Lessons from a VP: You Can't Turn a D Player Into an A Player | Craig Holbrook (nCino)

Carter (00:00.832)
Hey Craig, give the people a quick intro. Who are you and what do you do now?

Craig Holbrook (00:05.928)
Excellent. So, high level, I'm the vice president of new client acquisition sales at nCino. I focus primarily on the IMB side of things. And I have probably over a dozen years of sales in the mortgage industry. Been leading teams also as an individual contributor along the way. I've been a top producer, I think, for about eight of the nine years that I was an individual contributor. Before that, I've been a

know, sales marketing leader from small startups to Fortune 500 companies. And I've tried to learn a few things along the way that hopefully I can share today.

Carter (00:43.406)
Okay, excellent. So you've led teams of over 60 business development professionals and now manage a national team of RVPs. When you look back across 20 years of growing businesses, what's the biggest thing you've learned about developing salespeople that you wish you'd known earlier?

Craig Holbrook (01:02.678)
That's a good question. There's a couple of things that I've learned along the way. One is there are certain intangibles that you just can't coach and you have to take some of those. Another big one would be you can't take a D player and turn them into an A player. You can take a D, change it with C, maybe a C to a B, B to an A. But if you're expecting to go from multiple grades, that's really, really difficult to do. And then I think...

Every sales rep is different. Kind of what motivates them can be a little different. So you have to adjust your approach. So I give an example of that, right? So some sales reps, they do a great job. give them, you know, just take an extra day of PTO and just don't count it against your regular PTO allotment. It means the world to them. Others, congrats, here's a hundred dollar gift card for I appreciate all the hard work you put in. That means the world to them. Or others, it's just...

giving them kudos in front of the team and giving them the recognition and acknowledging their work and effort make all the difference to them. So those are just kind of a few key things that I've

Carter (02:09.848)
That was interesting what you said about intangibles. How do those things come up? Do you know immediately? Or are there certain things that you look for?

Craig Holbrook (02:17.482)
There are certain things that I definitely look for. So I'll give an example. One of the things that I'm working on right now at nCino is we're becoming very, very sophisticated in our hiring process.

So we'll do some, I basically have built out a project in Anthropic Clawed that will take some assessment testing that we do. I can run it through the AI. puts together a whole analysis on it and it'll even generate for me probing questions. We actually get to the interview process, but across the board, there's just certain things that a account executive has to have in order to find success that you can't really coach on. One is a work ethic.

They have to have a strong work ethic. They have to be kind of naturally curious and probing. They have to be assertive, be hunters. Some of those things you can't really teach. You can teach them like, here's some parameters, here's some metrics that'll lead to success. Number of phone calls you make in a week, emails, things like that. How many discovery calls you set up, demos. Those are all numbers that they can use as brahmers and metrics. But that's not gonna, it's not gonna be the those intrinsic.

features that's going to help differentiate them and drive success.

Carter (03:33.174)
And so you've worked at big companies, you've worked at startups. Does your coaching approach change based on company size or stage, or is it pretty universal?

Craig Holbrook (03:45.175)
It depends. There are certain things that do change. So for example, if you're a smaller company, you're having to wear a lot more hats. So you have to be more flexible, more adaptive. And if you're a larger company, there's more systems and processes that are built into that. A lot of it's around liability, right? So if you're a small company,

Give me an example, the legal process. So getting a contract through approvals in order to send that out to a client. I've been at small companies where it's just myself and the CEO that are looking through all the legal language and trying to tie up all the loopholes in those contracts and things. At a larger company, such as nCino and some of the others I've worked at, there's layers to that legal approval process and it can take a significant amount of time in order to get through all those approvals.

Carter (04:35.032)
When you come in to, when you get a new team and you like, let's say you're coming into the IMB segment, what does your first 90 days look like from a coaching standpoint? How do you like, what do you do? How do you figure out who needs what? That sort of stuff.

Craig Holbrook (04:48.374)
Are you talking about like if I'm building a team or if I'm like taking over a team or something like that?

Carter (04:52.684)
Yeah, well if you're coming into a team, like when you're coming into nCino, let's say you get this new team you've got to manage within this IMB segment. Yeah, yeah.

Craig Holbrook (04:54.986)
Mm.

