Chief Technology Officer

What You'll Do - Command the Platform and Delivery organizations as distinct operating units (each with its own culture, mandate, and accountability structure) and be the single point of accountability for the output of both - Own the Kaizen 2.0 architecture: sequence the build of 12 core modules in the right order, hold the line on abstraction, and ensure the foundation compounds rather than fractures under delivery pressure - Lead the Blacksmith initiative, which is Kaizen's internal AI configuration harness that transforms agency requirements documents into runnable, pre-configured repositories and eliminates the time-to-first-commit tax on every new federal engagement - Define and enforce the Platform-Delivery interface: module readiness maps, API contracts, and Blacksmith handoff protocols that keep Delivery fast and Platform honest - Drive federal technical strategy: FedRAMP posture, DoD IL4/IL5 readiness, and procurement-aware architecture decisions that keep Kaizen competitive in federal BD conversations - Recruit, develop, and retain builders who operate at the frontier of AI-native government technology, and who understand that shipping for government is different from shipping for anyone else What You'll Bring - Deep federal technology experience.

You've built or scaled production software at the intersection of modern engineering and government procurement (backgrounds like Palantir, Anduril, major federal integrators, or defense-adjacent tech companies are a strong signal) - The architectural credibility to make hard calls on platform discipline vs. delivery speed, and enough organizational authority to make those calls stick under pressure - A track record of running parallel technical workstreams across multiple high-stakes engagements without losing accountability on any of them - Native fluency with AI-native development.

You build with AI tools yourself, you've thought seriously about agentic pipelines and AI-assisted delivery, and you set the standard rather than follow it - Experience leading both product engineering and delivery engineering, with a real understanding of what makes each culture different and why conflating them produces the worst of both Strong Candidates May Also... - Have built or contributed to an internal AI tooling layer (agentic pipelines, AI-assisted scaffolding, or similar) that measurably accelerated team throughput - Have direct experience navigating FedRAMP authorization processes or DoD IL4/IL5 environments (the bureaucratic context, not just the acronyms) - Have led a technical organization through a platform re-architecture under active delivery pressure, and have the scar tissue to prove it Don't Apply If... - You need product and engineering to be separate reporting lines.

This role commands both, and the organizational separation between Platform and Delivery is load-bearing - Federal procurement cycles feel like a tax rather than terrain. FedRAMP, ATO timelines, and agency BD dynamics are part of the operating environment, not exceptions to it - You've operated exclusively in one mode (e.g., pure platform architecture or pure delivery execution) and have never had to hold both accountabilities without letting either slip - You think architectural rigor and delivery velocity are fundamentally in tension.

The entire Kaizen 2.0 model depends on them being complementary, and you'll need to demonstrate that in practice What Kaizen Offers Health & Insurance - 100% coverage across the board: medical through Oxford/United (Gold and Platinum PPO plans), dental through Guardian PPO, and vision through Beam - all fully covered for employees, with 100% coverage for dependents. - $100,000 in fully paid life insurance.

FSA and Dependent Care FSA. - One Medical membership, on us - same-day primary care, 24/7 virtual visits, and offices all over the city. - Fertility and family-building support through Carrot. - 401(k) through Guideline, with a 2% company match. Family & Time Off - 16 weeks of fully paid parental leave for birthing parents.

10 weeks fully paid for non-birthing parents. - Unlimited PTO, with a two-week minimum (we mean it when we say take time off!) - Closed for all federal holidays. - Company-wide winter break the week of Christmas. - Company offsites throughout the year. Office & Remote Setup - Up to $750 one-time home office or desk setup stipend for NYC-based employees. $500 for remote employees. - $50/month commuter benefit (company contribution). - Expensed lunch while in the office. - Company-provided laptop of your choice.

Wellness - Fully covered gym membership at Grindhouse - right across the street from our office at 47 W 17th St (and in Williamsburg). A $225/month value, on us. For remote employees, $100/month dedicated to gym or physical fitness reimbursement.

Stipends - $100/month utility stipend. - $500/year professional development. - $250/year recreation. - $300/quarter pet care stipend.