North Star Leaders Podcast

Lindsay Pedersen

The world needs what only your business can bring, and as a leader, it's your job to deliver. But where do you focus? Where do you direct your time, your team, your budget, and your emotional energy?

We're learning this together on the North Star Leaders Podcast. In this podcast, I talk to purpose-driven leaders about the choices that they make to create audacious economic value while also realizing their distinctive purpose. I'm Lindsay Pedersen, brand strategist, author of Forging an Ironclad Brand, and host of the North Star Leaders Podcast.

Let's get to it. Today, I am so happy to be joined by Doug Winter. Doug is the CEO of Seismic, the sales enablement platform.

Doug, welcome to the show.

Doug Winter

Thank you, Lindsay. I'm very excited to be here.

Lindsay Pedersen

Really glad to have you. To start us off, Doug, what is your favorite thing about what you do?

Doug Winter

Oh, my favorite thing is the team that we have built over the 15 years that we've been at this. I got fortunate to get to stand in front of an incredible team that's grown a lot over the years, but a lot of people that have been with me on the journey from the beginning or almost the beginning and being able to grow my career, watch them grow their careers, help service our customers, build a great product, and do it all together with people that you really, really like and care about. It makes all the difference.

Lindsay Pedersen

It's very gratifying. It's very gratifying. Seismic has really been a category creator.

You largely created this category of sales enablement. What's hard about being a category creator and what are the rewards, too?

Doug Winter

Boy, I'll tell you, it is a big challenge. Category creation, I don't think I had any idea when I started on this journey of what that meant or how difficult it was going to be, but really getting people to understand what it is you do, why it matters, the value that it provides. It's sad in some ways, but you got to put a name on it.

Otherwise, people lose track. They don't understand. You see companies all the time that this week, we call ourselves this, and next week, we call ourselves that.

You finally made it when you get a Forrester Wave or a Gartner Magic Quadrant or something like that, where the industry analysts are acknowledging that their vision of what this category is, what the space is, and the impact it can have lines up with yours. Those are pretty exciting milestones to hit, and it matters. When we started the word enablement, it's actually still not in some dictionaries, believe it or not.

If you go look at some dictionaries, it's not an actual word. We did sort of a tongue-in-cheek campaign a few years ago, quite a few years ago, to get it added to the dictionary.

Lindsay Pedersen

Oh, that's great. I love that.

Doug Winter

But now, you go out and on LinkedIn, and you do a search for people that have enablement in their job title, you get tens of thousands of people who have the term enablement in their job title. That, to me, is meaningful. This is something that they're really associating with.

They're part of who they are and what they do, and that's pretty exciting.

Lindsay Pedersen

Yeah. In some ways, that's probably more reinforcing than the dictionary. If people are associating their identity on LinkedIn, their career, something as important and weighty as their career, they're using the term enablement.

That's validating.

Doug Winter

Yes, it is. It's been a battle. We've got a lot of help.

Our customers, even our competitors, we kind of all did it together. But I'm pretty proud of the leadership role we had there.

Lindsay Pedersen

Yeah. Now, it is a category. It's not as elusive as it once was.

What are the rewards now that you're a creator of a category you've already kind of created?

Doug Winter

Yeah. I can tell you, when we started, we would spend our first period of time, small companies, it could be short, larger companies, it could be a year, convincing them that this was a problem that they should care about and putting budget aside for it. Now, they're like, well, we have to have an enablement solution, so let's pick the best one.

That is a very different conversation, I can tell you. That's one of the biggest rewards. As the leader who arguably had the most to do with creating the category, we have the ability to kind of keep changing the definition and keep growing the definition.

That's not in the dictionary. We can keep adding to what exactly enablement means by expanding our capabilities, expanding the value that we provide to our customers, and then kind of constantly redefining enablement as, oh, yeah, but it also does this. Oh, but it also includes that.

It also includes these capabilities. That's kind of been the fun.

Lindsay Pedersen

That's so cool. It's the empty vessel that you get to fill because you created the vessel and put it out there. Yeah.

