How to Scale a Sales Team From 19 to 100: Ashleigh Pepper's Kaizen Playbook
- The jump: In the stretch covered by this episode, Kaizen Promittere grew from 19 people and about $350,000 a month to nearly 100 team members and roughly $2.4 million a month.
- The engine: A structured leadership program turned 19 reps into 19 leaders, so the company could layer new recruits onto trained managers instead of stalling at the founder's capacity.
- The systems: A weekly meeting rhythm, a Tuesday-through-Saturday knocking schedule, a done-for-you recruiting machine, and a move from hourly pay to IRS tax code 3508 compounded into fast, durable growth.
Most home-service owners hit an invisible ceiling somewhere between 20 and 30 people. The founder is still the best recruiter, the best trainer, and the only real leader, so every attempt to grow just stretches that one person thinner. In this episode of the D2D Experts podcast, Ashleigh Pepper, CEO and founder of Kaizen Promittere, the direct sales arm of Renewal by Andersen, walks through how her company broke that ceiling and scaled fast without losing its people along the way.
The headline numbers from the episode are striking. The team went from 19 headcount toward crossing 100 in the week of the recording, and monthly revenue climbed from roughly $350,000 early in the year to about $2.4 million by the fall. What makes the story useful for other owners is not the growth itself but the specific, repeatable systems underneath it. Here is how it was built.
From 19 Reps to 19 Leaders: Build the Leadership Layer First
The single change that moved the business most was not a sales tactic. It was a leadership program. Kaizen rolled out an eight-week internal course, and the effect was immediate.
Ashleigh Pepper: that changed the business overnight because it gave a sense of growth within an organic ... ecosystem, if you will.
The point was to give people a path that was not just closing more and maxing out a commission check. A structured leadership track gave reps a reason to stay and a map for becoming a manager. As Pepper put it, people who did not even believe they had leadership qualities turned out to be some of the most natural leaders in the company once they were given the structure, the accountability, and the growth.
Her framing of what that leadership actually looks like is worth borrowing:
Ashleigh Pepper: it's okay to blend work and home life if it all works, right? Like if you're a good person at work, you should be a good person at home.
The math is what makes this the foundation for scale. You cannot run a 100-person team with two leaders. By putting people through a leadership development program in repeated cohorts, Kaizen turned its original 19 reps into 19 leaders. With 19 trained leaders, the company could layer roughly seven recruits onto each one and insulate the business. If someone leaves or has to be replaced, there is already a bench of people who know how to interview, train, and lead from the front. Leaders first, then recruits. That order is the whole game.
Put a Rhythm on the Calendar
Before the systems went in, the meeting cadence was thin. There was a national sales call once a month and no regular manager meeting. When asked why the national call only happened monthly, the honest answer in the episode was simply, "I don't know." That is the reality for most growing teams: the rhythm was never designed, it just happened.
The fix was a weekly operating rhythm. Executive calls on Monday set direction from the top. A weekly manager call on Tuesday then pushes that same information down through the leaders, so the whole organization is paddling in the same direction instead of each market guessing. On top of that, weekly rep calls now run with nearly full attendance, and the attendance is by choice rather than fear. People like the call.
The other calendar change was the week itself. Kaizen moved from a Monday-through-Friday schedule to Tuesday-through-Saturday knocking. Saturdays had been zero. Turning Saturday into a real production day while keeping a lighter Monday for new-hire training added a full selling day to every week without adding a single person.
Incentives That Last Longer Than Week One
Anyone who has run a sales contest knows the pattern: huge turnout the first week, then it fizzles. Kaizen built incentives to fight that decay. "Warrior Wednesday" earns reps the right to compete in a "Throwdown Thursday" competition, so they have to hit a goal just to be eligible. And a long-form summer contest called Summer Streets ran across the entire season with real swag on the line, including scooters for the top three.
Ashleigh Pepper: we were able to run Summer Streets literally for the entire summer and we saw week over week over week over week better and better and better and better.
The lesson for owners is that an incentive is a system, not an event. Structure it so people have to earn their way in, and so participation compounds instead of collapsing.
