Doug Winter, Seismic

Enterprise SaaS Sales From a Basement With No Category

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Episode Summary

In 2010, Doug Winter and his co-founders started building Seismic in a basement in San Diego. They had no venture funding, no brand recognition, and no product category to sell into. Despite that, they targeted enterprise sales from the very first deal.

Twelve years later, Seismic hit $300M in ARR, grew to 1,500 employees and 2,500 customers, and raised $450 million in funding. Doug shares how they created the sales enablement category from scratch, overcame enterprise objections as an unproven startup, and turned small footprints at big companies into million-dollar contracts.

Doug Winter is the co-founder and CEO of Seismic, a sales enablement platform that helps organizations better engage with customers and grow revenue.

In 2010, Doug and his co-founders launched the business out of a basement in San Diego. Their previous company had been acquired by EMC, and they saw an opportunity to bring the SaaS model to content management the same way Salesforce had done for CRM.

They initially focused on sales and marketing teams, but there was a problem. Sales enablement did not exist as a product category. For the first two years, they struggled to position the product. Enterprise buyers kept asking where Seismic fit on the analyst block diagrams, and the founders kept debating what to call themselves.

Rather than starting small and working their way upmarket, they went after enterprise sales from day one. Doug says the reason was simple: that was their comfort zone. They knew how to sell to large financial services companies and manufacturers, and they did the math on how many $10K deals it takes to reach $1M ARR.

But selling enterprise as an unknown startup brought serious obstacles. Compliance teams flagged them as a bankruptcy risk. Security checklists arrived with 47 tabs and hundreds of questions they could not answer. And on one memorable leap day in February, a cloud provider bug destroyed a critical executive demo just hours before they lost their biggest pipeline deal.

Doug explains how they survived those early setbacks, how they turned small pilot deals into million-dollar contracts by adjusting their roadmap without building custom features, and why being an "emotional counterbalance" became the most important part of his job as the company scaled to $300M in enterprise sales revenue.

Topics: Enterprise Sales|Positioning & Differentiation|Bootstrapping

Key Insight

Seismic co-founder Doug Winter grew the company from a bootstrapped basement startup to $300M ARR by targeting enterprise sales from day one, even before "sales enablement" existed as a product category. The team landed their first million-dollar deals by starting with small pilot deployments at large companies and expanding after proving value, rather than trying to close big contracts upfront.

Key Ideas

Seismic bootstrapped for the first two years before raising venture capital, reaching initial customers on founders' own capital during the 2009-2010 recession
The team targeted enterprise sales from the start because the math favored fewer large deals over many $10K contracts
Their first million-dollar customer came from the pharmaceutical industry after starting with a small footprint and expanding
Enterprise compliance teams flagged Seismic as a bankruptcy risk, but strong business sponsors overrode the objections
Sales enablement was not a recognized product category until two years into Seismic's journey, forcing the founders to create and define it

Key Lessons

🏢 Target enterprise sales if you have the experience: Doug Winter's team sold to large companies from day one because that was their comfort zone from a previous exit, and the math favored fewer large deals over hundreds of small ones.
📉 Expect enterprise sales compliance to question your survival: Seismic's early financials triggered bankruptcy warnings from enterprise procurement teams, but having a strong internal business sponsor helped override compliance objections every time.
🎯 Create your category by listening to customers, not debating internally: Seismic spent two years debating positioning before realizing customers were already describing the "sales enablement" problem - they just needed to own the term.
🏢 Start with small enterprise deals then expand from within: Seismic landed its first million-dollar contracts by getting small pilot deployments at large companies and proving value before asking for bigger commitments.
🧠 Become the emotional counterbalance as your company scales: Doug learned to project calm during crises and temper celebrations during wins, because every small shift in a CEO's behavior gets amplified across 1,500 employees.
🛠️ Adjust your roadmap for key accounts without building custom features: Seismic prioritized features that mattered to large enterprise prospects, balancing individual customer needs with long-term product vision for all customers.
🚀 Bootstrap first to maintain control, then raise when ready: Seismic self-funded for two years during the Great Recession, proving traction before taking venture capital on their own terms rather than desperate terms.

Watch the Episode

Chapters

00:00Introduction

01:44Doug's favorite quote and mindset on resilience

02:29What Seismic does and the sales enablement problem

04:57Company scale: 1,500 employees, $300M ARR

05:23Did you expect this level of growth?

06:10Sales enablement 101 and the Enablement Cloud

09:26Origin story: from EMC exit to basement startup

12:12Positioning struggles without a product category

13:51Building the MVP and getting in front of customers

15:21Why they bootstrapped instead of raising money

17:12Decision to target enterprise sales from day one

19:39Landing the first big enterprise deals

22:47Enterprise objections: compliance, security, risk aversion

25:49The worst day: leap day demo disaster and lost deal

29:30Becoming the emotional counterbalance as CEO

33:14Hardest part of the 12-year journey

35:18Lightning round

Episode Q&A

How did Doug Winter grow Seismic from a basement startup to $300M ARR?

