Deidre Paknad is the cofounder and CEO of Workboard which is an enterprise SaaS company that helps companies unlock growth by making alignment and accountability remarkably easy. The company has raised over $60 million from Andreessen Horowitz, GGV Capital, Crosslink Capital, Floodgate, Granite Ventures, M12, and Opus capital to name a few. 

In this episode you will learn:

  • When you should raise money
  • When it is hard to raise money
  • Why VCs told her she had three strikes against her before she even began pitching
  • Why not to accept startup capital from family and friends
  • The fundraising landscape for female entrepreneurs
  • Her top two pieces of advice for other young founders
  • How to turn around a company

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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.

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 Deidre Paknad:

Deidre Paknad is CEO and co-founder of Workboard, where she’s focused on helping managers improve their leadership capacity and team velocity. She is a serial entrepreneur who has founded and led several companies. 

Her last company created a new market category and inspired customer loyalty and was acquired by IBM in 2010. At IBM, Paknad ran a high-growth business improving information economics for enterprise customers. 

She has 16 patents (granted or pending) and has been recognized by the Smithsonian.

Connect with Deidre Paknad:

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FULL TRANSCRIPTION OF THE INTERVIEW:

Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today we have a very exciting female founder, and I think that we’re going to learn a lot today about turnaround on companies, about raising money as a female founder, about doing acquisitions, and you name it. So without further ado, I’d like to welcome our guest today. Deidre Paknad, welcome to the show. 

Deidre Paknad: Thank you. I’m so glad to be here.

Alejandro: Originally born in Stockton, California. So not far away from Mountain View. Your early beginnings and being born and being raised probably were not as easy. How were those early beginnings in your life, Deidre, and what kind of lessons did you learn from that.

Deidre Paknad: In some ways, Stockton is pretty far from Mountain View or Silicon Valley. It’s 100 miles, but it might as well be 1,000. There’s no overflow of the tech world, the scene, or the opportunities that the tech world provides into that region. I grew up a poor kid. My dad was an auto mechanic. There are five of us. My stepdad was an auto mechanic, my father had been killed in military service, and it was a bit messy growing up. I was very intent, for some reason, on finding opportunities and exploring the world and living a bigger life. I had a lot of urgency to go to college, and I had some financial constraints. I needed to go to college on the benefits that they pay you when your father is killed in the service. So I was trying to rush through college and through law school by the time I was 22. I left high school early. I left college early, and I got on my way out into the world as fast as I could.

Alejandro: Every card that we’re dealt with in life is there for a reason, and every experience shapes us to be who we end up being for our personality and also for our perspective. In your case, Deidre, the upbringing, and all these different events that were unfortunate, I’m sure that they had something for you to learn. What was that?

Deidre Paknad: You’re absolutely right about that. Among other things, I have a super-strong survival instinct. I’ll confess that I’m a pretty fierce person. I’m relatively short and small, so my veracity can surprise people because I don’t look like the package that is fierce. I think that veracity and tenacity are fabric that was woven in maybe even the first five years of my life because my father passed away when I was very young. My mom was also very young. It was a hardscrabble, and as I said, messy. But the orientation to move beyond that, and to see all there is, and to be all that I can be, that energy and urgency came early in my life. I would say as an entrepreneur, which I’ve been now for two decades, those things: energy, urgency, tenacity, and veracity. Those turned out to be really good ingredients for my adulthood, for my life. While they were hard-earned, I am glad that I earned them.

Alejandro: 100%, and probably during those years where there were limited resources and things like that, was there a point where — you said earlier that you wanted to live a bigger life. Was there a moment that for you was that moment where you said, “That’s it. I want to live a bigger life.”?

