Daniel Wikberg, Upsales

Outbound B2B SaaS Sales That Drove 90% of Revenue

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Episode Summary

Daniel Wikberg built his first CRM in 120 hours from his apartment. His server was literally a computer under his desk that crashed weekly, waking him up with customer calls at dawn. That scrappy start turned into Upsales, a B2B SaaS sales platform now generating $13 million in ARR with 1,800 customers - all bootstrapped.

In this episode, Daniel shares the outbound B2B SaaS sales strategy that drives 80-90% of Upsales revenue, how switching to a land-and-expand pricing model turned $5,000 starter accounts into $50,000+ deals, and why he took the company public in Sweden at just $6 million in revenue while keeping 74% ownership.

In 2001, 20-year-old Daniel Wikberg took a gap year before university, landed a sales job, and realized the tools salespeople used were terrible. Since he could code, he spent 120 hours building a basic customer database and to-do list. His first customer paid $50 a month for one user - and the "server" was a computer in his apartment that crashed so often the customer eventually figured out he was calling some random guy, not a company.

That accidental side project became Upsales, a B2B CRM and marketing automation platform now serving 1,800 customers with a 70-person team and around $13 million in ARR. All bootstrapped. No venture capital. Daniel built Upsales by doing B2B SaaS sales himself for years, starting with a brutal 1-in-20 close rate that gradually improved to 1-in-7 as he got honest feedback and learned to qualify harder.

The real growth came from a deliberate outbound B2B SaaS sales strategy targeting 1,500 named accounts. Instead of running hypothetical demos, Daniel's team onboards trial users with real customer data, skipping the sales theater and building trust faster. One client from their target list is worth 20 inbound customers, and outbound drives 80-90% of revenue.

Daniel also explains how switching from bundled pricing to a seat-plus-add-ons model unlocked a land-and-expand engine. Their top 20 accounts paying $50,000+ per year almost all started at $4,000-$5,000. Lower the entry price, simplify the first decision, then expand after proving value.

Along the way, Daniel took Upsales public on Sweden's Nasdaq First North exchange at $6 million in revenue - not to raise growth capital, but to let a co-founder exit while Daniel kept 74% ownership and full control. He shares why running a public company as a bootstrapped founder is simpler than most people think, and why advice from bankers in expensive suits is almost always wrong.

Topics: Founder-Led Sales|Bootstrapping|Pricing & Monetization

Key Insight

Daniel Wikberg bootstrapped Upsales to $13M ARR by running outbound B2B SaaS sales against Salesforce and HubSpot, targeting 1,500 named accounts where one deal equals 20 inbound customers, and switching to a land-and-expand pricing model that grew starter accounts from $5,000 to $50,000+ per year.

Key Ideas

Outbound B2B SaaS sales drove 80-90% of Upsales revenue, targeting 1,500 named mid-market accounts
Upsales onboards trial users with real customer data instead of running demos with fake data, shortening the sales cycle
Top 20 accounts paying $50,000+/year almost all started at $4,000-$5,000 - proving land-and-expand works
Switching from bundled pricing (gold/silver/bronze) to seat-plus-add-ons created 15-20 expansion upsell paths per account
Daniel Wikberg took Upsales public at $6M revenue on Sweden's Nasdaq First North while keeping 74% ownership

Key Lessons

🤝 Outbound B2B SaaS sales outperforms inbound for revenue: Upsales gets more customers from inbound and word of mouth, but outbound targeting 1,500 named accounts drives 80-90% of revenue because one enterprise deal equals 20 inbound customers.
💰 Land-and-expand pricing beats bundled tiers for growth: Switching from gold/silver/bronze packages to a seat-plus-add-ons model gave Upsales 15-20 upsell paths per account, turning $5,000 starter deals into $50,000+ annual contracts.
🛠️ Skip demos and onboard with real data to shorten B2B SaaS sales cycles: Upsales imports prospect data during trials instead of showing hypothetical demos, building trust faster and qualifying prospects by their willingness to engage with the real product.
📉 A 5% close rate is survivable if you keep iterating: Daniel Wikberg closed 5 of 120 prospects in his first five months selling Upsales, then doubled his effectiveness by getting brutally honest feedback and learning to drop unqualified leads faster.
🎯 Focus on the mid-market gap to compete with giants: Upsales found a gap between simple CRMs for small teams and complex platforms like Salesforce for Fortune 500 companies - mid-market B2B companies with 100-1,000 employees that neither end served well.
🧠 Hire for the stage, not the resume: Daniel learned the hard way that senior hires from large companies delivered polished presentations but no execution - set weekly milestones and verify output rather than trusting impressive backgrounds.
🚀 Going public as a bootstrapper can preserve control: Daniel took Upsales public on Sweden's Nasdaq First North at $6M revenue to let a co-founder exit and sell a small stake, keeping 74% ownership without giving a private equity firm influence over the business.

