Matt Benelli: This week on the Coach the Scale podcast, I sit down with Keith Rabkin, cro of PandaDoc and the seasoned go-to-market leader with an impressive resume featuring leadership stints at Google, adobe and Johnson Johnson.
Matt Benelli: Keith's unique path to sales leadership without ever carrying a bag proves that tenacity and curiosity can still drive extraordinary results.
Matt Benelli: He'll share his two-by three coaching framework, tackle the pitfalls of lone ranger sales behavior and explain why tough conversations that we don't want to have are the cornerstones of true customer centricity and solid coaching.
Matt Benelli: Whether you're scaling a team or leading from the front, this episode is packed with actionable insights for modern sales leaders.
Matt Benelli: Take a listen, oh yeah, please let us know you're out there.
Matt Benelli: Hit the subscribe button on YouTube, comment, like and repost on LinkedIn.
Matt Benelli: Let's go.
Matt Benelli: Welcome to Coach to Scale how modern leaders build coaching cultures.
Matt Benelli: I'm your host, matt Bonelli.
Matt Benelli: Join me as we build a community of like-minded professionals who share the belief that effective coaching improves the performance of every team member.
Matt Benelli: Our mission is to help leaders become better coaches.
Matt Benelli: The Coach to Scale podcast is sponsored by Coachum, the world's first AI coaching execution platform that leverages evidence-based coaching to increase quota attainment.
Matt Benelli: And with that let's get started.
Matt Benelli: Today's guest has amassed deep and broad-based go-to-market experience at iconic companies Google, johnson Johnson and Adobe.
Matt Benelli: Currently he's Chief Revenue Officer at PandaDoc.
Matt Benelli: Keith Rabkin, welcome to Coach to Scale.
Keith Rabkin: Thanks for having me, matt.
Keith Rabkin: There is nothing that I would rather talk about than coaching and talent, so this is the perfect activity for my afternoon and time well spent.
Matt Benelli: Awesome, all right, we are aligned.
Matt Benelli: So, keith, let's kick it right off with a MythBuster type question, and the question is this there's a lot of myths in this crazy business that you and I have been part of for a long time.
Matt Benelli: What's one of those myths, when it comes to coaching and leading salespeople, that you believe is misguided, maybe even complete BS?
Keith Rabkin: Yeah, I wonder if you've heard this one before, matt.
Keith Rabkin: I don't think it's total BS, but I think it's maybe misguided, which is that the only thing sellers care about is making money, and you know, I've heard that time and again right Coin operated.
Keith Rabkin: Just create the right incentive plan and then, you know, the reps will figure out how to get there.
Keith Rabkin: And I think, while there is truth, a lot of people want to be in this business to make a good living.
Keith Rabkin: There's a lot more, and I think salespeople in general have the same motivations that others do.
Keith Rabkin: They want advancement, they want recognition, they want to do a good job.
Keith Rabkin: I think a lot of sellers take particular pride in their craft.
Keith Rabkin: That's something that I've seen, certainly in the last two years at Panadoc.
Keith Rabkin: We have a lot of sellers who they want to obviously beat quota and hit those accelerators, but they also want to set personal records.
Keith Rabkin: They want to do the best job they can for the company, and so I think, as a coach, one of the things we have to do is make sure we're creating a system by which our reps can earn, but also dealing with more of these intangibles and identifying what is the one thing that makes my seller tick, and how can I lean into that to drive performance for that rep and help them reach their goals?
Matt Benelli: Yeah, and I appreciate you sharing that.
Matt Benelli: And yes, I have heard that time and time again and, like a lot of the myths, there is some truth to it.
Matt Benelli: It's not 100% false, but I like what you said.
Matt Benelli: It's misguided and I may you know years and years ago what motivates you Money.
Matt Benelli: I want to make the most money.
Matt Benelli: I probably said something stupid like that along the question.
Matt Benelli: What advice would you give to that hiring manager when he or she asks an interview question to get at the heart of what motivates somebody?
Matt Benelli: And that person on the you know, maybe newer in their career that wants to please, thinks saying making money is the right answer.
Matt Benelli: So they say making money is important.
Matt Benelli: That's what motivates me, and you and I know that that's not really the case.
Matt Benelli: What's the follow-up question to that?
Keith Rabkin: Yeah, I mean I would continue to dig how is making money going to make you a better seller?
Keith Rabkin: Or what other traits do you have that's going to make you a better seller?
Keith Rabkin: Because that's going to start to uncover that underlying motivation.
Keith Rabkin: Or what do you want to like?
Keith Rabkin: Maybe great, that's amazing that you want to make money, but tell me about what you want to accomplish in the next month and how you're going to grow in this role.
Keith Rabkin: Because, like that growth, if you turn it to growth, it's less about the outcome and more about the path, and I think what we want to understand is what path are they on and do they see themselves moving into?
Keith Rabkin: Because that's going to help us understand these inherent motivations.
Matt Benelli: Yeah, and those inherent motivations are really what makes the, what makes it all go, what makes where the rubber meets the road, if you will.
