legacy systems and extract data without APIs. Suddenly, the business had new life. But customers wanted more than data extraction. They asked if the bots could also enter data. This pivot to "digital workers" found product-market fit quickly, and by 2020, Briq had reached $1.5 million in ARR. Then came pressure from investors. VCs didn't like that no users logged into the product. They pushed Bassem to build something with daily active usage. So Briq pivoted again, this time to a forecasting tool. It was a disaster. Customers loved the idea of automated forecasting, but the product couldn't deliver on that promise. Less than two years later, they killed it and returned to their automation roots. As if that weren't enough, Briq had ballooned to 300 employees during the growth phase. The larger team created more problems than it solved, and Bassem says they "lost the plot." Painful layoffs followed in 2023 and 2024, reducing the team to 100 people. Today, Briq generates 8-figures in ARR and is targeting $100 million within three years. Bassem credits their turnaround to a counterintuitive enterprise sales strategy: skip the demos, refuse free POCs, and close deals in 9 days by selling vision and value to CFOs who control the budget.

Saket Saurabh, Nexla

Founder-Led Sales: How He Closed Instacart and LinkedIn

Saket Saurabh is the co-founder of Nexla, a platform that helps enterprises connect fragmented data across different systems, formats, and data models. Most founders start by selling to SMBs. Saket Saurabh did the opposite—he went straight to Fortune 500 enterprises like Instacart, LinkedIn, and DoorDash from day one. His reasoning was counterintuitive: if you architect for small companies first, you'll never fully understand the depth of enterprise complexity. Enterprises still run mainframes. They have fragmented data across dozens of systems. And that complexity is exactly where Nexla's value shows up. Saket closed the first 15 enterprise customers himself through founder-led sales. His approach was consultative: instead of pitching, he listened. Instead of demoing features, he asked questions. "My first goal talking to someone was not that I'm going to sell you something," Saket says. "I'm really passionate about solving this problem. Do you see this problem as well?" The breakthrough came when his co-founder live-coded a fix during an Instacart pitch. "We ended the session showing them something working," Saket recalls. "They said, 'You guys did this on the spot? It takes us weeks or months to solve the same problem.'" That magical moment closed the deal. Nexla has since grown to over $5M ARR, raised $33M, and serves 50+ enterprise customers with 6-figure ACV deals. But to get there, Saket had to cut founder salaries to zero and downsize the team to reach cash flow positivity before their Series A.

Bernard Aceituno, Stack AI

The Enterprise Sales Playbook That Took Stack AI to 7 Figures

Bernard Aceituno is the Co-Founder and CEO of Stack AI, a no-code AI platform that helps enterprises build AI agents to automate back-office workflows. Bernard Aceituno spent 10 years in academia, researching AI and reinforcement learning at MIT. He was on track to become a professor or join a research lab like DeepMind. But he realized that while research was intellectually stimulating, it wasn't solving the immediate, manual problems he saw in the corporate world. So he dropped out of his PhD program to build a startup. His first idea was a tool for machine learning teams to manage datasets. It got some traction, but he noticed his customers were struggling more with connecting data than managing it. That insight led to a pivot: Stack AI, a drag-and-drop builder for enterprise AI workflows. The launch was scrappy. They posted the MVP on Hacker News and Y Combinator's Bookface. It exploded. In just two days, they booked 20 customer meetings. But that early success created a new problem: everyone wanted it. For the first year, they tried to serve everyone - SMBs, startups, and enterprises. It was chaotic. SMBs churned quickly. Startups had small budgets. Bernard made the hard decision to fire his smaller customers and focus exclusively on enterprise sales in the mid-market segment - companies with 100-1,000 employees. This segment had real budget, real problems, and moved faster than the Fortune 500. The result: an 8x revenue multiplier in one year, with enterprise sales cycles closing in 2-6 weeks instead of months. Today, Stack AI serves over 100 enterprise customers like Nubank, has raised $16M, and is generating high seven figures in ARR with a team of 35.

Egidijus Pilypas, Exacaster

Enterprise Sales: 18 Months of Zero Deals to $7M ARR

Egidijus Pilypas is the co-founder of Exacaster, a SaaS company that helps subscription-based businesses grow revenue by turning customer data into actionable insights. As a statistics student, Egidijus worked part-time at a telecom company where he first saw the challenges of managing large customer bases. A university lecturer introduced him to cutting-edge machine learning research, and together they built trading algorithms for financial markets. When the trading experiment failed and Egidijus lost all his money, he pivoted. He called his former boss and pitched using machine learning to predict customer churn. The first company liked the idea but couldn't pay. The second said yes - and with no coding experience, Egidijus and his co-founder taught themselves to build a working platform in three months. What looked like early traction turned into years of painful enterprise sales lessons. Each new customer brought a flood of custom demands that buried their tiny team in delivery work. For nearly a decade, sales and marketing were neglected while they scrambled to stay afloat. When they finally hired an experienced salesperson and invested heavily in outbound enterprise sales, they spent 18 months burning cash and didn't close a single deal. Every RFP they entered, they lost - because by the time they received the request, they were already too late in the buying process. That failure was the turning point. Egidijus realized they weren't selling software - they were selling trust. Here is how Exacaster used three enterprise sales strategies to transform their pipeline: 1. Launched a niche podcast interviewing customer value managers (CVMs) at telcos - people who felt "lonely" in their roles and had nobody to share knowledge with 2. Published the CVM Body of Knowledge book with contributions from 30+ industry professionals across the world 3. Over-invested in enterprise sales pitches with 20-person teams responding to RFPs instead of sending 1-2 people Today, Exacaster is a $7M+ ARR bootstrapped SaaS business serving customers in nearly 20 countries, with close to 100 team members.

Alexa Grabell, Pocus

Pocus: From Founder Pain to First $1M ARR in One Year – with Alexa Grabell [430]

Alexa Grabell is the co-founder and CEO of Pocus, an AI-powered sales prospecting platform that helps sales teams generate pipeline more efficiently. In 2019, while building the sales strategy and ops function at Data Miner, Alexa was frustrated seeing sales data scattered across multiple tools and systems. She decided to hack together her own solution. During her time at Stanford Business School, she met her co-founder and they began working on a way to help sales teams spend more time selling instead of drowning in data. Through Stanford's Lean Launchpad program, they interviewed 350 sales leaders and professionals to validate their idea before writing a single line of code. It took them a year to build their first version of the product. But their patience paid off – within their first year of launching, they hit $1 million in ARR. Yet as first-time founders with no enterprise sales experience, they struggled with everything from building business cases to managing complex negotiations. They faced constant pressure to expand beyond sales into other teams, but stayed focused on serving sales teams exclusively – a decision that proved critical to their early success. Today, Pocus is a Series A company with 30 people, generating seven figures in ARR, and helping customers like Asana, Canva, and Miro.

Barb Hyman, Sapia

Sapia.ai: Rescuing & Rebuilding an Enterprise SaaS – with Barb Hyman [425]

Barb Hyman is the founder and CEO of Sapia, an AI-powered platform that uses smart chat interviews to help companies make better hiring decisions. In 2018, Barb was brought in to scale an existing HR tech startup. But within weeks, she discovered a harsh reality – the product wasn't working, and the business needed a complete reset. She made the difficult decision to fire the entire team, including the founder. With just six weeks of runway left, she had to quickly raise funding to keep the business alive. The next two years were a constant struggle for survival. Some months, Barb wasn't sure if they'd make payroll. She and her small team worked to rebuild the product from scratch, conducting countless experiments to find the right approach. Landing their first major customer, Qantas Airlines, took a series of 15 trial runs over several years before they finally signed an enterprise deal. And just as they were gaining momentum, COVID hit, making it even harder for them to close new business. But Barb and her team focused on building a product customers would love. Their persistence started paying off as more companies began seeing value in their approach. They won contracts with some of Australia's largest brands, with much of their growth coming through customer referrals. Today, Sapia is approaching eight-figures in ARR with a team of 45 people and has raised over $21 million in funding.

