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Hiring and Coaching Successful Sales Talent with Iterable SVP Jan Zeman

When Jan Zeman was hired as a sales development representative in the early 2000s, he had a unique background in management consulting and venture capital. Jan has since risen through the sales ranks, having helped his previous company,...

Kleiner Perkins
Go To Market Grit

Episode 42 w/ Jan Zeman, SVP Sales, America at Iterable

Below is a transcription of Jan and Joubin’s full discussion. Access the podcast on Kleiner Perkins, Spotify, or Apple.

Jan: Grit to me is running into a wall, falling down, picking yourself up, and brushing yourself off, reflecting on what actually happened, and figuring out how do you avoid that situation again, and just continuing to be laser-focused on that goal that is ahead, whether that’s building a company, whether that’s getting in the next job, whether that’s hitting your number, wherever that goal is, making sure that you keep that in mind, and don’t let anything stop you.

Joubin: Hi, I’m Joubin, go-to-market partner atKleiner Perkins and this is GTMG, a show that interviews world-class revenue and go-to-market leaders to explore how they operate, think, and deploy grit every day in order to build incredible companies. Now, let’s get to the episode.

Joubin: Jan, welcome to the show.

Jan: Thanks for having me.

Joubin: I’m excited. I usually start these things off the exact same way. I say usually; I start every single one off the exact same way, so I’m going to do the same for this one. I’m going to read your background back to you and you tell me what I screw up and we can go from there. Deal?

Jan: Sounds great.

Joubin: Okay. So, you got your Bachelor’s of Science in Foreign Service—I think I already screwed this up—from Georgetown. I don’t even know what that means, Foreign Service. And then you went to Planning Technologies Group as a consultant for almost two years. Then you went to Europ@Web—spelled uniquely—for about a year and a half as an associate. I think that was venture stuff if I’m not mistaken.

Jan: That’s right.

Joubin: Then you went to Datasweep; SDR for a year. And then Callidus, you were an AE for two and a half years. And then SAS; an AE for two years. Then you had a really good run at Responsys; you spent seven years there. Ultimately, that culminated as the VP of Sales for the East. That was from ’07 to ’14.

Then you got acquired by Oracle, and so you spent two years as the VP of Sales within Oracle’s Marketing Cloud. And then you went to Medallia, had another really awesome run, did about four and a half years there. And you did RVP for a year, and then the VP and GM for three and a half years. And now as of July 2020, you are the SVP of Sales Americas forIterable. How many times did I screw up?

Jan: No, you got it pretty right there. That’s fantastic.

Joubin: Okay. So, couple questions for you in your background before we dive in. You graduated magna cum laude from Georgetown; then you did management consulting, and then you did VC. Kind of like, you know, all the things that a mother would want you to do. And then you went to become an SDR. What gives? How did that go?

Jan: Yeah, it was a fascinating kind of early ride. So, both of my parents are academics, and so when I got to Georgetown, I was pretty set, like a lot of folks who arrived at the hilltop, that I wanted to be the next Bill Clinton or a senator. And starting to do work around Washington, DC, and realized pretty quickly that I was not cut for the public servant type of lifestyle. So, I started to pivot into business, working a variety of different jobs on campus. And then my senior professor, my thesis advisor—I actually did Econ within the Foreign Service school, so I had, like, a concentration on international economics—he one day approached me and said, “Hey, I have this student. He’s doing this consulting thing up in Boston, I think you should meet him.”

And that’s how I ended up doing management consulting. It was a couple-year ride right in the late ’90s when the first dotcom boom was happening. And that eventually brought me out to San Francisco where I heard about this thing called venture capital. And Europ@Web was Bernard Arnault, the chairman, and owner of Louis Vuitton Moët Hennessy. It was his venture, at that time, investing in internet companies.

And it was a fantastic opportunity until the whole world changed in the early 2000s. So, at that point, I found myself looking at what I wanted to go do, and what I found in meeting with all these companies as a venture or associate was I really loved B2B companies where I could understand the value proposition of what they were selling and delivering to their customers. And when I thought through what my path would be, I could do finance, I could do spreadsheets, but I didn’t really like it. I was not a very good coder, I learned some programming in consulting and I just was not very good at that, and I looked around at all my friends and everyone in my network, and everyone was in sales in some capacity. And so I said, “Hey, why not? Why don’t I give that a shot?” And started my journey as an SDR.

Joubin: So, you graduated top of your class at Georgetown. You did management consulting, then you did venture for, actually, what sounds like a really cool firm. And then you went to do cold calling. You did straight-up pretty much the worst job in the world, like, the hardest, I should say. What was that transition like when you got in there? Did you have an oh shit moment, like, “I can’t believe what I just did?” Or were you off and to the races?

Jan: I think I had multiple oh shit moments.

Joubin: [laugh].

