Joining Sprinklr

Alex Kracov: So you sent a cold email that changed your life and led you to join Sprinklr as the first sales hire. Why did you want to join Sprinklr, and do you remember what caught the founder's attention?

Jason Fishkind: Yeah, so, it's actually a funny story. I was in the printing industry for a number of years. Actually, I met a girl, and I realized she was quite expensive. She had expensive tastes. I said, you know what? I think I need to earn a bit more money than I had been.

I was in sales. My dad was in sales, actually. He had a whole list of recruiters. He gave me the list, and he said, hey, Jason. Why don't you call some of these folks? I was calling these recruiters. They all said, hey, Jason. You don't make enough money for me to qualify for the jobs that you want. I was like, oh, okay. So I went back to one guy and I said: well, what do you suggest I get myself into so that my next call is to you, and I qualify for it? He says big data something, something or social. I was like, oh, okay. He goes, you know what? I liked your question. Let me get you an interview with a company called Hearsay Social, which was run by Clara Shih. She's now a part of Salesforce, which is a whole story in itself. He goes, you know what? He tried to give me the interview. I never have had an interview. I was doing a bunch of research. I came across Sprinklr. I was like, huh, this sounds like an interesting company. I found one or two small articles or videos where they were looked at. I said, you know what? Let me cold email the CEO. That was a simple, simple short message. The subject line was: your next top sales athlete. If you're looking for your next top sales athlete, your search has ended... I put my little background in there. Three weeks later, I got an email back. Two weeks after that, it changed my life. I started. That was it.

Alex Kracov: And what was Sprinklr like when you joined? Was there revenue? How big was the team? Was there a working product? How early was it?

Jason Fishkind: Yeah, I mean, there was definitely a working product. They have been hacking at this thing for a while. Ragy bootstrapped the company himself. They had just taken Series A. 5 million ARR, $25 million valuation. He had bootstrapped himself. So they were going for a bit. He did all the initial deals himself. First handful of deals, like Nike, or Microsoft, or Intel, or Cisco. But yeah, it was on 13th Street, Manhattan. The office was disgusting. It had these green and red IKEA desks. It looks like Christmas threw up all over that place. And it's funny. Because I worked for this Fortune 200 printing company, and the CEO of that company was on my form, prior life. I used to wear a suit and tie every day. My boss at the time would be like, "Did you shave today?" I started trying to dress down. But I was walking to this office, and everyone there was - it was a small little tech company. They're wearing shorts and a T-shirt. They didn't like that too much. But yeah, it was interesting, for sure.

Alex Kracov: It's so funny, the difference of corporate culture versus startup culture. I remember growing up, my dad who's a corporate lawyer, the whole time, he would be like, "You're going to have to shave your beard. You're going to have to dress nicely and go to work." It's funny being in a startup where I can just be a gremlin and wear sweatshirts and as long of a beard I want. It's like a badge of honor to do that. So it's so funny how different of a culture is that.

Jason Fishkind: Hell yeah. It took me a while to get used to just being okay. There was a ping-pong table, whatever, all the typical things. But dressing down was a new one for me.

Early Sales at Sprinklr

Alex Kracov: I'd love to learn more about what early sales looked like at Sprinklr. Because, as you said, you're going from seed to series A. Ragy, the founder, was doing all the sales himself. And so what was that transition like from founder-led sales to you starting to do sales? Were you partnering with him on every call? Were you just running your own book of business? Can you take us back to those early days?

Jason Fishkind: Yeah, it was great. I started, and a few handful other folks started very shortly thereafter. They had hired a VP of sales that effectively started running around when I did. Ragy was phenomenal. Working next to him was like getting an MBA by osmosis just watching. I think I was 27. It was one of those where I wish I had more experience at the time just to really understood what I was soaking in. Hindsight, it's always 2020. But yeah, he was great. He just said, hey, go for it. They weren't really worried about me calling on the existing accounts, so it was just, go after net new. Go land logos and go figure it out. It's effective what we did. We tried to figure out what worked, what didn't work. And we did our best.

Alex Kracov: And social was like this new thing at the time, right? What year was that? Because I assume social media management wasn't really an existing category. What was the state of that market?

Jason Fishkind: Totally. This was 2012. This was Memorial Day of 2012 around then. This was legitimately when there was always the joke of like, oh, the interns running social. It wasn't really a joke. That was really what was taking place. What was actually fascinating about it was, especially, as time went on a little bit, you get into these rooms, and you get into these meetings with big Fortune 100, Fortune 500 brands. You'd literally have the intern or first year, first job out of college first year, and you'd have the social so real time in nature. You'd have the CEO in the room at the same time. It was pretty wild. But we just made it up as we went. We were trying to find - we certainly had some product-market fit with the big companies, but we were trying to now bring this to market. There was no brand. No one knew who we were, so we spent a lot of time trying to just get our name out there.

