Neil Patel

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Doug Winter is the co-founder and CEO at Seismic which offers a global sales and marketing enablement solution for improving close rates and delivering larger deals for sales. The company has raised $179 million at a valuation that is rumored to be $1 billion from investors like JMI Equity, General Atlantic, Jackson Square Ventures, Lightspeed, and T. Rowe Price. Prior to that, he co-founded Objectiva Software Solutions, a software outsourcing company that provides projects and products to help ISV’s and enterprise companies. The company was sold to EMC for $90 million.

In this episode you will learn:


  • The challenges of bootstrapping your startup
  • Fundraising techniques to optimize for a positive outcome
  • How to build a great company culture
  • Staying focused when distractions are always around you


For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

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The Ultimate Guide To Pitch Decks

Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400 million (see it here).

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Doug Winter:


J. Douglas Winter, also known as Doug, co-founded Seismic Software, Inc. and has been its Chief Executive Officer since June 2010.

Douglas Winter served as Chief Financial Officer of Objectiva Software Solutions, Inc. He served as the Chief Operating Officer at EMC Document Sciences Corp. Douglas Winter served as the General Manager of Technical Operations at EMC Document Sciences Corp.

Prior to joining EMC Document Sciences Corp., Doug Winter co-founded Objectiva Software Solutions, Inc. and served as its Chief Executive Officer.

Previously, he served as General Manager of ONEWORLD Software Solutions California client service centers, establishing their west coast operations and also served as part of their global operations committee, responsible for formulating and executing strategic operations.

Doug Winter also served as Program Manager for Qualcomms 3500 series of CDMA base stations and later was responsible for the product certification and testing of the QUALCOMM Thin Phone (QCP 860/1960).

He served as Chairman of the Board of Objectiva Software Solutions, Inc. He serves as a Director of EMC Document Sciences Corp. and Objectiva Software Solutions, Inc.

Following his undergraduate work, he worked for three years for Westinghouse where he was an instructor for the US Navys nuclear training program. Doug Winter holds an MSEE and an MBA from the Massachusetts Institute of Technology and a BSEE from Virginia Technological University.

Connect with Doug Winter:


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Alejandro: Alrighty. Hello, everyone, and welcome to the DealMakers show. I’m very excited about our guest today. We’re going to learn a lot about building and scaling companies, and also financing them. So, without further ado, Doug Winter, welcome to the show today.

Doug Winter: Thank you very much. I’m happy to be here.

Alejandro: So, originally from the Midwest from Ohio. How was life growing up there?

Doug Winter: Well, I lived in Ohio until I was about 13. That’s a fair number of years back now. I enjoyed it. I grew up in the country surrounded by farms. It was a great place to be a kid, and it served me well with lack of distractions at a young age.

Alejandro: Your CV is quite impressive. We’re talking Virginia Tech, and then from there, you do MIT. You did a couple of things at MIT. What did you do there at MIT?

Doug Winter: I was really fortunate in my education path. Virginia Tech was an incredible school for me. I studied engineering there, got an awful lot out of it. Went off and started working in the nuclear power field, and then at some point realized that it wasn’t the most exciting field that there was at the time, so I decided to look at going back to graduate school. I thought even though I was an engineer, business school would be a good background for me, a good change in direction. But my heart was still an engineer. So, when this particular program at MIT appeared, to me it looked like the perfect answer. The program at the time was called LFM program. Now, they call it the LGO, Leaders for Global Operations Program. It was a joint program between the business school and the engineering school. They took engineers, taught them business, and then attempted to grow better operations folks to work at large manufacturing and technical companies. It was an incredible program. It was very small. There were only about 50 students in the class and sponsored by some large U.S. manufacturing companies like Intel, Motorola, and Amazon, Dell, companies like that. It was a really unique chance to get exposed and to get a full MBA experience, but at the same time, go deeper in the technical world. It really opened my eyes to a very different universe than what I had been in as a very technical person prior to that.

Alejandro: Walk us through that first experience entering the employment market because it took you a little bit until you finally took the leap of faith and started your own business. So, why don’t you walk us and the listeners through what it was like being an employee first?