Matt Benelli: So we kind of hit on hiring and some things that have very high level here.
Matt Benelli: But, keith, when you think about your leadership playbook that you've developed over the years, is there a playbook or a framework you use with your leadership team to help better coach and lead your salespeople?
Keith Rabkin: I like to think I'm really big on structure, so this is a really structured approach that will work for some managers, may not work for others, but I like to create a two by three matrix and I may not like actually tell people I'm creating this matrix, but I use it internally and one of the columns is goals, and one of the columns is what do I need out of this team member?
Keith Rabkin: And the goals come from them, right?
Keith Rabkin: I'm asking them what do you want to accomplish?
Keith Rabkin: And the what I need is great.
Keith Rabkin: I may have some development areas for this person, right?
Keith Rabkin: Maybe it's they need to be better at pipe gen.
Keith Rabkin: Maybe it's they need to be better at closing.
Matt Benelli: Maybe, it's.
Keith Rabkin: They need to be better at driving cross-functional projects that actually have a bigger payoff for the entire organization.
Keith Rabkin: So those are my two columns, and then I have sort of three rows which are like what's the tactical, what am I going to do, what are we going to work on in the next three to six months, next one to two quarters, and let's understand your goals and how you're going to accomplish them in the next quarter or two, and then let's understand how you're going to raise your performance in the areas that I'm thinking about for the next one to two quarters.
Keith Rabkin: And then you've got this like middle bucket, which is like all right, let's look out over the next one to two years probably more, like you know, one, one and a half years what will indicate success for you and how do we get you there?
Keith Rabkin: Their goal may be to get promoted.
Keith Rabkin: Their goal may be to make it to P club Um, just start to like fill that out, and then my goals might be different too, based on my assessment of this person's talent, where I need them to get on their metrics.
Keith Rabkin: And then there's the long-term, which is what do you want to be when you grow up?
Keith Rabkin: You know, five years down the line, 10 years down the line, and how do I help you start to get there?
Keith Rabkin: And how does that fit in with my organizational plans?
Keith Rabkin: Right, If I've got a great enterprise seller who's crushing it and continually beating quota and driving new highs for the business, I want to make sure this person stays and I've got to figure out what are the motivators that then help this person continue to stick with my organization.
Matt Benelli: So when you talk about goals and you said that's what the employee, that's what the rep provides, let's say, and then it's what you, as the leader, need from that person, and you said they might need to ask better questions in discovery, whatever it might be, no-transcript.
Keith Rabkin: Like, does that skill that I think?
Keith Rabkin: Like, is there any alignment where I have to self-assess that I need to get better at discovery too?
Keith Rabkin: Or are you saying, hey, listen, I don't, it's not.
Keith Rabkin: You may not have thought about this, but I have and you is to get promoted and your goal like you can have goals that are, like, very tangible, like I want to get promoted, I want to make the club, I want to, you know, be the top rep, but then there's more amorphous goals.
Keith Rabkin: Like I want to be better in negotiation.
Keith Rabkin: I think one of your jobs as a coach or a manager is to make sure you can tease those apart and understand both of them.
Keith Rabkin: Like this box doesn't have to be one thing for each category.
Keith Rabkin: What I like to do and I think one of the beauties of this matrix is that if I can tie what's in my column to what's in their column, it's great.
Keith Rabkin: So if your goal is to get promoted, but my goal is for you to be do better discovery, then I'm trying to tie them together and say you know, your best path to get promoted is when you get better at discovery, because that's going to help you continue to generate pipe, continue to make sure you close deals at a higher clip, and that's going to lead you to the outcome you want.
Keith Rabkin: It's not that I'm telling you no to being a better negotiator.
Keith Rabkin: It's just tying what I want you to do back to the goal that you're explicitly asking for.
Matt Benelli: Okay, no, that makes a ton of sense, and thanks for sharing that.
Matt Benelli: Ok, no, that makes a ton of sense and thanks for sharing that.
Matt Benelli: Keith, one of the topics we talked about in our initial call together is that you pride yourself on being customer centric and leadingused.
Matt Benelli: When you talk about customer centricity, what does that mean to you in terms of how you lead a team.
Keith Rabkin: So I think there's this interesting.
Keith Rabkin: There's maybe another myth with sellers right, there's a few Sales is like a like it's a job for a lone wolf, right versus being part of a team.
Keith Rabkin: And I think this team aspect of selling really ties into customer centricity in a real way.
Keith Rabkin: When you're in sales, no matter if you're a new business seller, you're an str or you're an expansion sales rep who's doing renewals and driving expansion, or you're a combined rep that's doing all of this you're part of this like broader organization that has this goal of getting customers and keeping those customers and wanting those customers to come back for more.
Keith Rabkin: And I think when we approach from a standpoint of not being customer centric and just trying to get a sale, no matter what, we're actually putting ourselves above the organization.
Keith Rabkin: And it ties into that lone wolf mentality which may be okay for you know, hitting quota in a given quarter, but it's going to start to hurt you down the line, right?
Keith Rabkin: It's either your CSM team is going to start to get annoyed with you, your manager is going to realize their net dollar retention is suffering.