Jake Stein, Common Paper

Perseverance in SaaS: Navigating Pivots, Exits, and New Ventures – with Jake Stein [404]

Jake Stein is the co-founder and CEO of Common Paper, a platform that provides standardized contracts and contract management software for B2B software companies. In 2008, Jake and his co-founder Bob Moore started RJ Metrics, a business intelligence company, working out of Bob's attic without taking salaries for the first year and a half. Those early years were grueling as Jake and Bob struggled with finding product-market fit, acquiring customers, and generating enough revenue to stay afloat. By 2012, they finally found traction and grew the business, raising over $20 million in venture capital. But their success was short-lived. In 2015, their business model was disrupted when Amazon launched Redshift, causing RJ Metrics to stop growing. They were forced to do painful layoffs and eventually sold the company in what they described as an "OK exit". But the story didn't end there. In 2016, Jake and Bob spun off a small feature of RJ Metrics into a new company called Stitch. In a whirlwind 18 months, thanks to perfect timing and execution, they sold Stitch for $60 million – a far more successful exit than their previous venture. Drawing from these experiences, Jake launched Common Paper in 2021 to solve the widespread problem of contract standardization. But finding success hasn't been easy. Their initial product focused on NDAs, but it failed to gain traction, with months of enterprise customer conversations resulting in zero conversions. Forced to pivot, Jake and his team scrapped their initial model and refocused on more complex agreements for early-stage B2B SaaS companies. Today, Common Paper is a seed-stage company with 8 team members. They have 140 paying customers, and thousands of companies have used their platform to close deals worth tens of millions of dollars.

Evan Liang, LeanData

LeanData: Overcoming New Category Challenges to 8-Figures – with Evan Liang [399]

Evan Liang is the co-founder and CEO of LeanData, a platform that helps revenue teams manage all go-to-market motions. In 2012, while at Caring.com, Evan faced significant challenges integrating their CRM and marketing automation systems. He built an internal solution to address the pain, which sparked the idea for LeanData. So Evan decided to launch his startup. He brought on a technical co-founder, Kelvin, and as a former VC, Evan was able to raise funding before they even had a product. While raising money was relatively easy, finding product-market fit proved much more challenging. As the solo salesperson, Evan signed LeanData's first 20 customers. But growth was painfully slow. LeanData struggled to educate prospects and close deals as a new category creator. Sales cycles often dragged on for up to three years. If that wasn't bad enough, trhttps://saasclub.io/wp-content/uploads/2025/01/tools-and-materials-used-for-fashion-designing-4XD3MX3.jpgional marketing channels didn't work either. The founders had to get scrappy and creative. Finally, they found some success by attending events and meetups to connect with early adopters. On top of that, Evan and Kelvin were under severe pressure from investors to grow faster. But Evan stuck to his guns. He had to balance the board's expectations with the harsh realities of creating a new category. It wasn't easy, but Evan and his team kept at it. Today, LeanData serves over 1,000 customers, generates 8-figures in ARR, and has raised $42 million in funding.

Thomas Cottereau, SightCall

SightCall: The Long Road to Building a Scalable Enterprise SaaS – with Thomas Cottereau [394]

Thomas Cottereau is the co-founder and CEO of SightCall, a cloud-based platform that helps enterprises provide remote visual support for complex customer issues. In 2008, Thomas was working as a telecom engineer when he and his friend had an idea. They wanted to create a solution that could bridge the gap between the world of telecommunications and the internet. So, they started working on what would eventually become SightCall, spending their evenings in his friend's basement to bring their vision to life. They bootstrapped the company for 3 years, creating a prototype in just 4 months. However, building a scalable, enterprise-ready platform took 5 challenging years. In 2012, Thomas started showing up at Salesforce's San Francisco office every week, determined to get a meeting. Despite facing repeated rejections, he persisted until he finally secured the meeting he was after. Their prototype and unique approach impressed Salesforce, leading to a pivotal partnership that helped them land HP as their first major customer. Using SightCall, HP could remotely guide customers through printer issues, fixing problems without dispatching technicians or handling returns, saving millions in product returns. But getting to this point was no easy feat. It took years of hard work, constantly improving the product, and never giving up. And even after landing HP, it was just the beginning of the challenges they would face. As SightCall grew, they encountered numerous obstacles. Legal issues forced them to rebrand, sales and marketing teams clashed, and the pressure to scale rapidly intensified after raising significant funding. Today, SightCall is an 8-figure ARR business serving hundreds of global enterprise customers with a 100-person team. They've raised $54M to date.

Stephany Lapierre, TealBook

TealBook: Building an Enterprise SaaS Against All Odds – with Stephany Lapierre [391]

Stephany Lapierre is the founder and CEO of TealBook, a supplier data platform that helps enterprise customers make better procurement decisions. In 2014, Stephany launched TealBook, initially as a service where she sold $5,000 memberships to suppliers selling to enterprise customers. However, she realized this model couldn't scale when a larger customer wanted data on hundreds of thousands of suppliers, rather than just a few hundred. After years of bootstrapping TealBook from her living room while juggling the responsibilities of raising three children, Stephany faced a pivotal moment. She realized she needed to transform TealBook into a software platform. But fundraising was really tough for Stephany, mainly because investors were skeptical about her being a solo founder without a tech background. One investor bluntly told her, "You'll never raise capital on your own. You've got three kids, a funny accent (she's French Canadian), and you've never built a tech company." Despite these challenges and harsh feedback, Stephany rose to the occasion. She knew she needed a strong team to get investors on board, so she found a CTO who shared her vision for TealBook and together they got to work. By 2017, she successfully raised the funds they needed to grow the company. Today, TealBook is a 7-figure SaaS business, with over 100 enterprise customers. The company has raised $72M in funding and grown to a team of 60 people.

Thejo Kote, Airbase

Airbase: From Solo Founder to 8-Figure ARR SaaS – with Thejo Kote [381]

Thejo Kote is the founder and CEO of Airbase, a spend management platform for mid-market and enterprise companies. In 2016, following the successful exit of his previous startup, Automatic, Thejo began brainstorming ideas for his next venture. At Automatic, managing company spending had been a major challenge. This led him to explore potential solutions to this widespread problem. But instead of diving right into building a new product, Thejo spent 6 months interviewing CFOs to validate his idea and ensure it addressed a real problem. He hired a freelance designer to create software mockups, which he used to get feedback. After each interview, he iterated and improved the designs. Once his initial product was built, Thejo was ready to start his sales outreach. Despite his previous startup success, he faced struggles as potential customers were still apprehensive about trusting an unknown startup. It took significant persistence and hustle for Thejo to get those initial customers. Fast forward to today, and Airbase has surpassed 8-figures in ARR, grown to around 300 employees, and has raised over $100 million in funding.

Josh Ma, Airplane

Airplane: The Importance of Founder-Market Fit in SaaS – with Josh Ma [370]

Josh Ma is the co-founder and CEO of Airplane, a SaaS platform for engineers to build internal tools. In 2020, Josh and his co-founder Ravi began exploring new startup ideas. They were most excited about building internal tools for developers. However, after seeing how crowded that market was, the two of them began exploring other startup ideas. But they struggled to find another idea that resonated with them. Eventually, they realized that building internal tools was an area that both of them were most passionate about and where they had a strong founder-market fit. So, despite the idea not looking all that promising on paper and being a very competitive space, they decided that this was the idea that they were going to work on. The founders seemingly did everything right when they started out, including interviewing over 40 developers to better understand their frustrations and pains before writing any code. Armed with those insights, they shipped the MVP version of Airplane around 4 months later. But acquiring those initial customers wasn't easy. Their first attempts at targeting other tech startups fell flat. And their outbound sales efforts didn't get traction either. Through lots of persistence, experimentation, and customer conversations, they kept refining their messaging and positioning. And they began targeting and testing other markets. Today, Airplane is a 7-figure ARR SaaS startup with hundreds of paying customers. The company has raised over $40 million in funding.

