Chief Technology Officer

Who Are We?

Government technology has failed the public for decades, and Americans have been conditioned to expect websites from the 90s for essential public services.

Kaizen exists to strengthen trust in American public services by building technology that residents and public servants are proud to use. We partner with local, state, and federal agencies to replace legacy systems with modern, AI-native software that is worthy of the people they serve. We started in outdoor recreation, and now we’re building toward something much larger — the software layer that powers how Americans access any government service.

Our platform already reaches 40 million residents across 50+ agencies in 17 states.

The Role

Kaizen is building the constituent services operating system for the American government — and the 2.0 build cycle is the moment that determines whether we become a platform company or stay a vertical one. We have live federal deployments, real pull from USDA, DoW, DHS, and Commerce, and a product thesis proving out in production. What we need now is a technical general to command both Platform and Delivery: two fundamentally different operating modes that must run in parallel without collapsing into each other. Platform builds the reusable, compounding foundation — disciplined, architectural, built to last. Delivery wins and executes federal engagements at speed — high-tempo, AI-native, ships-or-dies. The CTO owns both, defines the interface between them, and ensures neither sacrifices what makes it effective.

Location

This is a hybrid role based out of our New York City HQ. Candidates must reside in New York or be able to commute to New York City to work out of our office at least three times a week (Tuesdays - Thursdays).

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 — 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 — 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
• Forty million Americans interact with government services that don’t work. If modernizing that infrastructure isn’t a sufficient reason to build something harder than you’ve built before, this isn’t the right mission.

What Kaizen Offers

Health & Insurance

• Comprehensive medical through Oxford/United — Gold and Platinum PPO plans, with 85% of premiums covered on the Platinum plan and a $0 employee premium option. Dental through Guardian PPO and vision through Beam, with 99% of employee premiums covered and 50% for dependents.
• $100,000 in fully paid life insurance. FSA and Dependent Care FSA. 401(k) access through Guideline.

Family & Time Off

• 16 weeks of fully paid parental leave for birthing parents. 10 weeks fully paid for non‑birthing parents.
• Unlimited PTO, closed for all federal holidays, and company‑wide winter break the week of Christmas.

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 3x a week while in the office.
• Company‑provided laptop.

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.
• $300/quarter pet care stipend.

Stipends

• $100/month utility stipend.
• $500/year professional development.
• $250/year recreation.

Kaizen is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, age, sex, national origin, disability, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local law. If you need an accommodation during the interview process, email us at View email address on click.appcast.io.

Compensation

$300K – $350K and Offers Equity