Watch the Episode

Chapters

00:00Introduction

02:05Favorite quote and background

02:24What Upsales does and who it serves

02:58Origin story - from sales rep to SaaS founder at age 20

05:25Building the first product in 120 hours

06:11First and second customers through word of mouth

06:58Current metrics - 70 people, 1800 customers, $13M ARR

07:36Bootstrapped - clearing up the funding confusion

08:15Competing against Salesforce and HubSpot

09:43Charging the first customer $50/month

10:39Getting to the first 10 customers in 7-8 months

12:27How brutal feedback improved the close rate

13:43Scaling to 100 customers

14:05How "Getting to Closed" doubled sales effectiveness

15:44Reaching $1M ARR in 2006

15:57Competitive positioning evolution

18:33Outbound as the primary growth driver

20:39The 1500 named account target list

21:25Outbound sales process and skipping demos

23:40Onboarding trials with real customer data

26:00Qualification through engagement

28:18Switching to land-and-expand pricing

30:51Hiring challenges and balancing junior vs senior

33:43Worst hiring mistake - impressive slides, zero output

35:08IPO story - going public at $6M revenue in Sweden

37:58Challenges of running a public bootstrapped company

40:54Lightning round

Episode Q&A

How did Upsales use outbound B2B SaaS sales to drive 80-90% of revenue?

Daniel Wikberg's team targets 1,500 named mid-market accounts where one enterprise deal equals 20 inbound customers in revenue. They skip hypothetical demos and instead onboard prospects with real data during trials, building trust and shortening the sales cycle.

How did Daniel Wikberg close his first Upsales customer?

While working as a sales rep in 2001, Daniel asked a prospect what CRM system they used. They had none. He spent 120 hours building a basic customer database and to-do list in his apartment, then sold it for $50/month per user - running the server on his personal computer.

Why did Upsales switch from bundled pricing to a land-and-expand model?

Bundled gold/silver/bronze packages frustrated customers who wanted one feature from a higher tier but not a 300% price increase. Daniel found that his top 20 accounts paying $50,000+/year almost all started at $4,000-$5,000, so lowering the entry price and adding 15-20 add-ons made more sense.

How does Upsales compete against Salesforce and HubSpot as a 70-person team?

Upsales focuses on mid-market B2B companies with 100-1,000 employees - a gap between simple tools for 5-person teams and enterprise platforms like Salesforce. Daniel says most prospects hear about a CRM category for the first time, so competition is less real than founders think.

What B2B SaaS sales tactic did Upsales use to increase trial conversions?

Instead of giving prospects empty trial accounts, Upsales imports their actual customer data and onboards them as if they were paying customers. This eliminates the friction of manual data entry and qualifies prospects simultaneously - those who engage with real data are serious buyers.

How did Daniel Wikberg improve his B2B SaaS sales close rate from 1-in-20 to 1-in-7?

Daniel brought a brutally honest friend to sales meetings who gave harsh feedback on his approach. The key shift was being selective about prospects instead of talking to anyone, focusing time on companies that matched the ideal customer profile.

Why did Daniel Wikberg take Upsales public at only $6 million in revenue?

Sweden has a stock-trading culture where even small companies go public via Nasdaq First North. Daniel wanted to sell a small portion of his 74% ownership, let a co-founder exit their 10% stake, and pay off a loan - all without giving up control to a private equity firm.

What hiring mistake cost Daniel Wikberg the most at Upsales?

He hired three super-senior executives at once who delivered impressive PowerPoint presentations but produced no results for months. The lesson: set clear weekly milestones and check-ins for senior hires, and do not get impressed by jargon, slides, or resumes from larger companies.

How did outbound B2B SaaS sales help Upsales reach $1M ARR by 2006?

Daniel spent five years doing founder-led outbound selling, starting with a 5% close rate that doubled after getting direct feedback and reading Steve Schiffman's "Getting to Closed." He focused on shortening sales cycles by being honest with prospects and dropping unqualified deals faster.

Book Recommendations

Getting to Closed

by Stephan Schiffman

The Hard Thing About Hard Things

by Ben Horowitz

Links

Upsales: Website | LinkedIn | X
Daniel Wikberg: LinkedIn
Omer Khan: LinkedIn | X

Full Transcript

Omer (00:09.760)
Welcome to another episode of the SaaS Podcast.
I'm your host Omer Khan and this is a show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
In this episode I talk to Daniel Wickwerk, 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.
And that's when Daniel had a light bulb moment and decided to ditch his university plans and launch Upsales instead.
Fast forward to today.
Upsells has become a 70 person team pulling in around $13 million in ARR with around 1800 customers, all while being bootstrapped.
In this episode you'll learn about the outbound sales strategy Daniel and his team used to drive the majority of their growth and close large deals.
How Upsell simplified the decision making process during trials and went the extra mile to provide more value which helped them significantly increase conversions.
How Daniel and his team used a land and expand sales approach to further accelerate their growth and simplify decision making for customers and the challenges and lessons Daniel's learned from competing in a market with some very established and well funded companies.
So I hope you enjoy it.
Daniel, welcome to the show.

