VP of Engineering

What you will do

• Define how we design, review, deploy, monitor, and hand work between discovery and delivery.
• Choose stacks and patterns that fit the job: existing systems, security, scale, and the next twelve months, not a fashion list.
• Keep platforms hosted, backed up, observed, and patchable as part of the monthly partnership.
• Hire and coach forward deployed engineers, developers, and AI engineers who ship with judgment.
• Be the senior engineer in the room when an integration, data model, or AI step is about to become a long-term mess.
• Protect quality without turning every client into a six-month architecture project.

What you bring

• A track record leading engineering while still building: services, data, cloud, and the unglamorous production work.
• Experience connecting or replacing real business systems, not only consumer apps or greenfield startups.
• You have run incidents, backups, access control, and the boring reliability work that keeps a client live.
• You already run an AI-first engineering practice: assistants, evals, code review, and internal tools that make the team faster.
• You can talk to a COO about a dispatch board and to an engineer about an API contract in the same afternoon.

AI-first, in practice

• You expect every engineer to use models as part of daily work, and you know how to review that work so quality holds.
• You have put AI into production systems with logging, fallbacks, and a human in the loop where it matters.
• You will not hire for “AI strategy” that never touches a repository.

Apply Mail career@upperplain.com. Put “VP of Engineering” in the subject. Include a short note on systems you have used and built, plus links to work you can show. Email this role