Keith Rabkin: Your customers may get you a reputation, especially if you're in a small industry, you know, or if you're an enterprise where there's just not that many companies out there like people talk, these things come back, and so the best sellers I've seen are the ones who continue to understand that this is a long game, right, and I'm going to be around as a seller for 20 or 30 years.
Keith Rabkin: The customers I have at one company are going to be my customers in the next company and the ones that I get to a really great outcome will come back to me for more.
Keith Rabkin: So we have a fantastic rep on my team today and he's actually won many of his customers from his previous company because they trust him so much, which only comes from getting them to a great outcome.
Keith Rabkin: If he had said, hey, I'm going to close the maximum deal I can, I'm going to sell them stuff they don't need, right, they're not going to come back to him because they realize, like he's out for himself, not for this, like mutually beneficial relationship, yeah, and so I think this pays increasing dividends over time right in terms of both the rep and the company.
Matt Benelli: Yeah, I really appreciate what you said about like no lone rangers and, um, you know one of, you know a counterpart, you know another revenue leader in this business, uh, mike Deloya.
Matt Benelli: He was on the show not too long ago and he commented.
Matt Benelli: He said if you, if a rep comes to me and says, hey, I closed this big deal and I did it by myself, um, the first thing I'm going to say is why you left money on the table and you didn't help the customer as much as you could have.
Matt Benelli: So I just I love the way this, our industry is focusing more on sales, being a team sport and that's a big part of being customer-centric and that there's no lone rangers.
Keith Rabkin: So I totally agree.
Keith Rabkin: I mean, I think sometimes it's hard to ask for help, but when you realize it's a team and a lot, of, a lot of great sellers come from sports backgrounds, right, so there should be this natural inclination that you can get help.
Keith Rabkin: Um, get your execs on a call, get your csm in there, get your se.
Keith Rabkin: I think the se?
Keith Rabkin: Ae relationship usually works pretty well.
Keith Rabkin: But the more people you bring I think there's some gong statistics that the more people on a call, the higher the close rate.
Keith Rabkin: So you know it's in your best interest to do it and it helps the customer get to that great outcome.
Matt Benelli: Yeah, I think it increases the close rate and it increases the deal size.
Matt Benelli: Those are two good things that we all want.
Matt Benelli: More of right, absolutely so, keith.
Matt Benelli: One of the topics that's come up well, it comes up a lot, but recently this is something that we've been digging into and peeling back the onion on is this whole notion of having difficult conversations.
Matt Benelli: Tons of books written about it.
Matt Benelli: The problem is not a new one.
Matt Benelli: What are the folks that impress you the most right, the most seasoned, successful sales leaders?
Matt Benelli: How do they deal with having difficult conversations?
Keith Rabkin: I would say that the best that I've worked with are very honest, but they don't and they don't hide, like they don't hide away from giving the bad news, but they give that bad news with compassion.
Keith Rabkin: You know, and personally I think this is one that took me a while to get used to, right, like I have this dread about having the hard conversation, like I don't want to have it.
Keith Rabkin: It's like it sucks, it's just, it's painful.
Keith Rabkin: But I think over the years, what I realized is you're going to have this conversation one way or another.
Keith Rabkin: So you know, it's like when you wake up in the morning and you're like I just want to lay Right, never, never.
Keith Rabkin: But like when you you just do it, like you just go get it done and when you get it done, everybody's in a better shape, right.
Keith Rabkin: Like you're not hiding.
Keith Rabkin: Then you don't have to have a conversation later where the person who's getting maybe this tough news was like well, why didn't you tell me this months ago?
Keith Rabkin: Like my behavior didn't change in this time.
Keith Rabkin: So it's like it's about being genuine and it doesn't mean like I think one of the challenges, too, is we say like well, when you're giving critical feedback, you're being harsh.
Keith Rabkin: Actually, you're not being harsh.
Keith Rabkin: Just just lead with the facts.
Keith Rabkin: Like it's not that you're a bad seller.
Keith Rabkin: Your close rate is low.
Keith Rabkin: You did not generate enough pipe.
Keith Rabkin: Yeah, I need to see this different.
Keith Rabkin: Like it's not.
Keith Rabkin: That's nothing personal about you.
Keith Rabkin: This is I'm.
Keith Rabkin: I have expectations for you and you didn't meet the expectations, but it's very honest.
Keith Rabkin: And then it's I'm here to help you.
Keith Rabkin: But, but you do need to hit these marks, um, and I think the more you can be upfront about that, the better situation you're creating and the better opportunity you're creating for this person to make a decision on their own part about what they want to do with this feedback.
Matt Benelli: Yeah, like most people, you mentioned that you don't love having these types of conversations.
Matt Benelli: I mean, no one does, but they have to be had.
Matt Benelli: Do you find, especially with all of the different data that's being aggregated and stored?
Matt Benelli: Do you see that the data sometimes helps have a more difficult conversation because you can point to the data as opposed to coming off as like?
Matt Benelli: Here's how I feel about you.