Daniel Wikberg (02:04.000)
Thanks a lot.
Good to be here.

Omer (02:05.520)
Do you have a favorite quote?
Something that inspires or motivates you that you can share with us?

Daniel Wikberg (02:10.400)
I think Ted Turner once said when asked what would you have done differently in your career?
And I think he said something like I should have hired slower and fired faster.
And yeah, I agree with that.

Omer (02:24.350)
So tell us about Upsales.
What does the product do, who's it for and what's the main problem that you're helping to solve?

Daniel Wikberg (02:30.510)
So we're a sales and marketing tool.
So we are a CRM and a marketing automation provider and we try to help like mid size B2B companies to grow revenue and we focus on a couple of key areas of the sales process where we believe that the industry in general has done a poor job of solving these specific problems.
So we try to solve them For a specific niche of the market, basically.

Omer (02:58.430)
Okay, great.
So I want to talk about kind of how you came up with the idea for this business.
You founded this company in 2001.
Before we do that, what were you doing before you founded Upsales and how did you come up with the idea for this business?

Daniel Wikberg (03:15.950)
Yes, I mean I was 20 years old when I founded Upsales, so I didn't have that much of a background to talk about.
But I mean I always been into programming.
I've been doing programming since I was 13 years old.
And then when I finished high school the plan was to go to the university and study some kind of engineering.
But I decided to kind of take a sabbatical year and ended up in a sales job.
And I realized that like sales and selling is like this huge industry which you never hear about.
I mean, you don't talk about being a salesman as a future career when you're a teenager.
So I started doing that and I realized that the tools that you were using, especially back then, were not, they were not so user friendly and they didn't do a good job in helping these non technical salespeople to do their job.
So that was kind of where I got the idea there must be a way to do this better.
And I actually just stumbled upon, I was talking to a customer in the sales job I had and I talked to them about what kind of system are you using?
And they didn't have any.
So that was kind of the first customer.
So I just spent a couple of days in my apartment building something and yeah, then we grew customer by customer after that basically.
And I never went, you know, I postponed indefinitely my plans for getting a degree in anything.

Omer (04:49.180)
Your background was basically programming, computer science.
And your sales experience was what, about a year or so of working as a sales rep before you founded Upsells?

Daniel Wikberg (05:01.480)
Yeah, I think two years.
I had two jobs and I mean I had the kind of.
I had the luck of ending up in a place where they had these super enthusiastic and professional sales coaches.
So those guys kind of sparked my interest in selling as a profession.
So I think that was a big part of it.

Omer (05:25.000)
Tell me about the first version of the product that you built.
Like how long did it take you and, and what did it do and what were some of the things that you were embarrassed about?

Daniel Wikberg (05:34.170)
Yeah, I think I was embarrassed about pretty much everything.
I mean the first version was like a super simple.
It was a super simple customer database and a to do list basically.
So the first customer was a media company and they had like five sales reps, you know, doing 100 calls a day to trying to close business.
So they just used this first version to keep track of all the calls and all the customers.
I think I spent 120 hours building the first product.
So it was very, very basic.

Omer (06:11.030)
And did you build it with just this one customer in mind or while you were building it, you were talking to other customers as part of your job, trying to gather more research and insights?

Daniel Wikberg (06:22.580)
I mean, I think that the first customer, I didn't really think of it as a business.
It was more like an experiment in a way.
Yeah, I just figured, you know, this is something I would use if I were, you know, I was also doing calls every day in my sales job.
So, I mean, sales is kind of a generic activity.
And then after that I found actually customer number two came.
Came by word of mouth from customer number one.
So that was also a media company.
And then everything evolved from that, basically 2001.

Omer (06:58.130)
So you've been running this business for over 20 years.
Can you give us a sense of the size of where you are right now in terms of revenue, number of customers, size of team?

Daniel Wikberg (07:08.530)
Yeah, so we're a team of 70 people.
We're serving 1800 customers.
And I mean, our customer base is kind of distorted.
I usually say that we have 900 customers and then we have 900 like very long tail customers, which we inherited from a former partnership with a white label partner.
So 900 like focus customers generating around 13 to 14 million dollars in ARR.

Omer (07:36.030)
How much money have you raised?
Because there was some confusion about this.
And I came in and said, hey, Daniel, you've raised this much?
And you were like, nope.

Daniel Wikberg (07:42.990)
Yeah, I know.
I mean, that's the problem.
We're a Swedish company and all of the data in all of these cool international databases are almost always incorrect.
So, I mean, we've been bootstrapped from the start to today.
We are a publicly listed company.
We did a small cap raise when we did the ipo, but never used that money was used to kind of pay off a loan that we had taken up a few years back.
So, yeah, we've been a bootstrapped company growing organically from the start.

Omer (08:15.650)
Bootstrapped to 13 million in ARR.
That's a nice accomplishment.
And especially in the market that you compete in with some pretty big players.
Right.
So who are like the top two or three competitors that you have to deal with every day?

