The Leader Who Gets You Here Won't Get You There

The same moment, over and over

Ty West joined a telecom startup with zero customers. The first ones came the way first customers always do: hustle, and doing everything himself. It worked. Then, somewhere around a few hundred thousand customers, it stopped working.

"By a few hundred thousand customers, that approach was holding us back," he says. "The company needed us to build teams, processes and leaders, not close deals myself."

SunCom Wireless grew past a million customers. Ty credits that to a decision he has kept making ever since: changing how he leads at each stage, before the company has to force the change on him.

Ask him for the moment that defined him as a leader and he pushes back on the premise. "It wasn't one moment," he says. "It was the same moment, over and over."

Learned it, proved it, scaled it

Learned it. At SunCom, Ty learned that the playbook that wins your first customers is not the one that wins your next million.

Proved it. At Imagine Learning, the same lesson arrived at a bigger scale. At around $5 million the company sold school by school. Ty helped shift it to selling district by district, then took on state adoption work alongside lobbyists. At about $30 million, private equity came in and the stakes went up. "The board wanted predictable growth, not heroics," he says. He rebuilt the sales organization and brought in leaders "stronger than me in their areas." The company passed $160 million.

Scaled it. At Age of Learning, Ty took Schools ARR from under $1 million to more than $15 million in 24 months. Then came a turnaround at a nine-figure managed IT company assembled from five acquisitions across four regions. Sales had been declining for 18 months, and the company was selling more than 100 vendor lines with no focus. Ty cut the vendors to about 10, concentrated on government, education and medical buyers, and ran the business on EOS: scorecards, quarterly Rocks and weekly accountability. Sales rose 30% year over year.

1M+

customers at SunCom Wireless

$5M → $160M+

revenue at Imagine Learning

<$1M → $15M+

Schools ARR in 24 months at Age of Learning

The trap of your own success

Ty is candid about the moment Imagine Learning nearly slowed itself down. The sales model that took the company from $5 million to $30 million was built for winning new logos. By the time PE arrived, about 90% of revenue was coming from existing customers, and renewals and expansions were eating the team's time.

The fix was to rebuild around the customer base. Ty separated hunting from farming, rewrote compensation around retention and expansion, and changed the board scorecard to match. That reset, he says, is a big part of how the company got from $30 million to $160 million.

"What gets you to $10M won't get you to $50M, and what gets you to $50M won't get you to $150M."

He now plans for those resets in advance. "I name the next milestone and design the next version of the organization before the current one stops working."

Why fractional, why now

"Most growth companies don't need a full-time CRO yet," Ty says. "They need someone who has already built the engine to install it."

The model also changes the conversation. As a fractional leader, he can have open and honest conversations with a CEO and board "without job security riding on it," and he is measured on results, not time in the seat.

Working inside The Proper Group matters for a simple reason. "CEOs rarely have just a revenue problem," he says. "It's usually tied to cash, people or operations." In a recent cash-crisis engagement, Ty owned revenue and renewals while TPG colleagues ran finance and operations alongside him. One problem, solved by a team that showed up the same week.

What Ty is seeing

Buyers have stopped waiting for sales. "Buyers now finish most of their research before they talk to sales," Ty says. "Reps who only pass along information are losing value fast." The data agrees. In a Gartner survey of 646 B2B buyers, published in March 2026, 67% said they prefer a buying experience with no sales rep involved, up from 61% a year earlier. But a May 2026 Gartner follow-up found that 69% of B2B buyers turn to sales reps to validate what AI tools tell them. That is exactly where an operator earns the seat.

Pipelines look full but don't close. The CEOs Ty works with worry most about predictable revenue. Pipelines look healthy, deals slip, renewals are at risk, and PE owners want growth and cash discipline at the same time.

Your existing customers are now your growth engine. What Ty saw at Imagine Learning is now the norm. Benchmarkit's 2025 SaaS benchmarks show B2B SaaS companies generating 40% of their new ARR from existing customers, even as median net revenue retention slipped from 105% in 2021 to 101% in 2024. Companies are leaning harder on their customer base while keeping less of it. "Who owns the customer after the sale closes?" is one of the first questions Ty asks a CEO.

The most common mistake. Hiring more reps to fix a pipeline problem. "If the ideal customer, the process and the metrics aren't defined, more reps just make the misses more expensive."

On AI. Ty sees real gains in account research, call prep and first drafts, saving reps hours a week. But "it doesn't fix a bad ICP or a broken handoff. It makes a good process faster and a bad one fail sooner."

Overrated: new tech stacks. Underrated: a weekly scorecard the leadership team actually reviews and acts on.

The operator's playbook

Ty's first three questions for a CEO:

1. Where did last year's revenue really come from?
2. What percentage of the forecast closed as predicted?
3. Who owns the customer after the sale closes?

His first 90 days:

Call Ty when

• the forecast keeps missing and no one can explain why
• revenue has stalled after a strong run
• you just closed an acquisition and need the sales teams combined
• renewals are slipping and you hear about it too late
• you need a go-to-market or sales leader but aren't ready to hire one full-time

Signs you need him before you know it: the founder still closes the big deals, sales cycles keep getting longer, every rep sells differently, and the CRM doesn't match what the board sees.

Work with Ty

Bring him in as your fractional CRO. Senior revenue leadership, typically for 6 to 18 months, with a planned transfer to your own team.

Start with a Post-Close Sprint. Just closed an acquisition? Combining acquired sales teams into one revenue engine is work Ty has done at multiple organizations.

Not sure where the gap is? Take The Proper Read. The 3-minute Quick Read shows where your leadership capacity gap sits.

Talk with Ty West

twest@theproper.group

Book a conversation with TyTake the Quick Read

Ty is one of the executives in The Proper Group. Tell us the moment you're in, and we'll bring the right operator.

Off the clock

Ty coaches youth basketball and softball, plays weekend pickup basketball and sand volleyball, and travels whenever he can. The best advice he ever got: "Begin with the end in mind," from Stephen Covey. The book that shaped how he leads: Patrick Lencioni's The Five Dysfunctions of a Team.

The Proper Group is a collective of experienced C-suite leaders serving organizations and individuals committed to growth. Through Collective Leadership, we embed at inflection points, creating lasting capability and sustained success. The Proper Way.