June 5, 2024

Sales and Leadership Mastery with Jacob Karp

In this Sales Therapy episode, Jacob Karp and Alper Yurder discuss modern business practices and leadership strategies for creating resilient and innovative organizations. The session highlights how leaders can navigate challenges, foster a positive work culture, and drive success in a dynamic business environment while sharing practical tips and real-world examples.

Meet our guest

Jacob Karp, Strategic Enterprise Sales at Rubrik

With over 20,000 hours of industry experience, Jacob not only excels in his professional role but also shares his expertise on LinkedIn, providing actionable, battle-tested sales strategies that drive success.

Key takeaways

  • Effective sales leadership involves coaching and leadership roles to enhance team performance.
  • Navigating large, complex deals requires a deep understanding of customer needs through strategic discovery processes.
  • The role of a strategic enterprise salesperson is pivotal, involving intricate stakeholder management and tailored sales strategies.
  • Building strong internal relationships across departments, like Customer Success, can significantly reduce friction and enhance collaborative efforts.
  • Successful sales teams are structured around clear roles and boundaries, fostering accountability and streamlined operations.

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Watch the highlights

Grit, growth, and sales mastery

In this episode of Sales Therapy, Alper Yurder interviews Jacob Karp, who leads strategic sales at Rubrik and is known for his expertise in closing complex deals. Jacob shares his personal background, growing up as the eldest of four in a challenging environment, which instilled in him the grit and resilience that have driven his successful sales career. 

He discusses the importance of building trust both internally and externally.

“In the role that I have today, a lot of my job initially was building trust internally. These other AEs that I work with, I want them to trust me and know that when I go into their accounts and have conversations, I'm doing it from a sensible perspective. I'm not doing anything that they wouldn't agree with. So you build trust with your internal champions and then you build trust with your external champions and in a perfect world you do it all together and that's where the wins come across.” 

Jacob also reflects on his career evolution from public relations to strategic enterprise sales. He candidly shares the highs and lows of his journey and highlights the value of learning, personal growth, and the joy of helping others succeed. 

“I'm still an individual contributor. I'm an AE in my own kind of little world, but I do my best to help people from a coaching perspective, give them kind of things that have worked for me. We see me do that on LinkedIn, but I'm doing that internally at Rubrik as well. I think you don't have to have a certain title to be a leader or to be a supporter of your colleagues, your friends, your peers. You should be doing that no matter what your title is, right?”

Navigating the highs and lows of software sales

In the next section of the episode, Jacob reflects on five years in software sales, recognizing the rollercoaster nature of the profession. While celebrating the learning opportunities and diverse connections it offers, he delves into the complexities of managing large deals versus smaller ones.

“I think my favorite part of it is just the strategic mindset you have to take to get into them. Because without that, you're probably not gonna get in the door because you don't have a POV or hypothesis that supports why you should be there to start. I love that.”

Jacob emphasizes the importance of strategic planning, stakeholder alignment, and rigorous organization in navigating the intricacies of sales. He underscores the value of genuine curiosity and meaningful interactions, advocating for continuous learning and persistence for sales success.

“In my younger career days and years as a seller for sure, I think I had a lot of those blind spots. I think you go forward and for those who are learning and building their career, you should always assume that your champion could potentially not be your champion a day later. So it's always like, you'll hear the phrase, trust but verify or trust but validate. And people talk about testing. I don't like that.”

Strategies for sales success

In the last part of the episode, Jacob Karp reflects on five years in software sales, recognizing the rollercoaster nature of the profession, delving into the complexities of managing large deals versus smaller ones. He underscores the value of genuine curiosity and meaningful interactions, advocating for continuous learning and persistence for sales success.

"Honestly, I think, and I always go back to this honesty, integrity, transparency. What it really is, is keeping it real. Like if I work with you, if I work for you, if you work for me, I'm going to be direct, but polite about things."

They discuss the importance of proactive problem-solving and collaboration between sales and customer success teams. Emphasizing the need for internal and external stakeholder alignment, they highlight the significance of a unified approach towards customer experience.

"In some of the biggest and best deals I've ever done, I've had CS involved in the last 25% of the cycle. Because when you're going to ask your customer to pay all of this money over three to five years, whatever it is, like I want my CS team there."

The dialogue underscores the importance of trust, communication, and a holistic view of the customer journey in achieving sales success.

Full episode transcript

Alper Yurder: So today in the Therapy Chair, I have Jacob Karp who leads strategic sales at Rubrik. After a decade in complex sales, Jacob is an elite seller and I love following his content around closing complex deals and go to market. We'll talk about his success, the joy, the pain and the journey. Welcome to Sales Therapy Jacob. How are you feeling today?

Jacob Karp: I'm doing great, Alper. Thanks for having me. I'm excited to be here.

Alper Yurder: Lovely, me too. Any good therapy starts with childhood and growing up because it shapes the person we are today as a person at work and in life in general, I guess. So can you tell us a little bit about your growing up experience, Jacob?

Jacob Karp: Yeah, definitely. So I am one of four children. I'm actually the oldest of four. I grew up in a household that went through a couple of different divorces, great parents, but they didn't necessarily need to be maybe married to each other, they found out. So yeah, so that was a part of it. And we moved around a little bit. I didn't grow up in the best neighborhood per se. But when I look back, what's interesting now, like as a nearly 40-year-old person, I'm like, that stuff was not easy.

Alper Yurder: Okay. Resonates.

Jacob Karp: But it kind of made me who I am today and instilled a lot of the grit and resilience that I have. So, you know, when you're going through it, maybe you're not thankful for it, but when you look back, you're like, those things made me a better person and who I am today. So.