Daniel Wikberg (08:34.250)
So, I mean, I think looking at our market, if you do a Google search for a CRM I mean, you get like a thousand hits and a lot of these are great tools if you're like a five man team or a really small company.
And then you have like Salesforce and all of the bigger players, which are great if you're a Fortune 500 business and you have like an IT department and a huge budget.
But if you're like a growing mid sized company like with 100 to up to a thousand employees, we believe there's a gap in the market.
So this is kind of the part of the market where we have our focus.
And I mean, our main competition comes from Salesforce and HubSpot.
So I think that's something we're very proud of.
I mean, we're a small team.
I mean, Salesforce, I don't know, 30, 40,000 employees.
And HubSpot is also like a huge company.
So I mean, a big part of our success has been to try to figure out which are the specific industries and types of companies where we feel that we can do something different and bring something unique to the table.
And that's the way we've always done it and that's the way we try to do it today as well.

Omer (09:43.430)
Okay, so that first customer that you got the product in front of, did you charge them?

Daniel Wikberg (09:48.790)
Yeah, absolutely.
I think they paid.
They bought like one user, 50 bucks a month.
And the fun thing was that back then the server was actually a computer in my apartment and the guy working there, the user was a sales rep.
He was calling customers in a different market.
So he always started like early in the morning because of the time zone.
And, and you know, downtime happened like almost every week because I had to reboot the computer, running the software.
So he realized after a couple of times, you know, usually calling me or you know, calling the number to upsales and literally waking me up.
And after a while he realized that this is not a company, this is just some dude I'm calling.
So yeah, I still know that guy, actually.

Omer (10:39.380)
That's brilliant.
All right, so how long did it take you to get to the first 10 customers?
So you said that, hey, you know, this was an experiment and I didn't really think of it as a business at that time.
But once you got this customer on board, you know, maybe got over some of those initial issues, at what point did it become a business in your mind?
And how long did it take for you to get those first 10 paying customers?

Daniel Wikberg (11:04.170)
Yeah, so what we did, we had this first customer and then rather quickly the second one.
And then I realized that, okay, this is just some super simple project I hacked together in 100 hours.
So I need to build something more robust if I'm going to sell it to more companies.
So I brought on my co founder, and I think we spent like four or five months building version two, and then we started selling that.
And I think in the first.
Yeah, I remember the first five months, we started in August after the summer, so August to Christmas, I closed five customers.
And I think I met with like 110 or 120 or something.
So, like, the win rate was horrible.
And I remember, like, the mental pressure of like, you know, 19 out of 20 people I meet is not interested in what I have to say.
So that was very tough.
But then after those initial.
Those first five months, something happened.
I don't remember exactly what was the main difference, but we went from like closing 1 in 20 to maybe closing 1 in 7 or 1 in 8 out of the customers we met.
So I think maybe in total, seven to eight months to get to customer number 10.

Omer (12:27.260)
You said you didn't know what changed.
Do you think it was just.
You were just getting better at kind of selling the product?

Daniel Wikberg (12:35.260)
Yeah, I think so.
I had a friend who's, like, very.
You know, everybody knows that guy who's, like, brutally honest when he gives you feedback.
So I had that friend, and he actually joined me on a few sales meetings, and he gave me some very harsh feedback.
So I think that was one of the key aspects.

Omer (12:53.740)
So.

Daniel Wikberg (12:54.460)
Yeah, and I think one of the key things was, like, I mean, in the beginning, you want to talk to anybody who wants to talk to you, but I think it's super important to early on be selective because, you know, you have 24 hours every day that's like you have the same currency as everybody else.
And it's important to be wise about where to spend that time.

Omer (13:20.040)
Yeah, everybody needs one of those friends who are harsh with the truth.
Because I was talking to a founder a couple of days ago, and she was talking to customers and trying to get feedback, and everybody was being so nice and saying, yeah, I love the product.
And she's like, I know there's something there, but they're not telling me.
So you need to find that friend.

Daniel Wikberg (13:43.040)
Yeah.

Omer (13:43.840)
All right, so we got the first 10 customers.
In terms of getting the next, let's say first 100 customers, did things change much or was it more about you guys just continuing to do the same, going out there, making the product better, kind of getting better at selling?
Like, did you do anything different to get to those first 100 customers.

Daniel Wikberg (14:05.900)
I mean, I don't think so.
I think, I mean, obviously a lot of things happen.
I mean, like a thousand things.
But I think all in all it was just about, you know, keep at it, you know, keep calling customers, booking appointments, meeting them, and try to figure out along the way, like, okay, where do we get success and where don't we get success?
I remember another, like, breakthrough moment I read this book about.
We had this problem with the selling cycles were really long and the deals were really small.
So to me it didn't make sense that all of these deals dragged on forever.
So I started googling about, okay, I need to find some information or inspiration about how to shorten sales cycles.
And I stumbled upon this book called Getting Too Closed by a guy called Steve Schiffman.
And that like, I think it doubled my effectiveness because it gave me this mindset about, you know, being brutally honest with all of your customers and, and not just pleasing them and make sure to spend time with the right kind of customers, basically.
So I think that was kind of an accelerator, actually.