Craig Holbrook (04:58.432)
Got it like a new role. Okay. The first, I think the first 90 days can be.

pretty critical because I mean, your boss or other people will give you an assessment of like, here's kind of what the team is, here's the rundown. So you have a little bit of framework on there, but you also want to learn for yourself on what you have, what you don't have. So when I come in, everyone has a pretty clean slate and they start from ground zero with me. And then I kind of work with them. You we do your regular one-on-ones and things like that. Within about six to eight weeks, you're starting to get a pretty clear picture of who you have and who's on the team.

what their strengths and weaknesses are. Are they good at their CRM cleanliness and hygiene? Are they good at prospecting? Are they good at building pipelines? Can they manage deals through the process? So you learn all those things pretty quickly. I will say that joining my team the first 90 days is a challenge for almost everybody. And the reason why is my general philosophy is like freedom with a framework. So here's my framework. I will give you a lot of freedom within that.

as long as you don't play too close to the electric fences on there, then you get zapped. And learning what my hot buttons are. Once you learn these five or six things and you work within that parameter, you're going to be just fine. And at the end of the day, it's all about results too. So if you're a top producer, you earn the right to have a little more flexibility. And I'm a big earn the right with me kind of guy.

So those first 90 days are a little bit challenging, but then once you learn what the framework is, what the expectations are, then it makes it very easy to align with that. And a lot of what those expectations are, they come from up above, right? So what's important to my boss is what's important to his boss. So what's important to my boss is important to me, and what's important to me is important to my team.

Carter (06:53.932)
Okay, that makes a lot of sense. And you maybe sort of touched on it a little bit in that answer, but when you have a sales rep who's hitting quota, maybe they have bad habits though, they're closing deals, but they're not going super deep with discovery, for example, how do you handle that conversation? Or is it just they're closing and you let them be in, you know, they're closing so it doesn't really matter what they do.

Craig Holbrook (07:18.678)
So they're closing, they're hitting their quota, but they're not really hitting their potential.

Carter (07:24.076)
Yeah, or maybe they have some bad habits where you think, okay, they can improve in these certain ways. Or yeah, they're closing deals, but their discovery skills maybe aren't really there and they would get up a level if they got around some of these bad habits, or they fixed some of these bad habits.

Craig Holbrook (07:37.591)
Okay, got it. There's a couple things that you can do if they have those bad apps. First of all is all good sales reps are naturally competitive and they have that drive to want to win and be the best. And so if you take a sales rep who is, they're performing well, but they can perform better.

That's where the coaching comes in. You just say, you realize that you can probably increase the probability of closing deals, have a higher velocity on closing those, and make a higher commission and more money if you do certain things. And I'll work with you on certain things that I've noticed. And then a lot of times I'll watch game tape from demos or discovery calls they've had, and I'll send them the good and the bad. It's like, hey, this little segment you did really well on. This, you know, let's talk about this piece here.

ask a more probing question.

Carter (08:31.19)
And you've promoted people from individual contributor to management. What do you look for in sales reps that signals they're ready to lead versus someone who's really good at sales, but wouldn't make a very good manager?

Craig Holbrook (08:45.782)
And there's a lot of things in there. So one is, they even have the aptitude to do it? Because some people love being an individual contributor and will never want to be in management because they're like, I just don't want to deal with the same pressures or things that you do. Others are, I look at and go.

Carter (09:01.581)
Yeah.

Craig Holbrook (09:04.918)
Could that person replace me? Do they want to replace me? If so, what can I do to help them to develop the skills to get to the next level? So maybe I'll share, we'll work together on a project together. And I started out, I kind of use this analogy, it's like, on this project, I'll be Batman, you be Robin, and then maybe on the next one, you're Batman and I'm Robin, so that they kind of learn that skill. But I I spend a lot of time in reports and Excel spreadsheets and crunching data and numbers.

part of the job and not a lot of sales reps want to do that. But if they want to and they're willing, I'm more than happy to coach them and help them out. And then you'll see some ones that are kind of natural leaders where the team members will gravitate towards them, go to them for advice and recommendations and how they do things. And then I think the last thing is when you look at someone and go, something were to happen to me, could that person step right in and not really miss a beat?

then that's when you know you really have a good AE who's ready to turn the corner and take it to the next level.

Carter (10:08.93)
You earlier, you were talking about nCino's hiring process. You guys are switching it up a little bit and you've hired tons of salespeople across your career. What's the one thing on a resume or in an interview that makes you immediately more interested in candidate and what's something that's an instant pass that you see?

Craig Holbrook (10:30.167)
Again, it kind of goes back to some of those, let's see, on our resume.

Carter (10:36.642)
Yeah, a resume, well both, on a resume or an interview that comes up. And I know you said you a little bit, you like work ethic and there are certain things that come up like that. yeah, anything that shows up on either of those things.

Craig Holbrook (10:39.763)
in an interview process.