Brett Turner, Trovata

Trovata: Navigating SaaS Enterprise Challenges to $10M ARR – with Brett Turner [359]

Brett Turner is the founder and CEO of Trovata, a fintech SaaS company that automates and simplifies cash management for businesses. In 2016, Brett, already a seasoned entrepreneur with three successful startup exits, launched a new endeavor: Trovata. But this wasn't just another startup for him; it was an idea brewing for 20 years. Launching a SaaS product in the enterprise space can be very challenging. So Brett spent over two years in the discovery phase talking to as many potential customers as he could. It was a long time, but he still felt it was worth it. However, one major obstacle stood in Brett's way. To deliver a successful product, he needed to integrate with banks. However, back then, most didn't have APIs. So he made a huge bet. He was going to start building the product and investing in the business with the hope that banks would start providing APIs soon. If they didn't, he was screwed. The banks eventually introduced APIs, but Brett had to wait over 2 years. And during that time, the pressure was growing as he was burning through cash. However, thanks to that bet paying off, Trovata has grown into a business that's currently doing around $10M ARR and has raised over $58 million.

Ulf Arnetz, Howwe Technologies

Howwe: Navigating the Tough Road from Services to SaaS – with Ulf Arnetz [358]

Ulf Arnetz is the co-founder and chairman of Howwe, a SaaS product that helps enterprises to accelerate strategy execution and financial results. In 2019, after running a successful services company for several years, Ulf made the decision to transition it into a SaaS business model. He and his team had been working on a SaaS product for a while. They believed there as a huge growth opportunity and felt ready to make the switch to SaaS. But the path to becoming a fully-fledged SaaS business was far more easy. Their annual revenue dropped considerably, going from $5 million to just around $2 million. While Ulf had prepared for a short-term drop in earnings, this turned out to be more substantially than he had expected. Selling their SaaS product to CEOs was also another big challenge. Although they eventually found a solution, they also realized that they were often losing deals because they hadn't figured out how to deal with other key execs who were resistant to using the product. And probably one of their biggest challenges was grappling with a jaw-dropping 60% churn rate. Their SaaS product just wasn't up to par and triggered widespread employee dissatisfaction. Despite those struggles, Ulf and his team persisted and eventually found product/market fit.

Neha Sampat, Contentstack

Contentstack: Scaling From Services to Enterprise SaaS – with Neha Sampat [352]

Neha Sampat is the founder and CEO of Contentstack, a headless CMS that empowers businesses to manage and deliver digital content across various channels and devices. In 2018, Neha seized an opportunity to transform a services-focused business into an enterprise SaaS company. Contentstack began as a simple form for editing mobile content without requiring developer involvement. Today, the business has raised $169 million, grown to a team of over 200 people, and is trusted by many of the world's top brands.

Daniel Wikberg, Upsales

Upsales: Bootstrapping a B2B SaaS to $13 Million ARR – with Daniel Wikberg [350]

Daniel Wikberg is the founder and CEO of Upsales, a CRM solution that helps B2B sales teams to uncover new opportunities and secure more deals. In 2001, when he was 20 years old, Daniel decided to take a sabbatical year before going to university. During that year, he worked as a sales rep and quickly realized that there was a lack of user-friendly software for salespeople. Since he knew how to code, Daniel quickly built a simple customer database and to-do list. Even though he was a bit embarrassed about the software, he got it in front of a prospective customer and managed to close his first sale. That's when Daniel had a lightbulb moment and decided to ditch his university plans and launch Upsales instead. Fast forward to today, Upsales has become a 70-person team, pulling in around $13M in ARR with 1,800 customers, all while being bootstrapped.

Nik Mijic, Matik

Matik: A SaaS Founder’s Journey from Refugee to Series A Startup – with Nik Mijic [336]

