Head of Product

Great Question, Inc.; Canada; On-site; CAD 150,000 - 210,000; Full time

Job summary

Great Question, Inc. is seeking an experienced Head of Product to own product and design end-to-end. You will lead two PMs and a design lead, collaborating closely with the founding team and engineering to turn customer needs into clear bets and outcomes.

You will steer strategy, drive ruthless prioritization, and ensure high-quality, on-time delivery. The role emphasizes AI integration and a data-informed, customer-obsessed approach in a remote-first environment.

Qualifications

• Has led product at a growth-stage software company (research, data, or dev-tools adjacent is a bonus).
• Experience building and shipping AI-native products.
• Ability to turn customer needs into structured bets and decisions.

Responsibilities

• Own strategy and decision rights for the product and design end-to-end.
• Lead a small senior team (2 PMs + design lead) and partner with founding, engineering, and GTM.
• Drive predictable, high-quality delivery and ship on time.
• Integrate AI into the product and team workflows for efficiency and leverage.

Skills

Leadership

PM management

Product strategy

AI product

Customer obsession

Communication

Technical literacy

Job description

About Great Question:

Great Question is the all-in-one AI customer research platform for understanding your customers. Our platform enables teams to recruit participants, run research, and share insights – all in one place. Backed by world-class investors and trusted by industry-leading teams like Gusto, Experian, Canva, and Brex, we're building the future of customer research.

We believe AI is a multiplier for creativity, speed, and scale. Everyone on the team is encouraged to lean into AI, not just to be more efficient, but to push boundaries and unlock new possibilities. Whether you're writing, designing, coding, or analyzing, we expect you to explore how AI can elevate your craft.

Our culture is built on high trust, high agency, and high emotional intelligence. If you're looking for a place where your voice matters, where work is fun, and where you're empowered to do your best - join us in redefining user research

The role

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. It's the operating muscle a fast-moving product org runs on. Get good things into the world to learn from, without letting quality slip.

An AI-native product and team. Build AI into the product and into how the team works: more done with fewer people, and a sharp eye for signal over slop. This is how we think and build, not a layer bolted on at the end. It's not that we can't hire more, it's that it's not the first tool we reach for out of our tool chest.

A small, senior team. Coach and lead two PMs and a design lead, raise the craft bar, and grow the team behind you. Design is a strategic partner, not a service function.

The founder and engineering partnership. Own crisp decision rights with a founding team that stays close to the customer, and keep a clear line to GTM on what's coming and when.

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, and you know where it creates real leverage versus where it adds noise or risk.

Think in structured bets and make decisions. You bring a framework, write things down, and are willing to be wrong and move, rather than please every stakeholder.

Are relentlessly close to customers, with a real system for where your signal comes from and how you separate signal from noise. You can defend your ground but equally believe in "strong opinions, weakly held".

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. You know when you can just get something done, and when you need more help; equally you know how to suggest alternative approaches to engineers in a credible way.

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

We keep it real and fast:

• 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. Taste and structured thinking show best in real context, so we lead with this.

• A short case study. Walk us through a product you led end-to-end.

• Conversations with the team you'd lead and partner with.

We'll move quickly for the right person.

Why You'll Love Working Here:

• 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.

Decisions related to hiring, compensating, training, evaluating performance, or terminating are made fairly, and we provide equal employment opportunities to all qualified candidates and employees. We examine our unconscious biases and take responsibility for always striving to create an inclusive environment that makes every employee and candidate feel welcome.