Alper Yurder: I love that. Things happen for a reason. And I think generally going through the experience, enjoying the experience is something that starts to finally tick with experience. I don't know if that makes sense. It's finally, by the way, I think we're similar ages. You're 38, right? Yeah. I mean, 85. Were you born in 85? 

Jacob Karp: Yes, correct. Yep, November of 85.

Alper Yurder: Yeah. Wow. Yeah. Hello, millennial. Love it. And it starts making sense. How am I going to enjoy this fucking terrible thing that's happening right now, but then you'll learn to enjoy it.

Jacob Karp: Yeah, I think, you know, you make a good point, right? Like I have kids now married. It's like, I didn't understand a lot of the stuff until I got older and like, it kind of comes to make sense to you. And you understand like the stresses of life, like the things that people go through and it just kind of shapes your view. Like I didn't grow up in a perfect scenario, but at the same time, I want to do the best for my family, my kids, like the people around me to make life better for them. So it gives you gratitude, right?

Alper Yurder: Yeah, it does give you gratitude. And I think sometimes because my natural self is not that gratitude person, I try to channel others I know that that know well to do it or friends. I had a friend and we were in a Greek island having an amazing time, but I was still the good old me three, four years ago and I was anxious about something. Maybe this was during covid sabbatical, whatever. And the guy told me, dude, you're good, you're fine. But it feels like every morning you wake up thinking about what to worry today.

Like, why do you do that to yourself? You ask me.

Jacob Karp: You know, honestly, I'm very similar to you. Like, it may not always come off that way to people who know me, because I can put on a pretty good face and like, Hey, I'm good. But up here, it's just always spinning. Like my wife will be like, you know, chilling, doing something she's like, I can just see that you're over there. Like, the wheels are turning. I'm like, Yeah, I can't stop it. Like, but what's interesting, right? Is like, that's some of the stuff that drives you…

Alper Yurder: You do, yeah.

Jacob Karp: …to do better, to always be trying to do more. I think we find a time in our life when we're like, we need to pump the brakes a bit, but it makes us who we are.

Alper Yurder: Yeah, it does. But I think I mean, I completely know where you're coming from. I think I had Patrick Trimpe and Angelina Mullins. They both said the same things like this, you know, driver personality success, success ties to love and affection and all those things like, you know, the better you are, the more calculated, not calculated, the more hardworking, the more you achieve and then you start seeing the rewards of it. And some of the rewards is affection and love and et cetera. But.

It becomes a little bit difficult when it's overly done. I think not everything has to be conditional. Not everything has to be about achieving. Even if you're just, you know, passing your day for a day, like you should have a free ride and chill and be comfortable and be happy. You should allow yourself to be happy, even if you're not achieving something that day.

Jacob Karp: I agree. I'm working on that every day. I think though, to your point, what I find is the days where I do that, where I, you know, kind of separate myself, like put the phone away, put the computer away. It's a Saturday, whatever. You don't have an agenda. You don't have places to be. And you're just accepting like what's going on and seeing the good. It's rare for people like you and I, I think, and a lot of people in these professions.

Alper Yurder: Yeah. Hard.

Jacob Karp: But like you realize how important it is and you're like, I need to prioritize that.

Alper Yurder: God, this is, I love the therapy bit of the sales therapy. I think a little more than the sales part of it.

Jacob Karp: Thank you.

We all need it, man.

Alper Yurder: Especially because I've been so I mean, recently I haven't been doing a lot of demos and stuff that's that's other people in the business. But obviously, I love the selling and but I guess the thing I love about selling other than the big commission checks is the relationship building, the conversation, the genuine interest in the others and all of that. You and I, we talked about this before. I very much admire how you are a very elite seller in your organization right now, like with decade or more of experience. You're one of the top performers, you coach others, et cetera, et cetera. And I think that's a great place to be. That's not necessarily leadership, but that's a senior person people look up to. I don't know. Is that the accurate way of putting what you're up to these days? Is that?

Jacob Karp: Yeah. I mean, I try to think of myself that way for sure. Like the title, you know, I'm, I'm still an individual contributor. I'm, I'm an AE in my own kind of little world, but I do my best to help people from a coaching perspective, give them, you know, kind of things that have worked for me. Like we obviously see me do that on LinkedIn, but I'm doing that internally, you know, at Rubrik as well. I think what's interesting is you get older is like, you don't have to have a certain title to be...

Alper Yurder: Absurd.

Jacob Karp: …a leader or to be a supporter of your colleagues, your friends, your peers. Like you should be doing that no matter what your title is, right?

Alper Yurder: And I think those people sometimes in an organization, I used to work in a training company like behavior change and stuff. And there's a lot of good science that goes into it. Sometimes in an organization to make change happen, you don't need to. People don't listen to the manager or the leader or whatever the title person is. They listen to who they see as the. The one they can trust, the one, the champion, basically, I mean, champion is sales language is different, of course, but.

It's a champion because people love respect. They see them as a subject matter expert, ombudsman, whatever you call it. So my career was going in that trajectory. Then I became a leader. Then I became in a startup, like the first man after the founder. And then I ended up being the founder. That's not something I chose, but you know, if I had the choice back then, I think I had decided to be a very senior IC.

And enjoy that as well, I think it's a very enjoyable position to be in.

Jacob Karp: Yeah, it definitely is. I mean, I think I don't know anything about being a founder, but I have like a high level of admiration for it. I think, you know, the IC world is so different, right? Because we kind of like own our own little world in your, in your role and the things you've done. You've got so many things to think about. What's beautiful about mine is I get to look at this one little spot and Hey, here's the things I need to do. But I think you can. 