Pay People to Grow: Hourly, Then Commission, Then 3508
Compensation evolved in deliberate stages, and the sequence matters. Kaizen started on hourly pay for setters. The advice shared in the episode was blunt: if you were launching a door-to-door program from scratch today, you would probably pay hourly at first and invest in the business to get it going, because you do not want to train people and watch them turn over while you are still learning the model.
Hourly pay bought something specific. It kept the first class of future leaders around long enough to build loyalty and trust in the process. Once that foundation existed, the company moved to straight commission under a 1099 structure. The people who were good at the job did not flinch, because they were going to make more money anyway. Production climbed, attrition stayed low, and the reps who left during the switch were probably not the right fit to begin with.
The most advanced step was a shift to IRS tax code 3508, the direct-seller classification that lets a company set standards like a uniform while still paying people as 1099 contractors. The tax mechanics are a conversation for your own advisor, but the leadership lesson inside that transition is universal:
Ashleigh Pepper: when we rolled 3508 out ... it took me a week to speak to every individual in the organization to make sure that they understood not only what they're moving to, but the why behind it.
Nearly 100 people moved from W-2 hourly to a direct-seller commission model and, in her words, nobody of significance left. That is what happens when the why is explained one person at a time.
Build the Recruiting Machine, Then Teach People to Recruit
Early on, recruiting was entirely manual. The VP of Operations, John Edwards, personally combed through Indeed resumes, set candidates up on the calendar, and squeezed interviews between running day-to-day operations and new-hire training. It worked, barely, and it did not scale.
The answer came in two layers. First, Kaizen plugged into a done-for-you recruiting offering that writes and places the ads, screens the resumes, books candidates into group interviews, and handles the offer letters, welcome sequence, and pre-training reminders. That turned a frantic calendar into roughly four or five group interviews a week and put seven to 25 new hires into training every single Monday. If your own recruiting is the bottleneck, a done-for-you recruiting engine removes the admin work that keeps owners from growing.
The second layer is the one most owners skip. A do-it-for-you funnel is powerful, but it is also expensive at national scale, so the real goal is to teach your leaders to recruit on their own. Inside the leadership development program, people learn to build a hit list, to talk to people at the gas station, and to fish for themselves.
Ashleigh Pepper: You eat what you kill, right?
The results speak to the balance. Six months before the episode, essentially none of Kaizen's recruits were organic. By the time of the recording, organic hires were running around 30 to 40 percent, and the company still valued it as the gold standard. The paid machine fills the pipeline today; the leadership training makes the team self-sufficient tomorrow.
The Outside Perspective Every Operator Needs
One thread runs under every system above: the founder did not figure it out alone. Kaizen brought in a fractional CRO from the D2D Experts as a consultant and mentor, and a standing Friday call became the pressure-release valve that a CEO rarely has.
Ashleigh Pepper: as a leader, as a CEO, there is no book on ... how to be the best CEO possible.
The value, she explained, is perspective. A founder can walk out of a tough call with investors feeling like a complete failure, then talk to someone who understands the industry and realize the controllable parts of the business are actually being crushed. Asking for help, in that light, is not a weakness. It is getting everyone collaboratively aligned on the best next move.
What Scaling Really Protects
For all the systems and tax codes, the engine underneath Kaizen's growth is loyalty. People do not quit friendships, they quit jobs, and a leader who genuinely cares is hard to walk away from.
Ashleigh Pepper: every decision I make affects not only the people that work for me but their families. And I genuinely care about every individual that works for my organization.
Asked how many of her people would drop everything for her, Pepper flipped the question: if anybody in her organization called and asked her, she would be in the car. That is the kind of trust no compensation plan can buy, and it is exactly what makes a 100-person team hold together while it scales.
Her ambition for what comes next is bigger than a revenue target. She wants to build a movement, one where a team united behind a single goal can, in her words, achieve anything, absolutely anything, and where people who were never given an opportunity finally get one. Kaizen, fittingly, stands for constant, never-ending improvement.
For home-service owners trying to break their own ceiling, the pattern here is repeatable: build the leadership layer first, put a weekly rhythm on the calendar, make recruiting a machine and then a skill, pay people in a way that rewards growth, and never stop explaining the why. The systems are what let a business run without the founder in every seat.
