Deep Dive with Sherisse Hawkins

Intro: Welcome to the Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster. And today we are here in deep with Sherisse Hawkins. Sherisse is the founder and CEO of Pagedip, and she is by her own branding a corporate escapee, which we will get back to in a couple of minutes. But Sherisse, nice to have you here. Welcome to the Daily Bolster.

Sherisse Hawkins: Nice to be here.

Matt Blumberg: Let's start by telling everyone what Pagedip is.

Sherisse Hawkins: Pagedip is a way to create interactive, engaging, but most importantly, measurable documentation. And we help people improve their sales outcomes by being able to measure the efficacy of their content.

Matt Blumberg: That sounds really interesting. Give me a use case.

Sherisse Hawkins: A great use case is either ESG reports where people want to understand how those are performing, or helping account executives for SaaS companies improve their sales playbooks and improve their revenue outcomes.

Matt Blumberg: Both of those are high impact in very, very different ways, and certainly the enterprise SaaS selling, which is a field that I know really well. If you have a product that's going to improve the velocity of enterprise SaaS selling, you have a very, very good product. So I am glad that Pagedip exists and that you're doing your thing there.

Sherisse Hawkins: Thank you. We're really excited about it. And a lot of startups, that wasn't our first use case, but it turned out to be the gold mine for both us and really making a difference for our customers.

Matt Blumberg: So let's come back to that because figuring out what your product market fit is, and pivoting is a great topic, but I'd love to start real quickly with your journey. Real quickly, what's sort of the arc of your career? We can get then at the end of it, to the founder journey after you started Pagedip, but how did you get where you got and why do you call yourself a corporate escapee?

Sherisse Hawkins: Yeah, I think I coined that term. I'm going to claim I coined that term because I've been talking about it for a long time. I'm an engineer and technologist by degree, and I think in ones and zero. So I got a couple of engineering degrees and went straight into corporate America. I worked as a Disney Imagineer designing theme parks around the globe. I worked with video systems and then I worked at Time Warner Cable leading up their software development group. And so inaudible

Matt Blumberg: But I remember when I met you, you were in that last job.

Sherisse Hawkins: Yes. Yes.

Matt Blumberg: You were saying you had a huge number of engineers reporting to you.

Sherisse Hawkins: Right, right.

Matt Blumberg: I've always thought-

Sherisse Hawkins: We were doing amazing things.

Matt Blumberg: Yeah, I mean, I've always thought that Imagineer is probably the best job title ever.

Sherisse Hawkins: I have to agree with you.

Matt Blumberg: And designing theme parks is pretty cool. Yes. How did you get from that into software development?

Sherisse Hawkins: Oh, every path is secure inaudible, right? I worked as the Imagineer, and the thing about being Imagineer is you're taking usually off the shelf equipment and technology in you're applying it in a really unique and creative way. And I'm one of those people that's a little crazy. I believe that engineering is one of the most creative jobs on the planet, and I think we should talk about it in that way. But it taught me that anything is possible and just had some great experience. It's also hard. It's also very hard to get things to work in unusual ways. Yeah.

Matt Blumberg: What's the most, the sort of most interesting or fun thing that you worked on at Disney?

Sherisse Hawkins: Well, I'll pose an open- ended question. There was a project that didn't actually turn into an attraction, but the problem was having to have the ceiling fall every, I don't know, couple of minutes, and then rebuild itself. And so those are the kind of things that, you get on paper and you're like, well, how are we going to do that from an engineering standpoint? And we figured out a way to do that. So just really creative, unusual problems to solve. It was a great experience, and that led me into more show design and ride design. And that naturally led into an interest in video. And so my next job after Disney was working for a company called Harmonic that did digital encryption for video streams and large equipment rooms. And from there, we sold to Time Warner Cable, and then they recruited me to work for them. And then I started becoming into more of a leadership role and taking more of the corporate leadership path, which was a great experience. We got to deploy to millions of people and start from a white sheet of paper and develop something completely new. I think that's where the entrepreneurial bug first started. That whole idea of starting from nothing and then developing something that got deployed to a lot of people.