In this episode I talked to Nik Mijic, the co-founder and CEO of Matik, a SaaS product that helps create personalized Google Slides or PowerPoint presentations using automated data driven content. In 2018, Nik was working as a program manager at LinkedIn. When he came up with the idea for his new startup, he saw that many companies were wasting time and effort manually collecting data from different sources to add to presentations. And he realized that software could streamline and automate a lot of that work, but he wasn't quite ready to quit his job. So Nik and his co-founder, Zach, who met through a mutual friend, spent six months researching the idea and trying to figure out if they were a good fit for each other. Eventually in January, 2019, Nik was ready to quit his job, but the hardest thing for him was telling his parents as refugees from the Bosnia Civil War. His parents thought their son had finally made it by getting a job with the great company, and now he was about to tell them that he was quitting. The co-founder started working out of Nik's apartment and it didn't take that long to figure out how to build the product, but the bigger problem was that neither of them knew anything about sales and how to get customers. In this episode, Nik shares his lessons as a first time founder. We talk about what he did to learn how to sell and get those first 15 or 20 customer. How he went from having no sales experience to selling the product, to eventually building and managing a sales team. We also talk about a technique that Nik uses to deal with the emotional highs and lows of being a startup founder and how he's used a somewhat unusual framework. To build a solid support structure around him. Today, Matik's customers include B2B tech companies such as Asana, Glassdoor, Greenhouse, and SalesLoft. The founders have raised 23 million, including a 20 million Series A round in 2021, so I hope you enjoy it. All right, Nik, welcome to the show. In PowerPoint or Google Slides today, the way that we kind of came up with this idea was I was at LinkedIn prior to starting the company. And before that I worked at a customer success software startup. And that was where the idea initially came from. We had a lot of our customers saying, Hey, we do these things called business reviews renewal decks, where we have these templates and PowerPoint on Google Slides, and there are placeholders that will say, Hey Nik, go to Salesforce to get this data point. Go to Tableau to get this chart. It'd be awesome if there was a one click button that pulled in all that data for a particular account and spit out a presentation and narrative. And so when I was at LinkedIn, I had worked on building out internal tools and narratives and had a opportunity to rebuild an internal tool. And that's really when it kind of got me thinking, Hey, there's probably other companies out there that have a very similar challenge where their sales and customer success teams are putting together this data driven collateral. , whether it's a QBR, whether it's a quarterly business review, an ROI deck, a business case, it's very, very impactful, right? When you share data with your customers and prospects, the likelihood for better business outcomes are there. But it's very tedious and it's very time consuming. And so our hope and our goal with Matik is to help alleviate that problem and, and help automate and streamline the creation of that data driven content within PowerPoint or Google Slides. I, I was really young when the war broke out. And we ended up fleeing the country and going to Hungary for about a year and a half. And then we ended up in Germany for about four and a half years and wanted to stay, but there were so many refugees that were coming up out of the region that we weren't able to get citizenship. And so, you know, parents decided to apply to a variety of places. We applied to Canada, Australia, US, and got accepted to the US and my mom and dad were like, Hey, let's do it. Let's, let's, you know, American Dream. Let's, let's go over there. So we were choosing between two cities. You know, when you'd come in as an immigrant or a refugee they'll ask you, Hey, do you have any friends or family that can help you get on your feet? And so we had some friends or cousins in Chicago, and then we had some family friends who went straight from the war to Salt Lake City, Utah. And my mom and dad ended up picking the cheaper options. So we ended up going to Utah, which was you know, went to school there high school, college, and then ended up coming to the Bay Area after, after college. I've been here for about almost 11 years. We didn't speak any English. And definitely, obviously I think a lot of people say, oh, tough upbringing. But at the same time, I think it's shaped who I am today. And I think it's a lot of those lessons of perseverance that I saw through my parents is one of the reasons why I started Matik, right? Because I don't think I would've had this opportunity to work at LinkedIn or start Matik if it wasn't for the sacrifices that that they made. And picking up, not just once, but you know, we went from Yugoslavia to Hungary, from Hungary to Germany, and then doing it a third time and coming to the US it really kind of showed me the sacrifice that they made. Right? So what was your parents' reactions to that? We have a cafeteria. They saw all the food, they had all these activities. Also, when you're, when you're an immigrant refugee, I think your parents want you to be like one of three things. They want you to be a doctor. They want you to be a lawyer or they want you to work for like a big company like Microsoft or Coke, Coca-Cola, LinkedIn, that they can brag to their friends back home. But honestly, I ended up flying back to Utah because that's where they're base out of right now. And I want to tell them in person. And the feedback I got from them was like, Hey, like do it like you're at the point in your life where you have the ability to go and take this risk. That's why we came to the US was to give you this opportunity. And if we need to sell our house, if we need to do anything, like we're here to support you. And I think that really gave me the confidence to be like, Hey, I know LinkedIn is great. The perks are amazing, the culture is amazing, pay is amazing. But I don't wanna have that regret later on in life knowing that like I, I wanted to try to do something and I never did. Right. And the other turning point for me was not just my parents. I had a nephew that was born right around that time and I remember being in the hospital with my brother and thinking, man, like, it doesn't seem like yesterday we were kids playing in the playground and now we're raising kids. And it was the first time in my life where I realized how quickly time flies, right? Like when you're in, in high school, you can't wait to get to college. When you're in college, you can't wait to become a working professional and time go by quickly, but you don't understand the magnitude of how quickly it goes. And then seeing my nephew born, it just really hit me. And so I think two reasons, right? One, my parents, I wanted to be able to show them that, hey the sacrifice you guys made, this is a sign of me of appreciation for you guys. And then two, I didn't want to have that regret later on in life to be like, Hey, I should have tried to, to start a company and never did. Right? And, and I know how quickly time flies. So him and I just kind of got together. I told him about the idea and I was like, let's just do some research, right? Like, I haven't worked with you, you haven't worked with me. I'm not quite ready yet, to quit my job. And we did that for about five to six months and we really just hit it off. I would say our core values really aligned. The way that we kind of worked together just worked. And so you know, at that point I was ready and I was like, Hey, this is me getting down on one knee proposing, like, let's do it. Let's, let's let's get a joint bank account and you know, start this thing. So that was kind of the, the initial starting point. So it wasn't just something that we thought was cool to solve for, but other people, other companies had this problem, right? So we were, one was just validating that this is a problem we're solving for, right? And the way we did that was a lot of conversations, right? And that doesn't mean that every conversation we had was positive, but majority of the conversations that we had were saying, Hey, Thumbs up, this is a problem that we have and we'd love to solve for. A secondary piece, which is more of Zach's realm, was kind of the technical components, like how are we gonna go and build this? Like what is the tech stack that we would use, right? What are kind of the base requirements that we would start to build a prototype? So that was kind of the, the, the secondary thing. And then I think the third was, I guess, him and I just kind of feeling each other out, right? Because we had never worked together before. We wanted to make sure that we were on the same page and we had the, we had the same goals going into starting a company. I had a roommate, a former roommate of mine who had just sold a company to Autodesk and you know, I caught up with him and I was kind of giving him the idea. I wanted to kind of run some things by him, and he was like, Nik, like I love this idea. Like, our company could use this. Like, I want to invest. And I'm like, well, we don't really have any customers. Like this is just, these are wire frames. Like we're still, you know, building prototype. He's like, I think there's something here. I think you should like, I want to invest. And so we did a safe, we did a small safe. $200,000. It wasn't, wasn't a big, big safe. And that kind of helped us build the initial prototype. And then we got a few companies that were crazy enough to like try out the product, right? Feedback was overwhelmingly positive and that's what led to us raising a 3 million seed round with Menlo Ventures and a few other seed funds. So that's kinda how we, we got our start. This is kinda what we're trying to solve for. We automate, you know, presentation building and PowerPoint, Google, and she's like, oh, our customer success team at our company could definitely use that. I'll send you an intro. And so she ended up sending me an intro to their enablement person and kind of showed them the initial prototype. They really liked it. And I remember them like, okay, great. What, what's next? Where do we sign? And I remember going back to Zach, I'm like, ah, we don't have a purchase order. We don't have like legal terms, like kind of contacted a few folks. I'm like, do I, what do I charge them? So I literally just came up with a number and I said, Hey, $2,500. Right? So it wasn't a lot. And they were like, great send us the DocuSign. And that was really our, our first customer. And then they ended up expanding from there. So they did test the product before they bought, but it was a, it was also, that was a huge milestone for us because now it wasn't just people trying it, people were willing to put their dollars and behind us, right. And actually buy the product. Was, was selling the product fairly easy despite that? We're gonna invest all these resources into implementing your solution and having our teams use it. Like how do we know that you guys are gonna be around? Right? And I think the raising a seed round helped give us some credibility, right? So like, Hey, there's institutional money behind us now. It's not just two guys working out of an apartment or a WeWork. It's legit. Like there are, there's backing here at at, at a VC level. So that was definitely a hurdle early on that we had to overcome. And I think another one is just we connect to data sources, right? So our primary persona that we go after is obviously customer success and sales teams. And for customer success in particular, a lot of the data that they show in these presentations is usage data where you're connecting to a CRM or you're connecting to a database and that's very sensitive information. And people security was really, really important. So we invested a lot in security upfront, whether it was getting certifications like SOC two, type one, SOC two, type two, investing in technologies for monitoring. That was a big part of how we were able to kind of handle that objection up front. How did you learn to sell? Were you just like winging it? Did you go out and find a mentor. Like what did you do? I think all the above. It is going. Yeah, I mean, it is all the above. So I definitely had some folks we had some advisors that had a sales background where, you know, SVPs of sales at, you know, pretty decent size tech companies and I would lean on them quite a bit, right? Like, 9:00 PM at night. Hey, I don't have an order form. Do you have an order form? Or like, Hey, I got this objection. What do I do? How do I respond to it? So a lot of it was mentoring and coaching from our advisors and folks in my network. And the other was iteration and, and just trial by error, right? So I would see what messaging would respond. I would see what messaging didn't respond. And again, you're iterating constantly, just like you're iterating on the product. We were iterating on that go to market process as well. So first basically target group was people in my network. Then I would look at former employees of LinkedIn that are at new companies, and, and that really resonated