Doug Winter

That's right.

Lindsay Pedersen

You mentioned, and to have noticed, you've really stuck with the term enablement, sales enablement. Was it hard not to shift to whatever was the flavor of the day, especially as others were trying flavors of the day?

Doug Winter

Yes and no. We definitely played around with other positioning and other terms at times to kind of describe what enablement was. But we always thought of it that way, as like describing what enablement does, not just not changing the category.

I think the biggest change that's happened is it's kind of gone from sales enablement to revenue enablement that sort of implies, hey, it's not just salespeople, but everyone who touches the lifecycle can be partners, can be customer success, can be services, sort of the bigger ecosystem associated with revenue and revenue generation. That's about the only real change.

Lindsay Pedersen

Is that a change that has been easy for customers and potential customers to grok? Are you ever met with resistance to its revenue, not sales?

Doug Winter

No, I mean, definitely larger organizations, things tend to be broken out a little bit more into smaller sub pieces and organizations. And so you may find like the partner team, for example, is a very different organization and kind of completely separate than the sales organization. But even in those cases, they're doing a lot of the same things.

They're sharing a lot of the same content and learning, etc. So connecting them together is not something that I think anyone really, really fought against. And certainly the enablement professionals that we serve, their stature continues to go up and having a footprint that spans more of the organization is good for them too, right?

So more budget, more resources, more respect, more ability to get things done.

Lindsay Pedersen

You're lifting them up. Yeah. I've heard you say in other contexts that you kind of hate buzzwords and buzz phrases and you cringe at the whole Sandhill encouragement to pivot fast, that there's value in sticking to the same thing, not changing and perseverance pays off.

Talk about this belief and how it's benefited Seismic to stay the course, to not be pivoting or following the flavor of the day.

Doug Winter

Yeah. I mean, I think the context you're probably referring to it, there are a lot of trends and buzzwords and people fighting for ears and eyeballs. I think that in those cases, sometimes it's something that's sticky or catchy or controversial even can accomplish those goals, but it's not the best way to run a business.

And there definitely are times where you need to pivot and go in a different direction than what you were on. And understanding when to do that is a skill that's really important, but there's a lot of times where, hey, we've got to trust our instincts here. We've got to trust what got us here.

Maybe we need to execute or fine tune around the edges, but we really don't want to reinvent. And so I think for us, myself and the other founders, we grew up selling to larger enterprises and that was in our DNA. And at the time it was really trendy to sell to high-tech startups, small companies that could write a check tomorrow and add lots of funding from the VCs, et cetera, but they weren't very and they weren't very committed to what you were doing.

We go work for some of our larger customers, their enablement teams are substantial, dozens of people, hundreds of people in some cases, they have a very strong opinion on what they want to do and how technology is going to help. And you better listen to them and you better service them the right way or else they're not going to ever go with you, let alone stick with you in the longterm. So it just kind of sets up a little bit of a different dynamic, a little bit of a different approach and methodology, and it's served us well because our customers tend to stick with us.

We've had a lot of customers now, well over 10 years, we've got now dozens of customers that are kind of in the million dollar plus range in terms of their commitment to us and to enablement. That shows, it's a nice stat that we love to quote, but it also just shows they're taking this very seriously. It's not a we have to match up with them in terms of our capabilities.

Lindsay Pedersen

It's like there's a commitment on both sides and therefore a durability than one wouldn't get if they're changing all the time. It actually kind of reminds me of what you were earlier saying about when you're creating a category and kind of sticking with the word enablement, that when you're trying to create something new in somebody's head, repetition, and maybe even to a boring extent, it really serves you. And interestingness or like variety actually makes it harder for the person to cognitively grasp and remember the idea like glamorous and sexy terms actually can be kind of fleeting.

Doug Winter

Yeah, that's exactly right. They can be fleeting if they're not really grounded in something real. You can make a really interesting point, but not have it be something that people remember if they don't relate to them.

And if that organization has committed to trying to solve that problem or solve it in that way, they can, yeah, that makes sense. So that's great. And then forget about it the next day.