Jan: Starting with the fact that I was in San Francisco and this is pre-remote work, of course, and Datasweep was based in downtown San Jose. So, I was doing that 53-mile commute each way, twice a day, which was painful, which was part of the reason why I ended up switching companies and moving to New York City and selling my car after that year of that experience. But what I loved about it was I really didn’t know very much about software. I mean, Europ@Web had been doing mostly, kind of consumer investments; we dabbled in some software, and I really wanted to learn the business, and I wanted to learn, hey, how do you go about selling a seven-figure solution to some of the biggest enterprises in the world, and how does that process start? How do you create an engine that can continue to scale? That’s what led me to that job and to take in that experience.

Joubin: So, you had a good seven years at Responsys. One of the themes that feels consistent among many of my guests is one good run at it, where they got to take the social and political capital that they built inside one organization, and that got them to a certain threshold where they got their butt over the bar far enough where it gave them access or keys to the kingdom in other places. Do you think that’s a fair characterization? Is that how it played out for you, a little bit?

Jan: Yeah, for sure. And I had no idea when I joined in 2007, that was going to end up being nine years, end-to-end, of the run. At that point in my career, I’d been carrying a bag for two or three years; I’d gone to a big company, SAS, which is a, kind of, legacy analytics provider, and just realized it wasn’t the pace of company that I wanted to be at. And I met with a lot of companies and started to think about what made sense for me, and I thought, “Gosh, digital. This seems like it’s going to be a growth area. I’d be a good place to be.”

And I met the management team of Responsys, Dan Springer, and Scott Olrich, who are now over at DocuSign, leading DocuSign, and it was pretty clear that these were outstanding executives who were on to something, and Scott Olrich, in particular, who became a mentor to me, he took me through his vision for what Responsys was today, and what Responsys was going to become, and really got me hooked. And then we just ended up getting together a fantastic team of people, where many of us were learning, an incredible amount from each other in terms of how do we take a business—which when I joined, was about $25 million in ARR—up through becoming a public company in 2011, and then through $200 million in acquisition. All of those were new steps in that journey, and we were going through those together, and I think if you look at the network of folks who came out of that company who are now at DocuSign, at [6sense 00:07:31], and other leading type of SaaS companies, it’s pretty incredible to see what we’ve all accomplished, based on that foundation.

Joubin: Scott, he wrote you a recommendation, and I’m not going to read the whole thing—or maybe I will and I’ll just scoot through it. There’s a few things that he mentioned that I think really encapsulate your run at Responsys. And then I want to ask you some questions about it. Is that right?

Jan: Yeah. Go ahead.

Joubin: Okay, cool. “Jan learned what it takes to build a winning high-growth SaaS selling organization during his run at Responsys. He started working for us as a rockstar AE closing early prominent deals, and by the time we’d taken the company public, slash sold it to Oracle many years later, Jan was managing half of our enterprise reps and over 30% of our yearly bookings in the US, was a key sales leader that we relied on for market insights, setting the quality bar, and always delivering the number on big deals. His professionalism and ability to navigate complex enterprise sales cycles is unparalleled. I hope to be lucky to work with him again.”

Really flattering. This is—now he’s the COO of DocuSign. Very, very nice note. When I asked you earlier about the run and having one good run at it, did you feel like when you were an AE, this was your breakthrough moment of like, “All right, Jan, go close some freaking deals so that you can go prove yourself and have some longevity at this organization?”

Jan: No, I wish I was that insightful at the time.

Joubin: [laugh].

Jan: I think, I think what I realized was I was having a lot of fun, and there was a moment, probably halfway through that run, that I got approached by a friend of mine who had started a company and he was like, “Hey, come on over here and help lead sales for this high growth company.” And I remember leaving that interaction going back to, I think we had at the SFO Marriott, a kickoff, and I went back and I just saw a bunch of people in the lobby, and after mingling with my teammates for about five or ten—and peers and other people for about five or ten minutes, I realized I can’t leave this. This is too special. We’re just getting started. We’re not done yet.

We’re not finished yet. And I think one of the things about me as I’m—when I get on something and I have a goal in mind which is building something or finishing a race, I usually stick to it and grind it out and figure out how to get something across the finish line. So, through that journey, there wasn’t a, “Oh, this is going to be the platform for me for the rest of my career,” kind of insight at any time; I just knew I was learning, I knew I was being challenged, I knew we were learning, and I knew that we had more work to be done.

Joubin: You know, I think that’s a very good anecdote for the audience. Especially, like, you know, there’s probably folks on your team that are getting poached by, pick your tech company right now, and a lot of the time, there’s an allure of a higher OTE or whatever, but the reason I wanted to highlight this run that you had is because it opened up so many doors, just grinding it out, and having some longevity, and some long-term perspective towards the opportunities, so I think it’s really good story. What didn’t work during that run? Talk to me about things that sucked, the failures, both personally, organizationally, like, what was bad?

Jan: Yeah, I mean, I’ll approach it in a couple of different angles. The first one is personally. So, I chose Responsys, and when I was hired, I was very clear with Dan and Scott that, hey, I’m a killer AE right now, but I do want to lead sales teams; that is my goal, and I’d like to do that sooner rather than later. And the opportunity, about nine months in, presented itself where there was an opening and a need for someone to step into a leadership role. And I did just that, and I failed miserably.