The best places I've ever worked are the places where everyone is moving in the same direction, moving together. It doesn't have to be rah rah. Like even from your position as a founder, like it doesn't have to be, and you're probably not like rah rah, right? But it's like, hey, we're all moving towards this one thing. We support each other. We're collaborating. If you don't agree with me,

Alper Yurder: Yeah, there's ra-ra and then there is ra-ra at times. But still at the end of the day, we're going towards a similar ra-ra, I guess.

Jacob Karp: Yeah.

Jacob Karp: And what people are looking for from their leadership is people who've been there done that, right? Like you kind of touched on it. The people you end up looking up to or wanting to spend your time with are like ones that you know, like they've gone through the same fights that I'm going through right now. When they go tell me to do something or ask me to do something, it's because they would do it themselves or they have done it themselves.

Alper Yurder: I don't know. I went straight into that topic. Generally, the flow is a little softer before I dive into the realities of the career, etc. But I went there because you and I, we had a few chats before and long ones, and I just love how you own your personal brand and the senior I see role. But you are currently helping others to build their pipelines or, you know, grow their deal sizes and how are you doing that? How is that experience nurturing you also?

Jacob Karp: Yeah. So I've made a little bit of a change this, this fiscal year and what I'm doing. So previously I had, I did strategic enterprise sales for 10 years. So I would have 10 to 15 to 20 accounts. I knew everything about them. You know, I did all the deep research, all this stuff. Now I actually am a subject matter expert on one portion of our platform and I aligned to around 10 different AEs. 

So I get to help them sort of with their overall go to market and accounts as it comes to the portion of the platform that I'm selling. And it's really interesting because I get to collaborate on pipeline generation. I get to run my own campaigns. You know, we're building our own champions together, but also separately. It's just like a really big mindset shift for me. But going back to what you were talking about earlier, Alper, like it gives me the ability to be, to do some leadership stuff, to do some coaching but also receive that from people who are in the same seat as me. 

Because previously it was like my first line sales manager was like telling me, hey, do this, do that, do this. Now I'm going to other reps like me and saying like, hey, what is the best way to get into this account? Like where can we find success? What partner is the best one? Who's your champion? Like it's fun.

Alper Yurder: The best, I mean, it's a win-win and I think the best work and environment is not, I think some businesses don't allow for this, but where there are like large complex sales, everyone's going after maybe like 10, 20 top accounts. There's so much to learn from each other. Verticals are well defined. So there isn't like, you know, conflict of interest and blah, blah. Then it becomes amazing. Like invite me to your call. I'll invite you to my call. We'll learn from each other. It's a very psychologically safe environment.

I guess not every business has the opportunity to do that, but once you have that ecosystem, I think it's a great place to be a salesperson because there isn't direct competition. You just really feed each other, isn't it?

Jacob Karp: Yeah, it's amazing. Like we talked about earlier, it's really everyone kind of on the same page going in one direction. I think what's interesting about it for me is that our jobs as sellers is to build trust with our prospects and customers. In the role that I have today, a lot of my job initially was building trust internally. These other AEs that I work with, like I want them to trust me and know that when I go into their accounts and have conversations, I'm doing it from a sensible perspective. 

Alper Yurder: Yeah.

Jacob Karp: I'm not doing anything that they wouldn't agree with. So you build trust with your internal champions and then you build trust with your external champions and in a perfect world you do it all together and that's where the wins come across.

Alper Yurder: Love that. To be honest, today I want to do something a little bit different with you. Like there's I collected maybe around 10 questions or so from our actual users and I added a bit of my my own things to it. So I'm going to go into a bit of a rapid fire situation in a minute where I'm going to ask you all about these like building, you know, allies, internal alignment, external and all these things that you have to do as an elite, elite seller. Somebody gave me this word. 

I don't know if I even like it, but complex enterprise seller doesn't have the same thing to it. And so I'll call you an elite seller. Okay. They just gave me that word and I'm going to go with that. But before I go into it, can you maybe summarize your career a little bit? How did you end up in sales? And from there, how did your career shape up to the moment that you are today?

Jacob Karp: I'll take it.

Yeah, for sure. So I actually, I have a journalism degree. I did not start in sales. I started in public relations. I did public relations and strategic media spokesperson stuff for the first five years of my career. What happened was I was working at a cable and broadband company. So I was like telling the stories of the company, the products, the services, the solution, do you name it? I was writing them. I was talking to the news about them. And I realized that like, I was actually kind of indirectly selling already…

Alper Yurder: Yeah.

Jacob Karp: …Because I was telling those stories, right? And so I had someone approach me in the same industry and said, listen, if you'd like to try sales, like you can take all the things you're doing today, you can come to this company that sells into the same arena and you can retell those stories, but you're gonna be doing a customer facing with a quota, et cetera. Now, full disclosure, I didn't know if I really wanted to do that, but the money definitely spoke to me at the time. Like the PR world, I wasn't making very much money. 

The upside was financially was much better, bigger in sales, but I had had a previous negative stigma, like a lot of people used to about sellers, like used car salesman. I hate to say that, but like people say that. Right. And I didn't know if I want to try it. Here's what was interesting. Before I took that role, I went inside the company I was working in and I talked to a lot of our sellers. Like I sat down with them, interviewed them kind of on a personal mission of mine to like understand like how do they operate?

Alper Yurder: It is what it is.

