Scratch Financial operates at the intersection of healthcare and finance, providing payment plans designed to help patients manage medical expenses. Its financing options cover amounts from $200 to $10,000 with 12- to 36-month repayment terms, and are presented with clear costs, no prepayment penalty, and no deferred interest. Scratch Financial serves borrowers in the United States and Canada; U.S. loans are serviced by WebBank. The company’s work centers on making medical financing more straightforward and accessible for patients and healthcare providers.
Chief Technology Officer — California Remote
Lead engineering, infrastructure, and security at Scratch Financial, a veterinary payments fintech. Drive scalable systems, stronger security, practical AI adoption, and organizational maturity through change.
United States
California$300,000 – $350,000 / year
RemoteFull-timeLeadEnglish RequiredChief Technology OfficerDescription
- Direct engineering, infrastructure, and security for a team of approximately 30 people
- Advance engineering processes and operational maturity across architecture, coding standards, CloudOps, GitOps, and security
- Strengthen monitoring, alerting, and observability across the technology organization
- Lead the security function, including audits, compliance preparation, application hardening, and incident response
- Define the engineering and AI strategy and identify practical uses for AI
- Develop and apply agentic security strategies
- Lead, delegate, and support a distributed, remote-first engineering team
- Review architecture, resolve complex technical issues, and establish engineering standards
- Connect technology investments and decisions to cost control and business value
- Communicate transparently with internal teams and external stakeholders during organizational change and sensitive matters
- Create the structure, delegation model, and leadership depth needed to prevent the CTO from becoming an operational bottleneck
Requirements
- Experience leading a company through a sell-side transaction, including hands-on diligence preparation
- Experience building observability, alerting, and security systems from near-ground-zero
- Direct experience leading a security function, including exposure to audits and compliance processes
- Hands-on experience developing agentic AI
- Background in distributed cloud backends, database scaling, and API architecture
- Recent hands-on technical or coding experience; candidates who have been away from technical work for a decade or more are not suitable
- Understanding of pragmatic, scalable architecture, including when to choose modular monoliths over premature microservices
- Strong FinOps discipline and attention to cloud costs
- Experience with Stripe-style payment infrastructure, including subscriptions, webhooks, and ledgering
- Experience designing secure integrations with third-party systems
- Commitment to rigorous software development lifecycle practices
- Ability to lead and delegate within a distributed, remote-first team
- Commercial and financial fluency
- Ability to communicate with transparency and discretion
- Comfort operating amid ambiguity and changing business or product requirements
- Ability to spend approximately 30% of the role hands-on and 70% on structuring, delegating, and managing
- Curiosity about the business, customers, and problems being addressed
- Proactive approach to identifying and resolving process and structural gaps
- Ability to work inclusively across a distributed, international team
Benefits
- Eligibility for the company's equity and leadership bonus programs
- Remote-first work flexibility
- Access to Pasadena office space for hybrid work, with snacks and beverages provided
- Unlimited paid time off
- Employer-covered healthcare
- 401(k) matching
- Cell plan reimbursement
- Monthly employee recognition opportunities
- Access to learning platforms and resources
- Equity retention policy
- Generous parental leave