Doug Winter: Sure. It was an interesting transition because when I was at MIT, it was the very beginning of the dot-com boom. I caught the bug when I was at MIT. I took some entrepreneurship classes. I was working on some side projects with some of my classmates. We built a small database for keeping track of our classmates and doing it all online. At some point towards the end of my second year, I turned to a few of my classmates and friends and said, “Hey, when are we ever going to be surrounded by so many really, really smart unemployed people? Let’s not take a job. Let’s go start a business.” And we had all kinds of different ideas. There were four or five of us that agreed “Yeah, we’re going to do this. We’ll take six months. We’ll go figure out what we’re going to do, and we’ll have a lot of fun starting our own company.” Then one by one, each of them took a job. McKinsey or Intel, or whatever it was. Had lots of bills to pay as a starving graduate student, etc. The next thing I know, I’m all by myself. The truth of the matter is, I didn’t have the courage at that point and time to say, “You know what? I’m going to go for it on my own.” So, I found myself in a little bit of scramble mode like, “I’ve got to find a job here.” So, I started looking around, and one of my classmate’s brother worked at this tiny little startup company out in San Diego called Qualcomm, tiny at the time. It wasn’t that tiny, but it was before Qualcomm really burst onto the scene. So, I came out having never been to California before. Came out and interviewed in San Diego with Qualcomm, and it had a really incredible culture and very fast moving, high growth, very entrepreneurial in its field certainly compared with some of the others that I had interviewed with. So, I was like, “Okay. This is what I’m going to do.” I moved out to San Diego, and I joined Qualcomm, and I was one of the first—I don’t know. I was like employee #3,000 at Qualcomm, but given where they are today, it was in early fund days.

Alejandro: I think they’re like 30,000 or something. So, I’m sure the experience was like a rocket ship. So, what was your biggest learning from Qualcomm?

Doug Winter: I got to Qualcomm, and I was in a rotation program for fresh hires and MBAs, people they thought had leadership potential. I rotated around into a couple of different roles. One of the things that happens at business school is they wind you up with “You’re a change agent. What would you do if you were the CEO of GE?” They kind of put all these thoughts in your head, and then they send you off into the world to change it. Then you quickly realize “Wow! There are a lot of really smart people here. Some of them work for me, and I work as peers with some of them, and I’d better listen to what they have to say and learn. Otherwise, there’s a lot of practical experience, and I’m going to miss what I can get from a lot of those folks.” I think that was one of my biggest learnings was it sounds good, and you learn a tremendous amount through the business school experience, but there’s no substitute for practical, real-world experience.

Alejandro: Why did you move out of Qualcomm and join OneWorld?

Doug Winter: Well, I was at Qualcomm. I was having a lot of fun. It was also though, got to be 1998, 1999, the dot-com boom was booming full force, and I was looking around going “Qualcomm’s a great place, but man, I really want to do something else.” I had gotten the entrepreneurial bug I think when I was in high school. My father had started a company. He was in the construction business, and he had started a company that was doing hazardous waste cleanup projects. It was every bit exactly what it sounds like, going out and cleaning up waste dumps and things of that nature, but it was his own company. There were three of them. They had started it. It was called Remcor. I remember in high school seeing him with hats and tee-shirts, and going to visit their new office, and how excited that they all were. I just remember very distinctly feeling “I don’t think I’ve ever seen him happier in his whole life, certainly professionally” than he was at that point in time. And thought, “Man, there’s really something to this.” So, I’d gotten the bug there, and I had always wanted to do that. I told you the graduate school experience where I tried to talk to some of my classmates into it. So, what happened, watching the dot-com boom go and seeing opportunity everywhere, being a bit of a geek and getting hands-on with the internet and all the different opportunities. One of my other classmates from graduate school at MIT had started a company. It was a services company of hired guns helping other companies build their products. I thought, “Man, I’d love to be part of it. So, he hired me to start up the West Coast operations for him. At that point and time, it wasn’t my company, but I was one of the first handful of employees, and I was on the West Coast, kind of the only one on the West Coast starting up operations there. I had the bug, and I got it bad.

Alejandro: What year was this?

Doug Winter: This was 1999, I think I started working there, and the company was called OneWorld Software Solutions. It was a great dot-com ride. It went up like a rocket ship and then crashed back down to earth a little bit like a rocket ship. I learned a tremendous amount. The relative safety of the front row, not being the CEO, but having a front-row seat to it.

Alejandro: What was the biggest takeaway for you?