Deidre Paknad: I don’t think there was a moment or an inflection. My mom and my stepdad, with whom I’m very close, they fed me a little bit of a different thing. They conveyed to me my father’s hopes. They gave me a kernel of “You can be whatever you want, and you can compete and win at whatever you want to compete and win on. It’s just hard work. Just do the work. But there’s no cap on you if you’re willing to do the work.” That, which is the ethic of maybe blue-collar Central U.S., Central California. It’s a good ethic. That was always in play. This will sound dorky, but I was a relatively smart kid, so schools were also taking care of, in a sense, making sure I got into this program and that program. Those things early on smoothed the path even though it was a bit of a rocky path. They did their best to smooth it. So there wasn’t “a moment.” That kernel, that idea that I could live a life as big as I was willing to work for, that was always there for me and that sense of being grateful for those programs that open the door. There are five kids in my family, and I’m the only one that went to college. In the town itself, at that time, was not a particularly college-bound community. It had a huge amount of drug problems. Right now, it’s got tons of drug and gang problems. The whole city declared bankruptcy. It’s not an awesome destination city right now for anybody. Now, people from Stockton are going to send me notes. [Inaudible 0:08:02] I was grateful for, and I am grateful for the people who early on saw potential, told me that I had that potential, which led me to believe that I did, and allowed me to then grow up with that concept as opposed to having to back into it or find it somewhere. They gave it to me quite early, and for that, I think I’m lucky. In some senses, every kid should have had that kernel, not just me, but I had it fairly early.

Alejandro: In your case, you went to college quite early. Also, you wanted to be a lawyer. That didn’t turn out to be as expected, and we’ll talk about that, but why did you want to be a lawyer?

Deidre Paknad: In those days, there were three models, or maybe there were five models of what you could be when you grow up. There was fireman, police officer, and nurse, which was one set. I’m none of those things — or doctor or lawyer. The images and the patterns that you could look to as a little girl and see yourself in the world in the future, and particularly pre-internet and coming from a blue-collar environment, there weren’t that many patterns out there of what to imagine your future self being. I knew I wanted to work and be professional. It was unbelievably clear to me very early on that I wanted economic independence. I was really committed to that economic independence. It was like, “Okay. Doctor or lawyer.” I’m not a doctor. I was reasonably articulate. I loved to write. I think I’m a rational, logical, person, thinker, and law resonated with me for those reasons. Then, I have this crusader veracity, and that all seemed to say, “Go be a lawyer.” Super early on in high school, there was a go sit with a judge for a day, or do that once a semester. All these things attracted me to being a lawyer, including working in a DA’s office when I was in college. I was a very single-tracked mind about becoming a lawyer, but I didn’t want to even know about the other possibilities, much less entertain any other possibilities.

Alejandro: And that’s something that happened because during the earliest stages of doing your JD, your law school, the tech industry came knocking, and that changed everything for you.

Deidre Paknad: Yeah. In the end of my first year at law school, I was living in LA, and I got a summer job at a semiconductor company. I spent my student loan buying a Mac and a printer and geeking-out on computers. I was working over the summer at this tech company. This was a long time ago, but at the time, big complex systems to draw complex semiconductor chip and packaging and assembly. The machinery to draw and to build those diagrams and detailed instructions were like a million bucks. I figured out that summer that if I use this Mac that, at the time, had spent a gross near $5,000 on, that if I took this Mac and this printer and I replaced the printer cartridge with this really cool thing in its day, which was a cartridge that read dot pixel-by-pixel and image. That, in a sense, was a scanner. If I used my Mac in this scanner and printer cartridge, I could actually create the equivalent power as this huge million-dollar CAD-cam systems at the time. I came up with this thing and told my boss. He said, “Write a proposal.” I didn’t know how to write a proposal, but I said, “Sure.” The next thing you know, I have a team of nine people. I had five Mac stations, and we’re now on the company tour when customers visit. “Like, oh! This is awesome, actually. I see something that doesn’t work very well, and I see a way to use technology to fix it. That results in more opportunity and an elevation in my career. This is great. I’m not going back to law school. This is too fun.” 

Alejandro: Obviously, this is what you dedicated the rest of your life to the world of hypergrowth companies, tech, enabled businesses. This was a nice segue, as well, into your first company, which you did in your early 30s. Tell us about this experience. I believe this company was called CoVia Technologies. Is that right?

