Case Study: How an Interim CTO Stepped In to Fill a Leadership Gap and Keep a Startup on Track

‍Taylor Crane is the founder of Fractional Jobs, a matching service for fractional executive talent. In this case study, Taylor sat down with Hari Raghavan, co-founder and CEO of Autograph, an AI company building agents for finance and operations teams, to learn how bringing on an interim CTO changed the trajectory of his business.

Hari Raghavan is the co-founder and CEO of Autograph, a startup building AI agents for finance and operations teams. Autograph works with companies of roughly 100 to 1,000 employees, deploying agents to handle the repetitive processes that eat up a team’s time: assembling reports, running reconciliations, chasing approvals, and pulling together analysis. Most of its work today centers on finance and HR.

Autograph is early-stage and lean. The company has just three people, and all of them ship code. Hari and his cofounder are both non-technical by background, which meant that when it came to engineering, Autograph leaned heavily on a single person to carry the technical load.

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A Unique Role

In the fall of 2025, as Autograph’s CTO stepped down and around the same time, the company had parted ways with its only other engineer. Autograph had recently brought on a contract engineer as a stopgap, but he wasn’t senior or strategic enough to carry the mantle of engineering lead.

“We had no really reliable engineering capacity,” Hari said. The company needed someone the buck could stop with, at least from an engineering perspective.

Filling this role was essential and time-sensitive. Autograph was in an important stretch and the engineering work in front of them was critical.

“There was no option not to. We had to hire this person,” Hari said. “It was a singleton role.”

Asked what would have happened if he hadn’t found the right person, Hari was blunt: “Without him on board, it is possible we would have had to wind down.”

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Why a Contract Hire, Not a Full-Time Employee?

Hari didn’t want to rush into a permanent, full-time hire, and not because of cost. Early stage startups are risky, and he wasn’t willing to make a long-term promise he might not be able to keep.

“Even with people we were talking to as potential full-time hires, I’d say, ‘I just want to let you know,’” Hari said. Some candidates bowed out. “But I’d rather do that than rug pull them.”

A contract engagement solved the problem. It gave both sides flexibility and optionality, and it fit the way Hari already liked to operate: with work trials.

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Why Fractional Jobs

Hari found Fractional Jobs through Taylor directly. He had tweeted about the need, and Taylor responded.

“I’ve worked with a dozen, if not more, recruiters, and I’ve had nothing but bad experiences,” Hari said. “You’re probably the first one I’d ever recommend to somebody.”

He pointed to three things that set the process apart. First, the quality and relevance of the candidates.

“You actually seemed to understand what I was looking for,” Hari said. “The people we ended up talking to were generally pretty high quality, and very few felt like a waste of time. The hit rate was pretty high.”

Second, the process itself was fast and structured. “Expectations were very clear. I knew I was going to send this out Monday, and by Tuesday or Wednesday you’d send me profiles. It was a very structured process,” he said.

And third, the model felt aligned. “Everyone else over-promises and under-delivers, charges an arm and a leg, and it feels slimy and transactional,” Hari said. “Here, it generally felt like you actually wanted us to succeed. We just felt aligned.”

He also valued that the contract model represented a way to test the relationship from both sides. “We can test out working together, and prove ourselves, and they can prove themselves,” he said. “That’s very interesting to me.”

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Clearing an Obscenely High Bar

There was really only one litmus test for the hire, and it belonged to Autograph’s outgoing CTO, who had what Hari called an obscenely high bar.

The departing CTO interviewed candidates as part of finding his own replacement. Jason Morganson was the first person, out of roughly eight, that he greenlit.

His conclusion, as Hari recalled it: “I can’t tell from just an interview process if he’s insanely good or very good, but he’s definitely at least very good.” It was a high bar to clear.

Jason brought more than raw engineering ability. He had built and run engineering teams before, so he thought naturally about what scales, and in conversation it was clear he’d already done work directly relevant to what Autograph was building.

The interview process was deliberately streamlined. It involved a conversation with Hari, a conversation with the CTO, and a third call that was less an interview than a frank discussion of comp and working style. “Especially with the concept of a work trial, you shouldn’t overdo the interview process,” Hari said. They quickly agreed to work together through the critical stretch, from October into the new year.