Doug Winter: Well, the biggest takeaway honestly was just I would say how important sales is. As a technical person, engineer, and getting into the operations of the business, you look at sales and think “Ah, what’s so hard about selling? It’s not that big of a deal. If you have a great product, it’s going to sell itself. You can hire anybody to come in and sell it. What’s the big deal?” The joining the startup company and finding myself as one of my main jobs is selling whether it’s selling to new employees that “Hey, you should join. This is a great company. You should be part of it.” Or it’s actually going out and calling customers. When I started on the West Coast, I started cold calling and trying to find opportunities. I realized quickly how hard that was and how important it was. The other big takeaway, honestly, was “This is a blast.” It’s hard. It’s absolutely hard. It’s tiring. You have to work your tail off, but it’s incredibly rewarding, and what you do every day when you come to work makes a big difference. To me, that was a huge—I felt that intuitively, but getting a chance to really get my hands dirty, that’s when I know, “Yeah, this the path I want to be on.”

Alejandro: Got it. Then from that, you moved to your last stint before you went at it on your own, and that was with Document Sciences Corp., which was later acquired, I believe, by Dell. Is that right?

Doug Winter: Yeah, so what happened is that after that company kind of crashed, I started my own company. It was called Objectiva Software. It was also a software services business. We ended up selling that after a couple of years to a company here in San Diego that’s called Document Sciences. Document Sciences was a small NASDAQ company. It was one of those companies that went public with almost no revenue back in the early 90s when it was kind of popular to do that. They acquired our company, and we joined to help them turn the business around. It was struggling quite a bit. We got involved in trying to help turn that business around. After being successful in doing that, we actually tried to buy the business. We tried to do a management buyout. We went and met up with some private equity partners, and we made a bid to the board and we said, “Hey, we’d like to buy this business because it’s too small to be public, and we think it’s a great opportunity, and we’d like to take it over and run it. The board said, “Nice. Good idea, but we think we’re going to shop the business around.” Then ultimately EMC, the Documentum team that’s up in Pleasanton here in the Bay Area, they were the ones that outbid all the private equity firms and ended up winning. So, I ended up selling the company to them and became part of the EMC team, which as you said is now Dell and OpenTech depending on which piece.

Alejandro: So, Objectiva. How big was the business before it got acquired?

Doug Winter: Objectiva grew to be—I think we were probably 100, 150 people. We were in the 5 to 10-million-dollar revenue range when we got acquired by Document Sciences.

Alejandro: And this is the business that you started as the first one right after OneWorld?

Doug Winter: That’s right. Yeah. That was my first real startup where I was the CEO. I had a couple of great business partners, and we took off and dove straight into the deep end. Our timing wasn’t exactly good. It was August 1st of 2001, so we had about a month before 9/11 happened, and before the economy screeched to a halt. So, our timing wasn’t good at all, but at the same time, we were successful in growing the business at a reasonable pace and had some great relationships with our customers’ companies like Document Sciences that we were helping out.

Alejandro: How did you meet the partners from this business?

Doug Winter: It was arranged. One was a friend from graduate school, a different friend from graduate school, and one was someone that I had actually met at OneWorld who had moved out to San Diego and had become my partner and kind of helping grow the West Coast in that business, and we became friends.

Alejandro: Really cool, and the terms of the transaction, did you guys make that public? Objectiva.

Doug Winter: No, we didn’t make that one public. It was largely stock. It was the opportunity to grow to help turn around Document Sciences which was public, so it was liquid which was good, but then try to help turn that business around, and grow it, and sell it. We ultimately did sell it. I think it was around 90 million dollars. We sold it to EMC. It wasn’t a huge transaction, but it was a solid single and one of those things that gives you an idea like, “Hey, we can do this. We’ve got the confidence. We can be successful.” It was a good foundation to grow.

Alejandro: Got it. So, basically, you did stay a little bit after the transaction of Document Sciences. I think it was almost two years until you went at it again. Is that right?

Doug Winter: Yeah, that’s exactly right. As part of the transaction, my former boss, the CEO of Document Sciences stepped aside and I became the GM that was in charge of integrating our product with the EMC product stack. So, as part of that, we had handcuffs that were for a year and a half. Then ultimately ended up staying a little bit longer through the transition, but it didn’t take too long, and the EMC is a great company. There are a lot of really smart people there, but I just didn’t feel at home. I didn’t feel that I had the impact that I wanted to have, and I started getting kind of hungry for what’s going to be next not long after we got there. So, there were a lot of discussions, a lot of weekend late dinners and other things where myself and the other founders of Seismic were bouncing around some ideas around what we could do before we decided to all jump together at the beginning of 2010.

Alejandro: Tell us about the founding team behind Seismic. How did you meet these guys and how did you all brainstorm and bring this to life?