Alex Kracov: It seems like you started with, definitely, as you said, bigger companies. I'd love to know what was that early pitch. Was there a lot of education? Did you have to teach people about social and then teach them about social media management? How did you convince people that this was a problem that they needed to solve?

Jason Fishkind: Yeah, so I looked at it - it's a good question. I looked at it as binary. At first, you start just trying to figure it out. Just trial the pitch, try different things. But after a little bit, you start to realize there was two conversations. There was the why Sprinklr conversation or the why social conversation. At that point, the whole entire world was greenfield. Every account doesn't have this. So if I have to go evangelize why social, like why anything period, probably not a great use of my time. So I really spent my time trying to figure out where are folks doing this, where there's some sophistication strategy, or there's more than a handful of people that are even thinking about social media within an organization. That's where I went and spent my time, in the why Sprinklr phase.

Alex Kracov: And what did that early product actually do?

Jason Fishkind: In today's world, it's actually not that fundamentally different from what Sprinklr's core product is, which was just social media management. If you put social into three buckets - organic or own social, earned, and paid. It was all things on social media. It was before Facebook built the walled garden. None of that existed, right? It was people. We would go explain it. Actually, it was one of those where we'd go to these trade shows.

I used to explain to people. Because a lot of us frankly did was helping people post things on social media, give them the automation to do that. There was permissions and calendars and monitoring and reporting. But I would explain to people. It's like the pipes in plumbing for how you operate social media for a big brand. Some understood it. Some certainly didn't. But we were really competing against the time, like Radian6 which did some listening, which was bought by Salesforce not long after I joined. It was competing at Buddy Media, if you remember 'sapplets' was a thing or these things on Facebook, and then HootSuite. So I would go to these trade shows. And people would go, oh, so you're like HootSuite? Im like, sort of. Are you like Buddy Media? Sort of. I'd say I don't know. We are Radian6 plus Buddy Media, plus HootSuite, all in one with reporting and governance. They'd go, oh, okay. Interesting.

Alex Kracov: Why do you think it resonated more with enterprise buyers versus SMB? Why did you deliberately go after that more up market segment? Was it just the contract sizes are more appealing, and that was kind of the answer? Do they feel the pain more?

Jason Fishkind: I think in Ragy's world, he saw this as - he was in the email space before. I think he saw this as an enterprise problem in that most companies would start with the SMB or start small. He's like, this social is really complex. Social media is not just one channel like email. It's many channels. It's Facebook, and Twitter, and then it's Instagram. What else? Instagram, and Tik Tok, and Reddit. And there's dozens, right? You think he realized the complexity of this. The real need was going to be for at scale when these big companies start to really get into this, they're going to need something that's purpose built for the large enterprise. And 1,000%, his vision was spot on and accurate. The dude was very much correct.

Alex Kracov: And you're telling me about how John McMahon was on the board of Sprinklr in the early days. He's an absolute sales legend. Can you share the story?

Jason Fishkind: Yeah, so McMahon was on the board or as an advisor to Sprinklr. I forget which one. I remember we were at this - I had sold print before. So I'm like two months into my software sales career. We're at this offsite in Westchester, in this place, this conference center, time forgot. It's like this wood-paneled place from the '80s. The entire Sprinklr US-based team, sales team basically. There's 25 of us. Everyone that was in the U.S. was there. McMahon starts training everyone on MEDDPICC. I remember he's a tall guy. He's imposing big energy. I remember him just walking over stalking a big U-shaped room. I remember him stalking over to me and saying oh, well, what's E? I remember saying economic buyer. He asked me a couple of follow-ups or whatever it was, and I didn't have the answer. Then he came back to me again. He was like, so what's the answer now? I remember I just blacked out, still to this day. That moment gives me agida. Like, Oh, God. Please never bring me back in that scenario again, though I've definitely had plenty of conversations with him afterwards in the years following.

Alex Kracov: Yeah, I've never met him myself, but I listened to him on some YouTube, and podcasts and stuff. There's a certain level of intensity about that guy, where I'm like, oh, wow. You must have been really hardcore to work for. I see why he's so successful as a sales leader.

Jason Fishkind: And he's getting more chill now. Actually, it's funny. McMahon was on our board. Then we were pretty early with force management, with John Kaplan. Actually, the fortunate thing. I messaged him twice. Being able to, it's like I don't know. A fun little fact that those are two big names in our world and our space. But learning what they do and what they've brought to bear to the market from them directly is a cool little thing to say.