Lindsay Pedersen

It also makes me think of trust and how maybe even like taking it out of the context of businesses, but people trust people who are consistent and don't change and show up the way they show, or maybe they evolve, but they're not like one day I'm kind of like this, another day I'm committed to this. It evokes a sense of I'm safe with you. Like I trust you.

And the same thing can kind of go, I mean, a customer and a business is just like a friendship in that way. Like there's a two-way trust that you can have by being consistent, which sometimes is sticking with something that's not flavor of the day. Sometimes it's sticking with something that others are deviating from.

Doug Winter

Yeah, I think that's a great analogy. And larger companies, they make big commitments. They move more slowly.

They plan their budgets on an annual basis. They have projects that last multiple years. And sometimes you look at it and go, gosh, why can't you go faster here?

But they're smart enough to know that like how you make a change is as important as what the change is, if it's going to stick. And that making sure you get it right, because you've got so many people that are counting on you that you can't make a misstep. And these are big established businesses that aren't going to die if one thing takes a little bit longer.

So they're thoughtful, they're methodical, they're thoughtful, but they're also very committed. And that leads to a long-term good partnership. They know we'll listen to them when they come back and say, we really need your product to do X, Y, or Z, because they've made a big commitment to us.

We're going to listen. If I had 10,000 tiny customers, I can't do that with 10,000 tiny customers. You just can't.

You have to make all the decisions with minimal input or aggregated input. So both approaches, I have a lot of respect for companies that have gone down the route with smaller customers and done more of the self-service model. I have a lot of respect for them.

But you got to know who you are, and that's not the path we took.

Lindsay Pedersen

Yeah. I've heard you say that the role of the leader is increasingly to be the emotional counterbalance of the team. Can you talk about that a little bit?

Doug Winter

Yeah. This is an observation from just earlier in my career that it's especially applicable at startups. The wins are so big and the losses feel so devastating that it's really easy to want to give up or to think you've won and the game is over.

It's fun to celebrate. You should celebrate, but you also have to be, as a leader, you have to be the one to pull the team back down to earth and say, okay, it's great that we had this big win, but that was yesterday. What are we doing today?

Because we want to win again tomorrow. The same thing is you have this devastating defeat. Something just goes completely wrong and everybody wants to throw in the towel and quit.

This isn't going to work. We give up. You've got to put on a smile, find some positive energy, and pick people up and get them back in the game.

Otherwise, you will. You can lose. Some of those losses can be very devastating.

That's how I always refer to it, the emotional counterbalance. Kind of stinks because it's a lot of fun to go celebrate like crazy and nobody likes the Debbie down or whatever kind of person coming in. But at the same time, it's a critical part of leadership.

Lindsay Pedersen

And it reminds me, it's very stoic. It's like the stoic philosophers. And it also reminds me, I'm in Seattle.

And if you're a football fan, you might know Russell Wilson. We had a really important, famous quarterback for a long time, Russell Wilson. And that's what you just said sounds so much like what he would say is it's all about being neutral.

It's about coming back to neutral because the wobbliness, as human as it is, is not energy begetting. It erodes energy over time. And so that's how he thought of leading that team as well.

It's so similar. Have you ever noticed the similarity to a sports coach in what you're doing?

Doug Winter

Yeah, I think coach probably more than player, but yeah, absolutely. Wilson as quarterback kind of leader on the field. Yeah.

People look to you like, how should I feel right now? And I, I'm the kind of person, I wear my heart on my sleeve. So you usually know how I'm feeling about just about anything.

So it's a skill I've had to work on to like really go into the office, scream at the wall, you know, try it out, whatever it takes, come back out and be like, here we go. And be very thoughtful about the image and the energy that you're putting out there. You don't want to read the team too and understand where they are, right?

Do they need, are they able to take another little push or do they need a minute or do they need a pat on the back and a hand up kind of a thing? Where are they? What's going to get the best out of them?

Like those are important skills for leadership.

Lindsay Pedersen

Yeah. Talk about the decision for seismic to stay in San Diego as a tech company went into that.