Keith Rabkin: Yeah, absolutely, like I said, grounded in the facts, because if it's a feeling based conversation like that's where it gets hard, because now it's how you feel about me as the person getting the feedback versus this is my expectation of anybody in this role.
Keith Rabkin: You have to generate this pipe.
Keith Rabkin: You have to close this much that you treat customers with respect right, like if you're mean or you're mean to teammates, like that's a, I have received X number of complaints or negative pieces of feedback.
Keith Rabkin: That has nothing to do with how I feel about you.
Keith Rabkin: I might absolutely love you as a person, we might have the best time like working together, but this is the expectation of the role and I think that makes it really easy for somebody to understand.
Keith Rabkin: Again, they may not like that feedback, but it is very factual, which at least allows them to internalize it and absorb it much more easily.
Matt Benelli: Okay, and that segues into a question I have about you know lessons learned right, have about lessons learned, painful lessons.
Matt Benelli: You've been doing this a while.
Matt Benelli: My guess is that it's not all rosy sunshine and rainbows.
Matt Benelli: Is there a painful lesson in this business that shaped how you approach leading teams today?
Matt Benelli: Maybe an aha moment, if you will.
Keith Rabkin: I think if you ask my team one characteristic about me, they would say urgency.
Keith Rabkin: I have an extreme level of urgency, so I don't like waiting for things to happen.
Keith Rabkin: But my lesson is that change always takes longer than you expect.
Keith Rabkin: So what do you do about that?
Keith Rabkin: You start planning ahead more and you start thinking about things you can do in advance and you signal to people who are doing a great job, you signal to the organization about the direction the organization is moving, and when you have critical feedback, you share it early, because the longer you sit on it, the longer that change is going to take.
Keith Rabkin: And so that's probably the biggest lesson.
Keith Rabkin: I mean, that's one of the things that drove me the craziest.
Keith Rabkin: When I started here at PandaDoc, we had a very transactional sale.
Keith Rabkin: We were pretty far down market.
Keith Rabkin: We just closed, closed, closed, and one of the changes we made was to introduce value selling and I was like, oh, this isn't going to be hard.
Keith Rabkin: I have really smart reps.
Keith Rabkin: I mean, I have a great team of AEs and AMs.
Keith Rabkin: I was like this is going to be easy, like they're super smart, they know this product inside and out.
Keith Rabkin: But changing that behavior just took a really long time and it just surprised me.
Keith Rabkin: So, repetition, planning ahead and continuing to like, draw that roadmap of where you're going is the best thing you can do to make sure you're bracing for that, that change that will take longer than you want it to.
Matt Benelli: Yeah, um, nobody loves change.
Matt Benelli: Uh, you know, some people it's easier than others.
Matt Benelli: And I remember a book written as a while back now by some folks out in the Bay area, I believe Chip and Dan Heath.
Matt Benelli: They wrote a book called switch how to change when change is hard.
Matt Benelli: And they, you know they talked about the repetition and shrinking the change, and you know it's just a just a super important book about, like, how change always takes longer than than you expect and so, but but then again, the, the other adage in our business is the only thing constant is change, right.
Matt Benelli: So so, um, I guess, when, when you were like, I mean, I'm curious, when you're focusing on value selling, right, when you rolled it out, you have smart reps, right, you know they get it.
Matt Benelli: It's not intellectual that that's going to knock them for a loop here it's, I guess, maybe it's comfort zone, things like that.
Matt Benelli: What are, what were some of the things I guess more specific that you did to hang in the pocket there and make sure that it wasn't treated as oh, this is, uh, the flavor of the month.
Matt Benelli: This too shall pass.
Keith Rabkin: So there's quite a few things you know.
Keith Rabkin: Start with great enablement.
Keith Rabkin: You've got to have an amazing enablement team and I think most sales leaders love their enablement team and I'm no exception.
Keith Rabkin: My team is fantastic.
Keith Rabkin: But you start with that as a basis to make sure they're grounded and they know what they're trying to get to.
Keith Rabkin: And then the second thing, back to team sport is my managers right?
Keith Rabkin: I want my managers constantly reinforcing this and they're going to be meeting with the reps all the time, so the more that they're telling them this, the more it's going to be top of mind.
Keith Rabkin: I think the challenge really is what you said, which is it's comfort zone.
Keith Rabkin: Like, yes, I get this, I know this is going to lead to better results, but in a moment when I'm on a call and I go into a Zoom meeting every single day in my job, I just go back to what I know Right and so, like you've really got to get them way past that point of change.
Keith Rabkin: So the team, the enablement, and then like, beat the drum.
Keith Rabkin: My sales staff is amazing at doing this Constantly.
Keith Rabkin: Every, all hands we have, we're beating the same drum of like these are our priorities.
Keith Rabkin: Here's why this matters, and it's not just the what, it's the why.
Keith Rabkin: So I think continuing to match those two things with great enablement and great management leads to these better results.
Matt Benelli: And I love that you brought up the other leg to the stool and enablement, because if you don't have a strong enablement team, it's hard to make anything stick moving forward, as we both know.
