Job Search Retro: Forward Deployed Strategist

James landed a Forward Deployed Strategist role at a growth stage AI agent company.

Hedgy Member Background

• Previously worked as a former consultant.
• Intentionally was targeting forward deployed roles that would allow him to be more customer facing while being hands on with product development.
• Received 7 intros and 1 offer through Hedgy.

Key Insights

"Forward deployed" is a label, not a job description

• James quickly learned every company means something different by it. For one interview process, he was already several conversations in before realizing that the company’s expectations of a forward deployed role were not a fit for him.
• As an example, one fork in the road for the role was how customer facing and hands-on versus internal and strategy heavy it was. Another is how technical the role can be or how close to the product and engineering team the collaboration is.
• He wanted continued technical exposure and optionality to move toward core PM work later.

An AI agent case study

• Unlike a forward deployed engineering role which may focus more on coding, James’ interviews focused more on how to think about agents behaving in production.
• A sample exercise: he was shown a fictional chat history between an AI agent and a customer whose flight had been canceled, and asked what went wrong and what should be improved.
• Typically an AI agent may want to jump straight into rebooking options. The irony is that this misses a human element that would be the hallmark of great customer service: acknowledging the customer inconvenience and apologizing for any mistakes the airline may have made.
• Lastly, expect eval questions as their own theme. You may be asked how you would test the agent: what samples you’d look at, and what success rate you’re targeting. Anthropic has written a blog post on this if you want to go deeper.

What the forward deployed PM role actually looks like from the inside

• His main counterpart on the customer side is customer experience leadership or similar, not engineering. Technical stakeholders get pulled in, but they aren't the primary relationship.
• Account load is inversely related to customer size. At any given time, he may have 1 or 2 large enterprise customers running multiple agent products (chat, voice) as his full-time responsibilities. Whereas he could have double or triple that if the customers are smaller.
• He also noted forward deployed PM and forward deployed engineer roles are converging. PMs are being pushed toward more technical readiness work like API integrations, and engineers toward more customer-facing work. To help accelerate this his company has an internal platform for building agents, which means the PM writes the prompts and guardrails directly rather than handing them off.

This post is part of our job search retro series where Hedgy members who have recently started a new job share learnings from their search. If we can be helpful as you navigate your search, email us at founders@hedgy.works