Omer (15:26.510)
I haven't heard of that book before.

Daniel Wikberg (15:28.030)
It's amazing.
I mean, it's like 25 years old, but it's the best book still.
I mean, I've read like several hundred sales books, but I think this one is the best when it comes to how to work effectively with your pipeline.
It's really, really good.

Omer (15:44.510)
Do you remember when you hit your first million in ARR?

Daniel Wikberg (15:49.870)
Our first million was in 2006.
So yeah, like five years.

Omer (15:57.790)
So 2006, the business is still bootstrapped.
You hit the million ARR when you founded Upsales.
I think Salesforce was still in the early days, right?
They had kind of been kind of noodling around with their product.
HubSpot didn't even exist.
I think HubSpot was going to happen later.
I want to kind of figure out this kind of competitive landscape you talked about.
Hey, this is where we think.
You describe that market in terms of these are the companies that we think are underserved, where we think this opportunity exists for us to provide value.
How did that change once products like HubSpot and Salesforce kind of became more mainstream?
Did you find yourself that having to spend more time with customers trying to explain where up sales fits in and how it's different or better?
Or do you feel like you'd kind of already, you know, the last sort of five years of building and selling the product, you'd already started to get some clarity around the sweet spot for where Upsells kind of fitted in.

Daniel Wikberg (17:07.730)
And your positioning, I mean, in a way, we're still trying to figure that out, to be honest.
I mean, it changes all the time.
Or I mean, at least it evolves.
In the early days, I mean, just talking about the basic stuff in a CRM was enough to convince a lot of customers.
And the market was like very immature.
I think in a way it's still, still very immature.
But as we have grown as a company, we've looked at, okay, which are the integrations we can do, like, what's the data we can add to up sales that no other provider has that gives us an edge.
That has been one very important thing.
And I think also, I mean, when I talk to people in our sales team and to other entrepreneurs, I mean, especially early stage entrepreneurs, I think that don't think so much about the competition because it's an illusion that all customers know about all providers.
I mean, most prospects you meet, you know, hear about your product or your product category for the first time.
So I think that's kind of, that's important to go out there and just talk to the customer, understand the problems and solve them in a better way than anybody else.
And don't worry so much about the competition.
I think a lot of companies make competition too big of an issue.

Omer (18:33.600)
First of all, I think that's a great point.
I think there's this danger with many founders to kind of spend too much time looking at competitors and while having some awareness is a healthy thing to do, you know, so at least you figure out where you fit in, how you differentiate all that stuff.
It can become problematic if you're spending too much time or obsessing too much over it.
I want to talk about like, you know, you went from like zero to, you know, 1800 customers that you have today.
What was the main growth driver?
Like the, what was the kind of the main marketing or sales channel that you are acquiring these customers through?

Daniel Wikberg (19:18.450)
We have had like a very deliberate outbound strategy.
I mean, we do a lot of marketing and we get quite a few leads every week.
We get a decent amount of customers from word of mouth and referrals from happy customers as well.
You can look at it in two ways.
If you look at it in terms of number of new customers we bring in, I think that inbound or word of mouth are probably like the biggest sources.
But if you look at revenue, like outbound is probably 80 or 90%.
And I believe that's the case in most SaaS companies.
I mean, for us Looking at the target list we have of like the ICPs we're going after, I mean, it's a pretty small list.
It's like 1500 named accounts and these are the accounts we're targeting.
One client from that list is the equivalent of like 20 customers coming from inbound channels.
So I think a lot of SaaS companies and also companies in other industries have this kind of this fantasy about how nice would it be if just the customers just came to us.
And I think succeeding with inbound for larger deals or deals that move the needle, I think it's very difficult and I see very few companies doing that successfully.

Omer (20:39.690)
So you said you're targeting around 1500 companies.
You have 1800 customers today.
I know you talked about the 900 that maybe fit that category.
So is that 900 part of the 1500?

Daniel Wikberg (20:53.130)
No.
I mean, we have a long tail.
I mean, we work with any customer who wants to work with us where we believe we can provide value.
So I mean, we get a lot of customers every month that finds us online and finds us through marketing.
But looking at this focused list of high value accounts, I think we may have sold to, I don't know, 5 or 10% of them now.
So it's still a long way to go.
A long Runway.

Omer (21:25.730)
Yeah.
So tell me about the sales process.
Not today.
We can maybe compare that to how you do it today.
But when you first identified this ICP and you said, okay, we're going to go out and we're going to do outbound and we're going to try and land some of these deals, what did that outbound process look like?
And typically like, how long was the sales cycle like, for you to get from like first touch to closing this type of deal?