Doug and his co-founders bootstrapped for two years, targeted enterprise sales from day one, and focused on landing small pilot deals at large companies before expanding into million-dollar contracts. They raised $450M in venture funding after proving initial traction.

Why did Seismic target enterprise sales instead of starting with smaller customers?

The founders had enterprise experience from their previous company acquired by EMC, and Doug calculated that closing fewer large deals was more efficient than acquiring hundreds of $10K customers to reach $1M ARR.

How did Seismic create the sales enablement category?

For the first two years, the founders did not know what sales enablement was. They started as a content management solution for sales teams, listened to customer feedback, and eventually realized the category they were building. They then chose to own the term and drive it forward.

What enterprise sales objections did Seismic face as an early-stage startup?

Enterprise compliance teams flagged Seismic as a potential bankruptcy risk based on their financials. Security teams sent checklists with 47 tabs and hundreds of questions about certifications the startup had not completed. Strong business sponsors helped override these concerns.

How did Doug Winter handle the worst day in Seismic's early history?

On a February 29th leap day, a cloud provider bug ruined a critical executive demo at a large insurance company. Hours later, their biggest pipeline deal called to say they were building the solution themselves. Doug describes the flight from Boston to San Diego as the lowest point.

What strategy did Seismic use to land million-dollar enterprise sales deals?

Seismic started with small pilot deployments at large companies, then expanded by proving value. They adjusted their product roadmap to prioritize features important to key accounts without building custom one-off solutions.

Why did Doug Winter bootstrap Seismic instead of raising venture capital immediately?

Doug had watched a previous dot-com startup crash after taking venture money with poor investor behavior. Combined with the 2009-2010 recession drying up venture dollars, he and his co-founders decided to self-fund and maintain full control of decisions.

How did Seismic's positioning challenges affect their enterprise sales process?

Without a recognized product category, enterprise buyers questioned where Seismic fit on analyst block diagrams. The founders spent half their sales cycle convincing prospects that sales enablement was important before they could discuss the product.

What does Doug Winter mean by being an "emotional counterbalance" as a CEO?

Doug learned to project calm and positivity during crises to prevent the team from spiraling, and to temper celebrations during wins by highlighting areas for improvement. He describes this as the hardest emotional part of leading a company that grew to 1,500 employees.

Book Recommendations

The 7 Habits of Highly Effective People

by Stephen R. Covey

Links

Seismic: Website | LinkedIn | X
Doug Winter: LinkedIn | X
Omer Khan: LinkedIn | X

Full Transcript

Omer (00:09.280)
Welcome to another episode of the SaaS Podcast.
I'm your host, Omer Khan, and this is the 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 Doug Winter, the co founder and CEO of Seismic, a sales enablement platform that helps organizations better engage with customers and grow revenue.
In 2010, Doug and his co founders launched their bootstrap business out of a basement in San Diego with the vision of helping companies solve their content management problems.
Initially, they decided to focus on a solution for sales and marketing teams, but at the time, sales enablement wasn't even a product category, so they really struggle to position their product in the minds of their customers.
In this episode, we unpack that story and share Doug's journey, including why Doug and his co founders decided to bootstrap the business for the first couple of years instead of fundraising and why that turned out to be the right decision, why they decided to target enterprise customers from day one instead of working their way up market, and the challenges they faced as a startup selling to large organizations.
And we talk about how they've grown Seismic from a bootstrap business to a SaaS company doing over 300 million in ARR, 2200 customers and having raised $450 million in funding.
I hope you enjoy it.
Doug, welcome to the show.

Doug Winter (01:44.630)
Thank you.
Excited to be here.
Appreciate the opportunity.

Omer (01:47.070)
Do you have a quote, something that inspires or motivates you that you can share with us?

Doug Winter (01:50.650)
Oh, my favorite.
My favorite quote.
It's.
It's John Wooden.
You've got to be a little bit certain vintage to know who John Wooden is.
But things turn out best for those that make the best of the way things turn out.
I think I've leaned on that one the last two years, two and a half years, I'd say more than.
More than I wish I had to, but I think it's a great quote.
It really talks about focusing on the things you can control and.
And not worrying as much about the things that you can't control.
And I think in these crazy times of COVID and pandemic and social unrest and now whatever this is that we're going through today, I think that one is one that really resonates with me.

Omer (02:29.570)
That's awesome.
So tell us about Seismic.
What does the product do?
And it's quite an extensive product.
Who's it for?
And what's the main problem that you're helping to solve?

