Case Study: How a Fractional CTO Rescued a Stalled Product and Went Full-Time in Four Months

Taylor Crane is the founder of Fractional Jobs, a matching service for fractional executive talent. In this case study, Taylor sat down with Kurt Chisholm, founder of LeaseUp, a commercial real estate technology company, to learn how working with a fractional CTO changed the trajectory of his business.

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Kurt Chisholm is the founder of LeaseUp, a data and transaction management platform that helps commercial real estate brokerages manage and facilitate their lease transactions with clients. The company is seed-stage with eight employees, and Kurt leads a small team that now includes Norm Metcalfe, who joined as a fractional CTO before becoming the company’s full-time Head of Engineering.

Kurt is a first-time founder who understands business, but he’s not an engineer. So when the technical side of the company started to face challenges, he needed someone who could not only diagnose the problem but actually fix it, someone who could write code, manage engineers, and think about the business at the same time.

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Code Red

LeaseUp’s previous technical leadership had made a call to rewrite the entire tech stack, and Kurt trusted the decision. But after months of work, not a single new feature had shipped.

“We spent a lot of time trying to build out a new tech stack without launching a single feature to the old one,” Kurt said. “Nothing got released. Nothing happened. It was code red.”

This left Kurt in a difficult position, with customers waiting for new features and the engineering team unable to make progress. And Kurt knew that if he didn’t act, the consequences would be severe.

“If we had decided to do nothing and stay the course, the business would have died,” Kurt said.

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Why Not Just Hire Full-Time?

Kurt needed someone with deep technical skill, real estate domain experience, and the business sense to understand the broader problem. That profile doesn’t come cheap, and hiring a top-tier executive full-time is difficult for early-stage companies regardless of price. LeaseUp wasn’t in a position to make a full-time executive hire, but needed someone highly capable.

“I knew we had a complex problem we had to solve, and we therefore needed someone who could do the pattern matching and help me figure it out,” he said.

People Kurt respected in the industry had recommended finding someone fractional.

“That piqued my interest to have someone who’s seen it before, can do the pattern matching, but doesn’t have to be full-time to diagnose what was going on and help us right the ship,” Kurt said.

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Finding Norm Through Fractional Jobs

Someone who was advising Kurt’s company informally referred him to Fractional Jobs. At first, Kurt was worried that a fractional hire wouldn’t be truly bought in and fully dedicated to helping LeaseUp.

“There’s always a concern that they’re not going to be bought in and therefore not going to give you the effort that you need,” Kurt said. “That comes from having worked with agencies or advisors who maybe instruct you to do a couple things but don’t have skin in the game.”

That concern faded once Kurt started talking to the candidates Fractional Jobs put in front of him.

“Every single person I talked to seemed like they could help me figure this out,” Kurt said. “I explained the problem, and in every case, it felt like the right plan.”

Norm stood out for several reasons: He had real estate technology experience, he’d been brought into exactly this kind of situation multiple times before, and he was deeply technical.

“As I explained the issue, he was starting to put pieces together before I even got to the next step of explaining the next part of the problem,” Kurt said. “He already knew it. That showed me he’d already seen this stuff before.”

Kurt also had Norm speak with technical people in his network, and the feedback was unanimously positive.

“Every person who talked to me afterward was like, yeah, he’s great. You should just work with him,” Kurt said.

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Stepping Into a Crisis

Norm started at 10 hours a week on a monthly retainer. The first few weeks were spent absorbing business context, meeting the engineering team, and getting oriented in the codebase.

Then, about three weeks in, the lead engineer had to suddenly step away, so Norm took over the project completely.

Kurt had been strategic about how he introduced Norm to the team. He didn’t call him a fractional CTO at first.

“I was like, hey, he’s a part-time engineer. He’s going to come in and help,” Kurt said. “When in reality, Norm had to go in and diagnose what was actually happening.”

It worked. “He’s an easy guy to get along with and easy to work with,” Kurt said. “Everyone kind of took to him pretty well. And then the other shoe dropped and he was able to step in and just take over.”

