VP of Product and AI Enablement

About Swimm

Swimm is an Israeli technology company focused on helping engineering organizations modernize complex legacy codebases.

We are pivoting from a pure SaaS product company into a product-enabled services company. We help customers execute high-stakes modernization projects: version migrations, monolith breakdowns, and AI-readiness initiatives.

We are not a classic services company. We deliver modernization services through a repeatable operating system: our own products, our own agent workflows & harnesses, and a human delivery team using a structured methodology. Our approach will enable us to move faster, validate harder, and deliver with transparency & predictability.

We are a small, sharp, VC-backed boutique at an inflection point. The next 12 months are about finding service-market fit, and scaling cleanly from there.

We are hiring a VP of Product & AI Enablement to own the products, and methodologies that power Swimm’s service work and business model.

This is a senior, hands-on role reporting to the CTO, with a seat at the management table. You will own two critical product surfaces:

Swimm Platform — our code-understanding platform, and the foundation for how we analyze complex legacy codebases in hours, and turn opaque systems into actionable insight.

Swimm OS — our agent/human delivery hub and the operating system for turning complex project work into a repeatable, product-enabled service.

You will sit at the center of the company: between the CEO, CTO, GTM, and Delivery. Your job is to turn Swimm’s products, agents, human workflows, and field learnings into a system that scales.

The product is what makes Swimm unbeatable.

• Own the product roadmap end-to-end. You decide what we build next and why.
• Directly manage the engineering team, working hands-on with the EM and technical leads.
• Own all internal and customer-facing product, deliverables, & delivery enablement aspects.
• Own the methodology behind our engagements: how we run assessments, how we define success, how we set test-coverage contracts, how we protect revenue margins, and what work we choose to take on.
• Act as a partner to GTM: translate use-case learnings into positioning, demos, landing pages, packages, and pricing tiers that close.
• Act as a partner to Delivery: turn field feedback into platform features, repeatable primitives, and operating playbooks, faster than anyone else in the market.

• 8+ years in product, including 3+ years as a VP Product, Head of Product, or strong Director who has effectively run a product organization.
• Deep technical fluency. You can reason about code and system architecture, understand agent architectures, and hold your own with senior engineers.
• Hands-on experience shipping AI based or agent driven products — not just wrappers. You have strong opinions about prompting, evals, tool-calling, MCP, observability, and where agentic systems actually break.
• A track record of taking 0→1 products from concept to first paying customers, including the messy middle.
• Excellent written and spoken English. You will be a leading voice with US enterprise customers.
• High ownership, low ego. You are happy doing the work yourself today and building the team tomorrow.
• Experience building or scaling a product-enabled services model — where software, workflows, automation, and human delivery are designed together to create repeatable, scalable customer outcomes.

• Experience with developer tools, developer platforms, or infrastructure.
• Engineering background: former engineer turned product leader is a strong edge.
• Experience supporting, selling, or shaping enterprise services engagements at $250K+ deal sizes.
• Familiarity with modernization and legacy-code environments: .NET, Java, monolith decomposition, and large-scale migrations.
• Experience supporting a Series A or B fundraise from the product seat.

• A seat in a small, founding leadership team.
• Meaningful equity in a company at an inflection point.
• Real impact on the company’s direction, business model, and path to success.