Jacob Karp: Integrity, transparency, honesty, like what's their go -to, how do they go to market? And I realized like there's so many good and brilliant people in sales, like that stigma needs to go away. So I decided to make that leap into sales, started in cable and broadband hardware. 10 years later, I'm in software for the last five years and the rest is history as they say.

Alper Yurder: So how has the last five years of software sales been? Have there been highs and lows, ups and downs?

Jacob Karp: Yeah. I mean, like the nature of this profession is highs and lows, right? Like I look at these people who are president's club every year, who are doing 200 % of their number every year. Like that is incredible. There are certainly those people out there. I'm not one of them. Like I'm going to be honest. I've had the ups, I've had the downs. I've had the big years. I've had the not-so-good years. the best part of the last five years is two things. 

One, like the amount of learning that I've been able to do and I, how I challenged myself and grown, and then also the people that I've met both in the companies I've worked for, but also my customers. You're not gonna get a better experience than being in sales for meeting all of these unique characters that you meet. So.

Alper Yurder: Yeah, I hear you. Actually, you pushed me to go into the next section, which is just extracting all the good stuff that you've learned throughout the years. And you are actually sharing your wisdom and preaching some of these things that I really like about, you know, large enterprise sales and how to be a good salesperson. So I'm going to be very direct and ask you a few rapid fire questions on them. And I would love to hear your tips, tricks, best practices, strategies, maybe like.

Jacob Karp: Let's do it.

Alper Yurder: if anyone is trying to accelerate their career and get to those bigger numbers, bigger deals, etc. quickly, like what they should do. OK, so I'll go with that in mind. So maybe let's start with these large complex deals. What's nice and what's not so nice about them like that? What are the highs and lows of, you know, bigger deals, complex deals, as opposed to maybe like smaller ticket, high velocity stuff?

Jacob Karp: Yeah, I think my favorite part of it is just the strategic mindset you have to take to get into them. Like people love to say strategic and strategy and all this stuff, right? But like you have to have a plan and it has to be based on research and understanding of the company, what they're doing, how do they make money? Are they worried about, are they worried about decreasing costs? Is it risk mitigation? Is it to grow revenue? Like you need to understand the basics of these companies that you're going into.

Because without that, you're probably not gonna get in the door because you don't have a POV or hypothesis that supports why you should be there to start. I love that. Remember, I'm a journalism major. I'm a guy who went to school to learn how to research things, write stories, come up with compelling narratives. So I use that in everything I do. The things I don't love so much,candidly, like I'm not great with the politics. 

Like I understand the org charts and the hierarchies and I've got to get this person to be neutral and this is a detractor. I don't love that because I want to just have very candid and honest conversations. But in sales, like you don't always get the opportunity to do that in the initial stages. Like you have to sort of hold your cards a little closer to your chest, right?

Alper Yurder: Yeah.

Can you give us some examples of that? That's intriguing. When do you have to be careful? When do you have to hold your cards to your chest?

Jacob Karp: Yeah, I think early stages, a lot of what you're doing is you're trying to understand who is a supporter of yours, who's neutral, who's a detractor, who's a potential champion. And before you know that, the information that you share with people, you need to be kind of cognizant of how that might affect you positively or negatively depending on their stance. So it really is kind of a chess game in the early stages. 

Like, listen, I firmly believe in being transparent, honest, and doing things with integrity, but you might not share everything when you're not sure how that person's going to take that information internally and either use it to support you or use it against you.

Alper Yurder: Yeah.

Yeah, I love that. And I think in every conversation, something you learn and sales, it teaches you really well is you don't assume things. Like you don't go into a conversation saying like, in your situation, this, that, like that can backfire very quick instead asking questions, but not an investigation. Like, what is a great discovery in your opinion? And I have my opinions of this, but.

Jacob Karp: Yeah, again, I think you come in with, to your point, you come in with a plan, you come in prepared, you understand some things, you know the questions you want to ask, but it's not like, hey, Alper, I have 17 questions I have to get through in the next 30 minutes, let's go. You need to start with what I firmly believe in is like a funnel of questions, but you're not gonna use them all. So you're gonna have like your high level overarching question of like, thematically, I wanna understand this.

If you go to a place that you want to learn more about, you kind of ask those second and third level questions, but it might be that you don't get to where you want to go and you go to the next thing. I will say this to my prospects and customers. Like I'm not here to interrogate you. I kind of use that as like breaking the ice, but I really mean it. Like the last thing I want to do is have someone get on a call with me. And when they get done with the call, they're like, dude, that guy just treated me like it was a hostage situation.

Alper Yurder: Yeah.

I can't even I can't even anymore. Like, you know, at the fourth question, I'm like, dude, I know you're very new. This that I don't want to break your heart anything, but let me give you the gift like that. This is how it's so horrible trying to sell to salespeople because, you know, like. Was that. Right, yeah.

Jacob Karp: Right. They know the game. So it's like, if you're, yeah. And I think the other thing too, right, is get rid of some of this wording that we see in discovery. What are your pains? What are your challenges? What keeps you up at night? Like get rid of that. Have a real conversation of like trying to understand where people are coming from in a real language.

Alper Yurder: Hmm. yeah. Yeah.

Yeah, I think for you to be able to do that, it's genuine, genuine curiosity, interest in others, time presence, you know, being comfortable in your own shoes, being confident to ask questions because, you know, those questions are helpful. But then, you know, when you have a buyer like me who is like been through that and da da da and you know, you're going through your four questions and I try to be patient and nice not to break anybody's heart. But at the fifth question, I'm like.

Where's this going? You have to give me something before I answer the next question. Hopefully it's I'm only zero point one percent of the buyers. Hopefully. But still, one percent is quite cruel as well. I've seen cruel people.