because they're like, oh, you know, I don't have those same tools internally here. I would love to take a look at your solution and what you guys are doing. What was that experience like? Was it, was it easy finding the right sales people? And what was the transition like to moving from founder-led sales to relying on a sales team to go out and sell for you? So again, leaning on our investors, leaning on our network of, of sales advisors to kind of help us. Made a hire really early on. Great individual wasn't there for very long. It was like right during Covid. And I think the hardest challenge is finding someone who wants to work at an early stage startup where there isn't all this infrastructure, there isn't product marketing, there isn't sales enablement, right? You don't have a ton of resources. But it's not just so junior where they're like leaning on you and that, that's kind of a tough hire to find. And so we ended up hiring someone who was a, had some big company experience but was really eager to get into startups and she did a fantastic job of just kind of building that initial playbook for our sales team. And she did some of that initial hiring on the SDR front and we worked really closely together to, to build that out. So it definitely was a challenge. And you know, like I said, one of the learnings that I had there too was you gotta hire in twos, especially on the sales side. I think a lot of founders are probably wary because it's costly, but at the end of the day, hiring in twos allows you to really see if it is the person that you hired or if it's the process. And having those two is a benchmark. You kind of know like, hey, one person's performing one isn't, or both are not performing. So maybe it is the process or the other way around. Right? So that's definitely a big learning that I had early on was higher in twos on the go to market side. So did you do that with SDRs and AEs? Like everybody was coming in two. Well initially, right? Like I think like your first hires, like hire, make sure that they have somebody that they can compare themselves to. So like when we hire the account executives, yes, hire twos. Same thing with SDRs, hiring twos because also they can learn from one another, right? And you want to build that culture of collaboration and it's hard to do that when you're just on your own. She was kind of, and I was helping out. Right? So still helping out on deals, right? And I think that's one of another key learning is you, you never really remove yourself from selling as a founder. So as you transition from founder-led sales to a more codified process, you're still going out there and selling, whether you're not necessarily managing the end-to-end cycle, but you may be coming in at the end, or you may be coming in at the beginning. And it also helps me kind of get a pulse on the market and the pulse on, on how our prospects are responding to our messaging, how our customers are responding to our products. So I've really enjoyed that aspect of it. Cause you're the founder, right? And especially if you're the tech guys as well, it's like, yeah, we could do that probably, whatever. But once you're then relying on a sales team to do that and they can only lean on a playbook or whatever training they've had, it's not as easy for them to navigate their way through some of the questions that customers may come up with that you haven't addressed so far. So how, how, how long did it take for you guys to figure out a playbook that you felt pretty comfortable with, that was working well? You're still learning. We're still in the early stages. We're still learning from what we're hearing from the market what we're hearing from customers and how we can constantly improve. So it does take time. But I think the key, key thing here is that that growth mindset, that iterative mindset where, and the hope is that the people that you hire, those account executives can embody that type of mentality where they're okay with ambiguity, they're okay with a little bit of, you know, chaos. But they can help provide structure to that chaos and they can help provide structure that ambiguity. And so a big part of it is not just the playbook or the process that you're implementing, but the people behind that, that can constantly go back and iterate and tweak based on the learnings that they're having. Right? And then we also saw a big expansion play as well. So a lot of those early customers that we signed on, we're getting a lot of value in our product and we're now starting to say, Hey, we only bought for a certain segment within customer success. Now we wanna buy for the entire team. Right. Or, Hey, we think our sales team could also use this. Yeah, they're not, their presentations aren't as like data heavy as maybe customer success, but they do business cases, they do ROI calculators. Some of the pitch decks are a little bit more dynamic. We'd love to use Matik to automate that process. So a big part of our motion too was also expansion which we've had a lot of success with this year. You, you brought on the, the sales team to, to start, you know, hopefully starting to scale the, the growth. What, what's, what's been the kind of, what are the hard parts of, of scaling? Right. That, that's what I'm trying to understand is like, it, it sort of, I hear the story so far and it's like the problem resonates with people. You didn't have that much of a hard time selling. Okay. You had some objections and things you had to overcome and, and certainly raising the seed round, as you mentioned, helped to build some credibility and maybe overcome some of the concerns people had. But beyond that, what have been some of the difficulties with trying to scale sales and get to some of these lands, some of these customers that you have today. Right? And so, as you know, this year as we've had the growth that we've had, you know, we raised a Series A last year with Andreessen Horowitz. We raised 20 million, 20 million series. . Now it's like, okay, we made a lot of these hires, but how do we continue to execute on our long term vision of where we want to go and how do we ensure that as a team continues to grow in size, they're not going into their own silos, they're all rowing in the same direction. So that, that's something that's like really top of mind for me, as well as just talent. Like I'm a firm believer that it's not the technology that wins, it's the people behind the technology that wins. And if you can build a great team, right, and you foster a great culture I think that is like one of the main ingredients to success. Like I said, I'm a first time founder, `so I may be naive in that, but from what I've observed in the startups that I've worked at that have been successful, the ones that haven't been successful, you know, I think culture is such a big part of it, and that stems from your core values, your mission, vision, all of that, and making sure that your team really knows where you want to be, not just today, but where you want to be five, 10 years from now. So tell me, tell me a little bit about that. What, what, what's the lesson you've learned? How do you try to be even-keeled as as you run this business? And it's unbelievable, huge milestone in the company. And then those are the days where, you know, maybe you have a bad meeting with a prospect or they didn't really understand what you're trying to say. Maybe at back-to-back meetings where that happened and you just feel like, wow, I'm just, you know. And so you don't really wanna be too high in the highs. You don't wanna be too low in the lows. And I think another. Thing that's been a learning experience is last three years, four years, not just in business but in society. A lot has happened, right? The pandemic, the war, social injustice and all of that is now like, is starting to collide with business. And so having to learn how to cope with that, with your team, how to address that with your team, how do you navigate a business through that type of climate that's outside of work, that's all been something that's been definitely a learning experience. And I think in times like that, you lean on your core values, you lean on your culture. And one of the things that Zach and I first did before we started writing any code, before we did anything was like, we literally wrote down, this is kind of cheesy, but we wrote down the things that were really important to us. Like what are the core values that you want to this company to live by? What are the core values that I want to, and what is that framework that we want everybody else to buy into? And I think that's really helped us navigate the last four years, not just from a business perspective, but also all the stuff that's going on outside of the business. Right? And one of my favorite sayings is like, trust is consistency over time. It's not one of those things that I meet you, you meet me, I hire you, or you hire me. Boom, there's trust. We are, you know it is your actions over time that prove to me that I can trust you and vice versa. The, second one that we really wanted to really focus on was compassion. And this is something that, that LinkedIn, Jeff Weiner the former CEO, the chairman, now, he would always talk about leading with compassion, and I really took that to heart because we all come from different backgrounds. I'm a refugee. My co-founder Zach grew up in Sonoma, right, and totally different backgrounds. That doesn't mean that his upbringing was better than mine or vice versa, but we may have different ways of looking at a problem. We may have different views on, on how to tackle a problem, and so that's fine. But we should always try to understand and put ourselves in the other person's shoes. You know, let's say you and I disagree on something. Well, maybe Omer had something happen to him over the weekend that I don't know about outside of work, or maybe in his past job they tried to solve for the same exact problem and they went down this route and it led to a disaster. Right? So those are probably the two. Like I said, we have two others. One is quality and the fourth is being customer first. But those are two examples. And you're gonna be testing, you're gonna be iterating, and you really need to have a good support structure. And he told me, he's like, go find a brother or sister. Go find a mom or dad or go find a grandma or grandpa. And so when he told me that, I go, what do you mean by that? And he was like, the brother or sister is the person in your, in your support structure that you can reach out to when you've had a long day and you're like, Let's just go grab a beer or let's go grab lunch or dinner. I just need to vent, right? And they're gonna give you that pep talk, like, Hey, remember why you're doing this? Push through it, right? The mom or dad is someone who is on the same journey, but they're may be two or three years ahead of you. So an entrepreneur that, like I said, is three years ahead of you, that can give you tactical advice. Like, Hey, I don't have a purchase order. What did you guys do here? Hey, I'm hiring for this role. Share some learnings that you had when you were hiring for a similar role. And then the grandma, grandpa is the persona or the person that can give you that 50,000 foot level. They've done it multiple times. Right? And they can kind of help you navigate that, that high level overview. And like I said, set those expectations. And the other is you, you wanna rotate them, right? So everybody has, you know, those friends who come to them constantly. Always complaining. And I, I didn't want to ruin those relationships. So, you know, I try to rotate every, you know, six to 12 months, try to get a new brother or sister, try to get a new mom or dad that I can lean on and a lot of that is just the people the relationships that I've built during my professional career. Things are not gonna perfectly align like you want. You're gonna make decisions. And even if it is a mistake, that is still progress because now you, you've learned something to hopefully not make that mistake again. So I'd probably say that's the biggest thing is don't, don't you know, don't be afraid to, to make mistakes and, and, you know, go, go for the home run. Like really push forward. There is not, you don't have a massive data set that is statistically significant that you can say, Hey, we lead, this is why we should make this decision. And I think this is where we're kind of at. At the life cycle of the company where a lot of the early decisions were gut, it was hypotheses. And now we've gotten to the point where we've collected some data. Now we've gotta change our mindset to now not couple that qualitative feedback and that qualitative data with quantitative data. Right? And so I would say now we're starting to lean more towards, okay, we have historical data, we have a data set that we can use to make decisions. But early on that was not the case. Right? And I think that that was hard, right? . When you're working at LinkedIn or you're working at other companies, you always have that data. You use data to go and make those decisions. And you know, when you're first starting the company, there is no data to lean on. It is all, `you know, research and, and that gut that you're kind of having to lean on. All right. Great. So we should we should wrap up and move on to the lightning round. I've got seven quick-fire questions for you. Just try to answer them as quickly as you can. You ready?

