Chief Technology Officer

Scratch Financial • Pasadena, CA

21h • $300,000 - $350,000 • Remote

About The Position

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.

Requirements

• 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 FinOps 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 Scratch's specific ways of operating (budgets, decision rights) even where they differ from past companies.
• Shares credit generously ("we" over "I") and handles high-pressure mistakes without assigning blame.
• Builds trust deliberately during a period of organizational change, and works inclusively across a distributed, international team.

Responsibilities

• Build engineering process and operational maturity from the ground up — architecture, coding standards, CloudOps, GitOps, 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.

Benefits

• Competitive base salary ranging from $300,000 - $350,000
• participation in the company's equity and leadership bonus programs
• remote-first company
• office space in Pasadena available for use (stocked with snacks & various beverages)
• unlimited PTO
• covered healthcare
• 401k match
• cell plan reimbursement
• monthly recognition opportunities
• learning platforms and resources
• equity retention policy
• generous parental leave

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed