Case Study: How a Fractional Head of Sales Built Sales Muscle for a Bootstrapped, Profitable Healthcare Cloud Company

Taylor Crane is the founder of Fractional Jobs, a matching service for fractional executive talent. In this case study, Taylor sat down with Gerry Miller, founder and CEO of Cloudticity, a managed cloud and AI company built exclusively for healthcare, to learn how a fractional Head of Sales helped his team build sales muscle through a leadership transition.

Gerry Miller is the founder and CEO of Cloudticity, a managed cloud and AI company built exclusively for healthcare. Cloudticity helps healthcare organizations modernize and secure their technology, and the team measures its work less by servers patched or breaches avoided than by the outcome underneath it. “We measure our success in, have they been able to treat more patients?” Gerry said. “Did people get healthier quicker?”

Cloudticity is 15 years old, around $20 million in revenue, profitable, and entirely bootstrapped, with no outside investors and no debt. The team is lean, roughly 20 people. A serial founder, Gerry has scaled companies before and knows that different stages call for different leaders.

That awareness is exactly what led him to Fractional Jobs. As Cloudticity grew, Gerry needed to jumpstart the sales function after a full-time sales leader left the company and prior engagements didn’t work out. This time he wanted fresh thinking instead of another full-time bet.

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A Sales Gap a Founder Couldn’t Fill Himself

Gerry is candid about where his strengths end. “One of my weaker points of leadership is sales,” he said. “I’m good at envisioning where we need to go and what we need to do to get there, but the mechanics of sales have never been my thing. I can sell, but I can’t lead sales, and that deficiency is really what led me to reach out.”

It wasn’t for lack of trying. “We’d been through a few transitions of heads of sales,” Gerry said. “I’d hired a few people who just never really got the engine running.” Each time, he'd been looking for someone to take the role over for good but this time, what Gerry wanted was different. He wanted someone to come in, get the sales motion working, and then step back once the job was done.

That context shaped the decision in front of him. “That was the inflection point where Taylor and I connected.”

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Why Fractional, Not Another Full-Time Hire

“What wasn’t on the table was hiring another full-time person, because I don’t have a good track record of being successful there,” he said. “So I looked at agencies and all the alternatives, and what Fractional Jobs presented was the most compelling.”

His only real worry was one that applies to any sales hire. “Sales always has a ramp period, and if we couldn’t generate momentum, that’s wasted time,” Gerry said. “But that would have been true of any path I chose.”

What the fractional route added was optionality. “What hiring fractionally gave me was the ability to easily shift gears if I needed to,” he said.

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Why Fractional Jobs

Gerry found Fractional Jobs through another company’s blog post on fractional executives that gave the company a shout-out. He booked a call and reached out to Taylor directly, and that was as far as his search ever went. “Once I met you, I trusted you and I liked your business model, and I never pursued anything else,” he said.

What stood out was how easy the model made the whole thing. “Access to you was great, and your business model made it friction-free, really easy to do business with,” Gerry said. “And you brought a great slew of candidates to the table.”

The flat fee, in particular, set Fractional Jobs apart from other arrangements he’d used. “I do work with other fractional organizations that don’t follow your model, and that ongoing burn is painful,” he said. “Every month it makes me reconsider, do I continue down this path or hire someone full-time? With you, I never had that debate. And the fee was right in the sweet spot.”

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Why Chris

The candidate slate made the final decision genuinely hard. “They were great,” Gerry said. “The hardest part was choosing. There were three that were phenomenal, and two I really had a hard time picking between.”

‍Chris DeNoia won out on substance. “His track record of 20+ years in healthcare sales  set him apart,” Gerry said. “He’d done great work with some very good organizations, and he knew our business intimately.”

The process was deliberate. “We talked several times. I did the initial vetting, then introduced the final two across my leadership team,” Gerry said. “We probably talked six or seven times over a few weeks. It was a measured decision, but Chris stood above.”

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Part of the Team From Day One

Chris came on under a monthly retainer of roughly 10 to 15 hours a week, though Gerry never tracked it that way. “I never looked at the number of hours. I just looked at the engagement and the output,” he said. “He felt like a full-time member of our team.”

That wasn’t just a figure of speech. Chris joined the company offsite, worked alongside the leadership team, and was introduced to customers simply as the Cloudticity head of sales, not as a fractional contractor. “He may have had other clients, but we never felt secondary in his priorities,” Gerry said.

