Head of Product & Engineering

Role Overview

• Define and evolve the product and technology vision in alignment with Housing Connector’s mission and growth strategy
• Clarify and validate product-market fit across key user groups and partners
• Define product success metrics and establish analytics to measure adoption, user behavior, and platform performance
• Integrate insights from partners, market teams, and platform users into ongoing product decisions
• Introduce product management discipline and decision frameworks across the organization
• Partner with executive leadership, market leaders, and operations teams to align platform investment with organizational priorities
• Serve as the senior internal voice for product strategy
• Shift the organization from reactive feature requests toward disciplined, impact-based prioritization
• Establish structured intake, prioritization, and roadmap planning processes
• Lead sprint planning, backlog refinement, and release cycles
• Improve engineering delivery predictability through clear planning and release cadence
• Guide the evolution of internal systems that support market teams, partner management, and program delivery
• Lead and grow a high-performing engineering team
• Establish engineering delivery standards that ensure reliable, secure, and high-quality product releases
• Partner with engineers on technical design and architecture decisions to support long-term platform scalability
• Guide evolving security and data protection standards as the platform matures
• Manage the product and engineering budget
• Recommend investment tradeoffs aligned with strategic priorities
• Partner with executive leadership on hiring and team growth

Requirements

• 8+ years of product and technology leadership experience
• Experience building and scaling B2B SaaS, marketplace, or multi-sided platforms
• Strong foundation in product management, including product strategy, roadmap development, and product-market fit
• Technical fluency and the ability to lead engineering teams and collaborate effectively with engineers
• Proven ability to translate user feedback and operational insights into scalable product direction
• Experience driving adoption across multiple markets or customer groups
• Experience leading lean engineering or product teams
• Experience transitioning a product from early traction to operational scale
• Ability to operate effectively in ambiguity and resource-constrained environments
• Strong judgment balancing speed, quality, and long-term scalability.

Benefits

• Comprehensive Health Coverage – Medical, dental, and vision plans. Housing Connector pays 100% of employee premiums and 50% of premiums for partners and dependents.
• 401(k) with Employer Match (up to 6%) – Plan for your future with a retirement savings program and employer match.
• Generous Paid Time Off – 22+ days of PTO in the first year, plus dedicated Community Service Leave.
• Extensive Holiday Schedule – Includes 11 paid holidays and a full week off between Christmas and New Year’s Day.
• Paid Parental Leave (12 Weeks) – Paid leave to support employees welcoming a new child.
• Employee Assistance Program (EAP) – Confidential resources for mental health, financial, and personal support.
• Life Insurance – Employer-provided life insurance coverage.
• Flexible Spending Accounts (FSA & Dependent Care FSA) – Tax-advantaged accounts for healthcare and dependent care expenses.
• Professional Development Reimbursement – Up to $500 annually to support professional growth and learning.