Doug Winter (02:41.600)
Yeah, it is quite an extensive product.
And, you know, 12 years into the journey now, we've got a team of almost 500 people that have been working on that product for over a decade.
And sometimes I see all the capabilities.
It's amazing to me.
But the fundamental problem is a simple one, which is selling, especially enterprise sales, is hard.
It's very difficult.
And it's harder than ever today where you have customers who are out there doing a ton of research about you before they ever call you as a salesperson.
So they know a lot of answers before they ever call you.
Where companies have more and more products and solutions in their bag.
So this, the actual knowledge base of what you're supposed to know about and sell has gone through the roof.
And it's tough.
You're now in a remote world where you're probably not going to be concluding deals on the golf course or over a steak dinner.
You're going to be face to face over a zoom call or a WebEx call or something like that.
It's made it really, really difficult.
And so we're really attacking sales enablement at the highest level.
In my mind, it's make sellers better through the use of technology and being able to do that in a way that they know what to say, what to share, what to do.
And they can navigate all the content that's used in the sales process, whether those are g slides of PowerPoint decks, white papers, videos, or just plain old questions and answers.
And being able to respond to those doing that quickly, doing that professionally, doing that in a way that's differentiated for your from your competition, Training and onboarding of reps is also a big part of being able to make them more effective.
So whether it's onboarding a new rep, which is doubly important in a world where there's so much turnover and a great resignation, or whether it's supporting training of reps when you launch a new product or go into a new market, being able to do that well, get reps more efficient, more quickly is a huge challenge and super impactful.
You know, there's probably not too many board meetings that happen where the board members aren't asking the CEO, how are you doing with your sales capacity and ramping up new reps and what's your rep turnover and what's your attainment rate?
And so our products really are focused on helping to solve those, those sets of problems.

Omer (04:57.020)
Now, you said you had about 500 people who've been working on the product for the last decade, but team size overall, you have about 1500 employees, is that right?

Doug Winter (05:06.830)
Yes, we're about 1500 employees.
Yep.

Omer (05:09.630)
And about 2,500 customers.
Where are you in ARR.

Doug Winter (05:16.030)
Yeah, we're, we're just at 300 million in, in revenue run rate now.
So it's crazy how, how we've grown over the years.
It's been a fun journey.

Omer (05:23.470)
Did you have any idea that the business would be this size when you started like 12 years ago?

Doug Winter (05:28.350)
You know what's really funny is I think all of us entrepreneurs create a business plan and you go into that wonderful feature in Excel where you can just grab the column in the corner and drag it to the right and watch the growth just happen.
And you see the customer count, you see the revenue, and you see the employee count go.
And I can tell you standing on stage and looking out at 1500 people is way different than looking at a spreadsheet and seeing the number 1500 in that column.
So on one hand, yes, absolutely, absolutely.
We, we knew this was a big opportunity and our vision and, and, and dream was to grow here and, and beyond.
On the other hand, it's, it is, it is definitely surreal at times.

Omer (06:10.490)
I want to talk a little bit about sales enablement, because I think.
Let's just do a quick 101 on that.
I think everybody listening to this has probably heard the term sales enablement.
They probably have some vague understanding of it.
Maybe others understand it better.
Obviously there's a technology aspect to this, and this is where seismic fits in.
But can you just tell us what your perspective is, how you see that, and what is the opportunity for businesses to really embrace and think kind of more strategically about how they approach sales enable?

Doug Winter (06:45.540)
Yeah, absolutely.
So we recently launched what we're calling the Seismic Enablement Cloud.
And it really is a step, function change in the field of sales enablement from being very tactical.
I'm creating training for my teams, or I'm organizing and creating content for a product launch to something that's much more strategic in that you now have the tools and the capabilities to have a plan of what you want your enablement programs to look like.
And where you need content and where you need training, you can track progress against that plan.
You can assign the pieces out.
Because enablement, you know, while it's a, it's a rich function on its own, it really relies on a lot of others, product marketing, for example, to build content that's going to be shared in support of the sales team and come up with the stories that are going to be needed and, you know, be able to Create the right set of materials and to support the training needs and onboarding needs.
So, so making that and understanding that it's a very strategic function and with targets and goal and timelines, you know, is a big change that really we enabled with the launch of the Enablement Cloud.
Any major strategic initiative has to have a closed loop.
You need to look at the results, you know, are they actually getting the results that you expected them to?
So if they said all the right things that you think they should be saying and they're still not winning the deals, well, maybe you have a different problem or they're losing deals, but you realize they're not using the content the way that you intended the content content to be used, then the problem that you have is one of training around your process or your playbooks.
So getting a very strategic and continuous closed loop view of how is my sales team doing and how are my individual sellers doing is really what the enablement cloud is all about.
And I think increasingly we see organizations of all sizes, but certainly bigger organizations, who view this as an incredibly strategic area.
You know, when we started on this journey, I'll tell you that we spent half the sales cycle, you know, convincing someone that enablement was important and they needed to spend money on it and build a budget for next year.
And now we routinely meet with a VP of enablement and she's got a team of 20 people and a significant budget, and they know they need these technology tools.
They're just trying to figure out who the right partner is to work with.
So the market has really come around to realize this is a strategic function.
And we believe, I believe strongly that with the Enablement Cloud, we're now putting in place some of the final pieces that enable you to take a very strategic view and not just be very tactical.

Omer (09:26.770)
Great.
So let's go back to 2010.
Where did the idea for this product come from?

Doug Winter (09:33.810)
Yeah, so it's kind of a fun story.
Previous company that we had were working at together was in this space of content, content management, content customization.
We ended up getting purchased by emc.
We were part of the EMC Documentum stack.
And, you know, what we realized was that the world was changing and that the new paradigm was going to be SaaS and it was going to be cloud.
And we looked at what Salesforce was doing at the time and said, what did they do?
Well, they took CRM, which was a known area.
They made it a whole lot easier to use, kind of consumerized.
It made it a lot easier to use.
They Used a new tech stack, which was a cloud, and they used a new business model which was a subscription and changed the world.
And what did Workday do?
Well, they took PeopleSoft some ways literally and redid that capability.
New technology stack, new business model changed the world.
And netsuite was doing the same for erp.
And we thought, well, nobody's really doing this for the problems of content.
And we looked around us and we saw really big, hard, important problems that didn't have great solutions.
You know, there were big businesses being built around those and I won't, I won't throw any of their names under the bus, but they had grown big businesses with products that customers really didn't like, but they needed.
And we thought, wow, we've got an opportunity here to do what Salesforce had done, but do it in the area of content, content management.
And we had also the experience of many sales and marketing organizations coming to us and saying, can you help us with the problem that we have in sales and marketing?
Sometimes they would say, can you help us with our PowerPoint problem?
We're drowning in PowerPoint decks.
We need to do better.
And the truth was that those products that existed at that point in time were terrible for the needs of sales and marketing, where things needed to move really fast.
Right.
You couldn't rely on your IT team and a one year project when you had a product launch to support or a big event that you were sponsoring, you needed to move a lot faster.
So we thought, let's start focused on sales and marketing and then we can build more and more content solutions over time.
And early in that journey, we realized sales and marketing was a huge opportunity by itself and we could go around content and add other capabilities and go much, much deeper there.
Until we, we kind of had the original vision and we shifted it to really just go deeper and deeper into sales and marketing.
I think a funny part is we didn't know what sales enablement was.
We never heard that term two years in to the journey before we finally settled on, you know what, that is, what we're doing and let's own that term and help drive it forward.

Omer (12:12.910)
How did you describe the product in those first couple of years?
Because if you're going into a new category or you're going into a category that you don't know how to define, it's kind of a challenging place to be and the positioning is all over the place.
How did that work for you?

Doug Winter (12:30.550)
Yeah, it's a really great observation that defining a category is a lot different and A lot more work in a lot of ways than replacing an incumbent, innovating around an incumbent in a well established space.
To be honest, we had many, many, many debates locked in our basement where we started the company, trying to decide what do we want to call ourselves and what category really going to end up being and did we need to be in an existing category or could we create a new one?
We had a lot of discussions and debates around it and it was a critical decision because you do, especially selling to enterprises.
If you're not in some category that one of the analyst firms is covering, then people are like, I don't know if I need you, why do I need you?
You're not on this block diagram anywhere.
Where do you fit?
But we just kept listening to the customers and the customers kept telling us we need this, this is important.
And although there weren't fit for built for purpose tools out there, there weren't many built sales enablement specific tools.
Everyone somehow dealt with the problem of, you know, all their PowerPoint decks.
And so the problem was real.
Nobody argued about that, what it was called and how to best solve it with technology.
That was where the action was and where the discussions really went.

Omer (13:51.220)
So you've got the idea for this product.
How did you get started?
How long did you spend going out and talking to customers and trying to validate this idea?
Did you start building a product fairly quickly or an mvp?
And how long did it take you to get something in front of potential customers?

Doug Winter (14:10.580)
Yeah, we, you know, we were most of the founders, three of the four of us were really product people.
Like that was what we love doing.
And if you would have locked us in the basement and kept paying us and just let us keep going forever, we probably would have been happy to keep doing that, having fun and innovating.
But fortunately, the fourth founder was really from the go to market side of the house.
And very early on he got us in front of a lot of prospects and customers and partners and just generally smart people who we could show our concepts to.
And then those became our prototypes and those became our early versions and those evolved into our mvp and some of them evolved into our first customers.
So that whole process, probably it was a good year of heads down work on building the product.
I think one of the good things was because of our experience, we kind of knew where at least a great starting point was.
And so we were really focused on that.
We knew that that was going to be something that companies would need.
And so we really focused on those core pieces and Then as about a year into it, started getting in front of customers to get real feedback and it was probably, it's probably 18 months or so before we signed our first contracts.

