Chief Technology Officer

Position Overview

We're looking for a Chief Technology Officer who can lead our engineering, infrastructure, and security functions (~30 person team) through that process — building the operational maturity, technical standards, and team capability needed to stand up to diligence, while keeping the organization stable and motivated through the change.

This is a hands‑on leadership role, not a strategy‑only seat. You'll spend meaningful time in the weeds — reviewing architecture, unblocking teams, and setting the technical bar — while building the structure, delegation, and bench strength that lets the org run without you as the bottleneck.

• Build engineering process and operational maturity from the ground up — architecture, coding standards, Cloud Ops, Git Ops, and security practices — closing our current gaps in monitoring, alerting, and observability rather than inheriting and coasting on what exists today.
• Revitalize and run our security function — own security as a first‑class function, including audits, compliance readiness (e.g., SOC2/GDPR/HIPAA‑type frameworks), application hardening, and incident response, not as an afterthought bolted onto engineering.
• Bring a credible AI and engineering vision — with a real, substantiated point of view on where AI creates leverage for the team and the product — grounded in hands‑on experience, not hype. Ready to hit the ground running with agentic security strategies.
• Lead a distributed, remote‑first engineering team — guiding and delegating rather than micromanaging, while staying technical enough to debug complex issues, review architecture, and defend technical decisions to outside parties.
• Operate with commercial and financial fluency — tie technology decisions to cost and business value, and move with speed‑over‑perfection when the situation calls for it, without losing sight of the underlying goal.
• Communicate with transparency and discretion — clear, tactful, and calibrated for the audience — whether that’s the internal team during a period of change, or external parties during a sensitive process.

• Has led a company through a sale on the sell side, including hands‑on experience preparing for diligence — this is not something we can teach on the job.
• Has personally built observability, alerting, and security systems from near‑ground‑zero — not simply inherited and maintained existing systems.
• Has led a security function directly, with real exposure to audits and compliance processes.
• Has hands‑on experience with agentic AI development and can speak to where it’s genuinely being applied, not just discussed.
• Comes from a background in distributed cloud backends, database scaling, and API architecture — this is not a fit for candidates whose experience is primarily mobile app or front‑end/client‑side engineering.
• If several years removed from a hands‑on technical or coding role, that’s workable; a decade or more away from technical work is not.

• Advocates for pragmatic, scalable architecture (modular monoliths over premature microservices) and strong Fin Ops discipline around cloud cost.
• Comfortable owning Stripe‑style payment internals (subscriptions, webhooks, ledgering) and designing secure third‑party integrations.
• Committed to SDLC rigor, especially if coming from an ops‑heavy background.
• Flexible on specific tooling — we’re looking for strong judgment and principles, not attachment to a particular stack or vendor.

• Comfortable with ambiguity and shifting business or product requirements; doesn’t need a fully specified brief to move forward.
• Operates roughly 30% hands‑on / 70% structuring, delegating, and managing — hands‑on enough to stay credible, but building a bench rather than becoming the bottleneck.
• Genuinely curious about the business, customers, and problems being solved, and treats being wrong as useful information rather than a threat.
• Proactive by default: when a process or structural gap surfaces, drives it to resolution with the right teams rather than stopping at a written recommendation.
• Low ego about role and process — comfortable with…