Alex Kracov: And so you spent over five years closing new business at Sprinklr, and you're a top 10 AE in company history. What made you so successful as an AE, and why did customers buy from you?

Jason Fishkind: I think it's really two key things. One, it's all that champion building. I realized that early. We used to have a stat at Sprinklr, something along the lines of, like, more than half the people that lead the person of Sprinklr were promoted within 12 months. To me, it's always identifying a personal win for somebody, whether it's to make their job easier, or, hey, they're seeking recognition or their career advancement or some combination of all the three. Building champions is everything.

I think the reason that folks bought from for me is, I'm always really proud of I always sold the right deal. I was always like the top dog on the scoreboard. Probably not, actually. A lot of folks, a lot of colleagues who are tremendous sales professionals just absolutely blew their numbers out of the water. I don't know if they always sold the right deal. What I was very proud of this, I think I did 50 or 60 logos in my five years. And nearly, all of them were still clients when I left, even five years after that. I was never about the short-term when putting money in my pocket. It was more about, how do I go sell the right deal? How do I go solve the right problem for the customer that they're trying to solve now prove value? Then in 6, 12, 18 months, they're growing with us and expanding versus trying to resell and save the thing that we oversold.

Alex Kracov: Who was the champion at Sprinklr? Was it a social media manager? Was it a VP of marketing? Did it change depending on who you're talking to? As you're trying to set meetings with people and find champions at companies, who were you reaching out to?

Jason Fishkind: I mean, in the early days, the title of social doesn't even exist. Sometimes. Sometimes not. So yeah, many times, it was a VP of marketing. It was probably the most common title. Then certainly, as time went on, it was a director of social because most of them didn't have VP titles. Then as organizations became really hip to it and really understanding the power of social, it certainly morphed over time. The other would be, as time went on, it was someone in care. So we'd get into these meetings. Oftentimes, remember early days especially, it would morph. Like the social marketing folks and care. The social won the first time. Those two groups were brought together, and they needed to do something instantaneous. That's actually a lot of what drove Sprinklr in its release.

Alex Kracov: Got you. When you say care, it's like people writing on social for customer support requests and things like that. Then you got to figure out, okay, how do I actually follow up with this customer? Because there's a whole new channel you got to manage outside of just like your email support thing.

Jason Fishkind: Totally. That's exactly it. But marketing own those channels. Marketing own it. They're like, oh, I got to solve this. How do I get this? I have to take a screenshot, drop an email, send it to customer support. Then it kind of goes back. This could ping pong back and forth, as opposed to saying, let me just do this in the system. That's where we would explain a lot of the pipes and plumbing analogies. That's where it really started to connect for people. That was really the first key use case that we found huge utility in. I wasn't expecting that per se, but it was big.

Alex Kracov: How were you able to get on the same side as your champion and not come across as sale-sy or trying to sell them something? How were you able to understand their problems? Were you building roadmaps with them? What were you doing with them that made you such a trusted partner?

Jason Fishkind: I've been in a leadership role now for a handful of years, and I think it goes to the same thing that I look for in the folks that I recruit. The number one trait, I think, is curiosity. So if you're in the room with somebody, and you're just trying to throw features and functions at them, I don't think that holds water. But I think if you have some natural curiosity, and you ask the right questions, and you genuinely show genuine care for the problem they're seeking to solve and, more importantly, why and with what benefit or outcome, I think that drives a lot of that relationship and for why some of these folks will go run through a wall to go get things done on behalf of the sales professionals that work with you.

Transitioning from AE to Management

Alex Kracov: You eventually became a sales leader at Sprinklr. I'd love to know what was the hardest part of that transition from AE to manager.

Jason Fishkind: The SVP at the time that was a couple that was above me promoted me. He said, Jason. He goes, you're going to be the sales leader. But you're not really going to be the leader. You'll just be the manager. He's like, you'll see. It'll take you a bit, it will take you a little while to learn how to lead properly. For now, you'll just manage the number more than anything. I was fortunate that I was already the de facto, like go-to, for my peers. I see a lot of folks who get promoted for the first time, and now they're responsible for their peers. That's a challenge. But I was fortunate that that wasn't a challenge for me.

I'll tell you one funny story about first-time leader. I'm being a first-time leader. I was that energy. Definitely, no one will ever accuse me of not having energy. I remember, on Sunday nights, I've never gotten the Sunday scaries. But Sunday nights, it's in this recap email. Hey, here's the recap from the prior week. Here's a look at the week ahead. One Sunday night, I'm sending an email, and I hit send. I call it 9:50 Eastern on this note. I walk in. This was pre-COVID. I walk back into the office. My whole team is there for the Monday morning meeting. And one guy, he looks at me. He goes, Jason. He goes, do you watch Game of Thrones? This was the height of it. I go, no. He goes, well, you sent an email in the last 10 minutes of the series finale of Game of Thrones. He's like, this guy better have something important to say, or I'm going to kill. So I was like, you know what? I learned my lesson, and I definitely do not do that anymore. The send-it-later button or Slack later button is my best friend.