Omer (15:21.260)
Now you decided to bootstrap this business, at least for the first couple of years.
Was there a particular reason that you took that route?
You had a successful exit.
So I.
Presumably funding wasn't kind of a major issue for you guys in terms of getting started, but were there any other reasons why you decided that you weren't going to go and raise money?

Doug Winter (15:43.820)
Yeah, I had the incredible experience of being part of a startup that it wasn't my company, I hadn't started it, but a close friend had started.
And I joined very early on in the, in the dot com days and had the opportunity to sit front row and watch a business go from, you know, 0 to 100 miles an hour and then crash and go back down to zero again in a very compressed period.
Two years.
Something along those lines and watching some of the investment left me with a feeling like, wow, that there just wasn't the kind of value add that you would expect.
And there was some pretty bad behavior that sort of helped make sure this business wasn't gonna make it.
You know, I didn't see the whole picture, but I saw enough to, to be left feeling like, is that something we even really wanna deal with?
We are in a situation where we're fortunate enough, we can get going with a small team for a while and then we'll bootstrap from there and, you know, and all the goodness that goes along with, you know, no dilution and being able to make your own decisions and that kind of stuff.
So we fell in love with that idea.
It was also, I'll point out, as you mentioned, 2009, 2010, so it was kind of majorcrash.com now or major crash of the Great Recession.
So it was also one of those times where it wasn't the best fundraising environment.
The venture dollars had dried up, especially for earlier stage stuff.
It was tough.
So we just put our heads down and said, let's just go.
And our intention honestly was will go all the way and just keep going and build the business that way.

Omer (17:12.239)
So you're building this product, you've been talking to potential customers, you're getting a sense of like where you want to take this business.
And you also talked about how sales and marketing look like an area that you could just focus on and go pretty deep there anyway.
You also decided pretty early on that you were going to target enterprise customers.
And as you and I were talking before we started recording, there are a whole bunch of challenges that come when an early stage startup, particularly that's Bootstrap, maybe has even kind of more limited funding, is trying to go out and sell to enterprise customers.
So number one, what was the reason that you decided that you were going to go direct to enterprise versus saying, you know, let's start with mid market or something and we'll work our way up.
And I want to kind of sort of unpack a little bit about what were some of the challenges that you faced when you started to do that.
So maybe just help us understand like the decision making process and why you decided to do that.
And then maybe we can talk a little bit about the process you went through to actually get enterprise customers to spend money with you.

Doug Winter (18:15.660)
Yeah, I mean, I'd love to say that it was, you know, a deep strategic discussion and debate and we had, you know, pros and cons.
The truth is that we knew how to sell to big companies, we knew how to service big companies and enterprises, and we knew how to solve complex problems.
And that was our comfort zone.
We knew what it took to sell to a large financial services company and, you know, huge manufacturers, and that was our comfort zone.
So we really focused on what we knew, you know, And I think I do remember going out when we did decide to take venture money and being asked, you know, consistently two questions when I went around up and down Sand Hill Road.
Given the pitch, the two questions were, number one is you're going to move your whole team up to San Francisco, right?
Because that's the only place you can start a company.
And the second question was you're going to do a freemium model, right?
Because that's the business model, you know, at the time du jour.
And you know, I kind of had to tap dance around because our answer was no to both of those questions.
But it was really what we knew and what we were comfortable with.
And you know, I also know at some point, doing the math of, you know, how many $10,000 customers it takes to get to a million dollars in ARR.
And you know, I'm not a math whiz, but it's a lot.
And so focusing on those bigger deals, you know, something that also I think really helped our growth.

Omer (19:39.670)
So let's talk about maybe the first big deal that you landed.
Maybe we can talk about who the company was.
If not, let's just talk just, just generally.
But what was the process that you had to go through to, to Land that first deal.
And then what was some of the, the challenges that you faced along the way?

Doug Winter (19:56.470)
Yeah, I've always thought of it.
You know, there's kind of a couple of different categories, right?
It's, it's relatively easy to sell a small deal to a big company.
You know, you'll, you'll look and you'll see certain logos, you know, on everybody's website.
You know, because it's really easy.
They're decentralized and you can get a small footprint there, you know, without a whole lot of work.
It's relatively easy to get a bigger deal at a small company, you know, where they're not as structured about their decision making process.
You build a relationship and they'll say, yeah, we're all in with you.
And you know, you get a decent sized deal when you know, the whole enterprise or something along that is only 500 people, the tough nut to crack is getting a big deal at a big company.
And you know, those decisions are made in a very structured way.
They're made very slowly, painfully slowly.
Sometimes they're made in the constraints of a budget that was created, you know, possibly when you were still in high school.
And so, you know, you really have to work around all of those things to be able to get a big deal.
There are also companies that are more risk averse, you know, for good reason, you know, big mistake.
A mistake for a big company is a big mistake.
So they're more risk averse and the bars is higher in terms of how that goes.
So, you know, when we were focused, you know, some of our early wins were small footprints at big companies, you know, where they were willing to give us a chance, but then being able to leverage that and turn it into the bigger opportunity, you know, the million dollar deal, the $5 million deal, you know, that that really requires a lot of engagement at an early stage.
So, you know, for us, I remember we had a couple that come to mind and I probably shouldn't mention names, but we had a big customer in financial services.
We had another one on the technology side that, you know, took a chance with us early.
A third one that became our first million dollar customers was also, obviously it was also in the pharmaceutical space.
So different needs, different sets of requirements.
But really what we had to do is be willing to dive up in deeply with them, listen to what their needs were, balance what we wanted to build long term for the benefit of all of our customers.
And the roadmap and the vision we had with what they needed in order to sign off on getting to that next scale of a deal.
And so you do you have to be nimble and agile in your product development, the art of not building things just for one customer, but adjusting your roadmap to be able to bring things sooner.
Perhaps because they're very important to a particular customer who's willing to step up for a big contract.
You know, that's something that I think, you know, takes some practice and some patience and, but is critically important if you want to get those first big customers in.

