Chief Technology Officer, Scratch Financial
$300-350k
+ Equity and bonus
Office located in Pasadena, CA
Healthcare financing provider
Open for applications
Healthcare financing provider
21-100 employees
Open for applications
$300-350k
+ Equity and bonus
Office located in Pasadena, CA
21-100 employees
Company mission
To help more patients and pets get access to the care they need to live happy lives.
Role
Who you are
- 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
- 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
- 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
What the job involves
- 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
- 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
Our take
Access to healthcare for both humans and pets can often be unaffordable, but the nature of the situation means people are forced to find a way to pay. This often involves unfair lending rates or hidden fees within payment plans, a tactic that unfairly preys on those least able to afford it.
Scratch Financial provides healthcare financing solutions for both human and pet healthcare, allowing customers to apply for payment plans across various time periods. The company provides its "Take 5" plan of five bi-weekly payments at zero percent interest, a plan which doesn't include hidden fees and is not subject to prepayment penalties or deferred interest.
The company has raised considerable funding which will be invested in developing new technology to help medical providers better connect with their clients and manage the end-to-end patient experience. Scratch is processing over $1 billion in payments annually, and is planning for further expansion as the popularity of buy now, pay later services continues to grow in the health care sector.
Freddie
Company Specialist at Welcome to the Jungle
Insights
28% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Sep 2022
$35m
SERIES C
Sep 2020
$0.8m
EARLY VC
Total funding: $58.9m
Company benefits
- 401(k)
Company HQ
Eagle Rock, Los Angeles, CA
Leadership
John Keatley
(CEO & Co-Founder)Experience as Director of Financial Planning & Analysis, Vice President of Finance, and CFO of Green Dot Corporation from 2004 to 2013. CFO of Klarna from 2013 to 2015.
Caleb Morse
(President & Co-Founder)Senior Analyst of FP&A & Revenue and Senior Director of Banking Operations for Green Dot Corporation from 2007 to 2012. Experience as CFO and Head of Growth for Meridith Baer Home.
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