Deidre Paknad: Yep. Same co-founder as Workboard. He had been working, at the time he was Adobe, and was one of the first five guys on Adobe Acrobat and really instrumental in that technology. This was before we all used browsers. Then he went to Netscape. So, really early inflection points in the internet. At the time, we thought that if we could communicate with our customers much faster and more freely than the generation before us, pre-internet, it would be phenomenal. This sounds so stupid right now because, obviously, it’s beyond phenomenal. But, we started a company then, and CoVia was very oriented around taking high-quality, high-value content that our customers cared about delivering to the world, and that might be broadly to the world. One of our customers was the U.S. Olympics. Or, it might be very precisely to the world of customers. Another one of our customers, WellsFargo, ADP, etc. were communicating to their customers that we sell this opportunity to take super-high value content and help companies deliver it with greater ease and without technical skill to their audience or to their stakeholders. Those were crazy and heady days, but effectively, the product that CoVia produced was Sharepoint, which was a super-smart set of ideas on publishing content, having conversations around them, creating micro-sites with that content, and doing that easily with a regular, ordinary, non-technical person. It was a little early for the universe, but it was successful in its day, but a little early for the broad success that I think it could have had and perhaps, theoretically, still can have in the universe. 

Alejandro: Here, you raised about 27 million, and you decided to hire an external CEO. That’s a very big deal as a founder because you’re bringing someone who is completely an outsider to lead your baby. I know that didn’t turn out as expected, perhaps for the time or the skill set. Can you tell us more about that?

Deidre Paknad: Yep. The company was started in the late ’90s. We raised money, and Adobe Ventures was an investor. We had some good success. American Airlines rolled out our product enterprise-wide with 100,000 employees. We were on a roll. We had some nice customers and success stories behind us. I think we raised around 9 million. Then, ’99 was this huge inflection. The company was growing quickly. I was a first-time CEO. I had never run sales or marketing. I had always been in operationally roles internally. I just didn’t have a lot of sales and marketing, particularly not enterprise sales and marketing chops. In those days, you had founders and CEOs. Then when the company would get to a certain scale, you would bring in a professional executive who knows how to scale sales. That was a fairly prevailing mindset at the time. In late 1999 and early 2000, we made a decision. It was a trip to Hawaii in December 1999. My co-founder and I made the decision to bring in a CEO who had a lot more sales scale and who had built and led larger sales organizations, which seemed to be the next stage in the company’s life. We announced that she was joining the company in April 2000. Of course, what we were bringing in was a person who had run much larger organizations from inside even larger organizations, so a person who could operate at high scale. What happened in the universe was the downturn of 2000, the financial, economic crisis. Unfortunately, two things: 1) She and I raised money in the fall of 2000 after the crash. We put about 26.5 million dollars in the bank on a fundraise, which was an actual feat to raise that much money after the crash. We did do that. However, as we moved into 2001, it became super clear that it was a time to be a scrappy entrepreneur, not a time to be a big company sales executive. The company just didn’t survive through the following two years, and ultimately, in 2002, it shut down. In 2001, I left the company. It actually ended in 2000 after raising the money. I left the company, and she led, but it was not successful. You’ve got to be super scrappy when times are tough and scrappy wasn’t in her resume. So we had just the wrong skills at a crucial period in the company’s life and in a macroeconomy. 

Alejandro: Your co-founder is now your co-founder at Workboard, which we’re going to talk about in just a bit. Obviously, your husband, so co-founder in life and in business, which is, I think, is an amazing trait, or an amazing thing to have because at the end of the day, your co-founder, you’ve got to trust them and the dynamics can be so clear. I’ve gone through that with my last company with my wife. In this case, the outcome was not as expected. I’m sure that for you and for your co-founder, in life and in business, Daryoush. I’m sure it was a tough pill to swallow. How was that warning process for you guys?