IPO Day at Sprinklr

Alex Kracov: Yeah, that's funny. I'm not the biggest sports fan. I like sports, probably not the biggest. And so there's some times I'm doing what are called big sports things. I'm like, I maybe shouldn't send this email during the World Series. People probably care more about that than whatever thing I'd be emailing them. Yeah, it was funny. Sprinklr had insane growth over the 10 years. You're going from like 5 million in revenue to 500 million plus, and the company went public in June 2021. What was IPO day like for you?

Jason Fishkind: That was a day - I mean, you work with leaders over time. They talk about, oh, we're going to IPO, right? You just kept sensing what's going to happen and always wanted to do it. It's like a dream, right? It's just out there. I remember we finally follow the s one. We were so excited. This was the middle of COVID, right? So we were really fortunate. It happened to be when we follow the s one and when it was set to IPO, the New York Stock Exchange lifted their protocol. They finally let people back on the floor. We were the first IPO, post-COVID, allowed back on the floor. So to New York City and through a huge part. It was great. I was on the floor ringing the bell with Jim Cramer right behind us. That was a day I will certainly always remember. It's what you join early-stage companies for. I would imagine liquidity that is probably fun in any respect. But the ability to be on the floor at the stock exchange and hear the bell rang, and cheer and chant, and seeing all those years later was just freaking awesome.

Alex Kracov: You spent so much time growing up at a startup. Looking at that iconic image of the stock exchange, you're just like, one day. One day. I can't imagine. I think about that with Lattice. No longer there. But I'm like, Lattice, knock on wood, is going to IPO someday. I'm just hoping I get invited to a sub-party around the New York Stock Exchange. That's my goal, yeah.

Jason Fishkind: I felt very fortunate to be a part of that.

Alex Kracov: What was this journey like for you on a personal level? It must have been crazy trying to go - you went through probably so many iterations of the company, so many different people, and the company changed so much. How were you able to keep up with this company growth curve and survive for 10 years there?

Jason Fishkind: I think it's a couple of things. One, it was rewarding in every sense, be it personally, professionally, financially. The company was always great to me. I got married. I had both my boys while working there. I went through sickness while I was working in the company. It was always great to me, provided me the opportunities to sell to the biggest companies in the world, travel the globe. Then certainly, to go through a liquidity event like an IPO helped set me up financially. So I felt really fortunate.

I think the biggest thing over that anyone thinking about having a big run in a company, or do I leave, or all those things that go through your mind, I think there's a few things. One, I used to say there's two constants. One is speed. The other is change. That's a definite constant at any high-growth company. You've got to have the growth mindset and just be open to challenges and open to learn. If you're not okay being humbled constantly, get knocked down, pick your ass up, just go figure it out. I think it's really, really critical. Then the other part is like I stayed for a long time. I remember having lots of colleagues who, they got off the bus early. They were like, "Oh, I found this opportunity. It sounded really interesting," and then it didn't work out after a year or two years. Then I'd see a bunch of folks, they're on job two or job three a couple years later. They were trying to constantly recreate this special thing we have with the people, the technology, the timing. It's just so hard to recreate. I'm filling the oil. So all of those things made for me sticking around for as long as I did.

Alex Kracov: Yeah, it's like there's only so many of these special companies out there that are going to grow that fast and change that much. It's like when you sort of have that seat on the rocket ship, you better strap yourself in and stay there as long as you can. I sort of felt like that at Lattice, where I was like, this is my chance. I didn't last 10 years. I lasted five because I want to go start a company. But it was still a really hard decision to leave because it was like, this feels special. I know this isn't going to just happen again at any other company.

Jason Fishkind: Yeah, for sure.

Alex Kracov: I'm curious, do you have advice for other people who want to go join a high-growth company, or maybe they're already? How can they navigate all the change that happens with the company, and not only navigate it but thrive in that natural chaos?

Jason Fishkind: Yeah, as what I said before, it's like the simplest thing is mindset. Just to use that term, mindset is everything. If you're not comfortable in that environment, it's not for you. And that's okay. In that environment, you can't wait around for people to do just things for you. I like the Extreme Ownership book from Jocko. You've read that? In small, small companies you have to have that mindset of extreme ownership and drive to completion, especially in small companies. The mindset of learning is a huge one. I always also had opportunities. I felt that when I wasn't learning, me being bored is a dangerous thing. Constantly go seek to challenge yourself within your current role, and just keep looking for the next challenge and the next challenge within the company. If it's something that you want to keep continue to do and that you can earn, you can go find great opportunity for yourself.