Doug Winter: The founders, there are four of us total. We were all working together and ultimately ended up together at EMC. Ed Calnan who is our president and head of sales, I had met him at OneWorld actually. We met at OneWorld when that company was in its infancy. He was helping lead the sales team there. Then we had gone separate ways, and then I had recruited him back to join us at Document Sciences and help turn the sales team around there which he had done successfully. Fred Shea, we had actually met also at OneWorld. He had worked with us from our China operations, our China team and had them immigrated to the states and was Chief Architect. He was working on some of the Document Sciences products, and he was a really solid engineer and architect and passionate about what he was doing. Then Marc Romano who is our CTO at Seismic had actually led the engineering team at Document Sciences as well as played a couple of other roles. There were people that I had met in previous jobs and previous lives. One thing that I have learned is that it’s a small world, and the relationships that you build today are really valuable for you down the road. That’s been the case whether it’s been college or grad school classmates that have joined the team, or whether it’s folks that I’ve worked with in other jobs building those relationships and having people that follow each other and really enjoy working together, it’s hugely powerful.

Alejandro: Got it. Did you find like any challenges being such a big number of co-founders?

Doug Winter: Not really. I think there are always challenges, but the other side of the coin is the benefit of having a more diverse group and a larger group and more opinions that come in. We all had a role that we worked at, that we knew how to play. Whether it was helping build the product or whether it was helping go to market efforts. I can tell you, I see all the time companies where they’re early on in their lifecycle, and you see they raised some money, and then the next announcement you see is they have four or five new executives coming in. I just kept thinking, “Man, if I was sitting here at the board room looking around the table at a bunch of faces and we’re all trying to get to know each other, how challenging!” What an additional challenge that would be at that early of a stage to have to deal with a bunch of people that you don’t really know, and do they like each other? Don’t they like each other? Who’s good? Which one did you make a mistake on? All that type of stuff. A lot of that was taken off the table because they were people that I knew, the strengths and weaknesses, and in your mind, we knew how to work together. That was a very strong foundation for us.

Alejandro: So, what ended up being the business model for Seismic?

Doug Winter: We’re a SaaS provider. We sell to enterprise companies. Larger enterprises are really where we focus. The business is called sales enablement, which is really around helping sales and marketing teams work together more efficiently, more effectively. In our particular area, it leverages our experiences really around the content. If you think about enterprise sales cycles, business-to-business selling, there’s an awful lot of content whether it’s power points or videos or Google slides or white papers, whatever it might be that are used through a sales cycle. Yet, if you go to most larger companies, you hear things like “I can never find what I need. It takes me forever to put together the presentation materials that I need for my meetings. I’m drowning in content, but I don’t know what’s good and what’s not good.” From the marketers, you hear things like “We create all this content. We never know if anyone uses it or if they don’t use it.” So, we’ve created a platform of Seismic to help solve that problem. We allow the marketers a lot of visibility into what’s happening. We provide them with very robust content management tools so they can scale up to thousands or tens of thousands of pieces of content, and yet deliver it precisely to salespeople in the field at the right time, the right content. Take advantage of all the data that’s available, collect a lot of data to be able to add a lot more intelligence and visibility into the process. We started selling the product in 2012. We had a slow start on the company as many companies do while we were winding down other things and starting to build out the product. We started selling it in 2012. We didn’t take any funding until late 2013, so we really ramped things up starting in 2013, and we’ve been going at it hard ever since.

Alejandro: So, you bootstrapped the operation until 2013 because you guys got started in 2011?

Doug Winter: We did. Yeah. We bootstrapped the business for a couple of years. Typical story: founders are “We’re not going to take salary for a while.” Hired a couple of people, but I gave them equity and less in salary. So, we were able to bootstrap, take some of the proceeds and profits off of the previous success that we had with Objectiva and Document Sciences and basically went all in. I kind of took pretty much everything that I had and put it back in the middle of the table and said, “We’re all in on this business. We think this is a great business.” To be honest, early on we thought “Let’s do this without any outside investment. We think we can grow a nice business. We could grow a 100-million-dollar business in a couple of years and have a lot of fun without the complexity and stress of having outside investors and accelerated expectations. Then what happened is we got to 2013, and we’d gotten a little bit of revenue. We had a product that when we showed it to customers, they went “Wow! This is amazing! I didn’t know you could do this.” The customers that we had were really loyal and incredibly zealous about what we were doing. I looked around the table, and I’m like, “Okay. We have two people in sales and no one in marketing. We’re going to watch the whole market go fly by us if we don’t accelerate and go a little bit faster. So, let’s go try to raise some money and see what we can do.” That’s when we went out and started down the path to trying to raise some venture funding.

