Sr Devops & SRE Engineer

Great Question is the all-in-one 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 🚀

At Great Question, we’re building more than just a product, we're building a culture grounded in values that drive how we work:

• Solve for the customer: Everything we do, from product decisions to marketing strategies, starts with a simple question: does this serve our customers’ needs?

• Quality matters: We balance speed with intention, aiming to build a product that people trust and love.

• We ship: Speed is part of our DNA. We prioritize getting valuable work into the hands of customers early and often.

• Continuous improvement: Feedback is fuel. We thrive on learning from peers, customers, and each other.

And we believe the best work happens in an environment that supports trust, creativity, and ownership:

• Froth: We leave room for fun. Work should be energizing, not draining.

• Disagree and commit: Healthy debate is welcomed. Once a path is chosen, we unite and move forward together.

• Sign your name: We take pride in our work and follow through on our commitments with excellence and accountability.

Expect your first few months to lean heavily on your devops expertise. Your work will likely touch Terraform, our CI/CD pipelines, observability tooling, and databases. Over time, your role will balance platform reliability with continuing to improve our overall developer experience.

Please note this is a contract position, with an initial

• Maintaining and improving our Terraform-managed IaC as we continue to scale

• Implementing automated and semi-automated scaling strategies to handle growth and evolving workloads

• Leading specific infrastructure improvement projects, such as implementing ephemeral staging environments

• Improving Observability, Reliability, Availability across the stack, including optimizing our use of tools like Datadog, Sentry, and others

• Working across teams to improve our signal-to-noise ratio, incident detection, and incident response

• Collaborating with engineers to diagnose and fix performance issues and harden security

• Monitoring and optimizing our cloud spend, including budgeting and forecasting

• Enhancing DX by reducing friction in local dev and CI, improving feedback loops, and investing in developer onboarding

• Have 7+ years running critical production systems in the cloud

• Know your way around AWS (EC2, RDS, VPC, IAM) like the back of your hand and always think about cost.

• Scaled and optimized PostgreSQL databases.

• Managed and improved CI pipelines.

• Enjoy building tools that make other engineers more productive.

• Thrive in high-autonomy environments where ownership beats process.

• Strong preference given to engineers who are familiar with the challenges of scaling enterprise Ruby/Rails SaaS applications.

• Cloud: AWS

• IaC: Terraform

• CI/CD: GitHub Actions

• Containers: Docker

• Monitoring: Datadog, Sentry

• Data: PostgreSQL, Redis

• App: Rails, React, Sidekiq

• 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

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.