Leading Sales at People.ai

Alex Kracov: After Sprinklr, you went and joined People.ai to lead their East Coast sales team. For those that aren't familiar, can you give a quick explanation of People.ai?

Jason Fishkind: Yeah, sure. So People.ai is a revenue intelligence technology that allowed go-to-market teams to win more revenue through improving pipeline execution. It did things like activity capture, so you'd have a factual understanding of what was taking place in an account or an opportunity, or by AE. Then the data can be used by leaders to coach reps in deals or do territory segmentation. Then some folks may be familiar with the name 'close plan,' which was part of people AI. Things like account plans or relationship maps and opportunity scorecards, all those things helped me help sales teams somewhere.

Alex Kracov: Got you. And what was this transition like for you? It must have been hard or at least weird. After being at the same company for so long, you have to go join an already existing startup. What was that transition like for you personally?

Jason Fishkind: Yeah, there's one thing I said before. I'm never without energy, right? So, for me, I was so energized to just go build again. I wanted to go build again. You think you'll learn a lot over 10 years, but you're never quite sure until you go try and apply. I was super excited about that.

Then I think the biggest thing is, most things in life come down to expectations. I knew what I was getting into, and I was ready to go build. The transition was great. It was just refreshing to go be at a small, nimble company again and dive right in. Quite frankly, the fact that it was in the sales tech space, to anyone in sales, especially in a leadership capacity, it's second nature. The value prop and the talk track was super easy for me to pick up. Quite frankly, I was on customer calls in the first few days because it was very natural.

Alex Kracov: How big was the company when you joined? What was the state of the sales team?

Jason Fishkind: The company was about 300 people or so. Sales team, the company was growing really tremendously. This was just before some of the world fell apart again. So it was definitely interesting. Yeah, the company was great.

Alex Kracov: And so you hired nine AEs in six months at People.ai. How did you approach your AE hiring, and what did you look for when you're hiring AEs?

Jason Fishkind: If there's one thing from this conversation, Alex, it's probably mindset and curiosity. I'm a big believer that there's a handful of fundamental things that just cannot be taught. Natural curiosity. Put anyone in the room. And if you have just the internal inertia and desire to go ask smart questions and understand what's being said in the room, and go seek for the second, third and fourth, you're always trying to get a business pain or getting to know somebody or what have you. But curiosity goes a long, long way. Then mindset of wanting to learn, trying to figure out how you go solution and to challenge yourself, all those things I think are just intangibles that can't be taught. I think it's those two things you combine, like an IQ with an EQ mix. It can't be taught. You can teach experience. I can teach you sales process or what have you. But the other things are so critically important. Those are, to me, the two absolute requirements in folks that I talk to.

Alex Kracov: Are there specific interview questions or situations you put people through in an interview process to test for curiosity? How do you actually do that?

Jason Fishkind: Yeah, my favorite question these days is, for curiosity, tell me something that you taught yourself in the last six months, and tell me how you did it. People would go, personal or professional? I'd go, I don't know. Pick one. You'd get some really interesting ones. One person the other day told me they wanted to get better actually at asking questions. He's like, I started a podcast. I was like, tell me more about that. How did you go do it? For me, you also got to know people just to understand what they talk about. But you can start to get an understanding of, is this person really a naturally curious individual and how do they go plot it for themselves?

Alex Kracov: I guess, why is curiosity so important for sales? Is it just because in qualification, you just have to ask deep questions and keep asking, and then you can put that back on the prospect? Why is that the single most important thing?

Jason Fishkind: It's a good question. I think that you can teach someone to go ask the right handful of questions in the deal. You got on the first call. We're going to do discovery. Mr. Customer, Mr. Prospect, I've got my list of my top 10 discovery questions. Fine. The thing is, when the customer gives you that first answer, the ability to not just say, you know what? Let me go from number one to number two. Let me go dig in on that, and go ask the next question. Go and ask the next natural question on that line to keep getting it, whether it's business pain, or why that person cares, or what have you. But the ability to keep asking questions on that initial one, that weren't planned. But that's just something that is very hard to teach. That's what's really intriguing about that as a quality for me.

Alex Kracov: I think it's also really hard to teach that coming across as authentic as you ask those questions. Like you're genuinely curious about the problem that they experience and how they're dealing with it today, as opposed to like, hey, I'm just reading my questions off of my notes tab. That authenticity just comes across in people's voices and the way that they ask and talk. It's super interesting. I'm interviewing a bunch of sales reps right now, so this is a very top of mind.