Daniel Wikberg (21:54.700)
I mean, so that's always also evolved throughout the years.
And I think that what always worked best for us has been to go out there, talk to the customer and try to get some initial understanding of their situation and then move straight from that to provide value instead of doing hypothetical demos and stuff like that.
I think that we always try to set up a trial account to get the customer's data into the account so they see the actual.
Basically we onboard them as if they would have been a paying customer.
I think that has always been the most effective way.
I mean, that's not always possible depending on what product you're selling.
But for us, that has always been the fastest way to win the deal.
And it's funny because this was basically what we were doing in the beginning because as a bootstrapped company.
I mean, you literally have a gun to your head and you need to close business to, you know, be ordered to pay the rent and buy lunch, basically.
So anybody who wanted to work with us, I mean, we would do whatever they needed.
So we did all these crazy customizations and all of these crazy stuff in the beginning, and then we moved to this more kind of, you know, professional selling process, if you will.
And then lately, the last two or three years, we kind of went back to the, you know, the initial way we used to work with customers of just skip all the sales stuff and just show them the value, because that's what matters for the customer.

Omer (23:40.200)
Give me an example of when you mean like skip the sales stuff and show them value.
So I think what you just described there in terms of saying, hey, we get their data in, even if they're just a trial.
And depending on the type of customer and the data they have, I assume could become quite a significant piece of work for your team to do that.
Well, but I can see the value in it because you give somebody access to an account and there's no data in there.

Daniel Wikberg (24:09.650)
Exactly.

Omer (24:10.530)
And they're thinking to themselves, okay, I can kind of play around with this, but I don't really know how this is going to work.
And the effort required to take all my data and put it into here for a trial, I'm not going to waste time doing that.
And so there's this, this risk that this trial never goes anywhere.
And so I think it's super smart to say, no, no, no.
We know this is a hurdle for potential customers, and so we're going to get, get past that and make it easier for them.
So I think that's a great, solid example.
But what do you mean by like, skip the sales stuff and do that?
So what were some of the things that you were doing less of?

Daniel Wikberg (24:51.880)
Most sales calls and sales meetings, you talk about, like, hypothetical stuff.
You know, you have a demo account with fake data and you're sitting there kind of discussing the.
You don't really get to the real stuff.
So I think like the typical software selling process, you have, you know, this workshop and you're sitting there talking about all of the stuff.
But it's always like that when you actually start to log into the account and to try to figure out exactly what the customer needs to do, that's when you get all the answers.
So I think this builds a lot of trust.
And when you sit in this hypothetical workshop discussions, the customer is always thinking, okay, this sounds really Good in theory, but I don't really know if it will work in reality.
And that's also one of the reasons why we spend so much time building integrations to the most common other tools that our target market is using to kind of accelerate the way to get the data in.

Omer (26:00.820)
How are you qualifying people before you were going and doing this work?
Like, you could have somebody who kind of looks like they're interested in it, and you spend a whole bunch of time getting their data into the product and then they never use it or try it out, versus someone who is a lot more engaged actively using the product, maybe giving you feedback, and is far more likely to become a paying customer.
What were some of the things that you were doing to qualify and to figure out which bucket somebody kind of fell into?

Daniel Wikberg (26:38.460)
I mean, I think that that's, that's the beauty of doing it this way, because engaging in the trial, in the way that you have to do to get value as a customer, you don't spend that time if you're not interested.
So I think that sell.
The process of doing that kind of qualifies the customer.
It's part of the qualification, I would say.
And obviously it's super important to make sure that you're not talking to some guy in the organization, in the customer's organization who just has a little too much free time on his schedule.
So we try to always include the CEO, or at least somebody reporting to the CEO to know that we're talking about something real.

Omer (27:29.130)
So you were basically any prospect that you're talking to, you were by default onboarding or moving over their data into the trial product.

Daniel Wikberg (27:39.450)
Right.

Omer (27:40.090)
Wow.

Daniel Wikberg (27:40.570)
So we had a fun example.
I think this was customer number five.
They were like very old school.
I mean, the opposite of tech savvy.
And when we were planning to do the implementation and we were talking about, yeah, we need to get your data into up sales, they actually literally went to get a physical, like a moving box with binders, like, yeah, these are our customer records.
Can you help us?
So, yeah, they actually had to do that themselves, but you get to see all kinds of examples.

Omer (28:18.870)
I know at one point you sort of, you changed your sales approach and you kind of went more towards sort of like a land and expand type approach.
What was the thinking behind that?
Why did you make the shift and how did that work out?

Daniel Wikberg (28:35.560)
So, I mean, we used to have these bundled, you know, this product bundles, which a lot of SaaS companies have, with, you know, like a gold, a silver and a bronze package.
And we Realized two things, that these bundles created a lot of frustration for existing customers.
You know, they wanted like one feature from the gold package, but they didn't want their bill to grow by 300%.
That was one thing.
And the other thing was that when we looked at our top 20 accounts who were paying us like north of $50,000 per year, most of them started paying like 4 or $5,000 per year.
So it made sense to kind of lower the threshold to make like the initial decision as straightforward as possible for new customers.
And then we moved to this pricing model where we have like a license, like a price per seat.
And then all of the other stuff we turned into add ons, which made it a lot easier for the expansion sales team.
We used to be like, you could sell more seats or you can sell an upgrade.
And that changed to you could sell seats or you could sell like, you know, a variety of 15 to 20 different add ons.
So it really helped accelerate the growth on existing accounts.