Omer (22:47.820)
So you said that you guys were comfortable selling to enterprise customers.
So that's the direction that you took.
But you were still a startup, new product, unproven.
We still got that, that category positioning thing and explaining it to people.
What were the kinds of objections that you were hearing initially from some enterprise customers?
As we know that a lot of them are also very risk averse.
So what were the top things that kind of look like the biggest obstacles you guys had to figure out how to overcome?

Doug Winter (23:22.570)
Yeah, you got some that came from the business that really related to are you going to be able to deliver?
Because you're probably not selling them something that you have that is complete in every way.
And so you sell them the product that you have, you sell them through the pilot or proof of concept that they did, but you're also selling them on.
Here's what we're going to do for you over the next, you know, six months.
So you really have to have credibility that you're going to be able to deliver on what your promises are and what you say you're going to do.
You know, there's, there's, there's that whole category from the business side of are they really, are they going to make me look bad?
Are they going to make me look good?
You know, and I can, they'll make me look really good because this is innovative and cool and no one's ever seen a way to solve this problem before.
But boy, if I make a bunch of promises to my leaders and peers and then it all falls apart because they can't deliver, I'm going to look bad.
So it's weighing that equation with the business and then you sometimes get from the, you know, from the compliance, if you will, side of the house, well, geez, you know, based on the spreadsheet you sent us, you're going to be out of business in, you know, any year, in a year and a half.
Right.
So for them to understand the venture world, the venture backed world, and some companies do, a lot of them don't you know, it's like, well, what's your bottom line?
What's your profitability?
How much cash do you have in the bank?
You know, they just do that very quick math and say, well, according to this, you know, you're going to be bankrupt in 18 months.
Why should I take a chance on you?
You know, you have that whole category as well.
I found that most of those, if the business is on board and excited you can get around, you know, the compliance side will flag it and they'll say, I did my job.
And I raised this.
If you've got the right business sponsor, that won't be a blocker, but it can be pretty scary.
I can also remember some of those big companies delivering, you know, the dreaded and security spreadsheet checklist with 47 tabs and 100 questions per tab and what seems like a foreign language of what those, some of those questions are.
And, you know, are you, you know, have you been through this certification and that certification, which in the early days, the answer is no.
And, you know, and, and what does that mean?
I don't even understand what you're asking me.
So there's that whole aspect as well, which especially in financial services can be pretty intimidating.
And, you know, really getting the right expertise on your team to, to help you with that early on is another probably piece of advice I would give to someone who was starting down that road.

Omer (25:49.630)
There was one day that nothing seemed to be going right for you guys.
I think you described this as, as one of those moments where it was like, okay, is this over?
This thing is done.
We're not going to be able to make this dream come true.
Tell us what happened there.

