[Hiring] Lead AI Engineer @Sierra Studio

Role Description

Our hiring partner is hiring their first engineer. The founder has already built the foundation himself using AI coding tools:

• A data layer that pulls Klaviyo data for every client into the company's own Supabase database.
• A set of AI skills and workflows the team uses instead of building reports by hand.
• A diagnostics tool made of agents that continuously QA client accounts and flag what's broken.

It works and it's validated, but it was built by one person and has reached a level of disorganization that isn't sustainable as the company scales. The products need to be rebuilt with scale in mind, and the whole system needs an engineer who owns it.

You'll own the architecture end to end:

• Auditing what exists, deciding what stays and what gets rebuilt.
• Turning it into a fully maintained codebase with clear guidelines.
• Pairing closely with the founder, who leads on product while you lead on development.
• Building agentic flows across nearly every area of the business.

This is a lead role: you set the technical direction and standards for everything that gets built, and as the engineering function grows, you'll be the one shaping it.

What You'll Own

• Architecture and Codebase:
  • Audit everything that's been built so far, define what stays, what gets rebuilt, and how it all fits together.
  • Take the current system to a fully maintained, documented codebase with clear standards and guidelines.
  • Design the data pipelines: ingestion from Klaviyo, Postscript, and Attentive, modeling and storage in Supabase.
  • Build for scale and clarity, so the business has a foundation it can execute on.
• Agentic Workflows and Internal Tooling:
  • Design and ship agents and AI skills for account diagnostics, reporting, QA, go-to-market, and internal ops.
  • Make internal AI tooling reliable and consistent.
  • Define the quality boundaries for the whole team.
• Products:
  • Evolve the early products into something clients can depend on.
  • Own the integrations with the email and SMS platforms.
  • Establish the workflow between you and the founder.
• Being the Technical Voice in the Room:
  • Be the engineering counterpart to the founder in product decisions.
  • Get in front of clients when it matters.
  • Set the engineering standards and practices for future hires.

Qualifications

• 5+ years building software professionally, with a track record of shipping things real people used.
• Strong full-stack engineering skills (TypeScript and/or Python, modern backend and frontend, Cloudflare, Supabase/Postgres, SQL).
• Cloud infrastructure provisioning experience (AWS, GCP, Azure, etc.).
• CI/CD workflows experience.
• Hands-on experience building LLM-based systems.
• Good taste for data pipelines.
• Comfortable with Supabase/Postgres (or equivalent) and owning data infrastructure end to end.
• Experience being the only or lead engineer somewhere.
• Ownership mindset.
• Proactive communicator in a remote, async environment.

Preferred

• Experience with email/SMS marketing platforms (Klaviyo, Postscript, Attentive, Braze).
• Background at a fast-moving martech or retention product company.
• Experience productizing internal tooling.
• AI coding tools are already part of how you work.
• Product instinct: you have opinions about what should be built.

What Success Looks Like

• The architecture has been audited, cleaned up, and documented.
• The internal AI tooling is reliable enough for the team to get consistent results.
• Agentic workflows across the business are built and maintained by engineering.
• The early products have moved from prototype to something clients rely on.
• The founder spends his time on product, clients, and growth.
• You've laid the groundwork for the engineering function to grow beyond one person.

Benefits

• 23 days of PTO.
• Generous maternity and paternity leave.
• Bonus structure.
• Fully remote with flexible hours and US overlap.
• Contractor engagement (no healthcare coverage).

A Note on Fit

The culture is built around ownership. Everyone geeks out on their craft, shares what they learn, and treats each other like adults. Because the team is remote, there's a lot of flexibility and an equal amount of accountability. People who take a full area, own it end to end, hit deadlines, and communicate proactively do very well here.

What makes this role different is where you sit. Here you're inside the agency: the feedback loop with clients is direct, the results are measurable in revenue, and you're never limited to what the software can do.