Deidre Paknad: It was challenging. So he stayed. I moved on at the end of 2000 after the fundraising, but he stayed as CTO and head of engineering. We each had the, if you will, fading out two years. We each had a different experience with that because he was in the business trying to help win new customers and so on. I was focused on other things and was doing a consulting gig at a Sequoia company. I think he was closer to the pain than I was. I was sad, but he was day-to-day immersed in the try-to-save-it. I think that’s super hard. That was quite a long time ago, and he went on to some interesting companies, and I went on to other things as well. With a lot of distance, now, I think we’re both much clearer about what we learned about ourselves, about our skill set, about company-building. For me, I was able to take some of my biggest learnings straight into my next gig, and I’m sure he did as well into his next. Maybe just because we were a bit younger, I think we valued what we gained. What we gained was in our understanding of ourselves and of company-building. We value that a lot. What was hard, then, and which maybe took us ironically the longest to get over was, in those days, there were a lot of friends and family investing. In 1999, there were friends and family who begged to put money in when we raised money. I still have an aunt and uncle who won’t talk to me because although they begged to put their money in, they’re still upset, however many years this is — 20 years later. I’ll tell you right now there are no friends and family investors to work for.

Alejandro: Lesson learned. Now, when you’re having the turkey at Thanksgiving, there’s no talking about valuation.

Deidre Paknad: Exactly right. You agreed; it’s your problem. It is not going to be my problem.

Alejandro: I hear you. In your case, you definitely bounced back. You went into doing some gigs with a company from Sequoia. Then, it’s interesting because you go from one storm to another. You went into turning around another company, but in this case, you actually turn it around. Tell us about that.

Deidre Paknad: I was recruited to a company to be a turnaround CEO, and it was a well-funded company. They had raised 30 million. They were two-and-a-half years old when I went in. The company was PSS Systems. It was backed by Lightspeed. At the time, it was very focused on securing documents and documenting encryption. The CEO, who was a very successful person, had decided that the idea he was working on wasn’t going to work and wasn’t going to pan out. Investors either needed to take their money back or go find a new CEO who wanted to do the hard work of figuring out what kind of company to build. I looked at that as a fabulous opportunity. The economy was down, but of the 30 million they had raised, they still had half of it in the bank. I had a huge appetite to go build a company and to make it super successful. I had a lot to prove, so I dove in, and it was super fun in figuring out what it could be. In some ways, I went in doing the same thing I had been doing at the Sequoia company I was consulting with, which was helping them figure out what market segment, what buyer, what solution they were going to pursue. It was a little bit unclear. I was pretty methodical about hypothesis for problem, hypothesis for buyer, hypothesis for value, threshold, and vetting those hypotheses with data before committing a substantial amount of capital and time. That’s what I had been doing at the Sequoia company, so I took the same approach as I came into this company, and said, “I’m going to take this much time to flush out the hypothesis. I’m going to take four months to go test that hypothesis. This is how I’m going to do the research. This is the approach I’m going to take to validate it, and at the end of that period, you guys either take your money back, or we invest and build this business. Between now and that, I’m going to cut spending way back, and I’m going to sit on as much of the capital that we have right now so that should we decide to go invest four or five months from now, we have plenty of capital to go do that. That was a super fun and interesting exercise looking for what are the problem spaces that are interesting? At the time, there was a huge rise in the amount of data being stored, so storage companies were not only getting funded but were growing like crazy and super successful. At the same time, this is 2003 and 2004, there was all the aftermath of the financial crisis. So there was a whole bunch of compliance things going crazy, firms that were destroying data and getting in big trouble for doing that, and destroying evidence, and so on. Is it either of those problems? Then, we had the novel idea that those problems are related, that if we have this massive growth in data, combined with a massive change in our obligations for that data, it’s not going to work out well unless we have a way to manage the two together. We had this idea that those things would intersect, and that we needed to give corporate legal and corporate IT organizations ways to balance the two: rising data, rising obligations for it. Actually, I loved that part of the four or five months of the company, working through that hypothesis and then met with 55 companies and tested the hypothesis. The companies were segmented, so we could figure out whether a large enterprise was a better place to start or mid-market. My hypothesis was mid-market. The data showed a large enterprise. This is kind of an old-school world where building software was harder and slower than it is today. About nine months later, customer number one was Citigroup. Customer number two was Credit Suisse. They were 48 hours apart in signing our first agreement, and PSS was off to create a category, which was super fun.