Doug Winter (26:07.780)
It is amazing, especially in the early days, the emotional swings that you can have in startup land, you know, and I think navigating through those is probably a key survival and success criteria for entrepreneurs.
I doubt there's too many that everything just works all the time.
That certainly wasn't.
Hasn't been my experience, but I think what you're referring to is I remember it clearly.
It was, it was, it was a time when we had one of those huge swings because I woke up in the morning and, you know, it was early days.
We had a few customers, we had gotten a demo with a whole bunch of executives at a very large insurance company.
We'd worked really hard.
Our business sponsor had really gone out on a ledge to bring all the key execs to the table with us for an hour and a half to do a demo and a Dog and pony show.
We had a pipeline with a couple of other really good opportunities and including what would have been our first million dollar plus deal that was also partnership that would have brought a bunch of other revenue with us, really would have put us, put us on the map.
And so you wake up in the morning, you're feeling great, you're excited, a little bit nervous.
And the reason I remember it so clearly is it was leap day, so February 29th.
And so we walked into the demo and practiced down in the lobby, in the Starbucks lobby where, you know, we're doing our practice walkthroughs, everything's working great.
We go upstairs and we get set up, settled in, signed in, you know, badged, connected in to the monitors and all that stuff.
And then suddenly the platform started having all kinds of weird, weird issues.
You know, just random things just weren't working or were giving weird results.
And you know, I started a little bead of sweat as, you know, the countdown timer started to when all those execs were going to show up and we're, you know, going on the side, going, tapping, going, hey, you know, back to our technical team back home, what's going on, you know, why are we having these problems?
And they're, we're trying to figure it out, we're on it, we're not sure.
And turned out that our cloud provider had some sort of an issue related to the fact that it was the 29th of February, which, you know, doesn't happen except every four years and someone had missed that use case and they're testing.
And so we were getting very weird intermittent bugs showing up.
And so the demo was not what we wanted it to be.
I did a whole lot of tap dancing and hand waving and we got through it.
But it was clear that we had not maximized that opportunity and maybe we'd blown it completely.
And then I remember my co founder Ed taking me to the airport and a long quiet drive back to Logan airport and the phone rang and it was one of that million dollar deal and that million dollar partnership that we were talking about.
And I'm like, great, let me put it on the speakerphone.
And like, at least we're going to get some good news here because we were right down to the final and it said, you know what, we really thought about it and we're going to go in a different direction, we're going to build some of this stuff ourselves.
And so in a period of, you know, less than a half a day, we'd gone from the highest Highs to the lowest lows.
And, and anyone who's ever made the trip from Boston to San Diego, you know, that's the longest, basically the longest trip you can take.
It's awful long, long, brutal trip.
Just thinking, I'm not sure if, if we're going to make it.
So, yeah, that was.
Thanks for making me remember that.
Not, not really.
I could have, I could have packed that one away for a couple more years and not had to remember.
It would have been okay.

Omer (29:30.230)
I mean, that's the kind of challenge that every founder faces at some point or another.
And we always talk about founder grit, resilience and things like that.
But as, as your company grows and especially where you are now with, you know, a team of like 1500 people, it's not just about your resilience.
It's also about how people see you behave in, in, you know, the, the, the good times and the bad times.
Someone once described it to me, it's kind of like, like these kind of cog wheels and, and you know, you as a leader is kind of like this little cog and you kind of make this kind of one degree shift and you think it's like no big deal, like in terms of your behavior, but the downstream impact is that there's a cog somewhere that's spinning like this.
Right.
Because of what you just did or said or didn't say.
And you, you told me that you sort of, kind of had to think of yourself as becoming an emotional counterbalance for the company.
What does that mean?

Doug Winter (30:34.680)
Yeah, I, I think that's, that's something that changes too, as you grow as an organization quite a bit.
You know, I'm, I'm the kind of person, I wear my heart on my sleeve.
People close to me, they know how I'm feeling about just about anything at all, at all times.
I'm not be a lousy poker player.
I don't even try.
And, but as the organization grows, you know, you, you realize that people are watching and people that don't know you very well and that you don't know very well are watching carefully.
And they're watching your body language and they're listening to the tone of your voice and you know that your words carry a lot more weight than maybe you think they do or maybe more than even you want them to.
Sometimes I'm also the kind of person that thinks out loud.
And so sometimes I'll go into a product meeting and say, wouldn't it be cool if we did this?
And then the next thing I Know, the product team is like, well, Doug said we got to drop everything and go do this.
I'm like, no, no, no, no, no.
It was just an idea.
So you do have to learn to be a little bit more guarded about what you.
You say and how you say it and who you say it in front of.
And that's a.
That's first.
And then the skill that you have to develop.
But I do think the emotional counterbalance is.
It's real, and I think it's one of the hardest parts, emotion, you know, of the job.
Because when things are bad and you want to curl up in a ball and cry and, you know, yell and scream and whatever it is that you do, you've got to smile and you've got to be positive, and you've got to point towards the successes and the path forward, you know, and you've got to bring positive energy and pick everyone else up off the ground.
You know, you just have to do that.
You can't let the company wallow and spiral down in a negative way.
And on the other side of the coin, when things are great, you know, and you've had a killer quarter, and of course you want to celebrate it, but you also have to bring the team back down to reality and say, don't get so full of yourself.
You know, we won these three deals, and that's great, and we had a great quarter, and that's great.
But, you know, here's five things that we need to improve on and do better.
So celebrate it.
Enjoy it.
It's great to celebrate success.
It's one of our core values.
But you also have to bring the, you know, keep a foot on the ground and pull the rest of the crew back down and point out the problems that you have and all the things that you need to do to continue to improve.
And that's.
That's emotionally tough because, you know, it's not.
It's not normal.
It's not what you want to do.
It's not what's fun.
You know, it's more fun to go lead the party from the front than, you know, throw ice water on it.
But sometimes you have to do that, and it's an important, important part of the job.