Matt Blumberg: Although, as you say, being an engineer and an Imagineer is an inherently creative job as well. So at the peak at Time Warner, how big was your engineering team that you've led?

Sherisse Hawkins: Oh my gosh. I know I had 12 direct reports and then-

Matt Blumberg: Oh, wow.

Sherisse Hawkins: ...how many people were underneath them? How many engineers and testers? I'm sure it was over 150, but I really don't know the total number. And what that also taught me was 12 is my favorite number of having a team of 12 is like the, it's not too big, it's not too small. You can get a lot of things done, you can move pretty quickly. So that was another little lesson that I've applied to career part two.

Matt Blumberg: Yeah, it's interesting. I know different leaders are comfortable with different spans of control, and for some people, 12 is way too many. I also like having a bigger team because it means that I'm sort of closer to the action, fewer layers.

Sherisse Hawkins: Yeah, a dozen. It's a good number.

Matt Blumberg: Yeah. All right, so let's continue. So you're at Time Warner. You're there for about 10 years, right?

Sherisse Hawkins: Yes. Yes.

Matt Blumberg: You're running a giant engineering team. What gives you the bug to start something and what did you start?

Sherisse Hawkins: Well, this is the part where people think I'm crazy. My husband still was in a little bit of dismay because imagine I've got this great team, I'm literally sitting in the corner office. It was one of those out of the movie things, the great benefits. And the theme of all this as we're talking is I like to start new things. And so once the product that we'd worked on for 10 years was out in the marketplace and it was at steady state and we were sort of making improvements to it, that's not the place that I get the most excitement and joy, even though on paper everything was the perfect job. And so that's where I get antsy and I wanted to start again. And so much to my husband's dismay on Friday the 13th, I put in my notice and I didn't have a really specific plan. I just knew it was time to do the next thing. And there was also some phenomenal opportunities when a full class of us left our executive roles and then a whole new generation of people got to move up into the ranks and take the company to the next level. So all of that felt really good, but also incredibly scary. Incredibly scary.

Matt Blumberg: I'm sure. Yeah. I mean, that's in theory, that's as stable a job as you get, and a cash inaudible job and everything else.

Sherisse Hawkins: Yes.

Matt Blumberg: Well, just curious, what was the 10- year project? What was the project that was done?

Sherisse Hawkins: So most people, including myself, have cut the cord from cable now, but at that time, remember, this is quite a long time ago, the software that's inside the cable boxes that allow you to record shows and to deal with daylight savings time, all of the stuff, all the interfaces that you have when you're looking at, when you're watching the TV, we built that from scratch. Yeah.

Matt Blumberg: Wow. Yeah. Talk about a mission- critical system for most people, right?

Sherisse Hawkins: Yes. Yes.

Matt Blumberg: All right, so you have the entrepreneurial bug. You leave the stability of Time Warner. How'd you get to Pagedip? Or you had a different name at the beginning, right?

Sherisse Hawkins: We had a different name at the beginning. I say we did one major pivot and four micro pivots to get to where we are today. The first idea was around adding interactivity to published long form content like eBooks. And again, this was a while ago, so eBooks were, I wouldn't call it a novelty, but definitely it was time for them to become a little bit more exciting. And we had a really fantastic... So we developed some software that allowed us to produce interactive eBooks, embed eBooks with a lot of different media components and really cool elements, and allow people to publish those on the major platforms. What I didn't know is how challenging the publishing industry is. The margins there, how difficult it is to be innovative in certain markets.

Matt Blumberg: I was going to say, having published a few books, it is a very entrenched slow thing.

Sherisse Hawkins: That's the word.

Matt Blumberg: Non- contemporary-

Sherisse Hawkins: Yes.

Matt Blumberg: ...Process.

Sherisse Hawkins: You're finding some great adjectives. Yes. But what it meant for us is after our first book won a major award at a book show, I came back and realized that we'd made no money. I'm like, okay, this was fun and was very creative, but this is not a business. And luckily we had another customer, a potential customer, met us at the book show, said, I want to apply that technology to a completely different use case, more of a business use case. We did some co- creation, some co- development with them, and that was the first small pivot towards more business content and content that is tied to revenue in some way.

