Director of Engineering

About Collective: Collective is on a mission to redefine the way businesses-of-one work. Our technology and team of trusted advisors help members achieve financial independence by taking care of everything from business incorporation to accounting, bookkeeping, tax services, and access to a thriving community, all in one integrated platform. We believe in empowering self-employed people to enjoy the same tax savings that big companies get, so they can focus on their passion, not paperwork. Featured in Forbes, Business Insider, Yahoo, Bloomberg, Financial Times, TechCrunch, and more. We are backed by General Catalyst, Sound Ventures (Ashton Kutcher and Guy Oseary), QED Investors, Google’s Gradient Ventures, Expa, and other investors who have financed iconic companies like YouTube, Substack, Twitch, Box, Hims, Instacart, and Lyft. About the role: We’re hiring a Director of Engineering to build and evolve the core product experiences that power Collective’s member platform. This is an engineering leadership role with high ownership across Product, Design, and Operations to lead the teams to ship fast and iterate based on real customer needs. You’ll be expected to encourage the use of modern AI tools and agent-based workflows to accelerate development, improve code quality, and unlock new product capabilities. What you'll do: - Act as a player-coach, balancing hands-on technical contribution and people leadership - Lead, mentor, and grow managers and leaders, fostering a culture of high-performance and empathy. - Work with teams of talented engineers, product managers, and designers to deliver a robust platform. - Define, own, and ensure the timely delivery of complex, multi-disciplinary, and highly visible engineering projects. - Drive clarity about architecture, design, and product decisions across teams, utilizing full-stack capability (e.g., Python/Django backend, React frontend). - Manage team processes and interface effectively with non-technical stakeholders, including Operations teams. - Contribute to engineering-wide initiatives and drive conversations from engineering teams to executive leadership. What you'll bring: - 8-10+ years of software engineering experience, including at least 4+ years of management experience. - Technical depth to drive end-to-end systems ownership, including architecture, design, and data modeling. - Demonstrated success in operating as a player-coach, maintaining hands-on technical proficiency. - Experience managing a team that has delivered a great product with solid foundations. - Organizational leadership experience, including experience collaborating with non-technical stakeholders and weighing tradeoffs. - A track record of encouraging a healthy work environment that is both supportive and challenging. What we offer: - Hybrid Work Model: Based in San Francisco with a balance of in-office and remote flexibility. - Fresh Lunch: Provided on in-office days. - Commuter Support: $150 monthly reimbursement for transit expenses. - Health & Wellness: $200 quarterly reimbursement to support your well-being. - Time Off: Flexible PTO plus 14 company holidays. - Comprehensive Coverage: 100% medical, dental, and vision for employees; 75% coverage for dependents. - Parental Leave: 16 weeks fully paid. - Retirement & Ownership: 401k plan plus an equity package. - Team Connection: Quarterly virtual events and an annual in-person summit.