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Owning the Hard Problems

Jason came in as the engineer the buck stops with, and his scope reflected it. He took ownership of the parts of the codebase that were less about any single feature and more about whether the whole thing would hold up: continuous integration and test suites, reconfiguring authentication, security, spinning up sandboxes with test data for new users, and building out CSV import flows.

His biggest project was building Autograph’s entire agent framework, from contact management to memory to tooling. That work included foundational, hard-to-reverse choices, like which framework the company should build its agents on.

“That’s a one-way-door decision,” Hari said. “I would trust him 10x more than me to do the investigation to figure out an answer like that.”

As trust built, Jason’s scope widened. “At first there were more discrete, self-contained projects,” Hari said. “By month three, it was more cross-cutting, very broad stuff.”

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A Difference of Kind, Not Degree

The agent framework was the most important thing Jason built, because it was the foundation everything else would sit on. And its value wasn’t incremental.

“It’s very binary,” Hari said. “It’s not like you add one more engineer and unlock a little more. It’s a difference of kind, not of degree. You could either do this thing, or you could not do this thing.”

Autograph had to answer a fundamental question by January: did the product, the architecture, and the team have the right to keep going? With Jason carrying the engineering, they got their answer, and continued to grow the business.

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A Contractor With an Owner’s Mindset

What surprised Hari most was that he never had to manage Jason.

“Once he got into a rhythm, I didn’t usually have to ask him to do stuff. He’d just do it on his own,” Hari said. In the absence of explicit direction, Jason would go off and tackle the things that should be done but that no one had asked for.

“If it weren’t for that, it would have felt like a temporary thing,” Hari said. “Whereas now it feels like a permanent thing. That, to me, is the difference between a contractor mindset and a teammate mindset.”

The fact that Jason was technically a contractor, Hari said, didn’t matter at all. He had become, in every way that counts, the company’s technical leader and a permanent part of the team.

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Hari’s Advice for Other Founders

For founders making a small number of critical hires, Hari is now a firm believer in the work-trial model.

“Unless you’re hiring large numbers of people, if you’re hiring for one or two people, you should almost certainly be doing work trials,” he said. “The risk of a false positive in the hiring process is so much greater than the risk of a false negative.”

The trouble, he noted, is that work trials usually aren’t feasible, because strong candidates already have full-time jobs. That is exactly what the fractional and contract model solves.

“The very nature of the matching you’re doing complements that,” Hari said. “It’s a way for us to de-risk that relationship when we’re making a singleton hire. That is honestly the main way startups should do it.”

Would he use Fractional Jobs again? “Yeah, totally.”

‍If this case study resonates with you, and you want to bring in a CTO like Jason, 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 Autograph?

A: Autograph is an early-stage AI company that builds agents for finance and HR  teams. Its agents automate repetitive processes like reporting, reconciliations, approvals, and analysis. The company works with organizations of roughly 100 to 1,000 employees.

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Q: How did Autograph find the right interim CTO for their needs?

A: Autograph worked with Fractional Jobs, a white-glove search service for fractional and interim hiring. Fractional Jobs presented a curated set of high-quality candidates, one of whom was hired as the company’s interim CTO on a contract basis.

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Q: What does an interim CTO do for an early-stage startup?

A: In this case, Jason Morganson became the engineer the buck stops with. He owned engineering best practices, continuous integration and testing, authentication, and security, and he built out the company’s entire agent framework, including foundational, hard-to-reverse architectural decisions. As trust grew, his scope expanded from discrete projects to broad, cross-cutting ownership.

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Q: What was the biggest result?

A: Jason built Autograph’s core agent framework, the foundation the rest of the product depends on. His engineering work allowed the company to keep shipping through a critical stretch and answer a make-or-break question about its future. The CEO said that without the right hire, the company might not have been able to keep going.

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Q: Why hire on a contract basis instead of full-time?

A: A contract engagement gave both sides flexibility and functioned as a work trial. On a fully loaded cost basis, he considered 1099 versus W-2 a neutral, trivial distinction.

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Q: How can I hire an interim or fractional CTO?

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