Matt Blumberg: Interesting. So it's a different use case, but really if I think about what you do today and what you originally started, it's a very similar theme.

Sherisse Hawkins: Yes.

Matt Blumberg: Making digital content, turning it from static to dynamic and doing the measurement around it and everything else. But completely different use case?

Sherisse Hawkins: Right.

Matt Blumberg: Yeah.

Sherisse Hawkins: The technology is more like a cousin. The business case is more another planet, another universe.

Matt Blumberg: So when did you start the company?

Sherisse Hawkins: We started the company very end of 2013. Yes.

Matt Blumberg: So coming on 10 years this year.

Sherisse Hawkins: Coming on 10 years. So this is the longest time I've held one job. We are now in that realm, but I think about it in terms of really having three companies because of how we pivoted. So Pagedip itself is about seven years old, six years old.

Matt Blumberg: Yeah. It is funny, I've tried to explain this to other people before, you can have the same business card for years and years and years, founder and CEO of whatever, and feel like you've had five different jobs.

Sherisse Hawkins: Oh my gosh, absolutely.

Matt Blumberg: Or even in your case, maybe feel like you've worked for a couple of different companies.

Sherisse Hawkins: Yes.

Matt Blumberg: So I'd love to hear a little bit about the transition from big company to small company. Obviously it took a lot of courage to leave and to start something. What was that transition like? What skills were transferrable, which ones weren't? What did you have to learn? What did you have to relearn? What do you wish you had known ahead of time?

Sherisse Hawkins: Oh my gosh, those are all really great questions. What I wish I'd learned, what I wish I'd known be ahead of time is when you're in a big company, you have a lot of support systems, a lot of support systems, not to mention your own personal assistant in some cases. And so the amount of energy that I put into ops right now, even though I have support in that area, still surprises me. So that was the first thing. The leadership skills were certainly directly transferrable. And I'm kind of a different breed. I started my entrepreneurial journey after having a corporate experience and a lot of leadership background and bringing products to market. I think there's some advantages to learning those things in an environment where you've got a lot of support and aren't worried about payroll, and you're able to go to some fantastic leadership opportunities. I think in some ways it's a good strategy to go and earn your chops, understand budgets, and have to balance a really big budget that's somebody else's to really get that experience. So I'm thankful for that. I think everyone tells you that your first idea isn't your best one as from an entrepreneurial standpoint. They talk about product market fit, they talk about being aware of cash flow, but you can't really appreciate all of those things in theory until you've lived them. And so just that there's on- the- job training that comes along with being an entrepreneur that you can't just can't learn in school, you can't practice. And so it felt a little bit when I was a good skier and I tried to snowboard. I know how to come down a mountain, but it's different.

Matt Blumberg: Those two things are very different. Yeah.

Sherisse Hawkins: So I wish that I sort of appreciated having to have that beginner's mind again and not having some conflict in my own psyche about that.

Matt Blumberg: What's an example of something you had to unlearn or relearn?

Sherisse Hawkins: I love being quick and agile, and I suppressed that in corporate because you have to do things by a certain process. And so Alex and I would change a presentation or make modifications in the car on the way into having the presentation with a customer or writing... Just the I idea of being really, really fluid and fast. I really, really enjoy that even to this day. And I think that's one of the things that why we've got amazing customers and some really large organizations that we work with, because that's the kind of thing that you can't do in corporate, but you can really exploit. It can be a little stressful if something's not working at the last minute, but there's a little bit of power and freedom associated with it that I really, really like.

Matt Blumberg: Yeah. How did you do with the transition around, I guess what I would call sort of scrappiness in engineering or MVP? So you go from leading a team of hundreds of engineers putting software in cable boxes. There's no room for error. It's not quite the same as programming a rocket to go to the moon, but it's there. It has to be bulletproof. And then the next thing you do, you're probably writing your own code or you have one engineer working with you and you're just trying to get something out the door. MVP. How did your brain make that leap?

