Head of Security

Tremendous is the global platform built for businesses to send payouts—gift cards and money—to anyone, anywhere, instantly. We're trusted by 20,000+ organizations, from startups to giants like Atlassian, MIT, and United Way, to reach millions of recipients worldwide. We're profitable and growing without outside investors. We're fully remote, with a high-documentation, low-meeting culture that leaves more time for the work that matters—and for your life outside it. Our employee NPS sits in the high 80s. We move billions of dollars through our systems. That makes security existential, and it's why we're making our first dedicated security hire. About the role You'll be our first Head of Security. There's already a real foundation here—bug bounty, pen tests, automated code and configuration scanning on the production and code side, phishing simulations on the people side. You’ll add to it across access and identity, SecOps and monitoring, incident response, vendor security, employee security practices, and policy. You'll own the whole posture. This is a player-coach role. Early on, you'll do the scoping and the hands-on work yourself; this is not a role where you direct from above. As the work demands it, we're fully prepared to build a team here—and we're looking to you to define what that team should be and when. You'll report to the VP of Engineering , Tremendous' most senior technical leader. We've deliberately placed security with Engineering so you're set up to drive real implementation fast—embedded with the people whose work you're securing, not siloed in a compliance function. As the security function matures, we'll revisit this. What you'll do Own Tremendous' security posture end-to-end, partnering with our engineering team on production infrastructure and code security. Assess where we have gaps, prioritize them, and tackle our highest-leverage gaps first. We’ll have opinions, but you own the prioritization and implementation. Treat incident response as core, not afterthought. We may not be able to prevent a breach, but your job is making sure it's small, contained, and that we know exactly what to do. Drive security as a cultural shift across the company—introducing controls incrementally, working with teams rather than over them. "Yes, and," not "no." Lead our AI-security posture. We invest heavily in AI tooling; your job is to manage that risk and enable it, not to ban it. Define when and how to staff up the security function, and hire your own team. What you'll bring Real, hands-on security experience at a company that scaled—ideally as an early security hire who grew with the business through high growth. Deep experience in at least one core security domain—product/production security, security operations, or access/identity and policy—with enough range to reason across the others. You defined the security posture, not just executed someone else’s playbook. An engineer's mindset. You reach for code to solve problems and can read our