Omer (29:52.780)
Okay, great.
So existing accounts, it worked.
How did it work out with lending new business?

Daniel Wikberg (29:57.500)
Yeah, that also improved because I mean we talked a lot about internally that don't worry so much about the initial contract value.
I mean just get the customer on board, just, just sign them and make the initial decision as straightforward as possible.
And I think there's a great benefit for the customer as well because when you start to use any software, I mean you can spend a hundred hours in a workshop trying to figure out exactly what you need, but when you start using it, that's when you realize all of the details.
So I think doing it this way, like kind of simplifying the initial scope, if you will, reduces the risk for the customer.
So it's great for us and it's great for the customers.

Omer (30:51.200)
Let's talk a little bit about hiring.
So you said the team is about 70 people today, right before we started recording, you were telling me about some of the challenges of kind of balancing not having too many junior people or senior people.
Just tell me about some of the challenges that you faced.

Daniel Wikberg (31:16.280)
I can attribute 100% of the success of the business having the right team.
I mean, it's a cliche, but it's so true.
And when you're a super small, when you're a startup, you need to get a lot of stuff done and the roles are never like clearly defined.
And if you're a five man team or a ten man team, everybody literally has three roles.
So I think that's a challenge because you need some outside perspectives and you need smart people with experience, but most smart people with experience come from way larger companies and most of them are struggling to adapt to this kind of chaotic environment of a startup.
So that's a challenge, like finding smart people who can really contribute and move the needle, but also have the kind of, you know, roll up your sleeves and just get your hands dirty.
That's a combination that it's rare to, it's hard to find.
So I mean we've had great success of hiring a lot of people early in their career, a lot of newly grads and training them.
And I mean it's a model that works, but it doesn't scale forever.
And after a while you get to a point where, okay, now the team is growing.
We need to promote somebody to a manager and we need to have all these kind of specialized roles and it's always easier to promote somebody from within.
But if nobody inside of the company has like any experience except from being at up sales, then you end up in a tricky place.
So I think that balance, it's a very difficult balance.
And now when we are hiring, we're trying to like the same way we have a very defined list of companies we want to sell to.
We try to define like these are the companies we want to hire from.
So try to identify which are the companies out there who have like a similar culture, similar size, like similar selling process and so on.
So that's one way of solving that.

Omer (33:43.020)
What was the worst hiring mistake you made in what did you learn from that experience?

Daniel Wikberg (33:47.830)
I mean, I remember one time a few years ago we actually hired like three people almost at the same time who were like super senior.
Two of them were part of the management team and these were like really smart people.
And you know, every month when we have like a town hall meeting every month, you know, going through the KPIs and all of the stuff that's happening and you know, boy, they had impressive PowerPoint slides.
But you know, a couple of months go by and you realize that none of them is doing anything.
So I think that was kind of don't get impressed by, you know, people's jargon or slides or you know, resume or background.
I mean, and I think one learning from that was that when you hire somebody senior for the first time, don't just let them go.
Make sure to like have clear expectations like weekly check ins and milestones and I mean you can't manage them in the same way you manage a newly grad, but you can't just let them go either.
So I think that was kind of the mistake I did.
It took me too long to realize that these guys aren't doing anything and I paid them a fortune.

Omer (35:08.109)
I think it goes back to like hiring the right person for the right type of company.
And if you're bringing in somebody senior who's working, maybe a much bigger company, maybe some of those PowerPoint slides are the expectation, right?
Because they are.
They're kind of delegating a lot of stuff out.
And the other thing I wanted to ask you about was this IPO that you mentioned.
Typically like, you know, when.
When I kind of look at a company and think of IPOs, it's usually, you know, yeah, they hit 100 million in ARR or something like that.
So for you, at around you, 30 million ARR, I don't know exactly when you did the IPO.

Daniel Wikberg (35:49.662)
2019.
So like four years ago.

Omer (35:51.600)
Got it.
So it kind of seemed early.
Is this something specific to Sweden or do I just not know what I'm talking about when it comes to IPOs?

Daniel Wikberg (36:01.280)
No, but it's a good point.
I think that Sweden actually has a culture of a very large part of the population have like a stock account.
So you have this culture of buying stocks.
I mean, you know, even if you have like only $1,000, you probably have like some kind of stock account and you trade stocks.
So this has kind of enabled.
You have actually a couple of them, like smaller lists.
So nasdaq, who operates the Stockholm Stock Exchange, they have like a smaller list called first north, where we are listed.
And I mean, this has enabled like very small companies to go public.
I mean, I think a lot of companies do it too early.
When we did it, we were at like $6 million in revenue.
And I mean, we were profitable.
We were doing like 20% EBITDA or something like that.
So I mean, at least we had some kind of stability and a business that had some predictability to it.
The story behind it was that, I mean, I had, I think I had like 74% ownership when we did the IPO.
So I wanted to sell like a small part of my ownership.
And I had a partner who wanted to exit, who had like 10% as well.
And then we had a loan I mentioned.
So we took on like, I think we did a share ratio of 2 and a half million dollars.
It was like a small issue.
And the pre ipo, which we did to get some more institutions and more famous people in the list of shareholders, that was actually a pure secondary.
So me and my partner selling existing shares So I think if you add those together, I think it actually becomes the number you see in Crunchbase.
But like two thirds of that were never like capital raised to the company was just me and my partner selling shares.