Sherisse Hawkins: Well, having some small wins in the beginning certainly helped. And there was a particular type piece of interactivity that we put into eBooks that if you read all the forums that said that's not possible. And we did it. And I'll never forget, we had a little iPad when they were first came out and we had this interactivity working, and we were talking to somebody at a book show, and we said, " We've got this way to be able to touch on a word and have it expand and do these things." And they're like, " Well, that's not possible." And we literally pulled out the iPad and said, " Well, here it is." And the joy of being able to push the boundaries and try things. And then we only figured that out because we just kept trying unorthodox ways of manipulating an epub file. We just kept, it's one of those we didn't know any better because we didn't come from that industry. So we just kept trying. And that there's a high associated with that that keeps you going, that overcomes the fear of not having the inaudible chart project planned like I was used to in past life.

Matt Blumberg: Yeah, it is definitely a different world. So would you ever go back? Like let's say Pagedip is incredibly successful. Adobe acquires you, or someone big acquires and they say, " Oh, yeah, Sherisse, we want you to be the SVP of blah, blah, blah here, make your home here for the next five or 10 years." Do you do that or are you like, no, I couldn't possibly think about that again?

Sherisse Hawkins: I think because I had so many years in corporate, I think I would be a chameleon, and I think I would enjoy, again, you can see the grass is green on both sides. So you could see where you could bring that entrepreneurial spirit, that agility, some creative problem solving, but also have a great bonus structure or a 401k, whatever it is, and be able to help people even at a larger scale or internationally. So I'm not one of the people that says, oh, I'm not employable anymore. I think it would be a fun challenge and to bring that entrepreneurial energy, which I think employees in the large corporations really appreciate. They're hungering for that. So I think that'd be fun. Yeah.

Matt Blumberg: Well, you'll have to wind the clock forward a few years and see. All right. So let's back up again to the minute you decided to become a founder, to become a CEO. So it sounds like that to one extent it was driven by, okay, it's the right time for me to leave big co. You didn't have a specific idea, but you knew you wanted to do something creative. There are lots of things you could have done in life besides found a company. Why was that where you went?

Sherisse Hawkins: One thing I want to mention, especially for maybe women founders or people that feel like they are, I don't want to say caregivers, but have other roles. One of the things for me, I really wanted to make sure that my daughter's 529 was funded. And it sounds like such a weird tactical decision point, but for me, it was really important that if I was going to go off and follow this entrepreneurial dream, that I'd also put systems in place that I could feel comfortable with taking this risk. And I don't think we talk about that enough of what do you need to have in place for yourself, for your family, for whatever your ecosystem is to be able to take this. It's a wild ride, you strap in like a rollercoaster and there's a lot of twists and turns and upside down parts, right?

Matt Blumberg: Yes. And very, very limited cash generation for a number of years. Yes,

Sherisse Hawkins: Yes. So make sure you figure that out. Yeah. I'm an avid reader. I love words. I love how we communicate in different mediums. And that was actually a theme within my career, if you think about it from Disney through video. So seeing the potential of what digital content could look like, what long form text could look like, and just feeling like, wow, there's a huge disconnect between what's possible and what's actually happening drove me to explore that more. So it came out of a longing for what I wished there was in the world, and then it went from there.

Matt Blumberg: And what about actually becoming a CEO? What was the motivation there? Was it that you wanted to run something you wanted to lead other people?

Sherisse Hawkins: Yeah, I'm always been comfortable with being the leader. When you do the group exercises, I was always the person, well, I'll speak first, which I think is a little bit of a personality trait. But one thing that I've noticed, I'm not sure I'm answering your questions, but one thing I've noticed is I truly believe that we need to come into being a CEO or entrepreneurial journey out of a position of serving. Is there a pain point to help someone solve? Is there a need up there? And not from the ego place of, oh, I want to be CEO, I want to be founder. That's not very interesting or important to me. It's can I make a difference and make something better in a really earnest way? And sometimes I think the media gets that wrong. They make CEOs seem like these real egotistical... And some are, I guess... But egotistical, self- driven individuals. And I come our whole culture in our company, and I think bolsters the same as how can we really serve and make the world a little bit better?