Thor Olof Philogène, Stravito

Stravito: Lessons in Enterprise Sales for Early Stage SaaS Founders – with Thor Olof Philogène [320]

Thor Olof Philogène is the co-founder and CEO of Stravito, a knowledge management platform that gives organizations a secure and central hub for all their marketing knowledge and insights. Stravito is a Swedish-based startup that was founded in 2017. The company has raised $23M to date, and its customers include brands such as Comcast, Electrolux, and McDonald's.

Santi Bibiloni, COR:

COR: Moving a SaaS Upmarket from SMB to Enterprise – with Santiago Bibiloni [297]

Santi Bibiloni is the co-founder and CEO of COR, a SaaS product for creative and professional teams that intelligently suggests how to run their projects, finances, and resources in order to improve profitability. In 2015, Santi was running a successful e-commerce agency in Argentina. As the business grew, it became increasingly difficult to track the profitability of client projects. At first, Santi and his partners assumed that larger agencies had already solved this problem. But when they did research, they learned that this was a very common problem and there wasn't a good solution out there. So the founders decided to build a solution. Once they had built an MVP, they managed to get two other agencies in Buenos Aires to try out their solution. But those early users hated the product. It had lots of bugs and a poorly designed user interface. But even then, they were willing to keep using the tool because it was helping to solve a real pain. That helped them validate the idea and raise an angel round. But they spent most of that money on paid media that didn't really work. They tried running ads on Google, Facebook, LinkedIn, etc. But at the time they didn't have a robust solution and selling via ads wasn't a good way to spend money. They got to about $2K in monthly recurring revenue but growth was slow. What helped them find traction was to move upmarket and focus on enterprise businesses i.e. some of the largest agencies in the world, instead of selling the product to small and medium-sized businesses (SMBs). That helped them to get their revenue to multiple 7-figures and recently raised a Series A round. In this interview we cover some great topics: I hope you enjoy it.

Rohith Salim

Hard Lessons on Finding SaaS Product/Market Fit – with Rohith Salim [284]

Rohith Salim is the co-founder and Chief Product Officer of SpotDraft, a product that helps companies create, manage and review legal contracts. In 2017, SpotDraft's three founders teamed up to launch their new startup. They saw an opportunity to streamline the end-to-end contract management process and believed they could solve that problem. Initially, they built a product for freelancers and solopreneurs. But they quickly realized that most people in that market weren't willing to pay for a solution. So they decided to move upmarket and target Fortune 500 companies. But they didn't have the experience or credibility to win customers. Eventually, they struck a deal with a large reseller through which they got their first couple of customers. On paper, things were looking pretty good for them, and they were able to project out several million dollars in revenue from this one channel. But working with a reseller also created several new issues for the founders. They found themselves doing custom development work for each customer, which led to a higher onboarding and support overhead. But worst of all, they didn't own any direct relationships with customers – they were effectively a sub-contractor. It took the founders a long time to understand a fundamental lesson – as a SaaS business, you can't channel partner' your way to product/market fit. Eventually, the founders had to go back to the drawing board, do a bunch of customer interviews and try to figure out a completely new plan. In this interview, we talk about how they went through that process, how they had to deal with losing some customers and revenue, and how they've been able to turn things around and start growing again with a more focused strategy.

Rob Loewenthal

Whooshkaa: Launch & Differentiate Your SaaS in a Crowded Market – with Rob Loewenthal [265]

Rob Loewenthal is the founder of Whooshkaa, a platform that helps creators and brands to produce, host, and monetize their podcasts. In 2014, Rob walked away from a job as the CEO of a radio network in Australia to launch a SaaS startup. His idea was to build an end-to-end technology platform to help podcasters. He was getting into a market that already had a lot of competitors. But Rob believed that there was an opportunity to do a lot more to help podcasters than just hosting and analytics. And in a relatively short time, he's been able to build a differentiated product that's now used by around 9,000 podcasts and enterprise SaaS companies like Cloudera and Atlassian.

Jeroen Corthout

Salesflare: Finding Your Niche in a Crowded SaaS Market – with Jeroen Corthout [258]

Jeroen Corthout is the co-founder of Salesflare, a simple but powerful CRM that automates updating your data so you don't have to. Jeroen had to use a CRM system in his job and hated how much effort it took to keep everything up to date. And if you didn't, your CRM quickly became useless. He also realized that a lot of salespeople tracked deals outside of the CRM because they didn't want to be hassled by management until the deal was further along. He came up with the idea of a sales tool that could build off the data that was already there, make better use of automation and rely less on people having to manually update information. He built it not as a replacement but as an extension for a CRM application. But he had a really hard time selling it because his prospective customers couldn't see the value or benefit of having another tool alongside their CRM. And it took him some time to find the right market for his product. Eventually, he realized that smaller companies were using his product as a CRM system, not as an extension to it. For the first 18 months, he and his co-founder did a lot of things that didn't scale. He would do all the demos and personally onboard new customers. People couldn't even pay for the product online. They would send them invoices and wait to get paid. It was a lot of manual work to sell a product that was all about automation. But slowly, his efforts started to pay off. Today, Salesflare is used by over 2,000 companies and the founders have raised about $1M. We talk about how they acquired their initial customers, how they've scaled their marketing and sales, and the lessons they learned from selling their product on AppSumo. I hope you enjoy it.

Jafar Owainati

Loopio: How to Bootstrap an Enterprise SaaS Company – with Jafar Owainati [247]

Jafar Owainati is the co-founder and Chief Revenue Officer (CRO) of Loopio, a SaaS product that helps enterprises to streamline the way they respond to a Request for Proposal (RFP). This episode is a story about three co-founders who were all first-time entrepreneurs. One of them was working at a company as a sales engineer and spent half his time responding to RFPs. He realized that he was getting asked the same questions over and over again. Being an engineer, he decided that software could streamline the process and started building a product in his spare-time. But the idea went nowhere and his software just ended up collecting dust. Sometime later, the founders got together and came up with a new plan. Two of them would keep working full-time jobs and work on the product in their evenings and weekends. And the third founder (Jafar) quit his job to work on the business full-time. There were already products that helped companies respond to RFPs. But the founders believed there was an opportunity to modernize that approach with a SaaS offering. Jafar spent a lot of time getting introductions, interviewing potential customers, getting feedback on their product demo and learning how they could help companies to respond to RFPs more effectively. A lot of those meetings were a waste of time, and at that point, the founder didn't have a clue on their ideal customer was. They were just open to talking to anyone who would give them time. Eventually, that hard work paid off. They were able to build a good enough product (even though it lacked a lot of features) and win some early customers. They bootstrapped the business for the first 4 years before raising a $9 million Series A round in 2018. Today, they have a team of 140 people and are doing 8-figures in ARR. In this interview, you'll learn some great lessons – we explore how the founders figured out who their target customers were, what they learned about interviewing prospective customers, how they came up with their pricing and how to sell a SaaS to enterprise customers. I hope you enjoy it.

Jaleh Rezaei

How Mutiny’s Founders Launched a SaaS MVP in 2 Weeks – with Jaleh Rezaei [240]

Jaleh Rezaei is the co-founder and CEO of Mutiny, a SaaS product that helps B2B companies personalize their website for each visitor in order to close more sales. As a product marketer at VMware, Jaleh got to work with a lot of salespeople and soon realized one thing that made the difference between great salespeople and average ones. The best salespeople knew how to adapt and personalize the conversation for each customer. And so they were more successful at closing deals, which typically were worth over $100,000. In 2011, she joined Gusto when they only had around 10 employees. With an average deal size of just $500, Jaleh had to quickly become really good at online customer acquisition. She wondered if she could create a more personalized experience for people who visited their website. But quickly realized how hard that was with the tools available to her at the time. So when she eventually had the chance to solve that problem, she jumped at it. Jaleh and her co-founder were accepted into YC and built their MVP in just 2 weeks. It was a simple API and a pitch deck. They didn't even have a demo to show people. It's hard getting prospective customers to use your product – even if you don't charge for it. They have to learn how to use the product – which requires a time commitment. And since you're just starting out, they don't even know if your product will actually help them or not. So the founders decided to get really hands-on with their early adopters. They worked as an extension to their teams to create content, help them launch and measure the results. It wasn't scalable but turned out to be a great way to learn about their customers and find product/market fit. To date, the founders have raised over $3 million. There are some good lessons in this interview. For example, you may have a big idea, but you don't have to take months or years to launch an MVP. Think big, but start small. I hope you enjoy it.

Amos Schwartzfarb

Sell More Faster: A Playbook for SaaS Startups – with Amos Schwartzfarb [233]

Amos Schwartzfarb is a serial entrepreneur, managing director of Techstars in Austin, Texas and the author of Sell More Faster: The Ultimate Sales Playbook for Startups. Sell More Faster is a guide for founders seeking product-market fit, building their sales team, developing a growth strategy, and chasing accelerated, sustained selling success. In this interview, Amos and I discuss some of the key ideas in his book, including: By the end of the interview, you'll have some practical tips you can use to sell more faster. I hope you enjoy it.