Craig Holbrook (10:48.747)
Yeah, work ethic, attention to detail. Like if you see a bunch of errors on a resume, they're probably not going to be great at keeping their sales force clean. They're probably not going to have a very tight sales deck that they use. There could be all kinds of challenges there. The work ethic is a big one. And that's one of the things that I would always encourage, especially new sales reps that are coming in the business. So there's two things, right? There's two things that if you're new that you

Carter (10:55.864)
Right.

Craig Holbrook (11:18.257)
are, really, well, can really help anyone. One is the work ethic and two is how coachable are you? You give me those two things and I can coach up a lot in a lot of ways. Now, I'll give an example on the work ethic and what I mean by that. So, I think it was one of my very first sales jobs I had. I was talking to a coworker of mine and he's like, you know, one of the reasons why I got into sales is because I can make,

a of money, but also it gives me a certain lifestyle. And so about three o'clock every day, I kind of, I kind of not off, I quit for the day. And I start doing the math on that. go, okay, wait a second. So if you're, if you're leaving at three o'clock every day and say I work to at least five, that gives me another two hours a day that I'm working. So that's 10 hours a week. That's 40 hours in a month. So in a month, essentially, I'm working

Carter (11:52.995)
Yeah.

Craig Holbrook (12:12.511)
a whole extra week over you in a year that translate to over three months. So if I'm working that much more than you, I'm going to sell that much more than you. I'm going to make that much more than you. And there's a lot of things that can be overcome by working hard and just putting in that extra effort and time. And that's just if you're like an eight to five employee, which I'm usually still at my desk will pass five.

And most good sales reps are because they just have that drive that's built into them and that work ethic.

Carter (12:47.99)
Is there a way you would tell a salesperson that's trying to get hired to show those things? Because I feel like in an interview and on a resume, everyone says, I work hard and I'm coachable. there specific things you look for or things someone could say or do that would show that?

Craig Holbrook (13:04.983)
You know, I was actually listening to a podcast, I think it was about three, four months ago, and that work ethic came up. And one of the things that I learned that was kind of an interesting trick is, you know, because again, you want to be coachable and try and hone your craft every day, right? So one of the things the guy said was like, you know, say we're all sitting around the table at Thanksgiving dinner with your family.

and they're all just kind of like, you know, they're razzin' each other and everything and you ask the group, it's like, hey, you know.

Carter says he's a really hard worker. He's got a strong work ethic. Where did that come from? And then you just kind of listen to what that individual would say about, what would his family say about where he developed that work ethic from? Do you work on a farm? We have to get up early in the morning and milk the cows every day? There's a lot of different ways that you can work hard.

My dad had a business and I was working in his business ever since I was like 13 trying to do different things and working my way up within the organization, learning all the different skill sets there. So it's the stories that people ask or people will tell you that can be the most telling. And then what I do is I record all those conversations, all those interviews, right? And then I upload them into my little AI project and it will analyze and dive deeper into those as well. it's a.

Those are just some of little things that I've picked up.

Carter (14:34.456)
Okay, so yeah, there are some dead giveaways if you ask the question in a certain way, it's pretty easy to tell.

Craig Holbrook (14:39.095)
Yeah, and you gotta dig deeper too, because a lot of times they'll just give you a surface answer and you're like, well, tell me more about that or what about this? And then it's probing to ask for more details. Give me the numbers on that. What does that mean? What does that translate to? So it's not just taking that initial surface answer, because there are some people that are very polished in interviews. And if you're just taking the surface level answers, you're like, man, that was really good. But you start probing and digging. Don't be afraid to go down the rabbit hole in a big interview question.

Carter (14:58.766)
Yeah, right.

Carter (15:09.12)
What's one piece of advice you'd give someone listening right now who's earlier in their sales career and wants to eventually be in a seat like yours?

Craig Holbrook (15:17.811)
I think I'd go back to kind of those initial answers of outwork everybody. You don't have to be the smartest. You don't have to be the most handsome. You don't be the funniest or like that, but you can outwork because you choose to outwork somebody. So it would be work hard. Again, work hard on your craft every day to be a little better. Learn a little bit more. Try a little bit harder and then be coachable. Whatever advice, coaching or recommendations people have that will make you better and help you be a better sales rep. Do it.

And then don't be afraid to look for other opportunities to expand your knowledge and your growth. Don't be afraid to ask your boss, what do I need to work on? How can I learn this skill? What do you see that I need to work on? Because everybody has blind spots. Everybody has gaps. And we may not be aware of those. Your boss probably knows. Ask them, and they can work with you on things to shore those things up.

Carter (16:09.39)
Okay, perfect. Well, that's helpful. I think we got some good stuff here. I'll end it here.

Craig Holbrook (16:14.904)
Alright, sounds good. Thank you, Carter. Appreciate the opportunity.