Matt Benelli: So one of the things you shared with me before in our initial conversation was that you come from a non-traditional background.
Matt Benelli: You've worked at some great companies.
Matt Benelli: You know Stanford, wharton, great education but you didn't carry the bag.
Matt Benelli: And you know some would say, oh, why am I going to listen to this guy?
Matt Benelli: He's never carried the bag.
Matt Benelli: And some would say, hey, it's a superpower, you know I.
Matt Benelli: Sometimes it might be better not to know, right, you can find people who say both, but let me focus on the former one.
Matt Benelli: What do you say to those critics who might say Keith's never carried the bag?
Keith Rabkin: I.
Keith Rabkin: What I would say is you've got to study.
Keith Rabkin: You got to study to be good at anything and hard work is the number one differentiator.
Keith Rabkin: Like, how many?
Keith Rabkin: How many people hire sales reps based on what college they went to?
Keith Rabkin: I think very few.
Keith Rabkin: I think people want to see reps who put in the work and are good at their job.
Keith Rabkin: And I would say the same thing about me.
Keith Rabkin: Like, don't hire me because of my education, pedigree or the companies I work for, but hire me because I put in the hard work and trust me as a revenue leader because I put in the hard work.
Keith Rabkin: No one's watched more gone calls than I have.
Keith Rabkin: No one is reading more articles.
Keith Rabkin: Well, maybe Steph, my VP of sales, is.
Keith Rabkin: But you know, I think those are the things, right, and my way of selling is going to be different than the CRO who grew up carrying a bag for 20 years.
Keith Rabkin: But I also know where I'm not good, right?
Keith Rabkin: Don't, don't call me in to go sell to GE, like that's.
Keith Rabkin: I'm not going to do a good job there.
Keith Rabkin: I'm going to be okay.
Keith Rabkin: But if you want a CRO who's going to be really personal in a call and be customer-centric, which I think more and more buyers are looking for.
Keith Rabkin: Our expectations as software buyers has been raised in particular, as we expect technology that behaves in the business like it is in the consumer world.
Keith Rabkin: We want a customer-centric buying process, and when I get on calls, there is this level of authenticity and honesty that comes across that I do hope helps us win deals, and so I think that's a big piece of it.
Keith Rabkin: And then I think my team would say Keith's really done a good job of raising performance because he has been a student of the game and he looks at data all the time.
Keith Rabkin: I think that's the piece right, this understand, and I work hard to look at the data to say, you know, I see this trend.
Keith Rabkin: The reps that are top performing do these things consistently and that leads to better outcomes for these sellers.
Matt Benelli: Yeah, no, I really appreciate and I enjoyed the answer.
Matt Benelli: It's kind of funny because you always get people who say so-and-so didn't do that particular job, Like well, they don't have any street cred and as a sports fan, I'm a Boston guy.
Matt Benelli: I don't think Bill Belichick was.
Matt Benelli: He certainly wasn't a pro football player and I don't even think he played football at a high level.
Matt Benelli: And that's the case with most professional teams.
Matt Benelli: Many of them weren't players and they certainly weren't great players.
Matt Benelli: But you know, I really like the answer.
Matt Benelli: It's like you put in the work and you put in the work yeah.
Keith Rabkin: I mean one other point, like so I worked at Google back in its heyday, right when a lot of the great products were being introduced.
Keith Rabkin: You know, google Docs, which now I mean that's what I use in my job, that's what I used in my last job, it has become a mainstay of what we do.
Keith Rabkin: They introduced, you know, google Cloud.
Keith Rabkin: They introduced Chrome, the browser, all these YouTube.
Keith Rabkin: They bought YouTube and they turned it into this juggernaut.
Keith Rabkin: Back when I was there, we did not hire based on the resume.
Keith Rabkin: We were encouraged to look past the resume and the job on the resume and to hire for aptitude.
Keith Rabkin: And for me, that is a lesson that I take with me.
Keith Rabkin: Like yes, there are some jobs where you like experience is a good signal that somebody knows how to do something, but great interviewers will test for aptitude and use that aptitude score to make the hire.
Keith Rabkin: I would much rather hire a sales rep who is showing aptitude, who is at a non-name brand company, than a sales rep who doesn't work as hard, doesn't show insane levels of curiosity, but worked at one of the top SaaS companies.
Keith Rabkin: It's a very easy choice for me.
Matt Benelli: Yeah, you talk about curiosity.
Matt Benelli: One of the favorite interview questions that I stole from someone else along the way to kind of get at is someone really driven, are they ambitious, are they curious?
Matt Benelli: But if someone comes in with I don't know let's call it 15 years of experience this person says I want to get to the to understand.
Matt Benelli: Does this person have 15 years of experience compounded, or do they have one year of experience 15 times and you know?
Matt Benelli: And they really try to figure out like are they curious, are they ambitious, are they driven?
Matt Benelli: So you talked about Google or, as my father-in-law would say, the Google.
Matt Benelli: Put it into the Google.
Matt Benelli: You talked about Google.
Matt Benelli: You talked about technology.
Matt Benelli: Ai is all the rave these days and if anything comes to mind, what are the salespeople or sales leaders?