Doug Winter

Yeah. I mean, uh, I, you know, I used to joke that when I first went around Sand Hill road, they told me, you know, you're going to move the team up here. Right.

And then, you know, a year later I went back for my next round and they're like, you're not going to move your team up here. Right. And it's actually true.

I heard it, I heard it a lot and you know, look, nowhere can compete with the volume of incredible talent that the Bay area has. There's no question about it, but it's also insanely competitive environment to recruit top talent and hang on to top talent. So there's a trade off there.

I think, you know, we were really happy to be in San Diego. We were in San Diego, we were in Boston. Those were kind of our first two main hubs.

And we really grew most of our headcount there before we started expanding out a little bit. And then of course COVID changed everything, but you know, San Diego is a great town. There's a lot of tech here.

There's not as much software, but it's growing, it's grown. And I love that, you know, we've been a small part of helping put it on the map in that regard. Now there's a number of startup unicorn software companies here in San Diego.

And, you know, I hope it's something that continues to grow in the world where you can work anywhere, which is more so than it ever has been. Although, you know, we are seeing back to work kind of stuff, but you know, there's a lot of people in our neighborhood now that are Bay area refugees just like got tired of that grind and said, let's move down to San Diego. And they're still working for companies, you know, there or other places.

So it's become less of an issue and San Diego is a great place to do business. Great place to live.

Lindsay Pedersen

I'll say. There it is again, this slightly contrarian willingness to resist conforming to some other wind that's blowing. Like it feels similar to some of the other things that you've said about how you've built Seismic, even the choice of location is consistent with that.

Doug Winter

Yeah, I think so. You know, look, I believe that one of the things that's most important in life and leadership and as a company is knowing who you are and you're dumb. You don't listen to what the experts are saying.

They're experts for a reason. You're naive if you think that all your choices are going to be the best ones. But at the end of the day, the choices that you commit to, you're going to be much more successful with than the ones that you're constantly reevaluating and changing.

Even if they're not perfect, you got to commit to them or they have no chance. And I think that's true for where we are at Headquarters. It's true for the kind of customers that we went after and the way we kind of tried to grow the business or how we want to target.

I'm sure there's plenty of other examples that I could have done a better decision, but you got to commit to the ones you have and know who you are. And we knew early on, we know how to sell to these kinds of customers. We know how to deal with large companies.

That's what we're good at. Let's not try to be something else because we're probably going to not be very good at it. We're going to fail even if it's better.

And there were periods of time when other companies are growing a lot faster than us because the wind was blowing. The startup companies, they had so much money, they were growing like crazy and they signed a deal in five minutes. We sell to Oracle or IBM.

It takes a minute, but you got to stay the course and know who you are.

Lindsay Pedersen

Yeah. Well, there's that resolve again, the commitment to what you've chosen and resolve. And it makes me think of how employees and customers, for that matter, are looking for that resolve.

It gives air cover to them, right, to also commit to something and stay with something because they're seeing their CEO make that decision despite pressure to do otherwise.

Doug Winter

Yeah, I think that's right for the customers. They do. They want to know that we're not changing strategy every five minutes.

We're going to be their partner five years from now, 10 years from now. I say that with customers all the time. It's like, we're not going to make any money having you as our customer until year two, year three, year four.

So I got to earn my way to year two, year three, year four by doing a heck of a great job in year one. I'm telling that. Be honest with them.

It's like, if this is a one-year thing and we're not doing value for you, then I'd rather we just stopped right now. And I think they appreciate that as well, that level of commitment.

Lindsay Pedersen

Yeah, it's a partnership. Yeah, truly. You're both in the trenches.

You're both doing it. What has been the single most important thing that you've done to build the Seismic brand?

Doug Winter

You know, I think I'm not the flashiest person around. I am not wired that way for, you know, kind of the self-promotion or even company promotion. Too much Midwest in me, I guess.

But I think what we've done that has made our brand endure is deliver for our customers. You know, we have a great reputation amongst our customers. Even our competitors told me in the past, like, how do you get your customers to be so loyal and like, rave about you all the time?