Alejandro: That’s amazing. It did work out because the company ended up being acquired by IBM. The total amount of money raised was 40 million, so what a run, and this was, obviously, the segue into the next time you and your husband, Daryoush, will get together once again. Tell us about Workboard. How did you guys get together again and say, “Let’s give it another shot together.”?

Deidre Paknad: I was COO for PSS for seven years. Over the course of it, I was telling him the stories from work. There were inflection points where I was, “I wish you were my partner, and you’re building a product.” We had wishful thinking over the course of that journey. When I was at IBM, I ran the business group that I was acquired to go over the IBM portfolio related to it. I bought another company, and we were acquired in 2010. In those next three years, I drove a lot of growth and some very large software deals that were more than 10 million in software inside IBM. I got much deeper enterprise experience over the course of PSS, where most of the Fortune 50 were customers, and deeper still inside IBM. What was becoming clear to me was that the ability to drive the business with mission and metrics alignment where everybody is on the same page, everybody knows which needles need to move, and by how much, and everybody knows their part in that. That is so ridiculously hard inside large enterprises and large organizations. I was experiencing it running my business at IBM. I was seeing it happen in who my large enterprise customers and counterparts were. I was seeing them suffer from that as well. Getting everybody results aligned and getting the answer to how are we doing now on the strategic priorities? They were so hard, so opaque, so slow, so labor-intensive that I found it super frustrating, and it was starting to get exhausting due to how labor-intensive it was to give people’s results aligned and to get the facts on our results. At the same time, Daryoush, who is a hard-core cyclist and has been for decades, he was racing with the team. At the point where I was super frustrated on how I can get transparency on results and any enlightenment on results in my business, he and his buddies who had been tracking their personal performance in spreadsheets for years, they all moved into Strava, and they could all see each other’s results on Strava. As a team, they got stronger, and were more competitive, and moved into some of their best winning years as a team and how they performed in races. Because they could see each other’s results, they competed with each other to do better. He had this epiphany that once he could see those results in context of his peers, he could then optimize how he trained, so he could train fewer hours and come out at the same place in the race, which for both of us was like, “Oh, gosh! That’s it! Less effort and more impact.” He was getting all this lift, momentum, and benefit from results transparency across his team. I was dying from the absence of results transparency in my business and going nuts. Literally, it was like the peanut butter/chocolate Reese’s Peanut Butter thing, like, “Oh, wait. How come you can have that for cycling and team sport, and I can’t have that for work? Wait a minute, here. These things can go together, man. How would it look? What would it be like?” So he got started right away while I was still at IBM, and we set about. I was hypothesizing, “Okay. What would that look like? How would it be?” A bunch of the processes and cycles of aligning on the plan, driving the operations reviews, the business reviews that I was doing at IBM, we started to flush out what that would look like if it was digital, and you had the same transparency of team results, individual results, results over time, how smart you could be as a business. That’s worked for it.

Alejandro: What ended up being the business model? How do you guys make money?

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Deidre Paknad: We sell to large enterprises. We license the software application or subscription to it. Customers are Comcast, Cisco, Workday, Microsoft, IBM, Samsung, Trans America, really large enterprises that are not unlike the one I was working in when we had the idea. Quite a few startup companies that are about to go public or have just gone public like Seismic, Zuora, which are customers as well, where you’re starting to get to a scale where you have to be conscious of aligning on results, and you need to have more structure and velocity in how you understand what those results are because you’ve got more layers in the organization. The business model for us is enterprise sales in the classic sense. It’s been about three years in a row we’ve tripled sales, and that’s what, obviously, we hope to do this year as well.

Alejandro: Very nice. Here, you’ve raised quite a bit of money. How much capital have you guys raised to date?

Deidre Paknad: We raised an early seed round while I was still at IBM of about 2.75 million. It was five years ago or maybe a little more. We raised a Series A with Floodgate in the fall of 2017, 9 million. Then in 2019, we raised a Series B in March of 23 million. Then we raised a Series C in December of 30 million. So, 53 million total last year is our funding to date and low 60s total. 