Omer (37:58.730)
There are obvious benefits to doing an ipo, but as a bootstrap founder, where you kind of are running the show, you don't get too much interference.
There are no investors to tell you what to do or grow faster at any cost and that kind of stuff.
What has been some of the challenges of now running a public company?

Daniel Wikberg (38:23.690)
I think a lot of people overcomplicate.
I mean you have this view of once you go public, you have the, this monster of administration and all of this stuff you need to do.
I mean we have one person in finance and then we have like an outsourced partner helping us with the day to day books.
But we have a highly automated way of running our finance team.
I mean I have a few friends who've taken their companies public and some of them have had very poor experiences from doing that.
So I tried to learn from, from their mistakes.
And I mean, I think I wanted to sell some of my shares and my partner wanted to exit and I wanted to continue to be the majority shareholder and to maintain the control of upsells and run it the way I want to.
I wouldn't, I wouldn't have been able to do that by, you know, the other, the other, the other option would have been to sell like a minority stake to a private equity firm or something like that.
I think that would have been more of a hassle actually to handle compared to taking the company public.
So if you do it the right way, it's not that bad actually.

Omer (39:37.760)
Yeah, it sounds very like I thought you had a huge finance department and a whole bunch of overhead now that you had to deal with and things you have to, requirements that you have to meet in terms of how you're running the business.
But there you go, you learn something new every day.

Daniel Wikberg (39:55.350)
Yeah.
And I mean I think that the majority, the kind of, the trap that I think a lot of companies fall into is that when you go into that space, you know, you start meeting all these bankers and advisors and investors.
I mean these are smart people and all of them have like very strong opinions about what you should do once you're a listed company.
Almost all of them are wrong.
That was kind of, that was tricky in the beginning to navigate, like, okay, who should we listen to?
So I actually found a couple of mentors, like entrepreneurs who have, you know, taken their business public and had it public for many years and grown it into two larger, larger companies.
And the advice you get from people like that are, like, almost always exactly the opposite of what you get from these, like, you know, smart experts in expensive suits.

Omer (40:54.350)
All right, we should wrap up.
So I'm going to get onto the lightning round.
I've got seven quick fire questions for you, so just try to answer them as quickly as you can.

Daniel Wikberg (41:04.109)
Let's do it.

Omer (41:05.070)
What's one of the best pieces of business advice you've received?

Daniel Wikberg (41:08.350)
Trust your gut.

Omer (41:09.870)
What book would you recommend to our audience and why?
You can say the same book again if you like.

Daniel Wikberg (41:15.460)
Yeah, I mean, the book I mentioned is great, but I love it's behind me here.
It's A Hard Thing About Hard Things by Ben Horowitz.
I've got a ton of good advice from that one.

Omer (41:24.660)
What's one attribute or characteristic in your mind of a successful founder?

Daniel Wikberg (41:29.859)
Stamina.

Omer (41:30.740)
What's your favorite personal productivity tool or habit?

Daniel Wikberg (41:34.740)
Getting things done.

Omer (41:35.860)
What's a new or crazy business idea you'd love to pursue if you had the extra time?

Daniel Wikberg (41:40.810)
I don't know, something related to energy, maybe?

Omer (41:45.850)
What's an interesting or fun fact about you that most people don't know?

Daniel Wikberg (41:49.370)
I actually once was planning to compete in powerlifting and I was planned to be on the national competition actually when I was like 35 years old.

Omer (41:58.810)
Wow.

Daniel Wikberg (42:00.410)
And then I broke my back.

Omer (42:02.650)
Sorry to hear that.
And finally, what's one of your most important passions outside of your work?

Daniel Wikberg (42:07.350)
Skiing.

Omer (42:08.710)
Sweet.
All right, if people want to find out more about upsells, they can go to upsales.com if folks want to get in touch with you, what's the best way for them to do that?

Daniel Wikberg (42:19.190)
Danielupsales.com Beautiful.

Omer (42:22.390)
Daniel, thank you so much for making the time to chat, for sharing your story.
Always love talking to founders who who bootstrap and their SaaS business and grow beyond 10 million.
ARR.
So congratulations on that and I wish you and the team the best of success.

Daniel Wikberg (42:44.670)
Thanks a lot.
Thanks for having me.

Omer (42:46.110)
My pleasure.
All the best.
Cheers.

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