Jason Fishkind: Of course.

Alex Kracov: How did you earn trust with the People.ai team? Because I'm sure there was already a sales team. You're the new leader being brought in. How did you earn trust, and how would you describe your own leadership style?

Jason Fishkind: I think there's a handful of things. It's a critical question. Whether I did this at Sprinklr, or People.ai, or where I am currently, I think it's a handful five key pillars for me. I talked about myself that my biggest strength is also maybe my biggest weakness. That's empathy. I think it goes into number two which is, everyone is different. And act accordingly. Understanding how the team, what they individually care about, what their strengths or weaknesses are, what their situation is like at home, or with family, or what have you, how to have empathy towards that situation, and how to treat and work with and help develop the person professionally, all those folks in a way that makes sense for them, I think, is really critical.

I think number three is trust and accountability. Often used quote, trust is hard to earn. Easy to loose. I think it goes both ways. My goal is to earn trust. It allows you then to have a challenging conversation from time to time and hold each other accountable. But I think those conversations only go well when there's mutual trust and respect between the two people having them. For this, I typically tell the folks that I work with that I'm not going to ask you to do anything I wouldn't do myself. I find that to be disingenuous.

The fifth is, I try my best to be consistent. I try to be a four-to-six guy. I definitely have energy. I can get excited. I can get upset, what have you. But almost all the time, we've probably all worked for someone before. Maybe you have, Alex, worked with somebody that you give them good news, and they're over the moon. And you've given them bad news, and it's like someone just killed their cat. It's like they're just so on either side of it. It's unsettling, right? It's uncomfortable when that happens. So I really try to be as consistent as possible with my approach. Good news is good. Bad news is, okay, fine. Celebrate things, but you try to be consistent in approach. I think those have always served me as good pillars in how I work with a team.

Alex Kracov: I'm curious, do you feel like you mold your management or leadership style to the person who you're managing? Are you fairly consistent? Do you treat everyone equally the same? Or do you, I don't know, mirror back what they're sharing with you? How do you think about each person's unique quirks as you work with them?

Jason Fishkind: I think there needs to be some level of consistency. Just because there's not a time of the day to go be full-fledged individual to everybody. But being able to have an individual touch of, hey, I know this person. For instance, this person, his or her strength is in how they communicate, but they struggle with deck building. You know what I mean? Or, another person, they struggle to ask the tough question of a customer. Another one struggles with this, or this one has something's happening at home. Their family member is whatever. How I work with these individuals and how my day to day with them in those interactions, I really try and vary and, honestly, acquiesce. I adjust accordingly. But I do try to keep a level of consistency so that there's clear expectations and accountability on both sides.

Alex Kracov: I guess it goes back to your - I think the first leadership principle you mentioned was empathy and meeting people where they're at and understanding what they're going through, and then molding your style on how you work with them.

Jason Fishkind: Totally, yeah.

Sales Process

Alex Kracov: Switching gears a little bit to sales process, you wrote a great article about the messy middle. The messy middle is where deals are won and lost. Can you talk a little bit about what is the messy middle, why is that such a critical stage? How do you recommend people overcome it?

Jason Fishkind: Yeah, so the messy middle happened - I mean, quite frankly, the problem that people I solve. I just thought it was a great way to think about it. Because I genuinely think it's where deals are won and lost. It's the middle. People.ai is a great go-to-market tech, and it sits in an undefined space. That's a very crowded space, right? Lots of players in the go-to-market space. So there's Salesloft and Outreach. They do some outbound prospecting and high-volume sequencing. It's like the first 10% of the sales cycle. Then call the last 10% as the boost up to the world. I need to forecast my mind if I do to closure and forecasts my deal. But there's this middle 80%, these messy middles, I think, where the deals are won and lost.

For the AE, that's developing strategic account plans or relationship maps. Or, I got to do MEDDPICC, or band, or film, or my opportunity scorecard. Then for the leader, it's, how do I get an understanding of what's going on in the account and a factual set of data of what's taking place? All those things in the middle and how you coach against that, all those things in the middle, that's pipeline execution. That's the middle 80% of the deal. That's where deals are won and lost. That's all pipeline execution. That's the messy middle.

Alex Kracov: It's interesting. I think it's definitely some of the things we're trying to solve now at Dock. Because everyone has their classic opportunity stages. That's how you forecast and get a sense as a leader. These are the stages of my dealing where so much happens in between those stages. Whatever you call it, verbal qualification or whatever, there's so much process that goes there. And so much is hidden from a sales leader's view of what's getting sent to the client. How are we collaborating? Have we done security reviews? Have we done legal? How many product evaluations do we have? The list goes on and on and on. There's such a challenge when it comes to both. How do you standardize that process for the sales rep? But then also, how do you give the leadership team visibility into what's actually going on here that's sort of beyond just the stages in the CRM? It's an interesting problem.