I’ll be completely transparent about it. I did the classic, “Hey, I’m going to be the super-rep,” you know, just have the team get the ball to the 10-yard line hand it over to me and I’ll punch across the goal line, and worked myself harder than I’d ever worked to my entire career up to that point, and the results just didn’t follow. And so I realized pretty quickly, I had to just change my whole dynamic. A lot of it was around building amazing teams and finding talented people to join the team and helping them get to a place where they were better than I ever was as a rep. That was the goal was to have a rep and a team of all-stars, and to build that, versus be the person who’s classically the super-rep.

So, I think that was one, kind of, personal thing that was a difficult, probably, first 18 months as a manager to go figure out how to be a multiplier and how to, kind of, learn. And I see that with—I believe that promoting from within wherever you can makes a ton of sense. There’s just—it’s just great for the organization, and it’s a great way to grow people in their careers. And I think making that switch of how do you go from being an individual contributor to being an effective leader is a really difficult one because it’s a different job.

Joubin: Okay, what about organizationally? You said there was a couple?

Jan: Yeah, I mean, Responsys is interesting because it was founded in 1998, and gosh, that technology is still out there and being sold at Oracle today, but from 1998 to 2007 and then 2013, the world had changed pretty dramatically, and the product needs and use cases that companies needed to use Responsys for change dramatically, as well. So, we definitely had some situations where we were leaning into the vision and selling the vision more so than—while the product was catching up to the vision. I think that’s pretty common in software. And that was challenging at some times. There was one point in particular where we really had to get really good at selling our services capabilities, as we had some product gaps that we had to catch up on.

And all that stuff is like, those are the growing pains that you hear about in companies as they scale, and they’re hard. And you got to go realize it’s not the end of the world. Again, it comes back to the team, to the market. Do you have faith in the team, in the vision, and in the ability to ultimately execute? And at the end of the day, like we all did, which is why we had this just great nucleus and this great core of people who stuck through it.

Joubin: You mentioned earlier you told Scott and the team that you want it to be a leader. Why?e

Jan: You know, look, I love helping people. I always have had that back from early days in athletics and things of that nature, and I knew that I wanted to make an impact in the organizations that I joined, and that impact was going to be bigger and bigger as the companies that I joined, grew if I could be part of the leadership team. And so I always had this vision of, “Hey, I want to be an operator, I want to be part of a leadership team that is strategically growing a business and having a seat at the table.” And that was very much in mind when I came to Responsys.

Joubin: So, how long into your stint at the IPO happen?

Jan: About four years in.

Joubin: And then another three years after Oracle acquired you?

Jan: Yeah, like, two and a half years later.

Joubin: I’m going to ask you a question that I’m not sure you can actually answer, but were you happy or pissed when Oracle bought you?

Jan: Well, I [laugh]—it’s an interesting story. I was on the road in Toronto, and it was right before Christmas, and it was very unexpected. So, it was like a Friday morning and I got a text from someone, “Hey, check your email.” So, I think I was more surprised than anything. It had been such a long run at that time.

And I knew very little about Oracle. I knew it was a big software company, but I didn’t know very much about the culture. I knew that it was known for being a great engineering company and a great sales company. And I was very open-minded. I think a few of my mentors when we were going through that acquisition, they said there are typically three types of people when you go through an acquisition event: there’s the people that bolt immediately, there’s the people that stay with one foot in the water, and then there’s the people who really commit. And I’d say that for the first couple years, at least, I was very committed in terms of exploring what Oracle was going to be like and also just seeing what I could go learn.

Joubin: Okay, but in all fairness, if the handcuffs didn’t exist, would you have that same level of commitment out of loyalty to the business?

Jan: Well, what was cool about when we were acquired was Oracle made a pretty big bet of about $5 billion into marketing technology. So, they bought Eloqua about a year before Responsys; they also bought Maxymiser, and BlueKai, and Datalogix. And so there was a really, really interesting opportunity there to go learn how to go and transition from a single product sale to a base suite sale, which is something I had never done. I’d never led teams, Oracle, one of the first things they said is, “Here, your team size is going to double.” So, that was additional scale in my career. So, Joubin, I saw a lot of opportunity, a lot of things that for me, ended up being fantastic experiences that have helped me out since.

Joubin: Okay. That’s fair. Those are all pretty honest answers.

Jan: It’s a personal thing. I think—

Joubin: Totally.

Jan: —everyone evaluates their own situation. There were certainly people—because every company from an M&A perspective has different approaches. Some of them let the company that’s acquired kind of stay on its own. Other companies—and this is what Oracle did—Oracle kind of immediately plopped the sales organization in the sales organization of Oracle, they plopped the engineering team in the engineering part of Oracle, and I think for other departments where it was less clear what the fit would be, those decisions would be different for those individuals.

Joubin: Makes sense. Moving forward to Iterable. So, you joined in July of 2020. Is that right?

Jan: That’s right.

Joubin: Could you take 30 seconds to give the elevator pitch? What does Iterable do?

