Great Question is hiring a Director of Product

Great Question is hiring a Director of Product to define our product strategy and culture. This role reports to the CTO and collaborates closely with the CEO, Head of Design, and Director of Engineering. You will be a player-coach, guiding the team while personally owning key initiatives.

What You'll Do

• Guide and coach Product Managers while personally owning key product initiatives.
• Grow the product team from 2 to 4+ PMs over the next year.
• Help define the right product org structure to support autonomy and velocity.
• Collaborate with leadership to drive the product roadmap, refine strategic bets, and deliver impactful features quickly.
• Leverage AI tooling and shape product experiences infused with AI.
• Ensure the right data is tracked and used to inform decisions, championing outcome-oriented thinking.
• Be the connective tissue between product, engineering, design, marketing, customer success, and go-to-market teams.
• Bring a business mindset, thinking about growth, pricing, retention, and revenue impact alongside UX.

What We're Looking For

• 7–12 years of experience in product management.
• At least 2–3 years in a leadership role (e.g., Head of Product, Director, or similar).
• Hands-on experience building AI-driven products or a strong portfolio using AI tools in product development.
• Experience at early-stage, fast-growing companies — ideally from Series A through B/C.
• Proven ability to hire, coach, and retain product talent.
• High organization and strong communication skills; you bring structure to chaos and clarity to ambiguity.
• Commercial acumen — comfortable discussing growth models, pricing, and business strategy.
• Located in North America and able to work Pacific Time Zone hours.

Nice to Have

• Prior entrepreneurial experience, such as starting a company or building a product from 0→1.

Team & Environment

You will join a growing team of 2 PMs and help scale it to 4+. This is a player-coach role where you will refine our product org structure, reporting directly to the CTO.

Benefits & Compensation

• Remote-first culture with high trust and high autonomy.
• Annual team retreats and virtual events.
• Opportunity to work on AI integrations.
• Competitive compensation and equity.
• Generous PTO, health benefits, and a learning stipend.

Work Mode

This is a remote-first position. Candidates must be located in North America and available for Pacific Time Zone working hours.

Great Question is committed to providing a workplace free from discrimination or harassment. We examine our unconscious biases and take responsibility for always striving to create an inclusive environment.