Freelance Roller Coaster Engineer Jobs (NOW HIRING)

TITLE: Head of Security & AI Governance

REPORTING TO: CTO

LOCATION: Marina del Rey, CA (Onsite Monday - Friday)

Who The Flip Is Flip?

Ever call your favorite eCommerce brand or healthcare provider, and have a crazy good Voice AI answer? That's Flip. Hundreds of brands from Under Armour and Tory Burch in retail to Experity and Fast Pace Health in healthcare trust Flip to have millions of phone calls with their customers every month.

We've built our company on the idea that the best way to grow is to have a reference list as long as our customer list, and a constant belief that the team is the best thing we've built. Both are true today and increasingly so every day.

Many on our team would tell you this is their favorite place they've ever worked, and the hardest they've ever worked. It's ideal for people who want to go all-in, do the work, ride the roller coaster, and have a great Flippin time doing it. We're a small and mighty team of 50 today with offices in NYC, LA, and the UK.

At Flip, security and compliance are not checkboxes.

They were baked into the company early and helped us earn the trust of some of the largest enterprises in the world. As customers increasingly trust AI to represent their brand, make decisions, and interact directly with their customers, the security and trust model has to evolve.

We are looking for a hands-on leader to own Flip's security, compliance, IT, and AI governance program as we scale.

This is not a role for someone who only wants to answer questionnaires, manage an audit calendar, or operate at 30,000 feet. We need someone who can keep their head up and help define where AI governance is going, while also rolling up their sleeves and building the systems, controls, and processes we need today.

The right person can move fluidly between customer security calls, SOC 2 controls, Okta and access governance, internal IT operations, AI risk, vendor diligence, and emerging questions around LLM security, prompt injection, red teaming, data boundaries, logging, retention, and model risk.

We are not looking for someone who simply responds to security questionnaires. We are looking for someone who can look at a questionnaire and say, "They are asking the wrong questions," then help define the right ones.

• SOC 2, HIPAA readiness, audit evidence, access reviews, and security controls
• Customer security diligence, questionnaires, trust materials, and vendor reviews
• Internal IT and security operations, full stack
• AI governance frameworks around data flows, model/vendor risk, prompt injection, jailbreaks, evals, logging, retention, and customer data boundaries
• Security policies, runbooks, training, incident response, and internal control documentation
• Access governance, admin policies, role-based access, and separation of duties across IT, Engineering, DevOps, and business systems
• External security and trust conversations with enterprise customers and prospects
• Selection and management of tools, MSPs, and vendors that help Flip scale securely

• 6+ years across security, compliance, IT operations, GRC, infrastructure security, or corporate systems
• Experience owning or materially operating a SOC 2 program
• Experience with MDM, endpoint security, device lifecycle, SaaS access governance, and internal IT operations
• Comfort working cross functionally between engineering, sales, and other functions
• Ability to speak credibly with enterprise customers about security, compliance, and trust
• Strong judgment, high attention to detail, and low tolerance for sloppy access or unclear ownership
• Curiosity and fluency around AI governance, LLM security, data boundaries, model/vendor risk, red teaming, and emerging enterprise trust expectations
• A builder mindset: you can design the policy, implement the workflow, chase the evidence, clean up the process, and improve it over time

This role is for someone who wants the whole problem. Some days, that means joining a strategic customer call about AI governance. Other days, it means tightening an access workflow, cleaning up an Okta group, improving audit evidence, managing a vendor, or building a process that does not exist yet. You will not inherit a perfect machine. You will build it.

If you want a narrow GRC role, this is probably not it. If you want to help define the trust model for AI-native software while also doing the practical work to keep a fast-growing company secure, we want to meet you.

• We are international, with teams across the US, UK, and Canada
• We have raised $30M+ to date, including our recent $20M Series A
• Our investors include Ridge, Next Coast, ScOp, Bullpen Capital, Data Point, Forum Ventures, and founders and executives from companies like Amazon Alexa, Ada, Attentive, and Simon Data
• We offer comprehensive healthcare and unlimited vacation, including company-wide time off around July 4 and the end of the year
• We are an in-office culture and believe the best work happens when ambitious people build together

#FlippinLegend