Brynne Tillman

How to Use LinkedIn Social Selling to Grow Your SaaS Business – with Brynne Tillman [226]

Brynne Tillman is the CEO of Social Sales Link and the author of The LinkedIn Sales Playbook, a Tactical Guide to Social Selling. Brynne has been teaching entrepreneurs, sales teams and business leaders how to leverage LinkedIn for social selling for over a decade. As a former sales trainer, Brynne adopted all of the trhttps://saasclub.io/wp-content/uploads/2025/01/tools-and-materials-used-for-fashion-designing-4XD3MX3.jpgional sales techniques and adapted them to LinkedIn. She guides professionals on how to become thought leaders and subject matter experts, find and engage the right targeted market and leverage clients and networking partners for warm introductions into qualified buyers.

Shawn Finder

Autoklose: Launch a SaaS in a Crowded B2B Market – with Shawn Finder [216]

Shawn Finder is the co-founder and CEO of Autoklose, an all-in-one outbound sales automation platform. Competing in a crowded market can be really tough. Having a great product and clear differentiation is super important, but sometimes that's not enough. You also need a great product launch that helps you stand out in the market and drive rapid product adoption. In 2016, Shawn had an idea for a new SaaS product. He already had an existing business and realized that many of his customers were struggling with the same issue. So he started thinking about how he could build a SaaS product to help them. After doing some research, he decided he was going to go all in' with this new SaaS business. But there was one big problem. Shawn was building a sales automation product and so he was about to enter an extremely crowded and competitive market. No matter how good his product was, he knew it was going to be a challenge to stand out in that market. So he knew that a successful launch was going to be critical for his new business. In this interview you'll learn: As a result, the business has gone from zero to over a million dollars a year in about 18 months. There are a lot of great lessons and insights in this interview. I hope you enjoy it.

Rob Kall

SaaS Startup Lessons Learned as a Serial Entrepreneur – with Rob Käll [204]

Rob Kall is the co-founder and CEO of Cien, a product that helps sales teams get an edge using AI to enhance the quality of their data and improve their productivity. As every founder knows, building a SaaS business is rarely easy. And if you're doing it for the first time, it can be particularly hard and you often wonder if you should keep going or not. So can we learn anything from serial SaaS founders who've built and sold several companies? In 2001, Rob Kall and his co-founder talked about starting a SaaS business. They liked building websites and were interested in real-estate, so decided to build websites for realtors. They didn't put much thought into it. It seemed like a good idea and they thought they could build better sites for realtors than the ones they'd seen. So they started a business. 3 years later, they sold that business for $80 million. Rob says he was lucky. He had a great idea at the right time and sold the company at the right time. But then he started a second SaaS business and sold that a few years later for $15 million. Was it luck again? Was it really just about being in the right place at the right time? Rob is now building his third SaaS business. He seems to be a natural serial entrepreneur and on the surface, it seems like it's been smooth sailing from one company to the next. But when you look below the surface you start to get a picture of how tough it's really been for Rob. It's the same roller coaster ride experienced by first time SaaS founders. At every step, you're faced with a big problem and then you find some breakthrough. And then you hit another big problem and another one. It doesn't stop. While luck plays a factor, it's really about your mental resilience, having faith in yourself and the ability to keep going. Those are the factors that create a successful founder and company. In this interview we talk about that journey, some of the challenges that Rob has faced along the way and what keeps him going through the tough times. I hope you enjoy it.

Hampus Jakobsson

SaaS Success & Failure: Lessons from a $150M Exit & a Failed Startup – with Hampus Jakobsson [192]

Hampus Jakobsson is a serial entrepreneur, angel investor and venture capitalist. He's currently a venture partner at BlueYard Capital, a VC firm based in Europe and an angel who's invested in over 80 companies. In 2002, Hampus co-founded TAT a company that developed and licensed mobile user interface software to companies such as Motorola, Samsung, and Nokia. TAT was acquired by Blackberry in 2010 for $150 million. In 2012, Hampus co-founded Brisk, a SaaS product designed to make sales teams more productive. That startup failed and was folded 4 years later in 2016. In this interview, we talk about how Hampus and his co-founders built TAT and sold it 8 years later for $150 million. We also discuss the lessons Hampus learned from the failure of Brisk and what he wishes he'd done differently. And we talk about life as an angel investor and VC. And Hampus shares what types of companies and founders he likes to invest in. I really enjoyed my conversation with Hampus and I hope you enjoy listening to this interview.

Sangram Vajre

Drive SaaS B2B Growth by Building a Community – with Sangram Vajre [184]

Sangram Vajre is the co-founder and CMO of Terminus, a SaaS platform that enables sales and marketing teams to run account-based marketing (ABM) at scale. Before co-founding Terminus, Sangram led the marketing team at Pardot through its acquisition by ExactTarget and then Salesforce. He's also the author of Account Based Marketing for Dummies' and the mastermind behind FlipMyFunnel.com, a community for B2B marketing, sales and customer success professionals. This is a story about 3 first time founders who set out to build an account based marketing platform. In those days, most people didn't even know what ABM was. They didn't have much money and realized how difficult it was going to be for them to get the attention of their target customers (B2B marketers). So they asked themselves a simple question — How can we stand out? They did that by building a community first and focusing on educating their prospective customers, not pitching their product.

Oleg Rogynskyy

SaaS Sales: How to Use Consultative Selling to Grow Your Startup – with Oleg Rogynskyy [182]

Oleg Rogynskyy is the founder and CEO OF People.ai. People.ai is a SaaS platform that uses artificial intelligence to help sales teams to be more effective by automatically capturing all their sales activities and then giving them clear and actionable insights. People.ai was founded in 2016 and has raised around $7 million in funding. But back in 2010, Oleg was doing the 9 to 5 at another company, when he had an idea for a startup. He realized there was a need for democratized, cloud-based text analysis. So he left his job to bootstrap a startup called Semantria. It took Oleg and his co-founder George about 9 months to build the product and to land their first customer. And Oleg spent the majority of those 9 months talking to prospective customers using a consultative selling approach. He focused on two main things — listening more than he was talking and providing his prospects with real value before even talking about his product. And that approach paid off. The founders went from zero to $5 million ARR in just over 2.5 years. And then did no inbound marketing. They just focused on doing one thing — outbound sales really well.

Mike Taber

Single SaaS Founder: Getting it Right the Second Time – with Mike Taber [179]

Mike Taber is the founder of Bluetick.io, a SaaS product that automates the process of sending follow up emails, while keeping it personal. Mike is also the co-host of Startups for the Rest of Us podcast and he's the co-founder of Microconf, both of which he runs with Rob Walling, the founder of Drip. His last startup was AuditShark, a software product that helped regulate businesses such as financial companies to ensure IT security compliance. He tried for several years to get that business off the ground. It was a long, painful effort trying to make it work, but in the end, the business failed. Mike believes that it wasn't a product market fit issue, but a product founder fit issue. In other words, the business wasn't a good fit for him as a founder. For example, selling to enterprise customers typically involves outbound sales. Mike wasn't comfortable doing that and probably wasted a lot of time trying to acquire customers in different ways such as inbound marketing, that just didn't work as well.

Kyle Racki

SaaS Growth Lessons: From $800 MRR in 18 Months to $4.5M a Year – with Kyle Racki [173]

Kyle Racki is the co-founder and CEO of Proposify, a SaaS product that helps you create proposal documents, collaborate with your team and streamline your sales process so you can close deals faster. The company was founded in 2014 and is based in Halifax, Nova Scotia. Kyle and his co-founder Kevin came up with the idea for Proposify when they were running a design agency. But they didn't do anything with that idea for several years. Eventually they decided that they wanted to get out of the agency business and went back to their idea. They built a prototype and got a lot of positive feedback. But when they launched, the results were disappointing. They got to around $800 a month in MRR and flatlined there for almost a year and a half. Today, their business generates over $4.5 million in annual recurring revenue. We talk about what kept them going when they were only making $800 MRR. And we deep dive into specific things they did that led to their hockey stick growth. This is a great story and offers some valuable SaaS growth lessons.

