Haven't searched for a job in a decade? 36 interviews later

When I first spoke with this client, he had spent nearly 30 years in enterprise technology and product leadership, managed large teams, worked with Fortune 500 companies, and even taken a computer-vision startup to market before it was acquired.

He'd then spent another three and a half years helping integrate that technology into a global AdTech company's products, eventually moving into GenAI, LLMs and agentic AI initiatives.

His stock had vested, his tenure was coming to an end, and he was beginning to think about what came next.

There was no immediate urgency. He was helping a friend build a startup, had plenty of other commitments, and wasn't even sure whether he wanted to begin searching in January or wait until March.

He hadn't been in the job market for a long while

But there was one problem.

“To be honest, I've never been in the job market for quite a long while now.”

For most of his career, opportunities had come through relationships and professional connections. Naturally, that was the first approach he tried again.

When we asked how much success he was having with it, he gave us a simple:

“Not a lot.”

He wanted to explore VP and senior AI leadership opportunities in the Bay Area, ideally helping enterprises adopt GenAI and agentic technologies. He was open to startups, established companies, and even wanted us to explore ambitious targets like OpenAI and Anthropic.

Fair questions before he committed

He also had some very reasonable questions about whether we could actually pull this off.

He wanted to know how many executives at his level we'd helped, whether enough suitable opportunities existed, and what our market audit would reveal before he committed.

Fair questions, all of them. So we presented him with the data, after which he was eager to work together.

Positioning 30 years of experience

His background stretched across financial services, enterprise products, startup leadership and AI. He was particularly concerned that some of his earlier experience might get lost while updating his resume.

Meanwhile, he was finding interesting openings at companies like Adobe and ServiceNow and wanted to know how to feed them into our process.

So we worked on positioning his experience for the roles he wanted, identifying suitable opportunities, and managing the applications and outreach while he continued with his other commitments.

36 interviews and a Director of GenAI offer

That search eventually generated 36 interviews, including Visa, Adobe, Fiserv, Figma, Salesforce, GEICO and HighLevel.

And ultimately, he accepted a Director of GenAI offer with $250K in base compensation and $500K+ in total compensation.

Just like you, he was already an accomplished technology leader when we met him. He had the experience, the technical understanding, and a pretty clear idea of the kind of problems he wanted to solve.

He just hadn't needed to navigate an external job market in over a decade.

If you're in a similar position, that's exactly where my team can help. If you too want to wake up to notifications saying your target interviews have been scheduled without you doing anything, book a call with us.