Alejandro: Wow! Obviously, you guys have people like Andreessen Horowitz as well. So very good stuff. So you’ve learned quite a bit on fundraising. What would you say is the difference between fundraising on an economy that is on the upside versus on an economy that is on the downside?

Deidre Paknad: First of all, if you have the foresight or hunch that the economy is swinging to the downside, go raise money, which was what I was able to do at PSS. Our customers then included Citigroup and Merrill Lynch, and there was this discomfort in the air. I said, “You know, since I lived through 2000, I think I feel winter coming. I’m going to go get myself a coat of venture money and make sure that I can stay warm, which was super important in PSS through the harder downturn years. Even in 2000, raising money, revenue velocity, or sales velocity is the giant thing. If you’ve got it, good companies get funded whatever the macroeconomic environment is. By good companies, I mean people with sales velocity where you have consistent accelerating growth on the sales side. I think where I experienced maybe a bigger difference in fundraising was at PSS and at Workboard, we’re category-creating. So you’re creating something that there isn’t a name for yet that people haven’t heard of. Maybe they haven’t thought of the problem yet, or they haven’t ever given the problem a name. If you’ve got this new way of seeing issues, and a new label for it, and a new label for the solution to those issues, that’s harder to raise money on because it requires the people you’re telling a story to 1) agree and identify with the problem, and 2) to agree and identify with how you’re solving that problem. That’s hard. That is super difficult, and it was difficult for me in raising our Series A. The seed funding was a little bit easier just because I went back to investors that had invested in us before. But when I went to raise a Series A in the early part of 2017, there was no category; all the words were new. If people hadn’t worked in a big enterprise, they didn’t feel the pain. That was challenging. It was too early for us to have a lot of sales velocity at that time, so it couldn’t rely on external proof of problem and solution. I found it a lot more challenging as opposed to fast-forward to 2019. Our first meeting to term sheet on our Series B was three weeks. From Series B to Series C was seven months, and from the first meeting to the term sheet in the Series C was also three weeks. You’ve got a lot of sales velocity, so there’s a lot of external exogenous evidence of problem and solution. Then the solution category has matured so much more, and there are so many more customer stories, that it’s a lot easier for an investor, even if they haven’t felt the problem, it’s a lot easier for them to listen to other people, customers’ descriptions of the problem, customers’ descriptions of the solution, and then imagine that those two go together. This is really different than fundraising if you say, “I’ve got the 11th generation of video meetings or a CRM, and here’s how it’s better than the generation before it. People already know what video meetings are. You’re not starting with, “Meetings can be done differently.” But if you’re category-creating, and you’re solving novel problems, you have to start the education process so much farther upstream than something that is an evolution of a known or an existing solution to it, a well-understood problem.

Alejandro: Yeah. 100%. To expand a tiny bit more on the fundraising subject, what are your thoughts on raising money as a male founder versus a female co-founder?

Deidre Paknad: In the fundraising process, Daryoush is a geeky guy, and at this company, our enterprise customers and the narrative around enterprise and the business problem is so central to it that most of the fundraising I did, I took all the first meetings and the second meetings, and so on. I’m clearly a market-facing person. That belief I told myself a long time ago that I didn’t understand sales and marketing turned out to be false, I totally understand them, and maybe I might even be good at them. So I do most of the fundraising. I think in my Series A, 2016, 2017, I believe raising money as a woman was unbelievably hard. When I raised the A in early 2017, literally, a VC said, “Do you know what your problem is? You’ve got three strikes against you. First, you’re a woman. Second, you’re old, and third, you’re married to your co-founder.” I think he just told me out loud what lots of people were not saying out loud, but were thinking. In 2017, there were no women partners anywhere. Women CEOs were still 4% of total venture-funded CEOs, exactly the same percentage as it was in my first CEO gig in 1999. We weren’t making any progress on that front, but I felt it was the peak of negativity and a friction in 2016 and 2017 as a woman raising money. Then the dam broke.

