Great Question is on a mission to help businesses build better products by making customer research fast, easy, and scalable. We’re a Series A B2B SaaS company backed by top-tier investors and trusted by leading brands like Gusto, Miro, Brex, and Canva.
Our all-in-one research platform enables teams to recruit participants, run interviews and surveys, and analyze insights — all in one place. As we enter the era of AI, we’re pioneering automated qualitative analysis to help teams turn customer feedback into actionable insights faster than ever.
We’re a remote-first, customer-obsessed team committed to helping product teams deeply understand and serve their users. Learn more atgreatquestion.co.
About The Role
Great Question is growing fast — and we’re ready to bring on our first Director of Engineering to help scale our team, systems, and technical foundation for what’s next. You’ll help turn a strong product and ambitious roadmap into a durable, high-performing org.
You’ll work closely with our CTO to turn vision into execution at scale, while building a high-trust, high-impact environment that supports both rapid growth and technical excellence.
1. Org-Wide Delivery & Operational Excellence
Own the systems that power engineering delivery across all teams — from roadmap execution to internal alignment:
- Lead delivery across 4+ squads and 20+ engineers with consistent velocity, quality, and accountability
- Evolve the release process for scale: coordinated launches, post-release ownership, rollback playbooks
- Improve efficiency through cost awareness, tooling strategy, and cross-functional workflows
- Build and maintain visibility across squads without heavy process overhead – optimise for the teams time on tools
2. Technical Leadership & Platform Architecture
Uphold strong engineering standards while empowering teams to move fast with clarity and confidence:
- Define and scale technical quality across the org (instrumentation, testing, SLAs, postmortems)
- Partner with the CTO and shape architectural direction and platform investment
- Ensure strategic technical decisions are reviewed, documented, and socialized org-wide
- Advocate for “right-fidelity” development: when to build for speed vs. stability vs. scale
3. People Leadership & Org Design
Design and lead a high-performing engineering organization that can scale with the company:
- Align headcount and engineering investment with organisational priorities
- Structure teams to match product surface area, revenue contribution, platform ownership, and growth goals
- Attract and retain top-tier talent; maintain a strong hiring bar across all levels
- Develop IC’s into EMs, and EM’s into Directors
- Define career frameworks that support high performance, tenure and equity
4. Cross-Functional Execution
Be the connective tissue between Engineering and the rest of the business:
- Partner with Product, Success, and Design to align roadmaps and solve the right problems
- Create shared planning and prioritization processes that improve focus and reduce thrash
- Translate engineering investments into business impact — and help others across the org do the same
- Set expectations across departments around timelines, trade-offs, and capacity
5. Culture, Strategy & Executive Partnership
Scale engineering culture intentionally — without losing autonomy, quality, or accountability:
- Model calm, clear decision-making and foster a high-trust, low-drama environment
- Connect engineers to customer outcomes and business rationale
- Partner closely with the CTO to operationalize long-term vision, enabling the CTO to focus on technical differentiation and innovation
- Contribute meaningfully to exec-level planning, headcount strategy, and product direction
- Proven success leading engineering teams in high-growth B2B SaaS environments, ideally having scaled from Series A to Series B/C and beyond
- Experienced org builder; can scale systems and teams through ambiguity and change
- Deeply credible with senior engineers; understands architectural trade-offs at scale.
- Proven track record of hiring, coaching, and retaining high-performing leaders and ICs.
- Trusted partner to Product, Success, and Design; translates technical decisions into business impact.
- Low-ego, high-accountability. Balances urgency and empathy. Trusted by engineers and execs alike.
- Passionate about the opportunity around AI
- Competitive salary, equity and a benefits package
- High-impact work on meaningful, challenging projects — with the opportunity to lead and scale a fast-growing team in a dynamic environment
- Fully remote by default, with optional in-person meetups in your area if that’s your thing
- Generous time off : Four weeks of PTO, public holidays, parental leave and regular team events; our last all-company off-site was in Mexico City.
Hiring Process
We endeavor to deliver a great candidate experience, including notifications of your status in the hiring process throughout.
The hiring process includes the following steps and typically happens across 2-4 weeks from first interview:
- Initial phone screen for shortlisted candidates.
- Interview with Co-Founder & CTO, PJ Murray
- Technical Interview
- Cross-functional collaboration interview
- Final leadership interview with Co-Founder & CEO, Ned Dwyer
- Reference checks with a past manager and a person you have managed.
Note – Each interview is sequential, so you’ll only move to the next round if you pass the previous one. After each interview, we’ll aim to notify you if you’re progressing within 3 days of your interview taking place.
If this sounds like the opportunity you’ve been waiting for, we’d love to hear from you! Please submit your resume, making sure it’s a concise representation of your previous work experience.
Note, we will only ever contact you over email using a greatquestion.co email address.
