I joined David Dulany on The Tenbound Sales Technology Podcast to talk about something I lived and breathed for eight years: building and scaling a sales organization at Vendasta. As Chief Customer Officer and SVP of Sales, I had a front-row seat to what it takes to grow a sales team from scratch and turn a platform into something that serves over 50,000 channel partners.
David asked me to share the lessons I picked up along the way, and I was happy to dig into the real stuff: team growth, employee retention, and the systems that actually move the needle when you are trying to create what I call rocketship growth.
The Foundation: Getting the Right People on the Bus
When I think about scaling a sales team, everything starts with people. At Vendasta, we grew from a small team to a large, multi-layered sales organization. That kind of growth breaks things if you are not intentional about who you hire and how you bring them in.
The biggest mistake I see companies make is hiring for speed instead of fit. When you are in growth mode, the pressure to fill seats is real. Revenue targets are climbing, territories are expanding, and leadership wants results yesterday. But every time we rushed a hire at Vendasta, it cost us more than the empty seat ever did.
What worked for us was getting disciplined about our hiring profile. We looked for people who were coachable, curious, and competitive. Not just competitive in a “win at all costs” way, but people who wanted to beat their own numbers. People who took feedback and actually did something with it the next day.
Retention Is the Growth Strategy Nobody Talks About
David and I spent a good chunk of the conversation on employee retention, and for good reason. You cannot build a rocketship if people keep jumping off. Turnover in sales is expensive. You lose institutional knowledge, customer relationships, and momentum.
At Vendasta, we learned that retention is not about ping pong tables or free snacks. It comes down to three things:
- Career path clarity. People need to see where they are going. If a rep cannot picture their next role, they will find one somewhere else.
- Coaching, not just managing. The best sales leaders I worked with spent more time developing their people than reviewing dashboards. Reps who feel invested in stay longer and perform better.
- Winning culture. This sounds abstract, but it is not. Celebrate wins publicly. Address underperformance privately. Make the team feel like they are part of something bigger than their individual quota.
One thing I told David is that retention compounds over time. When you keep good people, they train the next generation. They carry the culture. They become the leaders you did not have to go recruit from outside.
Scaling to 50,000 Channel Partners
Vendasta operates as a platform that powers local businesses through channel partners like agencies, media companies, and resellers. Getting to 50,000 of them did not happen by accident. It required a sales team that understood the product deeply and could sell the vision, not just the features.
We had to build systems that supported partners at scale rather than relying on one-to-one relationships for everything. That meant investing in onboarding, enablement, and customer success alongside the sales team. The sales team could not just close deals and walk away. They had to set partners up for success from day one, because a churned partner is worse than no partner at all.
This is where alignment between sales, product, and customer success became critical. If we sold something the product could not deliver, we burned trust. If customer success was not looped in early, the handoff was rough. The organizations that win are the ones where everyone is rowing in the same direction.
What I Would Tell Sales Leaders Building Teams Today
Looking back at those eight years, a few things stand out as lessons I would pass on to anyone scaling a sales team right now.
First, do not skip the fundamentals. It is tempting to chase the latest sales tech or methodology. But if your reps cannot run a solid discovery call and your pipeline hygiene is a disaster, no tool is going to save you.
Second, measure what matters. Activity metrics have their place, but outcomes matter more. Are your reps having quality conversations? Are deals moving forward? Is your pipeline real, or is it full of stalled opportunities that nobody wants to clean out?
Third, invest in your managers. Frontline sales managers are the most leveraged role in any sales organization. A great manager multiplies the output of every rep on their team. A bad one drags the whole group down. Train them. Support them. Hold them accountable for developing people, not just hitting numbers.
Rocketship Growth Is About Consistency
Rocketship growth does not come from tricks. It comes from doing the basics exceptionally well, over and over again, while continuously improving. That is what I learned in eight years of building a sales team at Vendasta. And it is something I carry with me in everything I do today.
If you want to hear the full conversation, hit play on the episode above. David does a great job pulling out the nuances that are hard to capture in a written summary.