Matt Blumberg: I think that's right. For me, it was always about not just customers, but really employees. And I used to say when I started Return Path, that Return Path could have done anything. We could have been in the insurance business, we could have been a retailer. We ended up doing some really interesting stuff and in marketing technology. But that part of why I wanted to start a business is I wanted to create a different kind of workplace and really proud of the things we did there. So I'm with you. I think if you become a founder and it's all about you, or it's all about the money, it's a problem. If it's all about the customers, if it's all about your team, if it's all about making, as Steve Jobs said, the dent in the universe.

Sherisse Hawkins: Yes.

Matt Blumberg: Yeah. You're certainly going to be a lot happier and probably do a better job.

Sherisse Hawkins: Your expectations will be a little bit more aligned with the job. The CEO job's not an easy one, and often it's not a fun one. It's not as seen on TV.

Matt Blumberg: Yeah, right. It's not all Shark Tank.

Sherisse Hawkins: No.

Matt Blumberg: All right. So let me ask sort of one more question about Pagedip. You said a few minutes ago that you did one big pivot and three little pivots along the way, and you talked a little bit about one of them, I think, think that the term pivot is probably a little misunderstood by founders, and I think it's probably overused in the world of startups as well. So I'd love to hear you riff on that for a minute. So what did it mean to you to take a pivot? How big a shift was it? It sounded from your story, you were led there by a customer or a prospective customer. Yes. How did you know, it was the right time to do something different, and how'd you go about executing a pivot?

Sherisse Hawkins: Well, that first customer that found us at the book show was it literally a pivotal moment when they said, " We have an idea for what we think you could help us with and we've talked to Apple, we've talked to Microsoft, and we haven't found exactly what we're looking for." And jointly we created exactly what they were needed, and it was a fantastic, champagne popping project. So we thought, " Okay, we've made it. We've got this fantastic customer." It turns out that their use case was fantastic, and we learned a lot, and we were both very, very pleased with the outcome, and it went internationally. However, they had some characteristics that didn't make that particular use case as reproducible as we assumed. So we had to, in some ways a little bit go back to the drawing board. About the same time COVID happened. And so a lot of things shifted in terms of how people were consuming content and what they were willing to pay for. And so there's other dynamics that aren't always just around your technology. There's other outside factors that also can impact your business. And then we were doing a number of different pilots, and as soon as we did the sales playbook pilot for the first customer and then the second customer, and then the third customer, some consistencies of requirements came to be. And we learned, we had refined our, what we call granular analytic.s so we can really understand what someone's doing in the document. And when people started using the results of those analytics to create a virtuous cycle and improve their content, we're like, " Ah, it's not a one- time thing. It's a living thing, and it's a continuous thing." And we're seeing better results because of this concept of granular analytics that we really tried as just a, let's see how it goes. It was an idea that we decided to run with, and it wasn't fully baked when we first released it. There was a few pieces of data, and now we've got a ton of data. So it's listening to your customer and anticipating what they might need and be willing to try and be willing to be wrong. For goodness sakes. That's the piece of, if it doesn't work out, don't be so married to it that you won't let it go. Yeah.

Matt Blumberg: Yeah. It also sounds like, I think there's sort of a line between a pivot and a restart. The pivot, if you think about the definition of pivot, it is one foot stays in place and the other foot swings around to a different spot.

Sherisse Hawkins: Yeah. Yeah.

Matt Blumberg: It sounds like at least your big pivot, and presumably your smaller ones too, you still had one foot firmly anchored in what you were doing, but were trying some other things out around it.

Sherisse Hawkins: Right. And what we talked about... We used to talk about interactivity and engagement and how beautiful and polished and exciting a document can be. We used to lead with that, and it got some traction. We had some great customers, but when we added the element of how can you know, what can you know using analytics, that was the other leg of the stool so to speak, or the other pillar that really brought everything together. It clicked for us. It clicked for our customers, and it made the product even more unique and sticky. So we had the first two for a while, but when you get that last little piece, it falls into the jigsaw puzzle and it all clicks. That's a magical moment.