Jacob Karp: But at the same time, I mean, so have I, but at the same time, like you, based on your experience and also your current role as a founder, like you are a savvy buyer, right? Like you've been through a lot of these conversations and cycles. I think for those of us who have been in the profession for, you know, for me, like 11 plus years, I want the savvy buyers. I want to talk to you.

Alper Yurder: Hmm. Yeah, yeah.

Jacob Karp: Because I because you'll get to the point, like one of the hard things to an enterprise sales is when you're dealing with people who haven't ever made a purchase or are new to evaluating technologies. They're oftentimes too nice. They're willing to let the conversation go on too long. They're willing to take conversations, even if they're not really going to make a move. Like my guess is for you, you know, right away, like, Hey, I either want to work with this person in this company or not. And you're going to tell them, Hey,

Alper Yurder: Yeah.

Jacob Karp: This is a thing or get lost, Jacob. And I love that. I'll take it.

Alper Yurder: Yeah. I mean, it's the information asymmetry between the buyer and the seller and like, why do you need the seller? I mean, the seller's job is to, I think it was Andy Paul who introduced me to this concept of making good enough decisions. You're there to help me make good enough decisions. You know, it doesn't have to be perfect. It has to be a decision and it has to be good enough, which means, you know, we don't need to sit for five hours answering all these questions, but like, maybe you have to ask me the right questions. So we get to the answer quickly and all that.

Yeah, but it's hard. It's hard, especially when you're junior. It's you know, you don't have that same acumen. You don't know how to manage that difficult buyer. It's a tough job. Now.

Jacob Karp: If, if, if we went and looked back at my calls early in my career, which thank goodness, thank goodness call recording software didn't exist really back then. It would be horrendous. I would probably look like a deer in the headlights. I would probably sound like my voice was shaking because I didn't have to your point, the confidence. Like I didn't have the time and seat where you get like, you get very comfortable asking those questions and doing them naturally.

Alper Yurder: Hahaha.

Yeah, I agree. yeah.

Yeah. You met me more on the practical side of things. Let's talk about like managing client relationships and big deals and et cetera. So generally in your book, like how many accounts, how many deals, whatever ballpark do you have going on?

Jacob Karp: Yeah. So this year in this newer role where I'm more of a subject matter expert, like I could potentially be dealing with hundreds of accounts. They're all enterprise. They're all. What's that?

Alper Yurder: That's because you touch others through this

Jacob Karp: Right, right. So I aligned to seven plus reps and all of their accounts so I can do things in all of those accounts. At any given time, now I may be working 10 plus deals, five of which are very large. You know, they're either large POCs or they're just large engagements. So a lot of my job now is to understand the prioritization of those different deals, like which ones need more time and resources, which ones need less, which ones have more velocity, which is kind of what's based on the resources, right? 

And then time management, like we talk about this all the time, sellers talk about this all the time. The most elite sellers I've ever met, if you go look at their calendar, it is time blocked to the minute, like, and they are doing those activities during that time.

Alper Yurder: I love it. Hmm.

Yeah, sticking to doing, I mean, blocking this one thing and then sticking to doing is another. When you talk about like, you know, 510 and really large deals and et cetera, it makes me quite excited. It brings me back to the day and then there's the commission at the end of the quarter, hopefully as well. So how do you manage those multiple big deals? How do you know where to put your attention? What are the signals you look for? Maybe some practical tips on, you know, anyone who is new to complex sales or like, moving up market. What are the things you've learned over the time? What are your go -to strategies?

Jacob Karp: Yeah. I think, I think organization and your processes and tools you use are critical, whether that's something your company gives you or creating your own things that work for you. You know, everyone has a CRM. Everyone has some sort of methodology or most people do most companies. We use meddicc. I've used medic forever. People can say what they want about it. It works for me. I understand it. But at the same time, Alper, like I have teal trackers that I've made for myself. So it's a Google sheets and Excel spreadsheet. Maybe it's a tool that we actually have.

Alper Yurder: Hmm. Mmm.

Jacob Karp: And I'm tracking all of these things in like a slide. What's that?

Alper Yurder: What are you tracking? What are you tracking on those things?

Jacob Karp: Like, okay, so where are we in the stages? Obviously. What is the compelling event and timeline? Because I can then go put my stages up against like what I need to do. Paper process, like legal, like, do we have an NDA? Do we have legal paperwork going on? Technical win? Have we technically gotten the approval that yes, we're the right person or company? I'm kind of like all over the place with it, but it's like all of these different things.

Alper Yurder: Mm -hmm.

Jacob Karp: These are what people, when they go up market, what surprises them often is like, whoa, I'm like a project manager as a salesperson. I need to know about 10 different things happening in an account at any given time.

Alper Yurder: Yeah, yeah, yeah.

Yeah, all of that complexity.

Jacob Karp: Understanding all your stages, understanding like what gets you in and out of a stage, whether you create that for yourself or your company did like, Hey, I have pain. I have champion. I have a champion. Like I can exit this stage. Hey, we've got a technical win. I can exit this stage. Hey, the NDA is not done. I'm stuck. Can't move out of this stage until the NDA is done. So I do it. I'm like an old school. I'm doing it in like a Google sheet, but you could.

Alper Yurder: Yeah.

You are very old school and and I'm cringing inside. I'm like, this is exactly why I'm building Flowla. I should have done you a demo of it in all these time that we've been discussing and I. But we should get you to be a user definitely because all of these things are why exactly I'm building it..

Jacob Karp: I'm the use case, man.