Matt Benelli: How are they the best ones right now leveraging AI to be not more efficient, more effective?
Keith Rabkin: I think we're just in the beginning stages, right.
Keith Rabkin: As much as there are great tools out there, I do think the people who are leading now have a you know just as good shot of being completely irrelevant in three years from a technology perspective.
Keith Rabkin: It's changing so quickly.
Keith Rabkin: So for me, the best thing companies can do and individuals is to experiment.
Keith Rabkin: And it goes back to what we were just talking about Curiosity, the rep who is playing around with these technologies and I don't need to name names, there's tons of them out there.
Keith Rabkin: There's new ones coming up every day.
Keith Rabkin: The ones who are playing with it and figuring out what works are going to be the most successful, because they're going to find what works for them, and that may be different depending on your segment.
Keith Rabkin: It may be different depending on your motion Are you inbound, outbound, Are you channel driven?
Keith Rabkin: These are all going to create different permutations that different tools will serve at different levels, and so experimenting and trying things out to me is the best path.
Keith Rabkin: That's kind of what we're doing now.
Keith Rabkin: We actually have been playing around with about seven different tools to see which ones we want to bank on, which ones match PandaDoc style, which ones help our sales reps be more effective and actually turn into the end result.
Keith Rabkin: It's very easy to say this will make me more efficient, right?
Keith Rabkin: Oh, it writes my cadence for me, great.
Keith Rabkin: Did it actually result in an opportunity?
Keith Rabkin: How good is the pipe?
Keith Rabkin: Does it close at a different rate?
Keith Rabkin: Same thing with like intent data that's out there.
Keith Rabkin: Combining those makes me more efficient too, because now I don't even have to go do research.
Keith Rabkin: But does that actually make me better when I get on the call with the customer and I haven't done any research?
Keith Rabkin: So I think a lot of it will be customized and depend, and a lot of this is still changing so rapidly.
Keith Rabkin: So my advice is play around a lot, you know.
Keith Rabkin: Get different team members to try different things, share those learnings and then start to make some bets.
Matt Benelli: Yeah, no, I love the idea of sharing the learnings.
Matt Benelli: So, keith, you're over at PandaDoc, your chief revenue officer there.
Matt Benelli: For those who don't know what PandaDoc is, can you say what the?
Keith Rabkin: company does.
Keith Rabkin: And then also, what do you love most about working there?
Keith Rabkin: Yeah, so PandaDoc is a single solution for all your agreements and for sellers.
Keith Rabkin: That's super important because you send out sales agreements for Signature.
Keith Rabkin: I cringe every time I see on LinkedIn at the end of the month somebody says oh, we got our you know our DocuSign back.
Keith Rabkin: Uh, cause they're a competitor.
Keith Rabkin: What we have is a lot better for sellers, for several reasons.
Keith Rabkin: One, you know, we give you better analytics on people who view your agreement.
Keith Rabkin: So today I'm talking about AI tools.
Keith Rabkin: We've got a PDF that was sent over by one of these vendors, and this vendor charges around $200,000 a year.
Keith Rabkin: So this is a pretty solid sale.
Keith Rabkin: This PDF is getting passed around like no tomorrow, and we're like I'm reviewing it, my head of marketing is reviewing it, my VP of sales is looking at it.
Keith Rabkin: These are great buying signals.
Keith Rabkin: Now, because it's a PDF, this team has no idea that we're looking at this, which leads to two things One, they don't know how warm of a buyer we are, which means they can't forecast accurately whether we're going to close or not.
Keith Rabkin: And two, when I go back and negotiate, I'm going to play it cool, right, I'm going to say you know we're looking at five different vendors and you know you guys are just as good as the other.
Keith Rabkin: But if they could go in and see how often I was personally logging into this thing and seeing, that's an incredible signal.
Keith Rabkin: So that's one way that we're different.
Keith Rabkin: Another is we actually make the branding really unique on these proposals.
Keith Rabkin: You know how often do you get like an order form that's just like this kind of boring quote and then put your signature right.
Keith Rabkin: Ideally, your company has assets that they can put in front.
Keith Rabkin: Here's how many years of experience.
Keith Rabkin: Here's a case study and then the order.
Keith Rabkin: We bundle that all up and probably most importantly, the seller is we save you time.
Keith Rabkin: You know we actually prevent a lot of that back and forth with deal desk that sellers just hate working on.
Matt Benelli: Oh yeah.
Keith Rabkin: And so that value proposition makes us a really great sales tool.
Matt Benelli: Awesome.
Matt Benelli: And so what do you love about working with the team?
Keith Rabkin: The people at this company are amazing.
Keith Rabkin: We've got a global workforce.
Keith Rabkin: You know, employees from Ukraine, portugal, all over the US were fully remote, and we've just done this amazing job of bringing people together that have this goal of serving customers.
Keith Rabkin: Panadoc was founded as a company that was here to help small and medium businesses succeed Mm hmm with giving them a tool that was disproportionately powerful relative to what larger companies had, and so this mission of helping companies be more productive, close deals faster, is core to our being, and we talk about it a lot, and you know my team is here to do the right thing for the customer.