Alejandro: Something that’s very interesting there, Deidre, is that three strikes that that investor mentioned, to me, are like the three biggest blessings that you could ever think of because 1) there has never been a better time to be a woman, especially a female founder. 2) Your age gives you an experience and an edge that, as an investor, you’re going to be investing on earlier stage, first-time founders, and you’re really also investing in their education. So, in this case, you already have the education. 3) The fact that you’re doing it with your husband is also a major plus because you already have the dynamics, the communication, understanding, and the respect, and also, you go to sleep with it, and you wake up with it. So you’re literally producing the investor’s money either directly or indirectly.

Deidre Paknad: I agree with you. The first half of my buyers are women. At Comcast, our buyer, the person who we first met with, and who is our sponsor, he’s the president of Comcast Cable, TPx. At Workday, it’s the CEO and the COO. I’ll tell you what. They’re my age. So if I sit down at the table with them and talk about the way of running a business and driving growth is changing, I’d better not be 24. Also, I should not have on a hoodie. I need to look like, and I need to be a credible executive with real experience growing organizations both in startups and in large enterprises. I think I’m exactly the right CEO and founder for this company and the problem we solve here. I agree with you. Founder risk is huge. We already know how to argue. We already know how to grow things together, and we already know how to express our limitations to each other and work forward anyway. If you invest in founders who have known each other for two years in college, other than a lot of parties, I don’t know how much hard they’ve been through together and how much durability they have as they grow as human beings forward. 

Alejandro: 100%. How big is Workboard, for the folks that are listening?

Deidre Paknad: We’re about 150 people right now. A little more than 100 enterprise customers and close to 300,000 end users. A fairly large and good number of enterprise-wide of rollouts at Workboard at Juniper and Workday, Zuora, the Comcast Cable group where it’s every person in the organization has access to this solution. The solution footprint is pretty big. Actually, Microsoft and Workday are both substantial customers and also investors alongside Andreessen Horowitz and GGB Capital.

Alejandro: Very, very cool. One question that I always ask the guests that come on the show is, knowing what you know now — it’s amazing, the remarkable experience that you have been able to get over the years, especially with these two companies. If you had the opportunity to go back in time, and I’m sure you’ve done a lot of reflection looking back, especially with your co-founder, Daryoush, your husband. If you had the opportunity to go back in time and sit down with that younger Deidre, what would be that one piece of business advice that you would give to yourself before launching a business knowing what you know now and why?

Deidre Paknad: That’s a good one. I think there are two things that I wish I’d known earlier, and all the way back to the first company. One of those is, believe in yourself, which would have shifted the big decision that I made to hire a CEO. Just believe in yourself. You’ll figure it out. Then the second that I take super seriously is, as a CEO founder, pay incredibly close attention to the point at which, you can move from founder-led selling to sales-led selling and don’t try to accelerate that too soon, but don’t go past the point at which you needed to have made a transition out of founder-led to team-led or organization-led selling because the next big fail point is if you’re the only person that can sell it, the whole company constraints around you. I think founders make that mistake. I think I made that mistake early on. That very first company, I had hired this person to come in and lead sales, what I had also not done was make sure that there were people behind me and around me who are as effective at selling as I was. I had this odd thing where I thought I wasn’t good at sales, and I needed somebody else to scale it, and clearly, I did, because I hadn’t scaled it. But, second, also I was good enough at sales to get the company to where it was, and then no one else behind me could carry that forward or carry that onward. I recognize that in hindsight as fatal mistakes. For founders, the first time, in particular, you don’t have any hindsight. Borrow mine if it will help you.

Alejandro: I hear you. 100%. Deidre, for the people that are listening, what is the best way for them to reach out and say hi?

Deidre Paknad: I’m @deidre on LinkedIn. Twitter: @day_dree. I’m active on Twitter, so conversation there is awesome. Or deidre@workboard.com. I’m happy to chat any time.

Alejandro: Amazing. Well, Deidre, thank you so much for being on the DealMakers show today.

Deidre Paknad: Thank you. I’m delighted to have been in the conversation with you.

 

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