Jan: Yeah, you bet. So, it piggybacks very much on my Responsys experience. And if you think about it, every company knows that today, you’re in an experience economy, and you’re competing on how do you deliver that exceptional type of customer experience. And in a digital economy—which is what we truly are, I mean, software really has taken over the world—in a digital economy, that experience is oftentimes the communications that brands share with their customers, whether that be marketing messages, whether that be product messages, whether that be transactional messages, the emails, the push notifications, the in-app notifications, the SMS. And there’s a lot of different types of solutions and a lot of different systems that those communications come to from different types of brands.

Iterable essentially acts as the orchestration layer across an entire enterprise to be able to deliver and help companies take action on the data that they see from their customers and to be able to deliver a truly exceptional customer experience. It’s really hard for most companies because what they’ve found is that their channels and their products, they’ve evolved over time and so they’ve come up with, kind of, siloed approaches to dealing with different customer interactions. And really for Iterable, we’re that platform that allows you to take what’s happening—what do you see about a customer? Are they opening an email? Are they engaged in your mobile app? Did they just download something?—in one part of your business and be able to use that to personalize the type of communications that you provide across your entire business.

Joubin: Got it. Okay. So, I am a serious customer then. Okay. So, you guys are valued at $2 billion CRV. Index did the early rounds, most recently Viking Global and Silver Lake to the Series E if I’m not mistaken. This space is, like, red hot. It’s going. And to your point, it is an evolution of previous technologies.

One of the things that struck me was that since you joined, there has been a shitload of change. So, the company’s grown about 40%. In that time, your organization has probably grown around that same clip. You’ve got a new CEO, you joined in the middle of COVID. There’s a lot of things that are kind of crazy in startup world. How’s that?

Jan: Well, it’s been great. It’s been odd in that it’s been all virtual. So, the experience of going into the home office every day and talking to a screen, that’s certainly been an interesting wrinkle to it all. But we’re growing rapidly. We’ve got a fantastic product, fantastic leadership team, and fantastic vision, and a great, great brand reputation; our customers really, really dig the product. And so I think when you have those ingredients and you’re in a huge market, it’s a lot of fun.

Joubin: So, let me ask you this: you’ve seen change, right? You know what change feels like. You know when the ground shifts beneath you, that it’s generally a positive thing. If we’re not changing, we’re dying, right? Now, you might have younger reps, leaders on your team, folks that were excited to join the hot new startup that haven’t felt that change.

And all of a sudden, there is a unique confluence of multiple forces of change happening at the same time. Do you have any thoughts, I don’t know, communication style through all of this, that you’re like, “All right, how do I make sure that everyone continues to grow in the same direction, focused on our mission, independent of some of the things going on?”

Jan: Yeah, I mean, it’s a big, big theme in a lot of conversations and a lot of the communications that we have with the team. I always say, lean into the change; really be curious about it. As you grow and as you evolve as a company, you’re going to have to operate differently. Iterable just had its eighth birthday. The way that we sold those first four years versus how we sell now, it’s very different.

And it will be different two years from now when we’re twice the size that we are today. And so that’s really my mantra is lean into the change. We have four values at Iterable, and unlike a lot of companies that I’ve been a part of—you know, every company has their mission statements and their values; I’ve never seen a company that truly lives its values like Iterable, which are growth mindset, humility, trust, and balance. So, that first one of growth mindset is something that we screen for in the interview process, it’s something that we talk about in terms of constantly being learners, constantly thinking about, okay, how do we evolve? How do we get better?

And through getting better, we actually have our internal team focuses on a program called ‘betterable,’ which is really investments in the employee population to help us all work on business and life skills to improve. So, lean into the change, be open to understanding why that change is occurring, and speak up if you’re concerned about what that impact will be on you.

Joubin: How do you screen for growth mindset?

Jan: Yeah, sure. And this is actually something that I learned at Medallia because it was part of the value set of the founders of Medallia as well. A huge piece of growth mindset is what happens when you fail? And so we always—and I always ask, much like you’ve been asking me, give me a specific example, tell me an example of when you have encountered adversity. Maybe it’s a deal that you lost, maybe it’s a time when you thought you were going to hit your number and you didn’t.

How do you respond? What did you do? And I look for the details. I look for people who focus on where, this is what happened, but this is what I learned, and this is what I did to get better because of it. Maybe I’m not going to be single-threaded in a deal anymore, I’m going to be multi-threaded. Or maybe I’m going to be aware that I should have qualified that deal out. Things like that are great examples. So, those are things that we look for and we talk about when we assess talent.

Joubin: Do you think that the company values are independent from the characteristics and qualities that you look for in the team?

Jan: No, I think a big reason why I was so intrigued when I met the team at Iterable was that those values aligned with who I see myself as a person and as a leader. I think they’re very much in alignment with how I try to live my life and what I deem is important for me.

Joubin: And the next step that you took was to see if those values was just writing on the wall—literally—or if they actually meant it.