Alper Yurder: Absolutely. And a lot of people are talking about like multi-threading, like, you know, making sure that you bring more broader alignment. In a chat today, I heard like, you know, CFO was the person who is now appearing in every deal and now it's like CIO is also coming in, et cetera. How do you build consensus with all these different stakeholders? How do you manage that complexity?

Jacob Karp: Yeah, the multi-threading is key. And I think everything you just said is spot on for me. It starts with building like a perspective org chart from the beginning. Like I'm before I'm even in an account or before I'm truly in a cycle, I've already constructed what I think the org chart is because I'm already thinking like, Hey, if I want to go sell it to Alper, like who else do I need to get on board within his organization? And have I touched them yet? Am I truly like in a conversation?

So I already have all those targets on the board. I started with my initial team I'm with, you know, building a champion, a coach, whatever. And then I'm socializing those conversations. So I'm taking like, if you and I had a conversation and really well, I'm going to already have in mind three people I think I should talk to. I'm going to validate that with you to ask like, Hey, who else needs to be involved? Usually it's like this title, this title, this title, and your org, that's these names. You're telling me yes or no, or tell me, don't reach out to them at the end of the day, like my job is to go reach out to those people unless you explicitly are like, dude, if you reach out to those people, you're dead. Right. But like my job is to go try to get in front of those people because I want to tell them about the great conversation that you and I had so that they don't hear about it for the first time when I slide a PO across their desk.

Alper Yurder: Yeah. Yeah, it's a very, very tricky situation and you have to be careful at the same time you have to do it. Have there been any situations where you thought you were speaking to the champion, but they weren't or they were hidden stakeholders popping out at the last minute? Like, what do you do to avoid them now that you've become experienced, I guess?

Jacob Karp: Yeah, in my younger career days and years as a seller for sure, I think I had a lot of those blind spots, right? I think what you understand is you go forward and for those who are learning and building their career, you should always assume that your champion could potentially not be your champion a day later. So it's always like, you'll hear the phrase, trust but verify or trust but validate. And people talk about testing. I don't like that.

Alper Yurder: Yeah, yeah.


Jacob Karp: Language because like you're not like an AI model. You're not a robot. Like I don't, you know, you're not testing in that way, but you're always trying to understand like, are you really on my side? Are you going to sell on my behalf when I'm not there? And then also like the big thing that I've realized in these big deals, if there are people who are detractors who are against you, who don't want your technology, your job is to try to get them at least to neutral, right? Here's what happens, right? Like you and I have a great conversation.

Alper Yurder: Yeah, absolutely.

Jacob Karp: Let's pretend you're like, yeah, I want to buy your stuff. And then you push it to this committee and your organization. And there's seven other people. If I've never talked to those seven people, they're like, who is this guy and what is this? Or if some of those people do not like me, do not like my product or like my competitor, they might stand up when I'm not there and say, no, we're not doing it because we're using these people out for, I'm not doing it because of XYZ. So there's always people you are, can be influencing.

Alper Yurder: Yes.

Jacob Karp: I think, and I'm on a long -winded rant here and I'll summarize it here. If you think you've talked to enough people in the org, you probably haven't, add one or two.

Alper Yurder: I haven't. Yeah, no, absolutely. And it's one of the worst things like being ghosted as a salesperson. You think everything was going fine, but now, like for a month, you aren't hearing from anybody. You're in the dark. You have only one person to speak to and they're maybe changing their jobs. You have no idea. Yeah, I mean, honestly, all these things resonate a lot and what we're building into flow now, like you send the flow.

It starts beautifully circulating among different people. I think every digital sales room kind of at the basic offers this, but if you haven't tried it, I would highly encourage you to use something like this to, you know, build a few steps into a flow or whatever digital sales room you use. See how people are engaging with that, how much time they're spending, are they looking at your demo? And a lot of times, I think we've done some research into this and by increasing the number of stakeholders and a flow,

by doubling them, you increase your chances of closing a deal by 30 to 35 % on any deal that's under 100k. That is actual data that we have from Fola because, you know, anecdotally, people tell me all the time like, I thought this person was my champion, but I saw that they were checking my flow only two times, whereas somebody else popped out of nowhere. And apparently they're the CFO who was looking at it 14 times. So that kind of intent data, if you can get it somehow through products like ours or any other product, I think it really helps chances of closing the deal.

Jacob Karp: I totally agree. I think what you guys are doing matters in so many ways. And those signals are things that for those of us who may not have some of them or companies who don't have them, like they need them, right? Because to your point, we have a conversation. I send you something like I might lose track of what's happening after that, but like what you guys are building and these sort of technologies, it gives you those like, Hey, to your point, like Alper only looked at it twice, but the CFO like opens it every day.

Alper Yurder: Yeah.

Jacob Karp: They're passing it on to people clearly like it's on their desk and they're considering. They're considering. They're the ones that are considering like what do I need to do to move this decision forward? And so for a few of your, if you're a seller and you haven't talked to that CFO, nice little signal to say, I should probably reach out to them or have Alper introduce me.

Alper Yurder: Those are my best friends. The ones who are opening a flow every day. They are my best friends. Yeah.

Absolutely. And I think it happens a bit more naturally than trying to creep into people's, you know, LinkedIn's and stuff. One question I have around what makes a good salesperson a good salesperson, or actually I'll be even more personal. What do you think you excel at that makes you a sought after sales leader?

Jacob Karp: It's a great question. Honestly, I think, and I always go back to this honesty, integrity, transparency. What it really is, is keeping it real. Like if I work with you, if I work for you, if you work for me, I'm going to be direct, but polite about things. I'm going to keep it real with you. And I do the same with my prospects and customers. At the end of the day, if you came to me as a prospect and customer and told me, I don't want to work with you or we don't want to do this.

