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The secret sauce to your sales success? It’s what happens before the sale. It’s the planning, the strategy, the leadership. And it’s more than demo automation. It’s the thoughtful work that connects people, processes, and performance. If you want strong revenue, high retention, and shorter sales cycles, the pre-work—centered around the human—still makes the dream work. But you already know that.
The Unexpected Lever is your partner in growing revenue by doing what great sales leaders do best. Combining vision with execution. Brought to you by Vivun, this show highlights the people and peers behind the brands who understand what it takes to build and lead high-performing sales teams. You’re not just preparing for the sale—you’re unlocking potential.
Join us as we share stories of sales leaders who make a difference, their challenges, their wins, and the human connections that drive results, one solution at a time.
Jarod Greene (00:00):
Hello everybody and welcome to V5 where we spend exactly five minutes on our soapbox with some of the hottest takes in all of B2B SaaS sales and everything in between. I'm here with Andrew Berger, who is the VP of Revenue at Capchase. I don't know Andrew's hot take, I promise you guys, but I think we're getting into something spicy, so Andrew, you know the game, you know how to play it, what you got?
Andrew Berger (00:24):
Yeah, this is fun. Thank you for having me. I appreciate being here. So I was kind of thinking about a couple of different ways to take this. I could jump on the train of either saying AI is the greatest gift and sliced bread, or saying it's a demon in God going to take us all down, but I'm going to save that for the AI experts. My hot take is that quarterly territory planning or annual territory planning is a big performative waste of time, complete waste of time. There are elements that are really good structures and gets reps minds thinking the right way. You get to explore how you want to be creative. Penetrating an account or growing a use case or expanding an account or breaking into an account. It's like many hours of time. There's a sales leader and rev ops and probably marketing are spending a lot of time pulling in information.
Andrew Berger (01:11):
Then there is like what's the right format and structure and then you disseminate across the team and then you give everybody an hour, maybe sometimes 90 minutes depending on what your quota is, what your territory is, and then you spend four or five hours going through this. You have a team of six to eight on a per rep basis. So let's say everyone's having one hour, so that's six people times one hour, that's six hours. Let's say there's three or four teams in the segment or in the org you're talking like 24 to 30 hours, almost a full business week. Just kind of pontificating about what am I going to do the next quarter, two quarters, three quarters, four quarters, maybe even the next year to break into this account. I feel like they all have really good intention. I fall victim to it, I've done it, I've been a rep, been doing it, I've been a leader and asking people to do it and I just look around the room and I see eyes glazing over, I see uncomfortability in the hot seat and maybe that's part of the game to make people feel uncomfortable but get anxious about it and do I want to make my reps anxious about just a presentation that they're just given to me and their peers?
Andrew Berger (02:08):
And so I just think it's at the end of the day, it's kind of a waste of time and what I've started to do was look back of how are we mapping back towards the work that we have done and maybe this approach was the right process, 10, 15, 20 years ago. The velocity of information and how dynamic business environments are now. I just think that by the time you're on your eighth account that you're giving territory plan on that you like your P three account and maybe you'll get to that account in two or three months. Their world has shifted a full quarter later. So I think there's a few different ways to do it moving forward, but just this whole presentation aspect in front of everybody spending a ton of time. If we can get out of this mindset and maybe work on a better way of doing it, hello AI tools to collaborate all information for you, you can put in prompts to give you information and then have that be dynamically updated. I think it's a bygone era.
Jarod Greene (03:01):
It's a much better path. Yeah, I was going to ask what the alternative was because I think again, when we always talk about sales and sales evolution, nobody went to school and said, Hey, I want to be a B2B sales rep. We ended up in the space and we may have different skills for different, but we all learned from a playbook that someone else developed and then we evolved that playbook and we evolve that playbook. And to your point on velocity, everything has changed so fast so quickly. So again, when we think about these next practices and how they evolve, I think as leaders like yourself and other folks who just ask the obvious question, why the hell are we doing this? And ask it in a safe space and provide that alternative you've had success with say, look, we're not going to do this at this type of cadence. What results have you seen from breaking that book?
Andrew Berger (03:41):
I'll riff a little bit on the playbook stuff. I mean, I came up from the Aaron Ross, predictable revenue playbook, massive leads, inbound reps, outbound reps, and then just have this funnel go a wide to narrow funnel and that got us to some layer and then it's okay, now we're in the big leagues, we're going to go start to sell a hundred, 200, 300 K contracts, million dollar contracts, multimillion dollar contracts, alright, it's MEDDPICC or die. And so it's like predictable revenue to big opportunity qualifiers to then extrapolate that information into these presentations and whatnot. I wish that I had the answer what's next, but I do think integrating is best. Some things that we're playing with or that my peers and my friends are playing with is just connecting all the data systems together in a sort of prompt esque of mechanism to minimize all the collating information.
Andrew Berger (04:31):
I think the territory planning and account planning is all about just taking information that's in disparate places and putting on a spreadsheet, but guess what? There's agents that can go do that for you and there's systems you can go prompt against that. So I see it more as an efficient way for a rep or even myself to analyze the future of our opportunities and execute faster. A simple way of doing that is if you have the data flowing to whatever your favorite tool is right now and just prompt of pretend that I'm trying to crack into that account and that agent is trained on your data and your systems and how you operate, what are the three best ways for me to go crack into that account instead of just being like, okay, here's their revenue, here's their employee growth, here's their sales nav. It's like all that data lives already. Just make it queryable and then just leverage that as a prompt. That's stuff that I'm starting to play with on my own. I wish I had the right answer for you. Maybe I'll come back to see if I'm right or wrong in a year from now, but I think that's the next evolution in B2B sales for sure.
Jarod Greene (05:29):
Totally. Yeah. I always say once it's out in a spreadsheet of stale, there's also the book of best practices that we've all learned in the last quarter. And so what we might do in an account plan that was tried and true best practice before may have evolved completely. And especially in where we are today with the products and services we sell, they evolve fast, they evolve really quickly. So even what we thought we were going to sell 'em as far as this solution, it has this feature center solves this use case that may be completely obliterated. So the speed and the velocity on both sides I think warrants a new approach and we appreciate you pushing against the status quo so that we could all evolve accordingly.
Andrew Berger (06:06):
I say a year ago I was a little bit lost in the sauce of where things are going to go and now I'm just having fun building no-code apps for our team for efficiency or just playing with tools. And I'd say a year ago I was just exploring with ChatGPT and now it's my number one browser tab and the upswing of tools to make our jobs better and more informative and more accurate is pretty fun and revolutionary right now for sales.
Jarod Greene (06:35):
Yeah, it's what a time. I agree with the word fun. There's probably a realm of use cases I'm sure we all test and learn and as a community, as a group share those, we evolve those and everybody's got a new bag of practices, so we appreciate it. If folks want to find you and connect, learn more about you, where do they do that?
Andrew Berger (06:52):
Yeah, well I have an ex handle that is literally just retweeting Bay Area Sports, so that's not too fun. So LinkedIn, Andrew Berger, B-E-R-G-E-R. You can find me anytime.
Jarod Greene (07:04):
Awesome, you guys hit 'em up. Andrew, thanks for spending. Want to say man, appreciate you.
Andrew Berger (07:08):
Thank you.