Jan: That’s right. I talked to a lot of people, as you do when you go through any type of executive hire, and try to understand, okay, what’s the real situation here? And constantly had people provide examples of how, yeah, they wouldn’t necessarily say the value itself, but they would be curious and they would be asking for advice on certain situations which show that they had humility. They were looking for a thought partner; they were looking for someone to help solve problems with them, recognizing that they don’t all have the answers. They’d also talk about things that they did to keep themselves balanced, which during the midst of a pandemic is very important. So, it was clear that this was a company that, again, these were not just value statements on the wall, these are things that people thought about and that really represented the people at the company.

Joubin: What is the value of balance? What does that mean? Maybe, how do you interpret that for your team?

Jan: Yeah. I mean, I think—look, we’re all hyper-competitive, particularly in sales; we want to win. And when you do that, and particularly when you have folks who espouse growth mindset, they tend to work really, really hard, and they want to go and go all out all the time. And as you know, you can’t do that. I read today there’s a company Bumble; they’re having the burnout week where they just basically shut down the company for a week just to give people time to recharge.

And Iterable has balanced Fridays. Many other companies have this concept of having a day a month to just recharge. And I think for us, in particularly in this time when there’s no downtime for commuting, there’s no downtime—not as much downtime for socializing. It’s all meeting, meeting, meeting, meeting, you know, Zoom, Zoom, Zoom, Zoom, Zoom. Having that opportunity to be able to recharge, and to really reassess, and come back with a fresh mind and fresh energy for the job at hand is really, really important.

Joubin: Don’t you feel like sometimes it’s almost the hardest in sales to remind ourselves of balance because our input is so correlated to our output. Like, there’s always something more that we could do. Even thinking back to, like, a BDR; you could always make five more phone calls or emails, and if you want to be better, you’re competitive, you want to get to the top of the leaderboard, I think it’s a really tricky one.

Jan: It’s tricky for me personally. I have to work on it consciously because I get up at 4:30 in the morning and I just grind. I have a routine that I get into, and so recognizing that I need to pump the brakes every once a while and really just make sure that I’m not—you know, that I’m fresh and then I’m energized is incredibly important.

Joubin: Any habits that you’ve learned or developed over time to cultivate balance more effectively?

Jan: Yeah, I mean, I can tell you one that I started doing probably three years ago that’s been just revolutionary, which is I journal once a week on Sunday morning. I get up—I have three young kids, so my sacred time is Sunday mornings before the house is stirring. I’ll get up with a big cup of coffee and I just kind of write my reflections, personally and professionally, what’s happened last week, and then come up with my priorities for what I want to go and accomplish in the following week. And I found it just to be incredibly liberating. It gives me a sense of real kind of power and control over what the task is at hand for any given point in time. And something that, for me, has really made a big difference.

Joubin: Is it free form? Are you just writing? What does it look like?

Jan: I have a template in a Google Doc. It’s pretty basic. It’s like a cut-and-paste the week before. And it’s what happened personally, what happened professionally, and then it’s pretty freeform from there. And then I come up with categories of todos, just over time, things that I find helpful in terms of organizing my thoughts and my priorities.

And it’s helpful to go look back at the last week’s todo list. And these are usually big things; they’re not like, take out the trash, it’s big objectives of something that I want to go accomplish. And it’s helpful to go back and reflect and also just realize that I am making progress on the things that are important.

Joubin: And how long do you sit down and write for?

Jan: About an hour.

Joubin: And when you sit down, write, and reflect—to your point—that you’re making progress, does that quell the insecurity of an overachiever?

Jan: For sure. And certainly the anxiety around the end—you know, the being week, it helps with that significantly. So, the Sunday blues, or whatever they call it, that probably is what got me started out and doing it, and it helps with that significantly.

Joubin: Yeah, Sunday scaries. I’ve had a few of those. So, it’s funny, I do that—well, it’s almost embarrassing to say—I do that once a year. And I write down my goals at the beginning of the year, personal, and professional, and then health-related, and then health is bifurcated into mental and physical. And I generally have three or four—no more than that—highly quantifiable goals that I want to get across the line for the year.

The bar is 80%. If I do 100%, the goals weren’t good enough. If I get below 80, then I probably didn’t try hard enough, so that’s where I try and calibrate. And then at the end of the year, I spend many hours just writing down all my thoughts from the year, what I’m proud of. I actually spent a lot of time being positive about the year, like, trying to find the things that I’m actually proud of because I’m so damn tough on myself all the time, rather than talking about where I maybe came short to some of those goals. And then that’s my reset opportunity for the following year. Maybe I should do that 52 more times in a—

Jan: [laugh].

Joubin: —given year and I would be a little bit better.

Jan: Well, it sounds like you have a good process, so—

Joubin: Yeah. Yeah, it’s okay. Okay, so let me read you one more LinkedIn—by the way, I had my pick of the litter with these recommendations, they’re so flattering. I have one more; CEO of DocuSign Dan Springer who you had already mentioned earlier, and he says—I’m going to read his quote, and there’s going to be specific things that I want to pull out of that quote, and I want to get your take on that. Fair?

Jan: Sounds good.