Keith Rabkin: A lot of my sales reps will tell me they're like you know, keith, I didn't close this deal.
Keith Rabkin: And I'm like why didn't you close this deal?
Keith Rabkin: And they're like this wasn't the right solution for this customer and as much as I want that sale, at the end of the day I also run CX.
Keith Rabkin: So like I'm like, okay, you made the right call because I don't want this customer to turn all in it.
Keith Rabkin: Together we go to the right things and it's a fun environment.
Keith Rabkin: I mean, it's not always easy, right, we're coming from behind against some pretty large competitors, but the elegance of our tool.
Keith Rabkin: The great teamwork and the focus on doing what's right for our customer, I think makes it well worth getting up every morning.
Matt Benelli: So, keith, if somebody out there listening says wow, you know what We've been evaluating, so we need to evaluate something and we're interested and it sounds like PandaDoc sounds like it could be a good fit, and or someone says wow, it sounds like a great company, I want to work there.
Matt Benelli: Like, where can someone learn more?
Keith Rabkin: PandaDoccom We've got a very easy to find demo request form, which should make it very easy to get in front of a seller, and that is the best way to get into our pipeline and learn about the product.
Keith Rabkin: The websites we've done a really good job of making it accessible to understand what we do.
Keith Rabkin: There's some videos, there's some graphics, there's comparisons against other tools, and then we are constantly hiring, so our career site is on the website as well.
Matt Benelli: All right, constantly hiring.
Matt Benelli: I'm career site is on the website as well.
Matt Benelli: All right, constantly hiring.
Matt Benelli: I'm sure a lot of people might like to hear that.
Matt Benelli: So, keith, the podcast is Coach to Scale.
Matt Benelli: We bring people on who have a point of view and who care give a crap about coaching and developing other people.
Matt Benelli: People who care about that, like yourself, usually have had that behavior modeled for them somewhere along the way.
Matt Benelli: Can you tell us about someone whose coaching has had an impact on your career and your leadership style?
Keith Rabkin: Yeah, I've had three fantastic coaches maybe three and a half is maybe maybe three and a half, but uh, the one who was most recent was my executive vice president at adobe, brian lampkin, who's just an amazing human being and, again, really customer focused, very aspirational, like constantly challenging us to do better, and I can remember a couple times he really lit into me but did it in a way where he's like like hard but then like pulled me up at the end and I think I think a lot of sellers and go to market people in general appreciate that, which is this.
Keith Rabkin: I like I'm being hard on you because I know you can do this and I want to challenge you to do better.
Keith Rabkin: So, you know, brian helped me get into go to market.
Keith Rabkin: You know, again, took a little bit of a chance on me because I was coming from more of an operational background and really appreciate what he taught me and I think I'm much better for that, like really pushing hard and then pulling people back up, and then that continuing to be customer focused, which a lot of my mentors have done for me Awesome to be customer focused, which a lot of my mentors have done for me Awesome, well, yeah, I mean, whenever you describe someone that you worked for in this crazy business as an amazing human being, you know the shout out to Brian, for that that's, I'm sure he.
Matt Benelli: Have you ever told him that?
Keith Rabkin: I don't know if I've ever told him that All right.
Matt Benelli: Well, again, he knows I appreciate him, but I don't know if I've ever told him that.
Keith Rabkin: All right, well, again, he knows I appreciate him, but I don't know if I've ever said that so I should.
Matt Benelli: People love hearing that stuff.
Matt Benelli: So the who's your favorite coach?
Matt Benelli: So think of it a little differently.
Matt Benelli: Maybe a name a lot of people would know it doesn't have to be sports, but a lot of sometimes sports comes to mind.
Matt Benelli: Who's your favorite coach?
Keith Rabkin: out there and why what happened?
Keith Rabkin: I've got two maybe, and kind of similar in some ways, very different in other ways.
Keith Rabkin: So I'll start with the first.
Keith Rabkin: I went to Stanford.
Keith Rabkin: I went to Stanford when we went to the Final Four and I was a huge basketball junkie.
Keith Rabkin: Mike Montgomery was the coach, you know, and he put up a really good run in a very challenging environment at Stanford.
Keith Rabkin: I think what he did well was he recruited well and Stanford had really hard guardrails around recruiting there Did a great job there.
Keith Rabkin: Great X's and O's coach.
Keith Rabkin: You know, in some very tight games would just like pull out wins.
Keith Rabkin: That you know.
Keith Rabkin: I remember we beat, we beat duke like I think, two years in a row and it was just like what, how's that even possible?
Keith Rabkin: There's just no way this happened and he did it through like great coaching because I mean we had great players but they had like a ridiculous roster.
Keith Rabkin: So I think you know I love that about him and the x's and o's is kind of like that's how I think of myself as a CRO.
Keith Rabkin: Again, I'm not a salesperson, I'm more of like let me look at the data and figure out the plays we need to run.
Keith Rabkin: That would be like my back in the day answer.
Keith Rabkin: My today answer is Steve Kerr.