Omer (33:14.560)
Now, when people listen to your story, they're going to look at.
Okay.
Doug and his co founders founded this business in 2010.
They bootstrapped for a couple of years.
They basically, in that first 18 months or so, were able to start getting the product out there and selling it.
And from what started with relatively humble Beginnings has now grown into a business that's doing 300 million, almost 300 million.
ARR.
You've raised $450 million to date.
You've got a team of 1500 people.
Kind of sounds like a great success story.
And everything went well.
Maybe that day we talked about that was the one bad day you had in the 12 years.
When you look back at that time, what was one of the hardest parts of building this business and taking this journey over the last decade or so?

Doug Winter (34:02.430)
You know, honestly, the first steps are the hardest.
And, you know, I always say that.
I think a key to being successful as an entrepreneur is you can't be too smart, because it's so easy to see all the problems and all the reasons why it's not going to work.
And they're real, they're valid.
There's a million reasons why it shouldn't work.
And yet you've got to believe and you got to not.
You got to be naive enough to think this is going to work and we are going to make it be successful.
So I think that, you know, keeping your eye on the next set step, the next milestone, you know, breaking the big problem down into smaller problems, you know, if you would have sat me down 12 years ago and say, okay, you know, Doug, how do we build a $300 million business?
You know, no clue, you know, but let's get this product built and let's go get the first customers.
Great, we can do that.
We can focus on that.
And, you know, you want to keep your eyes on the horizon, but you can't trip over that step that's right in front of you.
And so I think as a team, as an organization, kind of occasionally looking up at that horizon and making sure you're going, you know, where you want to go, and you believe in where you're ultimately going.
But then you spend most of your energy on what's that next step and what do we need to do to make that next step step successful.
To me, that's the formula that's.
That's worked.

Omer (35:18.499)
Awesome.
All right, we should wrap up.
I get onto the lightning round.
I've got seven quick fire questions for you.
Just try to answer them as quickly as you can.
All right, what's the best piece of business advice you've received?

Doug Winter (35:30.310)
Do a great job at the job in front of you and trust your job, your manager, your boss, and your career is going to go well.

Omer (35:38.550)
What book you'd recommend to our audience?

Doug Winter (35:40.870)
It's an oldie but a goodie.
I love the 7 Habits of Highly Effective People.
I think there's some just really basic life lessons in there about knowing what you want to do and how to get there.

Omer (35:51.400)
What's one attribute or characteristic in your mind of a successful founder?

Doug Winter (35:55.720)
Yeah.
Unrelenting belief in your team and yourself and not being too darn smart to see all the problems that are inevitably going to get in the way.

Omer (36:06.120)
What's your favorite personal productivity tool or habit?

Doug Winter (36:10.120)
Ah, that's a good one.
I like to get up really early and have, you know, an hour, half an hour to an hour of quiet time before the day starts to really collect my thoughts and think about what it is I need to accomplish.

Omer (36:24.600)
What's a new or crazy business idea you'd love to pursue if you had the extra time?

Doug Winter (36:29.640)
I'm infatuated with, with the idea of transforming the food industry, and I'd love to get into the indoor farming space.
I might be too late now, but I love that idea.

Omer (36:39.160)
Well, what's an interesting or fun fact about you that most people don't know?

Doug Winter (36:43.080)
My.
My first, My first job was out of college, was operating a nuclear power plant and training others on how to operate a nuclear power plant as a contractor working for the Navy.

Omer (36:54.420)
Wow.
And finally, what's one of your most important passions outside of your work?

Doug Winter (36:58.180)
I, I grew up in Ohio and farmland.
My grandfather was a farmer, and I moved out to California where, you know, you're lucky if you can scrape together a quarter of an acre and.
But I built a nice little farm, and I love getting out there and growing stuff and trying not to kill it.

Omer (37:12.580)
Awesome.
Great.
Well, Doug, thank you so much for, for taking the time to, to chat with me today and, and trying to unpack the story of what's happened in the last 12 years.
I think we gave people a good sense of the journey that you've taken, some of the challenges you had along the way, and where you've been able to take this business.
At the same time, I feel like we only scratch the surface and there's so much more we could, we could talk about, and maybe that's another topic for another day.
If people want to find out more about seismic, they can go to seismic.
Com and if they want to get in touch with you, what's the best way for them to do that?

Doug Winter (37:45.610)
Probably best way is reach out to me on LinkedIn.
I'm, I'm happy to make that connection.
And, you know, it's a great, a great way to start and, and, and connect.
And I'm, I'm happy to.
Happy to do that.

Omer (37:54.850)
We'll include a link to your profile in the show notes.
Awesome.
Well, thanks again and appreciate you taking the time to do this.

Doug Winter (38:03.170)
Thank you so much for the opportunity and really appreciate it.
It's been an honor to be on this journey and get to stand in front of an incredible team that made this all happen.
So thanks for thanks for giving me the the chance.

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