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Scratch Financial
Scratch Financial
11 – 50 Employees
H1B Visa SponsorFinanceHealthcareInsurance
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.
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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.

USUnited StatesCACalifornia
$300,000 – $350,000 / year
RemoteFull-timeLeadEnglish RequiredChief Technology Officer
CloudMicroservicesSDLC

Description

  • 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

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