Joubin: Okay. “Jan leverages his disciplined preparation and his very strong business mind in combination with tremendous interpersonal skills to build strong teams and serve customers well. I enjoyed selling with Jan and I’m proud to have been his colleague.” This is the CEO of DocuSign, Dan Springer, right? There’s three things that I want to pull out of that. The first: disciplined preparation. What does he mean by that?

Jan: Yeah, I mean, I think it’s partly what we were just talking about in terms of Sunday journaling. I find that my best performance is always when I know that I’ve kind of put some thought into the task at hand. And I’ve carried that in as a rep and as a manager in terms of making sure that we had an outcome in mind and that we were thinking about, okay, how are we going to go and achieve that outcome in a particular customer interaction? And is a part of the discipline that really, I think, I helped instill in the team at Responsys that helped to see such great success.

Joubin: Okay. Number two, and maybe this one is going to be tough to answer, but he says very strong business mind. How do you think he’s qualifying that?

Jan: That’s incredibly flattering because Dan is one of the most amazing executives, I think, on the planet.

Joubin: Like, do you think he’s saying you can dive in and out at both levels? Like you’re both strategic and tactical?

Jan: Yeah, yeah. I mean, I’m incredibly curious, Joubin, and I think that’s part of what led me down this path of enterprise B2B sales was just, maybe it was the experience in management consulting working with different businesses, but I always enjoy understanding, okay, what is the value of the solution that we’re going to try to sell to this customer, and really understand the full perspective of the context. And so that’s something that I always just naturally have done, and as I’ve been doing this for a while, I’ve realized that you can help your teams incredibly by creating processes, and coaching to ensure that your teams are similarly having that kind of business mindset: not just selling features, not just selling on price, but really trying to understand, okay, how does this work, and why is this a business imperative for the customer?

Joubin: Earlier, I asked you about how do you interview and qualify for a growth mindset. How do you do so for curiosity?

Jan: Yeah, I mean, a big piece is just understanding and giving the candidate an opportunity to ask us about our business. I always do that. I want to see how have they researched us. How are they thinking—are they thinking strategically? I think that’s probably the most simple way to put it, Joubin, is do they have a strategic reason why the company, whether it’s Iterable or whatever other company I’ve been a part of, why this is the job that makes sense for them. And are they interviewing us almost as hard as we are interviewing them to really qualify, is this a company that they can be successful at? That’s what I know I’ve got someone pretty special.

Joubin: And are you particularly keen on understanding their curiosity professionally, or within your organization, or can you take curiosity in something else—if that makes sense—and apply it?

Jan: If you mean like in a hobby, that might be an interesting factor. I certainly want to understand, are they curious about people? Are they trying to understand where what are the different roles of the different people that they’re meeting? How would I interact with this person? Is this someone that I would enjoy working with? Is this someone that would teach me something? That piece of the curiosity for sure applies in addition to, is this a company that’s going to make it?

Joubin: Can I ask you kind of a dumb question? Like, obviously, you think so highly of Dan and Scott; they think highly of you; you’ve had a great run together; you all know what each other can do. They’re the CEO and COO of DocuSign. Company has been on a tear. Why didn’t you go there? There’s no way they did not try and recruit you—

Jan: [laugh].

Joubin: —probably many times over. And you’ve been—since Responsys, it’s been seven years. I don’t know when they joined DocuSign, but what gives?

Jan: Yeah, look, and many of our Responsys colleagues are there now in many different roles, and they’re doing fantastic, and certainly the success that they’ve had is not a surprise, given just the caliber of the people that they are. Look, for me, I was looking for a company in a different stage. I’d been at big companies, and I really enjoyed—what I found was, hey, the run that I enjoyed the most was that run from whether it was Medallia coming in around $100 million and going to $500 million, or whether was 25 to 200 at Responsys, that was what I was really looking for. And so DocuSign, while an amazing place to be, just it’s a different size and scale of a company.

Joubin: Yeah, where. That’s fair. You also earlier mentioned that there’s all these people that you were working with that went on to go—like, this pedigree, this lineage of people that came out of Responsys. We’ve had many of these, I think of them as kind of like, just amazing incubators for talent at these different companies. You know, PTC is one of the shining examples.

At the time, when you’re there—I think of my buddies who are on these sales teams now at Datadog and Atlassian, and—well, Atlassian’s maybe not a good example—but at these companies, when you’re sitting at the table, elbow-to-elbow selling with these people or working for these people, did you have any inkling of what they possessed in terms of talent and capability?

Jan: For sure. And I think, actually, we haven’t talked a lot about Medallia, but that’s—when I met Fougere, who’s the one who ended up convincing me to go join over at Medallia, that was exactly what I saw was, I had heard about the PTC myth in sales, and it’s really not a myth. It’s a process, it’s a mindset, it’s a methodology, and it’s a talent at work that’s just absolutely amazing. And I wanted to be a part of it. I wanted to learn what it was all about.

And so Scott Davis and Dan Fougere at Medallia convinced me to come on and join and it was an amazing opportunity to just see the discipline that they installed in the team, the ability to go and sell what is a pretty complex product that involves lots of different stakeholders. How do you go and systematically go and grow an organization who’s selling that product? I learned a ton from being part of that.