Like, that is the best form of marketing out there. And again, not the fastest. It takes more time to build that up, kind of one happy customer at a time.

But I think it's much more enduring. And it's what we focus on.

Lindsay Pedersen

Well, and that's brand too, right? And even you said, I'm not the flashiest guy. I've got too much Midwest in me.

That's brand. Like, that's something I as a customer can bond with. Why?

Because it's genuine. Like you said, it's your DNA. And the delivery, the actual experience of success as a result of their choosing Seismic, that's the ultimate reinforcement.

Doug Winter

My favorite customers are the ones that, like, go to their third company or fourth company and bring Seismic again the third or fourth time. It's like, we help them get that next job. We help them successful.

They helped us too, because they give us a lot of feedback, sometimes harsh feedback, that made us get better. But those are my favorite. Those are my absolute favorite.

Lindsay Pedersen

Oh, my gosh. Yeah. Like, what a testament.

What's the culture like internally at Seismic? And how intentional have you built it versus how lucky have you been?

Doug Winter

You know, it's a great question. I'd say it's a tale of two journeys. The early days, you know, it was really organic in that early employees, we were cut from a similar cloth.

We kind of really enjoyed working with each other, treat each other with respect, work hard, play hard, kind of fight for the customers and delivering value. And then as we grew, of course, it gets harder and harder to kind of bring in new people. You're bringing new people in 10 a week at some point in time.

Like it was, we were growing like crazy and it gets tough. And so at some point, you know, I think four years ago, five years ago, you know, we kind of got together and said, you know, we should write some of this stuff down. And I wouldn't call it, we wrote down, this is what we want to be.

I think it was more like we wrote down, this is who we think we are, you know, with a little bit of who we want to be. Right. And so we kind of came up with our values and we talked about them, we celebrate them, you know, all the time, every month in our all hands.

We feature someone who did something that really shows that. And we kind of put it out there and try to make it something useful. You know, it's like nobody wants the words on the wall, right?

It's not the words on the wall, it's the actions in the hall or something like that.

Lindsay Pedersen

Yeah.

Doug Winter

You know, it's that really make that happen. And, you know, we celebrate each other's success. That's one of the things I'm most proud of.

We send out an email when someone wins a deal. Salesperson goes and writes up an email and call it a push pin. Literally in the old days, we would pin a logo to the wall and then write up a push pin.

And it's all about all the people that helped me. It's not about, I'm so great. It's about all the people that helped me.

Right. And some of them are like, you know, this long for big deals. And they're like this, you know, it's like, all right, really?

All those people helped me, but it's incredible. Right. And that's part of the culture is like, yeah, these people and the people want to help because they know that it's appreciated.

Yeah. So that's just one example.

Lindsay Pedersen

I love that. As a leader, what's your growth edge right now? What are you working on?

Doug Winter

You know, one of the things that I love and hate both, I don't know, hate's probably too strong about being the CEO at a startup is you constantly have to ask yourself, what does my job need to be now? And, you know, you can go on the way back machine when we first started and, you know, I took the trash out. Someone told a joke at our company event lately about the fact that I used to actually take the, you know, we were too cheap to pay for trash in the office service.

So I load it up in the back of my car and take it home and throw it away. My trash at home, right. Or I'm writing, signing expense checks.

I'm building demos. I'm doing sales calls. Like it was a kind of everything.

And then as the business grows, you get people that are better than you at the next important function that you can afford to get somebody that's better than you at, and then you try to grow a month from them. And so in some ways the job gets smaller and smaller and smaller, and it becomes much more about how do you communicate to the team, right? How do you inspire, how do you lead, how to communicate, and how do you kind of think about like what's happening at a higher level and try to drive the right kind of direction.

So I'd say I'm constantly trying to evaluate, like, what do I need to work on next? You know, over the last few years, as we've gotten to be a pretty sizable company, it's, you know, hey, in addition to growing, we also need to get more profitable, more efficient. It, you know, started the mantra, you know, you got to get better, not just bigger.