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The Turnaround

The first major test was the project that had stalled for months: a flexible data model system that would let every client team build their own custom data structures. It was the most complex thing LeaseUp had ever attempted, and had been unable to ship it in months.

Norm built it in roughly six weeks.

“That was a really big undertaking,” Kurt said.

From there, the pace never slowed down. Norm built out a full AI pipeline that lets users drop in market reports and data, which the system then strips, standardizes, and normalizes for client reporting. That feature alone now accounts for half of all platform usage.

“Half of the usage of our platform is directly tied to any feature that he built with the AI,” Kurt said.

Beyond individual features, the overall trajectory of the company shifted. LeaseUp went from a team that couldn’t ship to one that customers now trust to deliver.

“We are now seen in the market as a group that deploys features quickly,” Kurt said. “We were the opposite of that before.”

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From Fractional to Full-Time in Four Months

Within four months of starting as a fractional CTO, Norm joined LeaseUp full-time as Head of Engineering. He now manages the engineering team, sets technical goals, and owns the company’s product development roadmap.

“He went from just writing the code to owning it all as a full-time employee,” Kurt said. Kurt has complete confidence in what the company can build going forward. “Anything that we want to try to do in AI, we’re going to do right because we put the right foundation in because of his work,” he said.

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The Network Effect

One thing Kurt didn’t expect was the value of Norm’s professional network. Through working with Norm, Kurt was introduced to other experts who helped with different parts of the business.

“One thing that people probably don’t underwrite strongly enough is a fractional’s ability to actually open their network and introduce you to others and what that can mean,” Kurt said.

“The most surprising thing to me was just to see the level of buy-in and effort that I had gotten from Norm before he came in and joined full-time,” Kurt said. “He wanted to do good work and he wanted to add value and adhere to the promises that he’d given us during the initial conversations.”

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Kurt’s Advice for Other Founders

Kurt recommends going into a fractional engagement with a clearly defined problem.

“As long as you have a well-defined problem and you know what you need to get done, working with a fractional leader will provide an outsized value compared to probably anything else you could deploy or invest in to try to solve that problem,” he said.

He also cautioned against skipping that step. “You’d probably spend too much time in initial conversations with fractional people with them trying to pull it out of you,” Kurt said. “It’s a good idea to go through an exercise first to figure out what you need to get done.”

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If this case study resonates with you, and you want to bring in a Fractional CTO like Norm, or any other kind of fractions 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 LeaseUp?

A: LeaseUp is a data and transaction management platform for commercial real estate brokerages. The company helps teams manage and facilitate their lease transactions with clients. LeaseUp is seed-stage with eight employees.

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Q: How did LeaseUp find the right Fractional CTO for their needs?

A: LeaseUp worked with Fractional Jobs, a white-glove search service for fractional hiring. Fractional Jobs presented LeaseUp with high-quality candidates, one of whom was hired as a fractional CTO.

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Q: What does a fractional CTO do for a startup?

A: In this case, Norm Metcalfe came in at 10 hours a week to diagnose and fix a stalled product development effort. He rebuilt a complex data model system, took over engineering leadership when the previous lead departed, and built an AI pipeline. Within four months, he transitioned to a full-time Head of Engineering role.

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Q: How long did it take to fix the stalled product?

A: Norm rebuilt the core data model system, which had been stalled for months under the previous engineer, in roughly six weeks. He then continued shipping new features at a pace that changed how customers perceived the company.

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Q: Can a fractional CTO work in commercial real estate specifically?

A: Yes, but domain experience matters. Kurt specifically chose Norm because he had prior experience building technology for real estate and had been in similar turnaround situations multiple times before.

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Q: Did the fractional CTO become a full-time hire?

A: Yes. After four months as a fractional CTO working 10 hours a week, Norm joined LeaseUp full-time as Head of Engineering. Kurt credits the fractional engagement with giving both sides a chance to build trust and prove the fit before committing to a full-time role.

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Q: How can I hire a fractional CTO?

A: If you want to bring someone like Norm in to solve problems at your company, learn more here about how the Fractional Jobs network can help.