Joubin: Do you feel like you got to step-function better when you went there and dove into the deep end? Because I will say that culture is also pretty notorious for being hardass. Like, it’s tough.

Jan: Totally. Yeah, I mean, step-function is the right way to put it. There are certain things that I felt like I was really skilled at, coming at that point in my career. There were are other areas where I walked in the door and immediately I said, “Wow.” This is another area, like pipeline generation—and I’ve actually carried this forward to our teams today, at Iterable—is celebrating and really just thinking about ways to get everybody in the repeated week-over-week grind of continuing to add to the top of the funnel, and Fougere and Scott Davis were fantastic at doing that and having a fun way to go and celebrate the successes. And of course, I’ve taken that and kind of personalized that along with the culture of the company that I’m at today at Iterable, but that’s a great example of something where I immediately saw something new.

Joubin: Okay, this is a good dovetail into the last recommendation that I’m going to read for you from the SVP of Global Sales at Datadog, Shaunt—is that how you pronounce his name?

Jan: Uh-huh.

Joubin: And I assume you met him at Medallia? Is that right?

Jan: No, actually, Shaunt, I hired at Oracle, post-Responsys. Yeah.

Joubin: Small world because he went to go, I guess, work for Fougere at Datadog.

Jan: Funny how that works.

Joubin: Yeah, exactly. Small Valley; reputation is everything. “Jan is one of the most effective sales leaders I’ve ever worked for. He’s so unique, et cetera. He’s incredibly smart. However, his coaching, both deal and people, is unparalleled, and he has a tremendous eye for talent.” So, those are the two things that I want to talk about. One, what does he mean, when he says coaching, both deal and people, is unparalleled?

Jan: Yeah, I mean, look, Shaunt was and remains a great friend like many of the folks that I’ve had the privilege of working with over the years, and I think, one of the things that when you’re in the trenches together, and when you’re trying to grow a business, or in trying to scale a team, there’s always obstacles. And so that’s something that, I try to be available, I try to be thoughtful, I try to listen, I try to provide a point of view based on my experiences, and that’s something that I’ve really worked at and also really leaned on in the places that I’ve been.

Joubin: And when he says tremendous eye for talent, what I was asking myself, is he’s saying that he’s excellent at recruiting known talent, or is he saying that he actually has a refined eye for undiscovered talent?

Jan: I’d say both are things that I work on. I think recruiting as you are in sales leadership, it’s probably one of the most important things that you do. I actually learned from the other Scott, Scott Olrich, earlier in our time together at Responsys. I think he found one of our top performers on an airplane; he met another one literally at some hotel, playing pool. Like, he always had an eye for, hey, who is someone that I can talk to that potentially could have a role that could go help us?

Having that curiosity and that always being thinking about, okay, how do we go find fantastic people? They may not have the skill set that we need today, but we can go get them into the company and help them become the future stars of tomorrow. That’s something that is part of who I am today.

Joubin: Do you think there’s anything more important that you do than recruiting talent?

Jan: I’d say there’s two pieces. One is recruiting talent, continually, as you scale out, the second piece is really operating cross-functionally with the rest of the leadership team, to be able to remove the obstacles and also to be able to be that feedback loop from the marketplace on what we’re seeing, and what obstacles either we’re presented with today, or we may see in the future. So, I’d say it’s those two things is being able to effectively work as part of the first team of the leadership team as well as being able to recruit, and build, and find great people.

Joubin: Do you think you’ve developed as a collaborator amongst leadership teams? I always didn’t think enough about this and I probably sucked for a really long time. Actually, if you ask my peers today, they’d still probably say I suck.

Jan: [laugh].

Joubin: Do you feel like you’ve gotten better over time, and it’s something that you’ve come to appreciate more?

Jan: Oh, yeah. I mean, of course. It’s something that the only way you can get good at it is continue to work at it and truly understand that different people, and particularly people in different functions will have different needs and different responsibilities. They see the world very differently, and so being exposed to that, and probably early in my career, I was a hard-charging sales leader who would come in and say, “The sky is falling and I need X, Y, and Z, and we need to go do it now.” I’ve learned how to take other approaches that may be more effective.

Joubin: Okay, I have a couple more questions than I think I got to let you run, unfortunately. Earlier we talked about, like, you’re just Iterable in the space, it is red hot; it’s a good space to be in right now. All boats are rising with the tide. My understanding—correct me if I’m wrong—is that one of the differentiators around the way that Iterable goes to market is its enterprise-focused orientation. So, your ASP is 100k plus, it’s upmarket from other competitors. It’s mostly top-down. Is that right?

Jan: We have three segments of our business, Joubin. We have an SMB segment, we have a mid-market segment, and we have an enterprise segment. I’d say it’s certainly true in enterprise, we’re going after larger types of brands that there’s an education process that needs to happen. The solution that we sell, it’s pretty radical. I mean, it’s built on the public cloud, it consumes and uses data in real time, it’s API first.

