Chief Technology Officer

Job description

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. What You'll Do 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. What We Are Looking For Experience & Track Record 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. Technical Approach 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. Leadership & Working Style 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. Why You'll Love Working Here 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. And if your family is growing, we offer generous parental leave, too! 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. 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. Who We Are 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.S. and Canada. Scratch has 2 main products: 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.