Alejandro: Got it. We’ll talk about fundraising just in a little bit. Let me ask you this: did you have any moment, Doug, where you were like—because, obviously, you were bootstrapping. It’s rough. When you have the financial muscle, then there’s obviously certain mistakes that you can do, and you may be okay and recover from that as well as you learn fast, but when you’re bootstrapping, it’s really tough because you’re literally always on your toes. So, did you ever have a moment where you were like, “This doesn’t look very well.”

Doug Winter: It seems like a million years ago. But absolutely, I would say there were lots of moments when I woke up, and I was like, “Wait a minute. What have I done here?” One that stands out in particular, I’ll never forget because it was Leap Day. It was February 29th, and I had a bit demo at a potential customer. I was there with Ed, one of the co-founders. Before the demo, we’re in the lobby, and we’re practicing. Everything’s going great, and then we go upstairs, and we get set up. We hooked up into the computer, into the screen and everything. All the sudden, everything is acting weird. Stuff just would work and then two seconds later, it wouldn’t work, and it was just all over the place. I’m on my phone. Ed’s on his phone, and texting with our CTO back in San Diego, “What’s going on? We don’t understand.” It turns out that our hosting provider had had a bug that was Leap Day-related. It caused some certificates to go out or something along those lines to where they were having intermittent outages. So, I’m in the middle of this room with 13 executives from our potential customer, and tap dancing like crazy trying to show what works and hide from what doesn’t work, and dancing all over the place. They ended up becoming a customer. They’re still a customer today all these years later. But we walked out of the meeting going, “Well, I can’t believe that just happened. That was terrible.” Then I’m getting a ride back with Ed back to the airport. On the way back to the airport we had this other big deal in the pipeline. It was a potential partnership, and we were looking at it as maybe a million or two-million-dollar partnership opportunity that was really going to accelerate what we were doing. In the car on the way to the airport, they called, and they’re like, “Yeah, you know what? We think we’re just going to do this ourselves rather than partner with you guys.” I remember that. I’ll never forget that day. Ed dropped me off at the airport, and we looked at each other like, “Oh, man. This is bad.” It turned out the partnership ended up to be—it would have been a cool opportunity, but it didn’t happen, and we ended up getting that customer, and as I said, they’re still with us all these years later. So, things turned around, but that was probably the darkest day I remember.

Alejandro: That’s amazing. Normally, when you’re dealing with those dark days, any advice? Because the people that are listening, there’s no such thing as a straight line. Right?

Doug Winter: No.

Alejandro: You’ve come a long way. So, how do you typically deal with those dark moments?

Doug Winter: One of the things I’ve learned over the years is as CEO, one of the toughest parts of the job is you have to be the counterbalance. Whenever everything is going great, you want a big deal. You crushed your quarter. You’re beating your competition. The customer’s super happy. You raise money. Whatever it is, everyone’s bouncing around the office. Everyone’s so excited, and the energy level is so high, you’ve got to be the one to kind of pull them back down to earth. You want to go celebrate. You want to pop the Champaign yourself, but you have to be the one to make sure that everyone remembers, “Hey, this is a temporary state, and we have to keep working if we want to keep going.” The opposite is also true. When you have, “Oh, we lost the deal,” or something’s not going well, you have to be the one that picks up the company, picks up the team, picks up your own team and lifts them up and say, “Hey, you know what? This is going to be great. It’s going to be fine. We’re going to keep moving.” Emotionally, that’s difficult because it’s 100% the opposite of what you want to do. You just have to find the strength to pull in the other direction. I think my advice to other CEOs and entrepreneurs is you’ve got to try to stay steady. Even when you really, really, really don’t want to, you have to be the one that can stay steady and keep the ship on track that it’s definitely not all up and to the right. It’s a marathon. It’s not a sprint. There are always great companies that go from zero to a billion dollars in a year. Those are amazing, and I have tons of respect for them, but far more success stories are built slowly with lots of effort, and continuous effort, and setbacks, and just never giving up. I think that’s the proven formula that most people need to be ready for.

Alejandro: Persistence. I love it.

Doug Winter: Persistence. Yes.