Alper Yurder: Mm-hmm.

Jacob Karp: I say, okay, thanks for your time. Like I'm here for you if I need you or if you need me in the future. I think like just being a real human. Like I know that's kind of like a can generalize answer, but we're what happens is for people early in their careers. And I was one of them, you get boxed into these like scripts or like parroting or robotting something back. And it doesn't resonate with people. Like just be a real human being and be like, if it doesn't work, it doesn't work. Cool. If not, I'm here.

Alper Yurder: Yeah.

Jacob Karp: Hey, if you want to move forward, just let me know. We'll get the resources for you. Like a real conversation, right?

Alper Yurder: Yeah. I think that that makes a lot of difference and I'll actually add something. And I thought about this very thoroughly. I think maybe I will define it as proactive or helpful. And let me elaborate. When you are the kind of salesperson who proactively thinks about potential roadblocks, difficulties, risks, alert the buyer on them, help them, you know, help your champion build that consensus.

empower them to be able to sell your thing internally, anticipate things and share that in advance. I think those things for me, they stand out like when I'm trying to buy and this person is coming like probably you're going to need this or probably somebody is going to object to this. So let me share that with you before you ask me. That is like a perfect salesperson.

Jacob Karp: It's so funny you say that and it's an incredible, kind of like segue into something. a younger seller who's younger in their career, who I'm, I've been helping. They came to me and they're like, listen, like we're in a good spot in this deal, but I have this feeling that these C level folks who I haven't talked to, who I can't get ahold of are going to come to me with these. A ton of objections about why we shouldn't do this. This person had a champion middle of the order, like director level, you got the C level, she hasn't talked to you. She's like, what do I do? I'm like, go to your champion and give them every single objection that you think the C level is going to say and give them the answers, the truthful answers. She did it. She sent it to the director. 

They talked about the C level and it execute the velocity of the deal went super fast after that because all the things they were worried about proactively was given to them of like, here's why you don't need to worry. And it's spot on. Like just make your buyer's life easier by giving them the answers to the test.

Alper Yurder: Absolutely. Just make their lives easier and then you'll hit better commission checks. On a less talked about topic, which comes up a lot in my conversations lately, actually, and I want to understand your perspective on this, client relation, blah, blah. That's all good. But internal relations matter, if not as much. At times even more to close a deal, I think. You have to have your internal champions.

Jacob Karp: Yeah, faster, hopefully.

Alper Yurder: How you work with other teams matters a lot in my opinion. So how do you build great relations with other stakeholders like customer success, for example, or I don't know how your organization works, but like those people who are going to potentially, you know, onboard the client to the product, handhold them, help them, you know, work on it. How do you work with them and how do you build good relations?

Jacob Karp: Yeah, great question. I mean, first off, you should be proactively building those relationships. Like whether it's early when you're at an org or even now if you've been somewhere a while, because the last thing you want to do right is go to someone within your org, who you've never talked to before and go make, go make an ask of them a big ask of them, right. So like for people early in their orgs or earlier in their careers, like build those relationships as quickly as possible. From day one. The other thing is this.

Alper Yurder: Yeah... Yeah...

Jacob Karp: When you are building your internal champions, we just talked about it with your external champions, make their lives easy. Do the work for them. Right? Like, and especially with CS, like I think it's so critical that sellers get into have good relationships with CS teams. Cause those are the ones when the seller sells the deal, that's the finish line to some extent, but it's really the beginning of the next part of the journey. And your CS or PS team, whoever deals with the customer from there is the one that then represents what you told the customer was going to happen. 

So in the best scenarios, like you do a fantastic handoff, you are on the calls, you provide all the information of what you sold and told the customer to your CS team. You go on to those first couple calls with CS with the customer and you're there as the bridge and you're making sure that there isn't a gap in knowledge or understanding. So the customer isn't like,

Alper Yurder: Yeah, yeah.

Jacob Karp: You told me this was gonna happen and then CS shows up and they don't know what's going on. And that's not CS's fault if that happens. That's the seller's fault.

Alper Yurder: Yeah. So you just, you know, already in my next question, what are those frictions between cells and CS in general that you observe and how do you overcome those? You mentioned communication. I think it's very important, but what else?

Jacob Karp: Yeah, I think it's communication. I think it's not providing the collateral, right? Like, like in some of the best orgs I've ever worked in, anything that the seller presented to the customer during the cycle is given to CS. And then you sit down and you have an internal handoff. Customer isn't in this yet. Sellers sit down with CS, you talk about what was the deal structure? What were the products? What were the use cases?

What are the timelines? Like what are the things, the success criteria they have to hit in adoption so that your CS team goes into it with the same talk track and mindset that you had when you were selling it. Because again, the worst thing you can do is have someone buy something for hundreds of thousands of dollars. And their first experience with CS is like, CS doesn't know what's going on. And usually that's on the seller who hasn't communicated it effectively to the CS team.

Alper Yurder: Yeah. And then it comes back hunting you on your performance review because you're selling fine, but everyone else hates you because you're not involving them and you're selling something. You're not using the latest and the greatest. And I mean, yours truly. I had those feedbacks and back in the day and I'm like, I'm going to sell them. They have to deliver like how terrible and arrogant. By the way, you mentioned an ideal handoff, which is great. 

But to me and something that we're trying to do with Fola, which is like looking at one source of truth every single moment, like one flow, every document shared, every content, every person, it's there. Do you think this handle thing has to be a one -off down the line or is it a better way to do it like maybe, you know, feed bits and pieces along the journey as things are getting real?