Jason Fishkind: To your point, some of those things, the annual paper process and something like, hey, I got to move my deal, and I got to get it done on time on the forecast. You can actually go back to the beginning and go, hey, did we actually do the right level of research? Did we map the right place in the org to figure out that we get the power? Are we more of just a coach? What does that role look like? All of those things really make a big difference at the end of the cycle. It was done in the beginning. That's where I think deals are won and lost.

Alex Kracov: Do you believe in mutual action plans? Do you introduce those in the beginning? Does that help this process at all, or do you find buyers don't actually want to use them?

Jason Fishkind: Well, I think that's the key word. It's mutual. In the mutual action plan, I think sales reps can put them together all day long. But if they're not mutual in nature, it's just your list of to-dos that the customer is not necessarily buying into. So I think that's key. It's, you need your champion bought in.

I think the other element is, especially I think if you're selling in IT space, it's one thing. But if you're selling to a line of business, not IT, especially in a large company, most times, the sales rep has more experience in how to procure technology around some of the gotchas that happened in a large deal cycle than the personnel in the other line. Now, many times the person in the line doesn't want to admit that they don't know the answer. They don't want to tell you they don't know. Or, they'll probably just tell you the answer they think you want to hear, which happened more times than not. Not because of anything malicious. They probably mean well. They just don't know. Thinking about how you position and frame that mutual action plan and think through all the elements and help guide that is really critical to getting a deal across the line with the deal closure.

Alex Kracov: I found the worst mutual action plan is the ones where it's all just the selfish steps. It's like, let's do legal review. Let's do security review. Let's close the contract. And that's where it ends. It's like, it's got to be anchored around the customer's problem. That you uncover it at the beginning. Like, okay, here's the roadmap of how we're going to solve your problem, not the roadmap of how we're going to close the deal and get my commission. It's like, you got to change the framing of it. That's when it works best.

Jason Fishkind: Totally.

Joining Cresta

Alex Kracov: At People.ai, and now at Cresta where you work, you've had really a front row seat to how AI is impacting go-to-market teams. And before we get into AI, can you tell me a little bit about Cresta and why you decided to join?

Jason Fishkind: Yeah, sure. Cresta is just in a fantastic space. It was an opportunity. Quite frankly, I couldn't turn down. Cresta is contact center AI technology. It just gets the best results in the industry with the biggest customers. Period. It was founded by Sebastian Thrun and two others in the Stanford AI Lab a number of years ago. If you know the name Sebastian Thrun, you know that he is the leader of Google X which was focused on Google's moonshot projects like flying cars, things like that. The contact center is really interesting. People in the contact center are typically low wage. It takes them a long time to ramp, and it's a stepping-stone job. By the time those people were productive and proficient, they're on to the next job. So it's a space that's just ripe for disruption.

Cresta has been doing GenAI for years well before ChatGPT came into the public view. We provide a chat copilot called Agent Assist that helps the contact center agents say the right thing at the right time to drive the objective that they're looking for. Then there's a whole host of data for contact center QA folks, and leaders and performance to optimize data. Lots of folks think about the contact center as care. But it's not a big use case as sales. A quick example is like a popular tax software company. They sell their products to consumers. They took Cresta. They gave it to 100 agents. Then another control set didn't have Cresta. In eight weeks, the agents on Cresta drove 2x sales conversions and 4x revenue, simply because the technology is helping them along. So it's really interesting and really, really fascinating.

Alex Kracov: So interesting. And so somebody is on a phone with a customer, and then the AI is essentially listening to the conversation and providing recommendations of what to say next. Is that kind of how it works?

Jason Fishkind: Exactly, yeah. Then you take that in a couple of different ways, yes. But in a nutshell, that's exactly it. It's super powerful.

Alex Kracov: Yeah, super interesting. Because I imagine. I was actually on the phone with Comcast the other day. It's like, I imagine those people you talk to, they just have this hard-coded script of like, say this, then that. The customer is complaining in this. Then it must be amazing to have AI that can provide recommendations on the fly based off what the customer is actually saying as opposed to this hard-coded script that I assume that everyone has.

Jason Fishkind: Yeah, totally. Then you think about, oh, it was good. You read the compliance statement. It's like, well, how many people actually do that? How do they check for that? There's lots of really interesting things that I think it's a space that is ripe for disruption.