Alejandro: Yeah. So, Doug, you guys have raised quite a bit of money. Why don’t you kind of make us insiders for a minute into how that process of fundraising has been for you guys? How much money did you raise in total?

Doug Winter: We’ve raised 175 million in total. As I said, we started out thinking, “We’re not going to raise any outside money. We’ll just do this ourselves and see what happens. When we decided this is a much bigger opportunity than we originally imagined that it was, we saw the opportunity in front of us to build a billion-dollar-business and 10-billion-dollar business. We realized “If we’re going to go faster, we’re going to need help. We’re going to need advisors who have done this before, and we’re obviously going to need capital. So, the first thing that I was worried about was fundraising can be incredibly distracting. You really have to dedicate yourself to it in order to be successful for at least a period of time. I was worried about that, so I said to the team and having a trusted team here, it makes this easier. I turned to the team, and I said, “Look. I’m going to go do this. I’m going to call you in when I need help. You guys, I trust you, run the business and do well. So, I went to a few friends that I had who had successfully raised money or had been entrepreneurs or had been in the bench world, and I said, “Who should I talk to. Here are the kinds of firms I think might fit. Do you have any good introductions?” So, I ended up getting 15 or so introductions. The early stage VCs, their job is to look for entrepreneurs, so if you have a half-way decent sounding business and you get a nice warm introduction, they’ll almost always take the meeting with you. But the bar’s very high because they’re looking at a couple of deals a day potentially coming in the door. Maybe more. So, the bar’s really high, and I’d never done this before. I had dealt with the private equity firms, but I hadn’t ever done traditional VC early stage. I look back at the old deck and think, “Wow. That was really terrible. What was I thinking?”

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Alejandro: It always happens.

Doug Winter: It always happens. Yeah, exactly. But learn through the process. Learn quickly what part of the message resonated, and what the best way to structure the conversations were. I talked to some great firms, and when I met with Pete Solvik, who is our Series A investor and Jackson Square, it just really clicked. I appreciated that there were a lot of operators there at that firm. They were all successful entrepreneurs or people who had been in operating roles at successful companies which meant a lot to me. They were a fairly small firm, not a lot of overhead. They liked to get hands-on with their customers. Pete, himself, had been the first investor at DocuSign, and I really appreciated what a great success story that was, and also how patient they had been, and that they had been in the investment for a fairly long time. I was expecting that we were going to build a big company. It wasn’t going to happen in three years. So, it really just lined up. I got a chance to meet the rest of the partners there who were also great, and we quickly settled on, “This is who we would like to be our investor out of the gate.”

Alejandro: How many rejections did it take to get to Jackson Square Ventures?

Doug Winter: That’s a great question. I probably at some point could have told you exactly how many, but you know, time heals all wounds. I’m sure there were ten, easily ten. There was a decent amount of interest, and everyone’s great and very professional, but the reasons varied, and my messaging and my story, I think got more precise and better tuned over time as well. I’m sure I heard ten noes before we ended up hearing a yes and joining forces with Jackson Square.

Alejandro: Do you think that perhaps one thing that made you guys click with Jackson Square Ventures is the fact that maybe out of those ten rejections you were optimizing your story and taking a look at maybe you had some holes in this story?

Doug Winter: 100%. I tried to learn from every one of those conversations, and I still do even as we’ve gotten much more mature and sophisticated about how we do later Rounds. You still listen and try to take feedback. The biggest thing that I learned is that most of the venture capitalists are so busy that he or she are looking at so many deals in such a short period of time, and they’ve seen a lot of different business models that you really need to get to the point. You can’t count on a long attention span. You really need to hit the highlights first. I remember being at a partner meeting and this was Series B. I’m going through my deck in front of all the partners, and some of them are on the phone, and some of them are in the room. I’m like two pages in, and I’m looking around, and everybody’s on their phones. People aren’t really paying much attention. Then I put our customer slide up, and I started telling the story of our customers and who they were. All the sudden everybody sat up, and everybody’s paying attention, and the questions started coming. They ended up being very impressed and wanting to work with us. Every presentation I did since then, I start with the customers. Like, “Here’s what our customers are.” Who they are and what they’re doing.

Alejandro: That’s amazing that you reacted like that, Doug, because anyone else, they would have grabbed the computer and thrown it at the guys with the cellphones. That’s unbelievable.

Doug Winter: I was a little bit tempted, I have to admit. I didn’t think that was probably going to get me too far.