Jon Ferrara

How a SaaS CRM Startup Found Its Way Into Office 365 – with Jon Ferrara [168]

Jon Ferrara is the founder and CEO of Nimble CRM. Jon is a serial entrepreneur, who started his first company in 1989 with just $5000 and went on to sell it for $125 million. Around 2001, a year after selling this startup, he was diagnosed with a tumor in his head. Life and his priorities quickly changed for him. Thankfully he made a full recovery and went on to launch another startup in 2009. He set out to build a social sales and marketing CRM product in a very crowded market. He had the vision of creating a product that you would live in for your email, social media and other communication. But that plan didn't work out, so he had to pivot. He also built great integration with Twitter, Facebook, and LinkedIn. But after a while, LinkedIn cut off their API access and Facebook severely restricted theirs. So he had to do a mini-pivot again. In other words, even though he had a very successful exit with his first startup, it hasn't made it any easier for him to build his second company. And he's faced a lot of challenges, like any of us would face or are dealing with right now. But he's kept going. And recently after years of trying, he has built a partnership with Microsoft which could be massive for his business in the next couple of years. He was one of the very first guests on this show in 2014. And I'm delighted to have had him back and given me the chance to catch up on the ups/downs of his business over the last 3 years.

Jim Brown

The 4-Step SaaS Sales Process to Hit Your Company Goals This Year – with Jim Brown [161]

Jim Brown is a sales coach, founder of Sales Tuners and the host of the Sales Tuners podcast. He's spent the last 10 years helping lead two companies from $1M to more than $10M in annual revenue. And has a founder he took another company from $1M in funding to zero. Today, he coaches tech companies and salespeople through his Skeptical Selling Method. And on his weekly podcast, he talks with great sales leaders and high performing individual salespeople about the behaviors, attitudes, and techniques that have lead to their success. This interview is a story about a sales guy who spent 10 years helping to lead two companies to over $10M in annual revenue. Then as founder, he took another company from $1M in funding to zero. Yup, you read that right. He shares with me some important but tough lessons he learned from that experience. And we talk about how losing other people's money was one of the hardest challenges that he has faced in his career. There are a lot of stories about how a founder went from zero to a multi-million business. And those stories are great because we can learn from those entrepreneurs and their successes. But it's equally important to learn from business failures. And I'm fortunate enough to have a guest today, who's willing to sharing it all. My guest also shares his sales expertise and takes me through a simple but powerful 4 step process to help you achieve the sales goals for your SaaS business this year. We do a deep dive into that process so you might want to be ready to take some notes.

Steve Benson

Lessons on Building a SaaS Sales Mapping App – with Steve Benson [160]

Steve Benson is the co-founder and CEO of Badger Maps, a SaaS sales mapping app that helps salespeople be more successful. The product enables sales reps to map their CRM customer data, integrate with their calendar, plan routes and find nearby leads. Badger Maps is a SaaS product and mobile app. Badger Maps was founded in 2012. The company is based in San Francisco and to date has raised just about $1M in funding. Prior to founding Badger Maps, Steve worked in sales for companies like IBM, Autonomy, and Google. In 2009, he was named Google Enterprise's Top Performing Salesperson in the World. This episode is a story about a sales guy who had an idea for a SaaS startup. He realized that there was a lot of time being wasted as salespeople drive from one customer's location to another. And he figured he could make them more efficient. So he started with a really simple idea — take all those customers that a salesperson has to see each day and map them as points on Google Maps. That simple idea has grown into a SaaS sales mapping app and business with over 6000 customers today.

James Gill

How 3 Teenagers Turned GoSquared from a Hobby Into a SaaS Business – with James Gill [144]

James Gill is the co-founder and CEO of GoSquared, an all-in-one platform for SaaS businesses. GoSquared combines analytics, CRM, live chat, and marketing automation in one seamless platform. The three co-founders started the company when they were 14 years old. They set to build an online advertising business inspired by watching the TV show 'Mad Men'. But nothing worked. As James told me, they couldn't even pay for lunch; and that was school lunch! However, as part of their advertising business, they also built a tool with a beautiful design which gave people insights about their web traffic. And people seemed more interested in this tool, than in their advertising business. So they turned the tool into a product and started selling that. And over time, they added live chat and CRM capabilities. Now, 10 years later, they've built a business with over 1000 paying customers and 10 employees. This isn't a story about rapid growth and raising millions of dollars. But it is a great story about persisting through failures, following your passions, listening to your customers and solving problems you discover along the way and most importantly building a great product.

Grant Miller

How Replicated is Making It Easier to Sell SaaS to Enterprise Businesses – with Grant Miller [141]

Grant Miller is the co-founder of Replicated, a service that solves the problem for companies who want to install and deploy a SaaS application behind their own firewall in a corporate data center or private cloud. Previously, he was the co-founder of Look IO, a mobile live-chat problem that was acquired by LivePerson just 9 months after launch for several million dollars. He and his co-founder, Marc Campbell, have already raised $6.5 million dollars for Replicated. And they're been making solid progress in growing this new business.

Matthew Bellows

How to Find the Right SaaS Distribution Channel to Grow Your Startup Fast – with Matthew Bellows [127]

Matthew Bellows is the co-founder & CEO of Yesware, a platform that helps sales people connect with prospects, track engagement and close more deals. Yesware serves more than 750,000 salespeople at companies like Adroll, Groupon, Salesforce, Twilio and Yelp. The company was founded in 2011 and is based in Boston, Massachusetts. To date the company has raised over $35 million in funding.

Aseem Badshah

Maximizing Your SaaS Customer Lifetime Value – with Aseem Badshah of Socedo [125]

Aseem Badshah is the co-founder and CEO of Socedo, a platform for sales teams that helps them generate relevant leads based on social media data. The company was founded in 2012 and has raised $1.5 million to date. Before launching Socedo, my guest founded and ran Uptown Treehouse, a digital marketing agency for Fortune 500 brands that focused on social media. Aseem shares how learned to maximize customer lifetime value (CLV) by asking his customers.

Mike Muhney, VIPOrbit

How a Failed Startup Helped Mike Muhney Find a $47 Million Idea – with Mike Muhney [094]

Mike Muhney is the co-founder and CEO of VIPOrbit Software, a company focused on building great contact management products. Their flagship product, Vipor CRM is available on iOS & Mac platforms. The company was founded in 2010 and to date has raised over $4 million in funding. In 1986, Mike co-founded a software business that eventually failed. And with only $15,000 remaining from an angel investment of $100,000, they had to come up with another idea or close down the business. The idea they came up with was ACT! Contact Management Software, which they eventually sold for $47 million.

Maciej Zawadzinski, Piwik Pro

How a Startup’s Using Open Source to Make Its First Million Dollars – with Maciej Zawadzinski [042]

Maciej Zawadzinski is the co-Founder & CEO of Piwik Pro, the business arm of Piwik.org. Piwik is an open-source alternative to Google Analytics, which puts users in control of their data, never shares data with other servers, and never sells data for ad targeting. Piwik Pro focuses on providing Piwik cloud hosting and extra paid services for enterprise-level customers.

Jon Ferrara, Nimble

How Jon Ferrara Sold His Company for $125M and Went Nimble – with Jon Ferrara [003]

Jon Ferrara is the founder and CEO of Nimble, a social CRM service for small businesses. He's a serial entrepreneur and a pioneer in the customer relationship management (CRM) industry. He co-founded GoldMine, one of the first contact management apps in 1989, which grew into a very successful venture that he eventually sold for $125 million. John shares with me how he started GoldMine with just $5000 and how they never took a dime of venture capital money or loans. He tells us about a big personal challenge he faced after selling GoldMine that changed his life forever. And he explains how Nimble is more than just another CRM solution.

Wade Foster, Zapier

How to Connect the Web, One App at a Time with Zapier – with Wade Foster [001]

Wade Foster is the CEO and co-founder of Y-Combinator startup Zapier. Zapier lets SaaS users create integrations that push data between hundreds of best-in-breed web apps without having to write any code or deal with APIs. Wade shares with me, how he and a couple of college buddies, took an idea that solved a problem that they were having themselves and turned it into a successful software product with over 300,000 users in less than 3 years. Today, Zapier is helping solve integration problems for over 350 SaaS applications such as SalesForce, DropBox and InfusionSoft.

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