How a product executive who had not job searched in over 10 years landed a Director of GenAI role at $240,000+ base

This client was a product executive with 25 to 30 years of enterprise experience, including leadership roles across technology, product, AI and enterprise transformation. Most recently he had spent more than three years at a global AdTech company, where he worked on GenAI, LLM and agentic initiatives. Before that he had taken a computer vision startup to market and worked with Fortune 500 customers. He had led large teams, worked across product and technology, and operated at an executive level for years.

He landed a Director of GenAI role with an IT services and consulting company, at more than $240,000 base and more than $320,000 in total compensation.

He had not been in the job market for over a decade

When we first spoke, he told us his biggest problem straight away:

“To be honest, I've never been in the job market for quite a long while now, more than 10 years.”

His previous moves had mostly happened through his network. When we asked how much that approach was producing for him now, the answer was short:

“Not a lot.”

He was also helping a friend with a startup, so running a full executive search himself was going to be hard to fit in.

“I have a lot of other things on my plate... my plate's full.”

What he was looking for

He was based in the Bay Area and wanted to stay there. He was targeting senior product and AI leadership roles, with compensation expectations of around $275,000 base plus bonus and equity. More than the number, he wanted his next role to connect to the work he had been doing in GenAI, LLMs and agentic technology.

He mentioned companies like OpenAI and Anthropic, and he was also open to established enterprises, mid-sized companies and interesting startups.

A broad career, packaged for today's market

His career was broad, and that cut both ways. He had experience across financial services, enterprise technology, product leadership, analytics, AI and startups, and he worried that narrowing his resume too hard would leave a lot of that behind.

Learning how a modern senior leadership search works, and then running one on top of his existing commitments, was more than he had time for, so he decided to partner with us. The first job was working out how to turn 25 to 30 years of experience into a story that made sense to the current market.

We centred the positioning on his most commercially relevant experience: AI transformation, GenAI, LLMs, agentic technology, product leadership and enterprise adoption.

Going after the roles directly

We stopped waiting for the right opportunity to come through his network. We identified the relevant companies and leadership roles ourselves and went after them with direct outreach, applications and follow ups.

His network was valuable, and it had carried every move he had made for years. What he needed now was a system that kept putting his profile in front of the people actually involved in hiring, week after week.

That search produced 36 interviews, at companies including:

• Visa
• Adobe
• Fiserv
• Figma
• Salesforce
• GEICO
• HighLevel

and many others. He accepted the Director of GenAI role at more than $240,000 base, with total compensation above $320,000.

If you have built your career the same way

He had spent more than a decade building enterprise AI and data platforms, so he had never needed to learn how the job market had changed. Most senior technology leaders who have spent 10, 15 or 20 years building their careers are in the same spot. Companies now lean on structured recruiting processes, online applications, recruiters, hiring manager outreach and very specific positioning. Your experience is valuable. It needs to be translated into a format today's recruiters recognize, and are ready to pay for.

The search in numbers

• More than 10 years since his last search, with his network producing "not a lot"
• 36 interviews, including Visa, Adobe, Fiserv, Figma, Salesforce, GEICO and HighLevel
• Director of GenAI at $240,000+ base, $320,000+ total compensation
• Level: Director. Function: AI and Machine Learning