Alejandro: Yeah, definitely no term sheet if you would have done that. Let me ask you this, Doug. The other people, the cap table is pretty cool. You have JMI Equity, General Atlantic, Lightspeed, and then also T. Rowe Price. So how did you meet the other guys? Was this like via perhaps Jackson Square Ventures, or other founders, or how did you get in front of those?

Doug Winter: Yeah, What I noticed is as difficult as it is to get in front the Series A investors, you need a warm reference basically and a good story. Once you’re in the system, once you’ve been plugged into the database in the sky, the matrix, people now know that some credible investor that they respect saw an opportunity here and suddenly they’re very interested in following up. So, from six months after the Series A Round closed, I started getting phone calls and emails from all kinds of firms saying, “Hey, we’re interested in what you’re doing. We want to learn more.” You get usually a junior analyst type of person from the firms. They want 30 minutes to learn about the business. I just made it a habit from very early on of saying, “Yes,” and trying to allocate an hour a week for a couple of those calls, or at least a couple each month where I would get on the phone. I would introduce myself. I would learn about their firm and some names that you’d heard and some names that you hadn’t heard, and I just kept a running list. I kept a running document where I just, “I met with so-and-so today. Here’s what I think about the firm. Here’s what’s the check size they’d like to write. They seem to be really knowledgeable of our space, or they had no idea about our space. They don’t follow it.”  I just kept those notes. Then over time, the ones that I thought were a better fit, I would proactively reach out to them periodically and say, “Hey, we had a great quarter. Would love to catch up.” They almost always would respond. So, it was a very non-structured, non-official let’s get to know each other process that I stretched out over basically the entire time between Rounds, and I’ve just kept doing that on an ongoing basis. The firms that called changed with times as we get bigger, and our profile changes. The investors who are a good fit, that also changes. So, over time, that list has evolved, but what happens is, as the business starts to accelerate and after a bit of time has gone by since the previous Round, somebody on the list starts to get really interested. They’re like, “Can we go faster? Can we pre-empt the process and jump ahead of everyone else?”

Alejandro: Yeah.

Doug Winter: So, at that point and time, you go back to the board and say, “Okay, I’ve got some real interest coming in. Maybe it’s a little bit ahead of one we were going to fundraise. What do you guys think?” If they come back and they say, “Let’s proceed,” then we’ll get a little bit more serious. We’ll put a deck together, and we’ll try to manage the process and accelerate a future Round. At that point and time, the existing investors and Jackson Square have been great about this, will make intros and bring folks to the table. In fact, even in this last round, Pete was instrumental in introducing us to the folks at Lightspeed actually. GA also introduced us to some folks at Lightspeed. So, all the sudden, Lightspeed who we really hadn’t been talking with was suddenly interested and showed up and ended up being one of the ones that we went with.

Alejandro: Really cool. That was the Series E. Right?

Doug Winter: It was. That was our last Round. Yeah.

Alejandro: That was 100 million. Right?

Doug Winter: It was. That’s right.

Alejandro: That’s great. So, shifting gears here a little bit, how many employees do you have not at Seismic?

Doug Winter: That’s a great question. Literally, I need to get one of those little timers on my desk or something. I think we’re in the 600-employee range now, 500 to 600. Getting closer to 600 employees scattered. We have several offices. Our headquarters are here in San Diego, but we’ve always had Ed Calnan as our president. He’s based in Boston. We’ve always had a Boston office where a lot of our sales and marketing are headquartered. We also have a fairly significant office in Chicago and New York. We just started expanding overseas, so we have probably about 25 or 30 people now in London and small offices in Sydney and Melbourne.

Alejandro: Got it. That’s a fair number. With such a big number of employees, how do you embrace culture, Doug?

