Head of AI-First Engineering

About Winter

Winter is a next-generation services firm helping enterprises become AI-native. We combine strategy, design, engineering, and GenAI tools to help clients build and operate modern, adaptive organizations. We are building real IP and have a prototype of our core product that is gaining traction with large enterprise partners. We are now looking to scale up engineering maturity, strengthen the codebase, ship faster, and lay the foundation for a new kind of AI-first platform and practice.

The Role

We’re hiring a hybrid engineering and product leader to own and scale Winter’s AI-first engineering function. This is a foundational leadership role reporting to a Founding Partner (Sean Middleton) that will shape both our internal platform and our client-facing delivery model.

Your first major priority is to take over engineering for our graph-based intelligence system that helps enterprises continuously sense external change and respond with AI-powered action. You’ll lead the push to improve velocity, stability, and reusability, while standing up the team and practices that can support long-term scale.

You’ll also define how we do forward engineering — building bespoke, high-impact client solutions — and how we use those engagements to harvest and harden reusable capabilities that flow back into the platform (our rear engineering loop).

We’re looking for someone who can operate at multiple altitudes, defining strategy and operating model, and also zooming in to write or review code, improve a pull request, or push a sprint over the line. AI-first to us means rethinking the way we build: pushing automation, enabling hybrid teams, and shaping new patterns of work. We want someone who understands where GenAI is now, but also has a clear, optimistic vision for where it's going and wants to be among the first to help define it.

What You’ll Do

• Take ownership of the DVM platform codebase, roadmap, and engineering team.
• Build and lead a lean, AI-native engineering team, with an emphasis on full-stack talent and modular reusability.
• Define Winter’s engineering model, including team topologies, delivery playbooks, and reuse pipelines.
• Deliver high-quality enterprise software fast across both internal and client-facing contexts.
• Shape a forward and rear engineering loop: custom client work informs and reinforces our core platform.
• Serve as a trusted thought partner to founding leadership on product direction, hiring, and architecture.
• Mentor hybrid squads of engineers, PMs, and designers, including early-career builders breaking into the new era.
• Promote 'reusable by default' practices across agents, workflows, and UI components.
• Help define and maintain a high bar for documentation, security, quality, and velocity.

What We’re Looking For

We don’t expect perfection across every dimension, but this role is uniquely cross-cutting. You should have meaningful depth in most of the following:

Product & Engineering Blend

• Proven experience leading full product delivery, owning both what gets built and how.
• Strong instincts around architecture, velocity, and modular design.
• Hands-on comfort with full-stack engineering (even if not currently coding daily).

Startup Agility & Enterprise Rigor

• Experience in ambiguous, high-change environments with lean teams.
• Familiarity with enterprise expectations around scale, governance, and supportability.
• Ability to navigate tradeoffs between short-term speed and long-term robustness.

AI-First Orientation

• Working knowledge of LLMs, RAG, agent orchestration, and vector-based retrieval.
• Experience using GenAI tools (Copilot, test automation, etc.) to reshape workflows.
• A builder’s mindset with a forward-looking, optimistic view on where this field is going.

Product + Services Mindset

• Background in product-led environments (especially infra, devtools, or platforms).
• Familiarity with consulting or professional services and how delivery informs IP.
• Belief in small, great teams and the power of cross-functional collaboration.

Leadership & Craft

• Experience recruiting and mentoring high-caliber engineering and product talent.
• Can zoom in to improve a story, a system, or a sprint and zoom out to set vision.
• Thoughtful, direct, humble, and driven by substance over hype.

Why Winter?

• Work closely with the founding team in a high-trust, high-autonomy partnership model.
• Define what modern engineering leadership looks like in the GenAI era.
• Help shape a product that blends platform thinking with real client value.
• Grow a practice that opens the door to a new generation of technologists.