[Hiring] Chief Technology Officer @Scratch Financial

Role Description

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.

What You'll Do

• Build engineering process and operational maturity from the ground up — architecture, coding standards, CloudOps, GitOps, and security practices.
• Close 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.
• 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.
• Lead a distributed, remote-first engineering team — guiding and delegating rather than micromanaging.
• Operate with commercial and financial fluency — tie technology decisions to cost and business value.
• Communicate with transparency and discretion — clear, tactful, and calibrated for the audience.

Qualifications

• Has led a company through a sale on the sell side, including hands-on experience preparing for diligence.
• Has personally built observability, alerting, and security systems from near-ground-zero.
• 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.
• Comes from a background in distributed cloud backends, database scaling, and API architecture.
• 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.

Requirements

• 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 — looking for strong judgment and principles, not attachment to a particular stack or vendor.

Leadership & Working Style

• Comfortable with ambiguity and shifting business or product requirements.
• Operates roughly 30% hands-on / 70% structuring, delegating, and managing.
• Genuinely curious about the business, customers, and problems being solved.
• Proactive by default — drives resolution with the right teams rather than stopping at a written recommendation.
• Low ego about role and process — comfortable with specific ways of operating 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.

Benefits

• Competitive base salary ranging from $300,000 - $350,000, with participation in the company's equity and leadership bonus programs.
• Scratch is a remote-first company, giving ultimate flexibility to today's nomadic work style.
• For those who prefer a hybrid model, we do have an office space in Pasadena available for use.
• Unlimited PTO, covered healthcare, 401k match, cell plan reimbursement, and monthly recognition opportunities.
• Learning platforms and resources for all to keep growing.
• Equity retention policy to ensure you grow as the company grows financially.
• Generous parental leave for growing families.

How to Apply

Ready to join our team? To apply, please visit our Scratch Careers Page. Be sure to:

• Submit your resume.
• Answer the custom questions provided.
• Feel free to add any additional information or documents you believe are relevant to your application.

We look forward to reviewing your application!

*Our team will ONLY contact you from the domain @scratchpay.com or @ats.rippling.com

Our Commitment

We’re innovators who care deeply about the lives of pets, their owners, and veterinary professionals. We believe diversity strengthens our team and drives better solutions. Scratch is committed to diversity in its workforce and is proud to be an equal opportunity employer.