Doug Winter: Yeah, that’s a great question, and I think it’s so important. Especially being spread out the way that we are, the Boston office, The Chicago office, New York office, San Diego, London, they all have their own feel. They all have their own culture, and I think that’s a great thing. I think that diversity makes us a better company, but at the same time, you want to make sure that there are common threads, that it still feels like Seismic even if it feels like a slightly different flavor in each office. To me, those things run, and they start with the leadership team. They go through to being careful around who we hire and keeping that going, but you know, the things we care about. We care a lot about the transparency. I always feel like I want my door to be open. I want people to be able to ask me any question that they want, and I’m going to give them an honest answer even if the answer is, “I can’t really share that with you.” People appreciate that. We try to overcommunicate. I have a board meeting, and then after the board meeting, I have an all-hands meeting, and I share as much as I can about what the board said, and what we talked about, and a lot of the content. The other thing that I think is really critical to our culture specifically is the culture is built on the fact that people celebrate each other’s success. We have a tradition called Push Pins. It started in the early days when we would win a deal, literally they would print out the logo of the company, cut it out with scissors or tear it out of the paper, and they would push-pin it to the wall. We started adding logos to the wall. That doesn’t scale particularly well, especially when we have 500, 600 customers. So, now, it’s an email that goes out, but every time a salesperson sends out an email, she’ll highlight not just “This is what I did to be successful,” but she’ll call attention to all the other people who helped. “I had help from the marketing team putting together a great RFP response. So-and-so really helped me out. Customer Success went the extra mile to help with the onboarding conversations and preparation of some of the paperwork and SOWs. Contracts helped me, and Product Team had to get involved and do a roadmap discussion.” The fact that the person is celebrating a win, but they’re celebrating that win by giving everyone else credit, I think is an important part of our culture. It’s things like that that go across the company that we try really hard to keep going that really, I think define the unique aspect of our culture. But it does certainly get harder and something I worry a lot about because to me, that’s what makes the company who we are. If we ever lost that, I would feel terrible.

Alejandro: I hear you. I mean, nothing like acknowledging others. That’s super powerful actually. So, where do you see, Doug, the sales and marketing space heading?

Doug Winter: I think it’s a really exciting time where we are right now because technology is evolving and it’s enabling things that just weren’t possible not that long ago. When we talk about this space, we talk about the evolving dynamic between marketing and sales, and how it used to be that marketing was tasked with eyeballs, the Mad Men era if you will. It was all about impressions and just go get the name out and do advertising. Then marketing evolved not that long ago, 10 or 15 years ago, started into it’s all about leads. Give me leads, give me leads, give me leads. Now what we see is that as more and more of that process has been automated with the Marketo’s and HubSpot’s of the world automating the top of the funnel, that marketers are being asked to reach further down in the funnel and help sellers’ directly and are being held accountable for revenue, not just impressions or eyeballs or leads. So, I think that is what’s driving the industry forward. The sales enablement space has really exploded. If you look at the number, statistics I found while we were doing our fundraising is that if you look at the number of people at LinkedIn who have sales enablement in their job title, and then you look at the number of people of open job openings for people with sales enablement in the job title, they’re almost the same which means that the number of people and opportunities there are in that space is doubling at a very fast rate. Every three, four months or so, the number of people in that space is doubling. We certainly can’t take credit for that. I think although, hopefully, our success and the success of our customers is contributing. The fact that the market is really ready for solutions like ours and that the technology now allows things to be done that couldn’t be done before, it makes for a very exciting time.

Alejandro: Got it. Really, really cool. I always ask this same question to guests on the show, Doug.

Doug Winter: Ut oh.

Alejandro: Be ready. Be ready. Brace yourself for impact. Knowing what you know now, this is your second rodeo as a founder, you’ve come a long, long way, and you know quite a bit. You’ve failed quite a bit, you’ve learned from that, you’ve had a lot of successes too in the journey. So, if you could go back to the past and give yourself one piece of advice to your younger self before starting a business, what would that be and why?

Doug Winter: Yeah, that’s a really great question. I think it would be to even get as far as we’ve gotten, you really have to believe in yourself. You have to believe in yourself, and you have to not question and dwell on all the reasons why you can’t do something. I think that even though I now see that so clearly, there were many times in the past where you run into the doubt. “Can we really do this? Can we really be successful? We’re not as smart as that company that did this amazing thing.” My advice would be you’ve got to trust yourself. The only way you can possibly be successful is you go all in and you trust in your own judgement and your own ability to execute, and you realize that you can be successful and that making mistakes is part of the process and not to get too fixated on those things.

Alejandro: Absolutely. So, Doug, what is the best way for folks that are listening to reach out and say hi?

Doug Winter: You can certainly reach me on LinkedIn. That’s probably my social media connection of choice. Or, I’m also on Twitter. I’m not quite as active on Twitter. All the craziness that you see on Twitter from entrepreneurs scares me away, but I’m on Twitter as well. Then you can certainly also send me an email at [email protected], and I’ll be happy to get back to folks that way.

Alejandro: Amazing, Doug. Thank you so much for being on the DealMakers show today.

Doug Winter: Thank you. I really appreciate the opportunity, and it’s been great speaking with you.


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Neil Patel

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