Keith Rabkin: I'm in the Bay Area Warriors.
Keith Rabkin: I gotta love them and like, how can you go wrong?
Keith Rabkin: He's, he's got this amazing team, but, um, so got great talent, recruited great talent.
Keith Rabkin: But then again back to the X's and O's.
Keith Rabkin: He finds a way to maximize the talent, or he, you know, I think the other piece about him that's maybe different is he finds a way past obstacles.
Keith Rabkin: So grit, um, you know, curry goes down with an injury and somehow they still win, right, because he's figuring things out.
Keith Rabkin: And I think any good leader is going to continue to find obstacles.
Keith Rabkin: Any good coach is going to have obstacles, right.
Keith Rabkin: People plateau at different times.
Keith Rabkin: People have life changes, right, whether it's getting married or God forbid illness or a pregnancy, like.
Keith Rabkin: But people good coaches find ways to solve through those problems and help maximize the potential of their team.
Matt Benelli: So those would be my two Great player, great coach, great results.
Matt Benelli: Hard to argue with Steve Kerr, except I'm a Boston guy and I don't like what he did to Jason Tatum.
Matt Benelli: I don't understand it, but topic for another day.
Matt Benelli: Last question, keith, just have a little fun with it If you had to give a TED Talk tomorrow about one topic to a huge group, ted Talk style, what would the topic be and why?
Keith Rabkin: So one person who worked for me said that he's never experienced more growth than when I managed him directly and we would talk about how he experienced this and he would say a couple of people who've worked for me have had this and I think, as I've sort of dissected what that is more, and it doesn't work for everybody, but it is almost this sink or swim viewpoint on new talent, and one of the things I do which, again, you have to hire the right kind of person for this to work is I like give them all the pressure.
Keith Rabkin: I just I'm like here's everything you've got to do and go get it and I'm here to help you, but like I'm going to keep giving you more until you tell me, uncle, like when you tell me to stop, I will pull back and I'm just going to give it to you.
Keith Rabkin: But through these experiences like I think of, like the term forged in a crucible, like that crucible of the pressure, it's either going to cause somebody to drop out, which is why this is not the right approach for everybody, or it's going to challenge them to reach new heights, which is why this is not the right approach for everybody, or it's going to challenge them to reach new heights and for me and the way I hire and the way I manage, I've gotten really good results out of that.
Keith Rabkin: So I would probably talk about that and you know how you match the hiring with people who succeed in that coaching style.
Keith Rabkin: You know, and maybe your follow-up question is going to be how do you hire the right people?
Keith Rabkin: You hire people who like challenges, you hire people who are curious and you hire people who have a tenacity to want to go and overcome obstacles because, like they don't want to give up when you're putting this on them.
Keith Rabkin: Like eventually, everybody, even the most tenacious people I've hired, are like OK, this is enough, please stop.
Keith Rabkin: At which point, like we load balance and we figure things out, but it just produces so much growth with people.
Matt Benelli: Well, I love the connection.
Matt Benelli: You're right, it does segue into about hiring, and if you hire the right people, you can do things like that.
Matt Benelli: You know one of the big programs in Marine Corps leadership training, you know they actually call it the crucible, and one of the principles within the crucible is to give people, to give the students, the aspiring Marine leaders, absolutely much more than they could possibly accomplish in the allotted amount of time.
Matt Benelli: They can't do it.
Matt Benelli: They can't do it all.
Matt Benelli: So they have to think, they have to prioritize, they have to maintain even keel, they have to ask questions.
Matt Benelli: But in order to do that, you have to have, you have to bring certain ingredients to the table, which means you have to have the right recruiting process.
Matt Benelli: And so, yeah, no.
Matt Benelli: Thanks for sharing that.
Matt Benelli: I loved it, keith, we covered a lot of ground, you know.
Matt Benelli: We talked about the crucible, we talked about hiring.
Matt Benelli: We talked about having difficult.
Matt Benelli: We talked about the crucible, we talked about hiring.
Matt Benelli: We talked about having difficult conversations, customer centricity.
Matt Benelli: Really appreciate everything you brought to the table today.
Keith Rabkin: Thank you, thanks for having me on.
Keith Rabkin: There's very few things I like talking about more than talent and getting people to great results, so I appreciate you having me on.
Matt Benelli: Well, likewise and it was obvious that you like talking about it and I noticed on LinkedIn there was somebody fairly recently wrote a review for you and you know they just talked about how you help them and you care about them and that's why they followed you from company to company and that's a huge vote of confidence for for any leader.
Keith Rabkin: That's the person I was talking about.
Keith Rabkin: Who is the one who is like you've challenged me so much and I guess he kept coming back for more challenges, but I've tried to get him over here to Pandadoc, but so far he's resisting.
Matt Benelli: Ah, all right, I missed that.
Matt Benelli: I thought he was there, but yeah, but still, he followed you to multiple companies, so that's a huge testament to your leadership.
Matt Benelli: Keith, thank you very much, and also thanks to everyone out there watching and listening.
Matt Benelli: Appreciate you being there.
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