Matt Blumberg: Yeah. All right. Let me switch to one last topic. So you've been a founder/ CEO now for almost a decade.

Sherisse Hawkins: Yeah.

Matt Blumberg: That's a long time. And I know, I've been there as well. How important is it, and how do you think about the fact that you're in a marathon, you're not in a sprint. How important is self- management or self- care to keeping yourself going and keeping yourself effective as a leader of your team and a visionary at work day in, day out, after 10 years?

Sherisse Hawkins: Yeah, it's paramount. It really is. And I think I was no different than most inaudible, which I didn't listen to that. I didn't heed that advice everywhere. It's just everywhere.

Matt Blumberg: It is now, I'm not sure it was everywhere 10 years ago.

Sherisse Hawkins: That's true, that's true. But my motto was, I can sleep when I'm dead and I can just work and I can finish this up. I'll work, I'll do the second shift, and then I'll do the third shift and then I'll get up early. It just went on and on and on. And there's always one more thing. And it's not sustainable. You are human and it's not sustainable. There was periods of high blood pressure, just like health issues that your body's telling you, this is not sustainable. But now there's just a few simple things that I do that I wish I would've told my prior self, just get on the bandwagon and do them. Now, the first is planning for the next day with a small, what's important, what I'm going to accomplish, and setting some goals. The second is making sure that of the things that I'm going to do, what are the three that I'm going to absolutely get done? And it's only three. I used to have a list of 10 or 11 or 12. Just make sure that there's a small number that are the really important ones and get those done. And the third thing is sleep. I really was like an anti- sleeper before, and there's studies now that show that not sleeping is the equivalent of trying to function when you are under the influence of alcohol or drugs. And the clarity, the focus, and the productivity that comes when you have a decent amount of rest. I'm not saying go crazy, but having consistent sleep is definitely a life hack that I didn't believe in before. And I'm here to tell the world that you should sleep more.

Matt Blumberg: That is certainly true. More sleep, and quite frankly, more exercise, which usually leads to better sleep and more sleep.

Sherisse Hawkins: Yes. Yeah.

Matt Blumberg: I always think of both of those as those are investments in your own productivity, and at some point the marginal hour is better spent getting yourself more productive in the other hours than it is doing another hour of work.

Sherisse Hawkins: And interesting about the exercise, I've always been a huge exercise person. That was something that I would not forego, even if it meant I'm going to run the treadmill at 11, because that's the only time I've got. I noticed that the things that I like to do from an exercise standpoint changed. So now I love to do what's called aerial silks. When you climb a silk fabric to a high point in the ceiling and then do a bunch of different wraps and then unfurl in a really cool way, sort of Cirque du Soleil esque.

Matt Blumberg: Very Disney. I'm seeing.

Sherisse Hawkins: Yeah, it is very Disney.

Matt Blumberg: ... like an imageof Rapunzel or something.

Sherisse Hawkins: Yeah. But one of the things that compared to running and cycling and swimming and triathlons and things like that I did in the past, it's one of those activities where you have to be fully present. And I've talked to more and more entrepreneurs-

Matt Blumberg: Because it's dangerous. It's dangerous if, you're not?

Sherisse Hawkins: Your life depends on it. And I've found that more and more CEOs and entrepreneurs that I know say that they've found another physical activity or meditation where they practice being fully present. And that was a really big shift for me from a long run where that's a great time to ruminate about what's working and what's not. When you're about ready to do a double star drop, you are in the moment.

Matt Blumberg: Yeah. And look, both of them, I don't think there's a right answer. Both of them can be good to clear your head, but those are very, very different things.

Sherisse Hawkins: Yes.

Matt Blumberg: All right, Sherisse, it's been great talking to you. Thank you so much for being on The Daily Bolster and our first season here. And Sherisse Hawkins, founder and CEO of Pagedip, and by her own definition, corporate escapee.

Sherisse Hawkins: Thanks for having me.