How Zach Miller Built a $22M Pipeline in a Year

Building a new sales motion from scratch—where do you start? 

In this episode, Jarod Greene sits down with Zach Miller, CRO of VanillaSoft, about the real challenges of creating an enterprise sales strategy without disrupting a successful SMB pipeline. Zach shares the hurdles of transitioning to long-cycle, multi-stage deals and the importance of surrounding yourself with the right team.

In this episode, you’ll learn:

1. Building an Enterprise Sales Motion from Scratch: Establishing an enterprise sales motion requires careful planning to maintain an existing SMB pipeline, balancing new processes with proven success in smaller markets.
2. The Power of Team Alignment: Having the right people with clear objectives allows for efficient scaling and helps tackle challenges as they arise.
3. Challenges of Long Sales Cycles: Staying focused on core priorities is essential to managing the complexity of multi-stage deals without being overwhelmed by details.
4. Filling Knowledge Gaps as a CRO: Broadening expertise beyond traditional sales, especially in marketing and SDR functions, can be crucial for a CRO stepping into an enterprise role.

Things to listen for:
(00:00) Zach Miller’s hot take on building an enterprise sales motion

(00:28) The challenge of balancing enterprise and SMB sales

(01:15) Tackling the hurdles of starting an outbound motion from scratch

(02:15) Keeping priorities straight while adapting to a constantly changing sales landscape

(02:41) The importance of team alignment and focusing on key outcomes

(04:07) Advice for first-time CROs on filling knowledge gaps beyond traditional sales

What is The Unexpected Lever?

The secret sauce to your sales success? It's what happens before the sale. It's the pre-sales. And it's more than demo automation. It's the work that goes on to connect technology and people in a really thoughtful way. If you want strong revenue, high retention, and shorter sales cycles, pre-work centered around the human that makes the dream work, but you already know that.

The Unexpected Lever is your partner in growing revenue by doing what you already do best—combining your technical skills with your strategic insights. Brought to you by Vivun, this show highlights the people and peers behind the brands who understand what it takes to grow revenue. You're not just preparing for the sale—you're unlocking potential.

Join us as we share stories of sales engineers who make a difference, their challenges, their successes, and the human connections that drive us all, one solution at a time.

Jarod Greene [00:00:00]:
Hey, Everybody. Welcome to V5, where we spent exactly five minutes getting on our soapbox with some of the hottest takes and topics in all of B2B sales. This is gonna be a fun one because I'm here with somebody I go way back with. This is Zach Miller, chief revenue officer of VanillaSoft, and I'm gonna let him explain his hot take. This was pretty good. So, Zach, I'm gonna start the timer. You get going, tell the people your hot and spicy take.

Zach Miller [00:00:28]:
Okay, here's my hot take. I joined as CRO of a software company, VanillaSoft about a year ago. My mandate was build an enterprise sales motion where one didn't exist, but don't screw up the SMB inbound. We got a marketing machine that's dedicated towards inbound fast twitch like get them in, get them closed, and then we got to go build a whole new organization and whole new mental mindset for the whole company around long, complex sales cycle, in-depth discovery, in-depth, multistage selling and multi-threaded deals. And turns out when you got to do that from scratch, there's a lot to it, man. Yeah.

Jarod Greene [00:01:15]:
What did you find to be one of the bigger hurdles?

Zach Miller [00:01:17]:
The zero to rolling. Just an outbound motion, right? Like literally just picking out your target. We're good in this category, and turns out that category isn't on the SIC pick list in any of the tools if you're really good at being the tool for a third-party SDR company. Third-party SDR company is not one of the industries tracked by Department of Labor. Anyway, so it's all these little things where I've never considered myself to be dumb. I don't think. I'm not the smartest guy in the room, but I'm not the dumbest guy in the room. But turns out there's just every time you turn another corner, there's another detail you got to go figure out. And keeping all that stuff straight with a small team and a small team that you're trying to kind of teach at the same time as you're building and then trying to teach, you know, the rest of the organization at the same time you're building, turns out there's a lot of stuff there.

Jarod Greene [00:02:15]:
I feel that I resemble that remark. One of the things that I think is difficult, Zach, is while you're doing all that, it's not as if the world's standing still. The best practices we might have used three, four years ago are the old things now. And the tools and the processes that, you know, we grew up on aren't the cool ones anymore. And so as the whole world evolves, we're just trying to catch up and keep pace. How are you dealing with it? How are you keeping it all in perspective?

Zach Miller [00:02:41]:
I'm trying to just keep the most important things at the forefront, right? The things that if we do them right, we'll look back in a year and say, okay, that was worth it. And not get too bogged down in the minutia, I think, is the most important thing that always comes down to the people you put around you. If you put the right people around you and you give those people the right tools and you trust them to go, you know, accomplish the tasks and the outcomes you need them to accomplish, then that's a really good start. You know, being clear with the team on what, what the desired outcomes are and when we need those desired outcomes and then giving them the latitude to go make those things happen, and then to make sure that you're, you're getting the things that are maybe the bottlenecks out of the way for them is the most important thing. And then it is kind of cool to turn around in a year and say, oh, wow, we started with zero pipeline, and we've built 22 million in pipeline in a year. Like, okay, you kind of take moments and you look out and you're like, wait a second, this is, this is where I'm kind of getting some of this done, right? And so you kind of feel like you're in the weeds, but then, you know, when you kind of stop and look back and take stock, you know, given that you've gotten people moving in the right direction, you've gotten the right people moving in the right direction. It's kind of fun to stop and see some of those things as they're.

Zach Miller [00:04:07]:
As they're happening.

Jarod Greene [00:04:08]:
So absolutely, yeah, look back, see how far you've gotten. That's awesome. Zach, what would you give a first-time CRO as advice? What would you tell someone who was a very successful sales leader, who's leveled up like you have about the journey and what it takes?

Zach Miller [00:04:25]:
Go get smart on the things that aren't in your wheelhouse before you get going. If you're a traditionally a sales leader and you're coming into a CRO role, go get smart on marketing. Go get smart on the SDR functions. Go get smart on product and product marketing. And if you're a CS led, go get smart on pre-sales. Right? Figure out where your gaps are in that broader space and get a plan you don't need an expert, but to get smart and to get well-versed in that broad. Certainly more broad aperture. Yeah.

Jarod Greene [00:04:59]:
Sound advice. And we're at time. Told you that would fly by. It's just like the year you just flew by.

Zach Miller [00:05:04]:
You just look back and you go, it's a year.

Jarod Greene [00:05:07]:
That was awesome, Zach. Well, thanks for hanging out five minutes playing the V5 with us. Appreciate you, man. All the best of luck to you and the team this year. Keep cranking.

Zach Miller [00:05:15]:
Thanks, buddy. You too. Got it.