Director of Engineering

Description

• Leading the Engineering Organization
You'll own the health, performance, and growth of our engineering team. This means building strong Engineering Managers, establishing clear career paths, running calibrations and performance cycles, and creating an environment where engineers do their best work. You'll directly manage 3 Engineering Managers and several senior individual contributors, with ~26 engineers in your organization overall.
• Setting Technical Direction
You'll shape our technical strategy in partnership with senior engineers and cross-functional leaders. This includes making decisions about architecture evolution, AI/ML integration, platform scalability, and technical debt prioritization. You won't be writing code day-to-day, but you'll provide technical guidance through architecture reviews, design discussions, and mentoring senior engineers. Your technical judgment will help teams make the right trade-offs.
• Driving AI Integration
We're integrating AI throughout our platform to bring AI-powered features to 10+ million small business owners. You'll champion AI adoption across the engineering org—ensuring teams have the skills, tools, and architectural patterns to ship AI-powered products effectively. You'll also drive AI-assisted development practices (AI coding tools, automated testing, workflow automation) to accelerate engineering velocity. Whether it's LLM-based features for customers or AI tools that help engineers ship faster, you'll guide the strategy and remove blockers.
• Driving Delivery and Operational Excellence
You'll ensure we ship high-quality products on predictable timelines. This means optimizing how squads work together, establishing engineering metrics that matter, improving our incident response and reliability practices, and removing organizational friction that slows teams down.
• Partnering Cross-Functionally
You'll be a key voice in product strategy, partnering with Product and Design leadership to balance business needs, user value, and technical sustainability. When the CEO wants to understand engineering capacity or a PM needs to make a build-vs-buy decision, you'll be the person in the room.
• Building for Scale
As we grow, you'll evolve our engineering organization—hiring senior talent, establishing new squads, improving our technical interview process, and ensuring our org structure supports our product roadmap.

Requirements

• Engineering Leadership Experience: 8+ years in software engineering with at least 4 years leading engineering teams, including experience managing managers. You've built and scaled teams of 20+ engineers at growth-stage companies.
• Technical Credibility: You've been a strong IC in your past and can still go deep on architecture, system design, and code quality. You don't need to be the best coder in the room, but you need to earn the respect of senior engineers through your technical judgment.
• Delivery Track Record: You've shipped products that matter at companies with real scale. You know how to balance speed and quality, manage technical debt, and keep teams focused on outcomes over output.
• People Development: You've grown Engineering Managers and senior ICs. You have a track record of retention and promotion. You know how to give hard feedback and have hard conversations.
• AI/ML Familiarity: You've shipped AI-powered product features or led teams integrating LLMs and ML into products. You're excited about what AI can do for small businesses—and for engineering productivity.
• Cross-Functional Partnership: You've worked closely with Product, Design, and business leadership. You can translate between technical and non-technical stakeholders and influence without authority.
• Experience with our stack is a plus: Ruby on Rails, Elixir, React/TypeScript, AWS. But we care more about your ability to learn and lead than matching every technology.

Benefits

• Smart, supportive co-workers
• Competitive compensation
• Equity
• Health, dental, and vision insurance
• Unlimited vacation policy
• Virtual working environment
• Flexible working hours
• Paid Parental leave
• Professional Development Program
• 401(k)