Onboarding ran through Cloudticity’s standard process, which is rigorous by necessity. “We serve healthcare, so there’s a lot of regulatory work, background checks, vetting, the whole thing,” Gerry said. “There was nothing different about bringing Chris on than anybody else.” From there, the working relationship was constant. “We’re a remote organization, and our culture is very communicative. He and I probably exchanged a hundred Slack messages, checked in on the phone, and joined each other on sales calls. The weekly one-on-one was more of a formality.”

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Building Sales Muscle

The mandate was clear from the start: stand up the sales function Gerry couldn’t build himself. “I needed somebody to act as a fractional head of sales, primarily as a coach, building the sales process and sales muscle, all the way down to auditing phone calls,” he said.

Chris didn’t stay in the coaching lane. “He took it upon himself to be more than that and started making his own sales calls,” Gerry said. “He led as a player-coach, and he did a really good job.”

The result was forward motion the company had been missing. “He helped drive sales, which is what we brought him on to do,” Gerry said. “During his tenure, we focused on the GTM plan, added pipeline, and closed some good deals.”

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Success with a Fractional Role

After several months, the engagement wrapped up, and Chris had done what he came in to do. “It was mission accomplished,” Gerry said. “We brought him on temporarily to do a particular thing, and he did it well.” For him, that clear engagement worked incredibly well. Results were delivered as expected, and the sales motion he'd brought Chris in to jumpstart was finally up and running.

The relationship even outlasted the contract. “He and I still communicate,” Gerry said. “He sent me a note just the other day.”

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Gerry’s Take: Fractional as a Tool in the Kit

Gerry would work with Fractional Jobs again without hesitation. “For sure, 100%,” he said. “I wouldn’t refer people to you if I wouldn’t use you again.” And he does refer people, on both the hiring and the candidate side.

His advice to founders weighing a fractional hire is, “Why not? You don’t have a lot to lose,” he said. “At that price point, if things go catastrophically wrong, so what? The candidates are great, the risk is minimal. There’s no reason not to do it.”

He has little patience for founders who insist every team member be full-time. “I’ll be blunt: that’s silly,” Gerry said. “As business owners, we’re here to achieve a mission. Be fanatical about why you’re doing what you’re doing, not about doing it one single way. You’ve got to take advantage of a huge variety of tools in your toolkit, and fractional talent is part of that toolkit.”

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If this case study resonates with you, and you want to bring in a fractional Head of Sales like Chris, or any other kind of fractional leader, learn more about how Fractional Jobs can help connect you to the right person for the job. You'll be working with Taylor directly.

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Frequently Asked Questions

Q: What is Cloudticity?

A: Cloudticity is a managed cloud and AI company built exclusively for healthcare. It helps healthcare organizations modernize, secure, and run their technology on the major cloud platforms while staying compliant, so they can focus on treating patients rather than managing IT. The company is 15 years old, profitable, and bootstrapped, with around $20 million in revenue and no outside investment.

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Q: How did Cloudticity find the right fractional Head of Sales?

A: Cloudticity worked with Fractional Jobs, a white-glove search service for fractional and contract hiring, after discovering it through a First Round Capital blog post on fractional executives. Fractional Jobs presented a slate of strong candidates, several of which the founder described as phenomenal, and Cloudticity hired one of them as its fractional Head of Sales.

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Q: What does a fractional Head of Sales do?

A: In this case, Chris DeNoia came on at roughly 10 to 15 hours a week to bring a fresh perspective to the sales function that the founder couldn’t do himself. He acted as a coach, built sales process and structure, audited calls, and then went further as a player-coach by running his own deals. During his tenure the company added pipeline and closed new business.

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Q: Does a fractional engagement have to be long-term to be successful?

A: No. Cloudticity brought on a fractional Head of Sales for a specific, time-bound goal: building sales muscle through a leadership transition. He accomplished it, the engagement reached its natural endpoint. A fractional role is a tool for a particular stage or problem, and a finite engagement can be a complete success.

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Q: Can a bootstrapped or mature company use a fractional hire?

A: Yes. Cloudticity is a profitable, 15-year-old, bootstrapped company with around $20 million in revenue, not an early-stage startup. A fractional hire gave it senior sales leadership with the flexibility to shift gears as needed, and without the long-term commitment of a full-time executive.

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Q: How can I hire a fractional Head of Sales?

A: If you want to bring someone in to build your sales function the way Chris did at Cloudticity, learn more here about how the Fractional Jobs network can help.