Head of Engineering

We’re a growing, 50-person startup transitioning from founder-led engineering to building scalable systems and structures that will support our next phase of growth. Our product has hit critical scale and is evolving rapidly. As we grow, our engineering team is looking for steady, values-driven leadership that supports autonomy, shared accountability, and quick, thoughtful execution—while continuing to uphold a high standard of technical quality.

Role Overview
As Head of Engineering, you will guide our transition from our scrappy startup roots into a thoughtfully scaled, high-performing engineering organization. Your focus will be to establish trust and build a solid foundation of leadership, systems, and processes that enable the engineering team to scale their impact. You’ll report to and closely partner with our founding CTO to bring clarity, mentorship, structure, and decision-making frameworks that support both immediate and long-term business objectives. You'll also be a collaborative cross-functional leader—someone who values the role of product and works in close partnership with product leadership to ensure we’re building the right things in the right ways that reflect shared goals and thoughtful tradeoffs. We are looking for a seasoned technical leader and people manager who brings curiosity and wisdom to guide complexity and scale, balanced by a collaborative and people-first approach. You’ll support two engineering managers, offering mentorship and helping create an environment where engineers can thrive and do their best work.

Key Responsibilities

• Drive Execution: Partner with the Founding CTO, Director of Product Management, and Engineering Managers to shape a shared technical and product vision that thoughtfully supports our company’s goals and evolving market needs.
• Foster Our Engineering Culture: Cultivate a culture of ownership and shared responsibility, where teams care for the systems they build, prioritize observability, and view iteration and post-incident reflection as essential parts of learning and growth.
• Build Scalable Systems and Processes: Partner with Product leadership to co-create simple, effective frameworks for planning, prioritization and delivery. Support the adoption of sustainable practices for quality, reliability, and architecture that help teams build with both care and momentum.
• Develop and Empower Managers and Technical Leaders: Support emerging leaders as they navigate technical and team-related decisions, while fostering an environment of psychological safety, growth, and shared learning. Encourage mentorship and development tailored to individual needs, and actively champion inclusive practices that welcome diverse perspectives and approaches.
• Lead with Pragmatism and Empathy: Practice servant leadership grounded in transparency, humility, and care. Balance thoughtful technical progress with business needs, focusing on what’s meaningful. Prioritize the well-being of the team through people-first practices that support sustainable, inclusive growth.

Experience & Qualifications

An Experienced Engineering Leader

• 10+ years in the software industry, beginning as a hands-on engineer and growing into senior leadership roles.
• Proven track record of leading engineering teams through phases of organizational growth and change.
• Extensive experience managing both individual contributors and engineering managers, with a clear understanding of the distinct needs and dynamics of each.
• Prior experience in a Director-level (or equivalent) role, with direct reporting to executives or C-level leaders. Brings a strong sense of ownership, strategic alignment, and clear, transparent communication at the leadership level.

Culture-Driven Leadership

• Recognized for building engineering cultures that balance autonomy with accountability.
• Leads with humility, pragmatism, and a people-first mindset—focused on supporting others to thrive and do meaningful work.

Strong Communicator & Cross-Functional Partner

• Skilled at aligning engineering priorities with broader company goals and building collaborative relationships across product and business teams.
• Communicates with clarity and empathy, adept at navigating complexity and fostering shared understanding across stakeholders.

Deep Technical Expertise

• Hands-on experience scaling distributed systems and applying modern software development practices, including CI/CD, observability, and service ownership.
• Familiar with AWS or other cloud-native platforms.
• Comfortable working with and improving legacy systems, managing technical debt thoughtfully.
• Proven ability to support innovation and improve developer experience while staying closely aligned with business outcomes.

Nice To Haves:

• Leading engineering teams through transitions from founder-led to more structured, scalable organizations.

Why This Is The Perfect Time to Join Us:

We're at a critical inflection point in our company's journey with unprecedented market opportunities ahead. You’ll have the opportunity to shape the future of our engineering organization at a pivotal time in our journey. If you’re passionate about building resilient systems, empowering teams, and fostering a culture of excellence, we’d love to hear from you.

Competitive Compensation Package:

• Base Salary: $200,000 - $300,000 annually, commensurate with experience
• Performance bonuses tied to company valuation milestones as we scale
• Equity: Meaningful equity grant with opportunity to increase based on performance and company growth
• Benefits: Comprehensive healthcare, 401(k) matching, Unlimited PTO, Sabbatical, Free Coworking Membership, Office Stipend and more!
• Strategic Leadership Impact: As a leader in the organization, you'll have direct influence on company strategy and decision-making at the executive level.
• Market-Disruptive Technology: Lead efforts for cutting-edge technology that's solving critical challenges in the digital ecosystem.
• Collaborative and Dynamic Environment: Work alongside passionate innovators in a high-energy startup culture with significant growth and advancement potential.

We want to hear from you if you’re an experienced engineering leader with a passion for building high-performing teams, scaling systems thoughtfully, and fostering inclusive, collaborative cultures. Join us at a pivotal moment as we evolve from our startup roots into a more mature, resilient organization—help shape the future of our engineering function while making a meaningful impact on the company and the industry.