The legacy solutions that we displace, it’s a different paradigm for those users of those platforms, and in fact, in many times, they’re surprised about the fact that something like Iterable exists. So, in the top end of the market, I would say it’s very much a top-down approach, we certainly do have some digital-native companies like DoorDash, for instance, where they get it because they were architected as a modern type of company. In our SMB space, I would say it’s actually more of the bottoms-up. We have about 850 customers today, growing really rapidly, and we have tremendous [unintelligible 00:42:11] and a lot of referrals, we have a fantastic partner ecosystem of both technology and services companies that recommend us to their customers. And so, we see a lot of our lead flow come from folks who’ve heard of us and are interested in hearing more.

Joubin: Thank you for clarifying that; I did a good job butchering it. One of our portfolio companies is in a probably equally hot space right now, and the CEO, always past 9 p.m., texts me and—

Jan: [laugh].

Joubin: —probably a few times a week and is complaining, or just he’s really hopped up on how there’s such a convergence of everything in the space because it’s so hot, right? So, the pitch starts to sound the same; the website start to look the same; customers start to get confused with what’s actually what. Products, features, functionalities, speeds and feeds all start to converge, and the customer or the competitors started undercutting us on price. And he says, “What do we do? How do we get rid of the FUD? How do we make sure that we’re beating them?”

And my perspective—and I’m really curious to hear yours—is like, it’s you against you right now. This market is so bi, that there’s going to be a lot more people that come in here as well. And if you’re constantly—you, as the leader—are distracted with all of the other people, you’re not focused on your own four walls, and hiring great talent, and continuing to innovate on the product. And if you lose your focus to go worry about all the other guys, then you’re not going to move your own business forward. How do you think about it?

Jan: Yeah, I think we’re aligned there. I mean, there was a report that came out this morning that there’s, in our core category, like, one of the categories that we get considered in his email marketing, email service providers, there’s something like 68 vendors.

Joubin: [laugh].

Jan: Which wouldn’t be a surprise because that was—when I was at Responsys in the early days, there were something like 68 vendors at that time, too. There’s everything from MailChimp through Salesforce and Adobe, and everything in between. And then you add in mobile marketing, and then you add in the data component of it, well it becomes even much bigger and more complicated. I believe, and it sounds like you do as well, ultimately, it comes down to the experience you provide your customers in terms of being able to educate them and help them navigate through all that noise. That’s what’s most important.

That plus having a product that has true differentiation. So, you need to know what that differentiation is and you need to know what the value is of that differentiation to the customer. That’s something we talked about PTC. That’s something that PTC really talks a lot about in their sales methodology and that school sales leaders talks about is really understanding where, how do you understand what you do that is different from anyone else that you can go and prove with, actually, hard evidence, and also that has value, making sure that everybody is on the same page about that, and understanding it. And it will change because your competitors will copy you, as you mentioned, so you need to constantly be evolving on what is that unique differentiation and then building a team that can go and qualify for customers that would benefit from that unique differentiation. That’s how you differentiate at the end of the day.

Joubin: So, how much time are you spending educating your team on enablement?

Jan: Yeah, I mean, a ton of time. We demo certify every single, actually every single employee, but every single member of the sales team is able to do a demo of the product. That’s incredibly important so they have that foundational knowledge. And then we have an enablement team that is continually working on specific initiatives around either a specific part of the market where we want to be more articulate about how to compete in that part of the market or a specific value proposition that we want to go and make sure that we’re talking about and qualifying for early in the sales process. So, it’s something that we are just continually trying to make sure that we can—because your top performers, they’re going to figure it out, but to scale and to get that consistency, particularly as you bring new people in the business, you need to make sure that foundational knowledge is there for everybody.

Joubin: Thank you. I appreciate your time. This was awesome. I always wrap up the same way; two questions. The first, what does the word grit mean to you?

Jan: Grit to me is running into a wall, falling down, picking yourself up, and brushing yourself off, reflecting on what actually happened, and figuring out how do you avoid that situation again, and just continuing to be laser-focused on that goal that is ahead, whether that’s building a company, whether that’s getting in the next job, whether that’s hitting your number, wherever that goal is, making sure that you keep that in mind, and don’t let anything stop you.

Joubin: That’s a great answer. If someone wants to be a part of the next phase of growth with you and Iterable, are you hiring? And if so, what’s the best way to get a hold of you?

Jan: Yeah, come join us. We’re hiring across the board. We need great people. So, find me onLinkedIn, and we’d love to meet.

Joubin: Thanks for the time, Jan.

Jan: Thanks, Joubin. Great to talk to you.

Joubin: That’s it. Thanks for listening. If you’re just discovering the podcast, we have a lot more episodes with CROs from organizations like Snowflake, Twilio, Slack, LinkedIn, Box, et cetera. If you want to keep up or support the show, the best way to do so is by following us on Spotify, subscribing on Apple, and leaving a review. Thanks. Talk soon.

Interested in working with leaders like Jan? Join our growing sales team! View and apply to open roles on Iterable’s careers page

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