Jacob Karp: Yeah, no, I think that the latter of what you said, like in the, some of the biggest and best deals I've ever done, I've had CS involved in the last 25 % of the cycle. Because when you're going to ask your customer to pay all of this money over three to five years, whatever it is, like I want my CS team there, one, because it's like comforting to the customer, but I want them there to speak about exactly what's going to happen the moment that contract is signed and the moment we start having to deliver value to the customer.

Because if there's a gap, like I've seen it, where people sell a deal and then like a month goes by before CS gets involved, it's like, what, how is this happening? Like they need to be your partner on the deal before it even closes, both for you, for the company, but also for the customer, right?

Alper Yurder: Do you think then a salesperson has a role in onboarding, customer onboarding as well? Or not really?

Jacob Karp: I think that their role needs to be more internally focused again, like communicating, providing the right information. And then I think like, if you're a salesperson who doesn't, isn't on those first customer onboarding calls, after you sold the deal, like you, you, you might not have the best, that your customer might not have the best experience because they're going to think of you as someone who just sold the deal, got their commission and pieced out. Like I want to be there supporting and especially in enterprise, like.

Alper Yurder: You turn around, yeah?

Jacob Karp: …the money is made in the expansions, right? Like the land is important, but like it's the long-term LTV and like more money that comes from doing the right things once you sign the deal.

Alper Yurder: So what can do? I mean, I think this is my last question and I think it's a very juicy topic. I've seen the best and the worst experiences where CS will be like, well, I'm doing all the work, so I should get the commission. And then, you know, sales should be like, I brought in like, what is a new business? What is an expansion? How do you I mean, this is a very loaded question to be a final question, but like, how do you avoid those situations? I guess like, how do you make sure in a team people know their roles well and they're doing the right things. How do you build those boundaries between the two? It could be a topic on the phone.

Jacob Karp: Yeah, that is a juicy one. I think it's on the company that you work for to incentivize all the parties correctly, right? You have clear rules of engagement and lines of how things should work. Now in a perfect world, the seller can still be compensated for some things. If there's an account manager, they can be compensated. CS, like if you're compensating all of them the right way, then they should theoretically be collaborating and working together on the right things.

Alper Yurder: Mm-hmm. Mm-hmm.

Jacob Karp: I haven't always seen that happen. I'm sure you haven't either. But I think like going back to what you and your team is building, consistency of the way that things happen and communication is key. So like having a flow even just for customer success plus the seller for the customer is so important. It's in one place, it's uniform, it's the same thing they saw over and over. It's not some deck that CS made after the fact that doesn't have any.

Alper Yurder: Yeah.

Jacob Karp: Like trace back to what the sellers called. So it's incentivizing everybody right, but also like consistency of communication deliverables.

Alper Yurder: Yeah. Yes.

I think it's transparent, it's visible and it touches on the point you mentioned in the beginning. It's all about trust. And when there's no trust, when there's no psychological safety, everyone's trying to do their own things, you know, bring things at the last minute. Even the buyer does it. They'll be like, your seller told me this. Whereas you as the seller never told them that. Yeah, we all know it. We've been there.

Jacob Karp: That also comes in right because they're like, yeah, he said that this part of the platform was included. 

Alper Yurder: Yeah, not really. Yeah. So how do you keep track of that? How do you make sure that everything is aligned without breaking hearts? Basically, like, have everything in one place, just one flow to rule them all. That's what we're trying to build. All right. This has been a great chat. Thank you very much, Jacob. And are there any closing remarks? Actually, are there any questions that I haven't asked you that I should have asked?

Jacob Karp: I know, I like it.

I don't think so, man. Honestly, I've appreciated the conversation. I think the things that you guys are building and what we talked about, the way you guys are thinking about it, it's right. We need to improve some of these things for our buyers if nobody else, right?

Alper Yurder: Thank you.

Absolutely. Yeah, for the buyers and also for ourselves, I think, yeah, I mean, I always have the buyer in mind. But when you say that, my gut feeling is we also can do a better job to each other as a team working together on a deal to be able to see everything together, look at the same source of truth. Somebody, I think in customer success roles, leaders understand this even better.

Like we sales first, we see it like stages and processes and you know, now I'm doing the handoff to you and it's your thing. Even if we have the best intentions, we see it in that way because we have to move on to the next opportunity. But customer success sees it more holistically, I guess. It's like, and the buyer actually sees it as just one flow. They don't have a sales CS implementation, whatever. So for the buyers, you just need to give the perfect experience, which is frictionless.

They don't care about talking to Jacob. They don't care about talking to Alper, CS. They just want one frictionless experience and we should strive for that.

Jacob Karp: It's a really solid point. I completely agree. Sometimes you brought up something that I forget sometimes. Your buyer, they don't really care about you. They don't even necessarily care about your product and they don't care about your process. It's like, can you help me achieve the outcome I need by whatever means necessary?

Alper Yurder: Yeah?

Help me.

Yeah, exactly. Help me achieve the outcome I need, whatever it means necessary within my budget and timeline and constraints I'll end. Wonderful. This has been a great chat, Jacob, and I look forward to having you again on the show. But thank you very much. Any closing remarks before we go?

Jacob Karp: Nah man, I appreciate the time, it was a good conversation. Thanks Alper.

Alper Yurder: My pleasure. So that's a wrap on this episode of sales therapy. If you enjoy the show, follow us on your favorite podcast platform until we speak next time. Be good. Bye bye.

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