And so like that was a new muscle for me, right? I was like, oh, wait, we just worry about growing and doing awesome job and don't worry about, you know, how efficient it is or how, you know, cost effective it is. It's like, all right, now we actually have to be great at running the business too.

And like, that's been an evolution. That's something I've had to really had to work on. Doesn't come now.

Lindsay Pedersen

It's like stages of development of a human being in some ways, right? Like there's the things that you're working on when you're 12 or different from what you're working on when you're 19 and same thing. It's always going to, and the best you can do is like bring self-awareness to it and get feedback and all of those things.

Awesome. Okay. Before we finish, I have a few rapid fire questions for you.

Doug Winter

Uh-oh.

Lindsay Pedersen

Uh-oh. Are you, are you up for like some kind of one word, like no pressure. One word.

Doug Winter

I have a slow brain though. So rapid fire, we'll see how it goes.

Lindsay Pedersen

Are you a morning person or a night owl?

Doug Winter

I am a morning person. I'm up usually four in the morning, like it or not.

Lindsay Pedersen

You are a morning person.

Doug Winter

You'll find me in a Starbucks reading, doing emails at four 30 or five when they open.

Lindsay Pedersen

I didn't even know that Starbucks opened that early. Okay. Wow.

Doug Winter

That's why I go there because they open.

Lindsay Pedersen

Because what book do you find yourself recommending a lot to people?

Doug Winter

You know, I read biographies, I read science fiction and I read kind of history, like history that I didn't know, you know, African-American history or stuff that I didn't learn when I was in high school. So I kind of rotate between this. One that really stuck with me that I read not too long ago is called destiny of the Republic.

And it's a biography of James Garfield who was president for six months and then he got shot. He got shot after three months and it took him three months to pass away. It's a fascinating, fascinating story and a fascinating person that you would probably never, ever think would be interesting.

So try it out on.

Lindsay Pedersen

Okay. I love it.

Doug Winter

Destiny of the Republic.

Lindsay Pedersen

What is a place that you've always wanted to travel to?

Doug Winter

I have always wanted to travel to Greece and I've never been. Greece.

Lindsay Pedersen

Me too. Are you a dog person or a cat person or neither or both?

Doug Winter

I used to be a dog person and I married a cat person. So now I'm more of a cat person.

Lindsay Pedersen

You're so adaptable.

Doug Winter

Yeah.

Lindsay Pedersen

Okay. And finally, what is your favorite comfort food meal?

Doug Winter

Ooh, my favorite comfort food meal. Well, I have a big garden in the backyard, so I like to grow stuff. And right now it is asparagus season.

So I am pulling so much asparagus out of my backyard and it's absolutely delicious when it's fresh.

Lindsay Pedersen

That's a very high brow comfort food. Asparagus. I love that.

Wonderful. Power to you. You're lucky because you live in Sydney.

Doug Winter

Yeah, I guess I missed the word comfort in there. It's probably not.

Lindsay Pedersen

Oh, that's okay. You didn't say like hot dogs or macaroni and cheese.

Doug Winter

It reminds me of being a kid too because we always had a big garden in the backyard in the summer. All about the vegetables.

Lindsay Pedersen

It's so nourishing. I love it. Well, Doug, this has been great.

Thank you for taking the time. Where can folks learn more about you and about Seismic online?

Doug Winter

Definitely come to our website, seismic.com, and you can learn a ton about enablement and our products and get little demos and all kinds of great stuff. And if you want to learn about me, start with LinkedIn and reach out. I'm happy to connect with folks and really appreciate the chance.

This has been fun.

Lindsay Pedersen

I've really enjoyed it too. Thanks for listening to this episode of North Star Leaders. Make sure you don't miss an episode by subscribing on your favorite podcast app.

If you know of a North Star Leader whose insights would be valuable for this community, please message me on ironcladbrandstrategy.com. Also on that website are show notes, transcripts, and a way to sign up for our monthly newsletter. I hope you join us again for another episode of North Star Leaders.