Head of Engineering

Reflex is building the infrastructure that powers modern retail labor. By 2030, Reflex will look like the largest retail workforce in the world without owning a single store.

More than sixteen million Americans work in retail stores today, yet staffing remains reactive, inefficient, and costly for both retailers and workers. Retailers struggle with unreliable coverage and limited visibility into labor performance, while workers face unpredictable schedules and inconsistent income.

Reflex addresses this problem through a real-time, on-demand retail labor marketplace that connects national retail brands with trained, high-performing workers. The platform enables stores to flex staffing dynamically as demand changes, while creating performance-driven opportunities for workers. We’re scaling fast with some of the most notable brands in retail and are live in over 1,200+ active stores in the US.

This is a structurally complex, two-sided marketplace with real-world operational constraints. Reflex has demonstrated that the model works, with national retailers, growing marketplace liquidity, and rapid expansion. Backed by leading investors and operating at the Series A stage, the company is now focused on building durable systems that scale.

Notable Investors: Indicator Ventures, Canaan Partners, Precursor Ventures, Sugar Capital, ATX Venture Partners, Clutch VC, Active Capital, Red Swan Ventures, Gaingels, and several industry thought leaders.

Reflex is hiring a Head of Engineering to own the technical strategy, delivery execution, and operational maturity required to scale our platform for the next stage of growth.

This is a foundational builder role, not a caretaker position. You will partner directly with the Founder/CEO, and lead an existing engineering team of approximately 5-8 engineers. There is no CTO layer today, as such this is a high-visibility role, including Board/Investor exposure.

Your mandate is to architect and implement a resilient foundation of systems and processes that allows Reflex to scale and carry us into our next stage of growth.

You will be responsible for:

• Build and Lead the Team: Manage, mentor, and develop a team of five engineers. Conduct regular 1:1s, provide meaningful feedback, and create growth paths that retain top talent.
• Establish Engineering Culture: Define and model engineering best practices, code review standards, and technical decision-making frameworks that scale as we grow.
• Drive Technical Hiring: Partner with leadership to recruit exceptional engineers, from writing job descriptions to conducting technical interviews to closing candidates.
• Strategic Technical Partnership: Collaborate with the Technical Lead to navigate the complexities of a two-sided marketplace, including real-time dispatching, matching algorithms, and high-concurrency data processing.
• Refine the Software Development Life Cycle (SDLC): Partner with Product to optimize how features are defined, scoped, tracked, and delivered to ensure high velocity without burnout.

• Engineering Excellence & Standards: In collaboration with the technical lead, define and enforce the standards for code quality, documentation, and system reliability. You own the accountability for the team’s adherence to these best practices.
• Operational Oversight: Lead the strategy for DevOps and infrastructure (CI/CD, cloud spend, security compliance), ensuring the foundation is stable enough for the team to ship rapidly and safely.
• System Health & Risk Management: Own the technical debt backlog and incident response protocols.
• Pragmatic Hands-on Contribution: Contribute to feature implementation and code reviews alongside the team.

This role requires hands-on ownership and fast, high-quality decision-making.

You should expect to:

• Personally ensure the stability of the system through sound technical decision making
• Work daily with exec team & engineering on priorities, tradeoffs, and technical direction
• Move quickly while maintaining a high bar for quality and leverage

Reflex has validated its model and is scaling rapidly. At the same time, marketplace complexity is increasing.

Decisions made in the next product strategy phase will determine whether Reflex compounds its advantage or accumulates long-term friction. This role exists to take the engineering team to the next step in operational maturity and technical excellence, transforming a high-growth group of builders into a disciplined, scalable organization ready to tackle the next frontier of innovation.

• You have built a predictable delivery engine where the CEO and stakeholders have full confidence in roadmap timelines and the trade-offs required to meet them.
• You have implemented clear career paths and a culture of continuous feedback, resulting in high team engagement and the successful retention of top engineering talent.
• The platform remains resilient and performant under increasing marketplace load, with a clear strategy for managing technical debt and infrastructure costs as we scale.

We are looking for an exceptional technical leader with high standards.

You likely bring:

• 9+ years in software development, including senior leadership experience
• 6+ years managing and growing high caliber engineering teams
• Deep, battle-tested experience in modern backend ecosystems (e.g., Python/Django, Ruby on Rails, Go)

You are someone who:

• Is passionate about growing engineers and their careers
• Is a strategic thinker, you see the Big Picture
• Loves technology and applying it to solve challenging problems
• Is comfortable owning ambiguous, high-stakes decisions
• Moves quickly with a strong bias toward action
• Cares deeply about craft, clarity, and outcomes

This role is not a fit for:

• Desire for pure management with no participation in implementation
• Desire for pure development without people management
• Candidates who prefer consensus-driven, low-intensity environments
• People unwilling to engage deeply with technical and operational details
• Anyone optimizing primarily for title or stability

Our customers and workers come from every background, and our team does too. Reflex is proud to be an inclusive employer. All qualified applicants will receive equal consideration.