Head of Security

Bad software is everywhere, and we’re tired of it. Sentry is on a mission to help developers write better software faster so we can get back to enjoying technology.

With more than $217 million in funding and 100,000+ organizations that believe we’re on to something, we're building performance and error monitoring tools that help companies like Disney, Microsoft, and Atlassian spend less time fixing bugs and more time building products.

Sentry embraces a hybrid work model, with Mondays, Tuesdays, and Thursdays set as in-office anchor days to encourage meaningful collaboration. If you like to selfishly build things that make your digital life better, come help us build the next generation of software monitoring tools.

About the Role

Sentry’s users trust us to develop, ship, and operate a secure open-source product and a secure SaaS offering, so they can focus on their own applications worry-free. We’re looking for an experienced Head of Security to build and scale Sentry’s security program—starting with early adoption (bug bounty, penetration testing, red teaming) and growing into a high-impact organization that protects both our multi-tenant SaaS and self-hosted products.

This role is not for the faint of heart. You will adopt, improve, and expand our current protocols, breaking down barriers to create a secure environment for all users. Because Sentry will always provide an open-source option, success in this role requires creative, outside-the-box thinking to protect diverse deployment models.

In this role you will

Ensure security for our SaaS platform —establish and operate the controls, guardrails, and monitoring required for a modern, high-scale, multi-tenant cloud service.

Partner deeply with IT & Compliance on identity and access, endpoint / security baselines, vendor risk, policy, and audits; drive secure-by-default corporate foundations.

Collaborate with executive leadership to fine-tune and evolve Sentry’s security strategy, set multi-year roadmaps, and communicate risks, tradeoffs, and outcomes.

Build application and product security programs with support from the CTO and IT / Compliance orgs, including managing external parties for penetration tests and bug bounty programs.

Prioritize automation and tooling over manual process; measure outcomes and continuously reduce risk and toil.

Partner with Recruiting to build a world-class security team across AppSec, ProdSec, and GRC capabilities.

Influence product roadmaps and customer-facing security features (e.g., MFA, session audit tooling, data controls).

Explore future security-adjacent product opportunities where Sentry can add value to developers and security teams.

Define security objectives and key results (OKRs) for SaaS security posture , corporate security, and compliance outcomes.

Collaborate with leaders in Engineering, Product, IT, and Compliance to align investments, policies, and incident response.

Communicate security posture to leadership and contribute to board-level updates as needed.

You’ll love this job if you

Are passionate about creatively building out security solutions for both open-source and SaaS environments.

Seek ownership and high impact at a company whose customers are deeply technical.

Have a knack for finding weaknesses and automating them out of existence.

Enjoy mentoring and upleveling teams across engineering, IT, and compliance.

Are driven to make engineers’ lives easier and more efficient through secure defaults.

Qualifications

Deep understanding of modern security domains with expertise in at least two of : application / product security, infrastructure security, corporate / IT security .

10+ years relevant experience, including 5+ years in security-focused roles and prior management experience.

Strong technical background (CS degree or equivalent software engineering experience).

Proven experience building and managing security programs (bug bounty, pen testing, red teaming, secure SDLC, training).

Demonstrated success in SaaS security (multi-tenant architecture, cloud controls, customer-facing assurances).

Extensive collaboration with IT & Compliance on identity / access management, endpoint posture, and policy.

Experience working directly with auditors (e.g., SOC 2 / Type II, ISO 27001) including evidence collection, remediation planning, and closing findings.

Self-motivated owner who can both set strategy with leadership and execute through roadmaps, metrics, and teams.

The base salary range that Sentry reasonably expects to pay for this position is $240,000 to $300,000. A successful candidate’s actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans / programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits for more details about the Company’s benefit plans / programs.

Equal Opportunity at Sentry

Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally-protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry. We strive to build a diverse team, with an inclusive culture where every teammate can thrive. Sentry is an open-source company because we believe that everyone, everywhere, should have the ability and tools to make great software. Software should be accessible. That starts with making our industry accessible.

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