Head of Product

Role Description

You are an experienced, hands-on Head of Product who owns product and design end-to-end and is as comfortable in a customer call as in a pull request. You'll lead a small, senior team of two excellent PMs and a design lead, partner closely with a hands-on founding team and engineering, and bring structure to chaos and a spine to the hard calls.

We want someone who can run the function like a clock, is willing to get in the weeds on customer needs, or debate strategy with the founders or engineering teams to get to the best outcome. You are a rock-solid operator grounded in reality, competition, and the customer. Not a pure strategist who orchestrates.

What you'll own

• Strategy and the hard "no." Turn a dozen competing customer demands into a coherent set of bets, deciding what we don't do as clearly as what we do.
• Predictable, quality delivery. Make "we ship what we commit, on time, at quality, at an increasing pace" true.
• An AI-native product and team. Build AI into the product and into how the team works.
• A small, senior team. Coach and lead two PMs and a design lead, raise the craft bar, and grow the team behind you.
• The founder and engineering partnership. Own crisp decision rights with a founding team that stays close to the customer.

You'll thrive here if you

• Bias hard to action and "prioritize finishing." You close open loops and ship at pace without dropping quality.
• Are genuinely AI-native. You use AI as part of how you think, build, and operate.
• Think in structured bets and make decisions. You bring a framework, write things down, and are willing to be wrong and move.
• Are relentlessly close to customers, with a real system for where your signal comes from and how you separate signal from noise.
• Are technical enough to be dangerous. You read the codebase, wire up your own tooling, ship a small fix, and hold a credible line on tech-debt versus velocity.
• Communicate with unusual clarity. Your writing makes decisions obvious across time zones.
• Partner with founders without deferring to them. You challenge assumptions, make the recommendation, then commit fully once the call is made.
• Have led product at a growth-stage software company (research, data, or dev-tools adjacent is a bonus).

Our process

• An initial set of calibration conversations to understand the opportunity, what you’re up against and how you fit in.
• A live working session on a real GQ strategy tradeoff.
• A short case study. Walk us through a product you led end-to-end.
• Conversations with the team you'd lead and partner with.

Benefits

• A culture of customer obsession and curiosity
• Opportunity to shape and scale a critical business function
• Remote-first culture with high trust and high autonomy
• Annual team retreats and virtual events
• Opportunity to work on cutting-edge AI integrations that matter
• Competitive compensation & equity
• Generous PTO, health benefits, and learning stipend

Equal Opportunity Statement

Great Question is committed to providing a workplace free from discrimination or harassment. We expect every member of the Great Question community to do their part to cultivate and maintain an environment where everyone has the opportunity to feel included, and is afforded the respect and dignity they deserve.