Head of Technology - Remote

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.
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, CloudOps, GitOps, and security practices — closing our current gaps in monitoring, alerting, and observability rather than inheriting and coasting on what exists today.
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. 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.
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; Advocates for pragmatic, scalable architecture (modular monoliths over premature microservices) and strong FinOps discipline around cloud cost.
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; 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.
Builds trust deliberately during a period of organizational change, and works inclusively across a distributed, international team.
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 (which is stocked with snacks & various beverages). We offer unlimited PTO, covered healthcare, 401k match, cell plan reimbursement, and monthly recognition opportunities. We also provide learning platforms and resources for all to keep growing. Not only that, but we have an equity retention policy to ensure you grow as the company grows financially, as well. 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. Scratch considers qualified applicants without regard to race, color, religion, creed, gender, national origin, age, disability, veteran status, marital status, pregnancy, sex, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
Scratch Financial (“Scratch”) is a late stage venture‑backed financial technology business based in Pasadena, California. At Scratch, everything starts and ends with our mission: being the payment partner of choice for veterinary practices and helping pet parents access the care their animals need without financial barriers. Driven by our award‑winning technology, Scratch has become the fastest growing financing provider in veterinary care, with a partner network of 15,000+ practices across the U.Scratch Pay: Point‑of‑sale client facing lending, including a BNPL offering and longer‑term payment plans
# Scratch Checkout: Payment processing that is integrated with the veterinary practice management software

We are a company built on the foundation of transforming the way pet healthcare payments are done, and we are looking for innovators who share our commitment to shaping the future of veterinary care financing. If putting compassion first, helping tell the story of groundbreaking products and continuously learning & refining to achieve exceptional outcomes sounds like you, then we encourage you to apply.
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