The Secret to Selling AI

Alex Kracov: Yeah, really cool. What's the secret to selling this AI technology? Because, as you're talking, it's like, whoa, this sounds amazing. You just blow someone's mind with a demo. Is there an education problem? How do you think about selling such innovative technology to companies?

Jason Fishkind: I've referenced a few books. I don't read good, but I referenced a few books. I was reading Nate Nasralla's book the other day called Selling With. It was on my bag. I was on a plane the other day. He talks a lot about buyer enablement, which I couldn't agree more. The concept of buyer enablement is, how do you go enable your champions to go sell internally? Especially, if you work at a large company - Excuse me. If you're selling to large enterprises, your champion is really selling tremendously internally. Especially, in a new space in AI that has so much confusion and a lot of unknowns to it, how you go enable your buyer, I think, is so critical. We're spending a lot of time focusing on how we're doing that today.

Alex Kracov: What does enabling a buyer actually look like or mean to you? Is it just co-creating a presentation, giving them videos? Do you organize a bunch of assets in one place for them? How do you actually tactically enable the buyer?

Jason Fishkind: Yeah, it's all of those things, but there's a tremendous amount of nuance to it how you work with your own. For the product marketing, how you go create the right types of content, the right elements. You choose the right word, Alex. It's co-creation. That's the real key. How you go understand the business problem, how you understand all those key elements, and you go build the right elements to deliver alongside your champion.

Alex Kracov: I'd love to end today's conversation just hearing a little bit from you. Because you're so deep in this AI world now. What are the trends you're seeing across the marketplace as respect to AI? Then maybe how it's impacting your own go-to-market efforts? Are you using this technology to close more business yourself? I'd love to hear about it.

Jason Fishkind: I'll take the last one first, actually. On a personal level, actually, we've done a bunch of sessions with the team. I'm sure I'm not alone in this. Just the thought of using ChatGPT or Google Bard to help with prospecting or research is really fascinating, really interesting. There are some great things out there to help enable sales reps to prospect better and do better research.

But when I'm thinking about AI in the large enterprise impacting go-to-market efforts, there's a handful of key observations. One, what we're trying to do or what we can is attach to some level of GenAI initiative in a large company. I'd bet you, 8 or 9 out of 10 companies, if not 10 out of 10, they have some version of some AI initiative, some GenAI initiative. I think it goes into the second point. There's so much confusion, and folks just don't know where to start. Nobody quite knows what is what. Everyone says their AI, but you need to stand out and be clear. Then there's this element of, well, do we want to use the public elements like ChatGPTs or a private version of that? Do we want to go use the golden private bottle, which will take years? Personally, I think the domain specific LLMs that are focused on a single line of business and a single handful of use cases that have tremendous firepower, I think it's really interesting. I think that's where it will begin, actually, and where you're going to see a big pickup.

The other thing we're really seeing right now is, in almost all these deals, is we're seeing companies say they have an AI Council. There's always paper process and InfoSec. Now, the AI Council is part of that process, where an existing customer, we're seeing brands come to us and say, hey, I know you already have an MSA, but we need to add this amendment in the MSA for AI. It just adds. It's just a long-gating deal cycle entirely. It's interesting. It's exciting though.

Alex Kracov: And everyone is just figuring it out. Everyone knows they need to do something about AI, but the landscape is changing so quickly. And it's like, we're even thinking about how do we build AI technology into Dock. It's like OpenAI is a clear choice. But then, Google Gemini gets released last week. And it's like, okay. Wow. Maybe we build into that. Then the costs involved. AI is an expensive computing power. So how does that change business models and how we sell it, our pricing and packaging? It's like, everyone knows we need to do something. But how you do it? And because it changes so fast, I'm paranoid I'm going to make the wrong decision, choose the wrong vendor, whatever it is. Then, oh, this new thing comes up, and it's even cooler and better. And so, yeah, I don't know. But it's a fun puzzle. It's cool to have a frenzy to innovation.

Jason Fishkind: Totally. I think it'll be interesting to see. I was reading one of those VC predictions for 2024. Certainly, AI was a big topic. No surprise. Some of the stated beliefs was like, the hype around GenAI will give way to focus on results. I think that'll happen sooner than later. I think the companies that can separate themselves in the AI space - there will be separation - it'll be the ones that can show that they can really be additive technology and can show that they can go make money and focus on business results with really tangible use cases, will be durable. So certainly, making that bet right now myself, and I'm excited about it.

Alex Kracov: Well, thank you so much for the wonderful conversation, Jason. If people want to check out Cresta, if they want to follow-up with you and ask questions, where's the best place for them to find you?

Jason Fishkind: Ping me on LinkedIn. I'd be more than happy to connect and chat.

Alex Kracov: Awesome. Thank you, Jason.