Head of Technology & Product (US or Europe, remote)

Role overview A senior leadership role unifying product direction and engineering ownership for an AI-driven operations platform serving short-term rental property managers. The position exists to settle competing priorities between a standalone SaaS product and a live shared services operation, and to bring a single accountable leader to a small, profitable team that has outgrown its current structure.

Responsibilities - Own the combined product roadmap and prioritization across the SaaS product and the live services operation - Define north star metrics, including how automation coverage is measured against actual resolution quality - Run discovery with property managers and customers, then prioritize the right problems ahead of engineering - Scope work sufficiently ahead of the engineering team so delivery is rarely surprised - Design and implement pod structure, ownership boundaries, and a formal performance framework - Act as the bridge between engineering and the rest of the business, converting pressure into useful context - Partner with operations and customer success to decide what gets built rather than absorbing requests reactively

Requirements - 10+ years of experience across product and engineering, with direct ownership of both functions - Hands-on engineering background, including writing production code and credibility with engineers - Direct management experience with product managers, engineers, or both - Industry experience in short-term rental, vacation rental, or property management, including working knowledge of reservation alterations, OTA compliance, and manager priorities - Track record of restructuring a team and improving how it delivers - Scrappy, hands-on style suited to a small team without an existing product organization or analyst layer - Experience shipping AI or automation products where coverage and quality trade off

Nice to have - Experience at a competitor or adjacent platform in the short-term rental space - Background building tools for internal operational users alongside external customers

Benefits and work setup - Remote within the US or Europe - Quarterly in-person meetings, which may be held in the US or Europe - Base compensation determined by location and experience - Equity included