OLarry AI-Native Security & Quality Engineer Remote · Full time Company website

Apply for AI-Native Security & Quality Engineer

With deep expertise in tax and technology, we're a team driven to change the landscape of tax by making it more accessible and efficient for all involved. Join us! OLarry only hires individuals based in the U.S..

About Us

OLarry is shaping the future of tax by bringing together tax experts and technology leaders to create a tax practice that provides exceptional service supported by leading proprietary technology for high-net-worth and ultra-high-net-worth clients.

The Role

We are not hiring for a traditional QA role, nor are we hiring a senior security specialist.

We're looking for a strong software engineer who loves automation, uses AI deeply, and wants to grow into security ownership. You don't need to have led a SOC 2 audit or built a security program before; we're looking for engineering fundamentals and the ambition to own this area, not a résumé that already covers all of it. You'll become OLarry's security and quality expert over time, and we'll invest in getting you there.

Your first job is helping the team ship more confidently: better automated tests, better CI gates, better release checks — built with AI, at the speed our engineers ship. Over the next few years, the role will grow into ownership of our security posture and SOC 2 readiness.

Our goal is not to slow engineers down. It's to make the safest path also be the fastest path.

What You'll Do

The scope grows with you; you won't be expected to master all of this at once.

1: Quality and automation

• Build AI-assisted testing workflows across our backend services, web apps, and integrations — generating, reviewing, and expanding coverage rather than writing every test by hand.
• Own and mature our CI quality gates: what runs on every PR, what blocks a merge, what blocks a release — and keep raising the bar as the codebase grows.
• Grow our end-to-end test coverage and kill flaky tests before the team learns to ignore them.
• Turn recurring bugs and production issues into automated checks.
• Evaluate AI-generated code and tests for correctness, maintainability, and security, and continuously improve the team's AI-assisted engineering workflows.

2: Security engineering

• Review product changes for common security and privacy risks: authn/authz, access control, secrets, data exposure, injection, dependency risk.
• Run our vulnerability workflows: dependency scanning, secret scanning, static analysis, triage, and remediation tracking.
• Partner with engineers on secure defaults for sensitive customer data — tax documents, identity data, financial records — across services, storage, and third-party integrations.
• Introduce lightweight threat modeling for new features while they're still on the whiteboard.

3: Compliance and security ownership

• Partner with engineering leadership to build the technical foundations for SOC 2 readiness: controls, evidence collection, access reviews, incident response, and change management.
• Help us meet the obligations that come with tax data (GLBA Safeguards Rule, IRS Publication 4557).
• Mature our secure development lifecycle and become the engineer the team trusts to balance speed with security and quality — helping teams ship safely rather than creating unnecessary friction.

Our Stack

A modern, cloud-native stack built around Python and TypeScript services, with infrastructure managed as code and mainstream identity and data-platform tooling. AI tooling is deeply embedded in how we build. You don't need to have used this exact stack; you need to be able to read it, reason about it, and automate around it.

What We're Looking For

• Roughly 4–8 years of software engineering, test automation, or SDET experience with strong coding ability and comfort reading production code.
• Real experience with automated testing and CI/CD: you've designed test strategy for a live product, not just executed someone else's.
• Practical knowledge of modern web application security basics OWASP-level familiarity with auth, secrets, access control, injection, and dependency risk.
• Heavy, genuine AI-tool usage for coding, testing, reviewing, or automation as a default, not an experiment — and you can show us.
• Genuine interest in security and compliance, even if you haven't owned those areas before. Wanting to own an area — not just implement tickets — is the core of this role.
• Startup judgment: you improve systems without creating unnecessary process, and you ship process improvements the way engineers ship code small, fast, iterated.
• Clear communication with engineers, founders, and non-technical stakeholders.

Nice to have

• Experience with modern test automation frameworks, static analysis and dependency-scanning tools, and mainstream CI/CD platforms.
• Exposure to SOC 2 or similar compliance frameworks, access reviews, audit logs, or security questionnaires, at any depth.
• Experience in fintech, tax, healthcare, or another trust-sensitive domain.
• Experience testing AI-assisted or AI-generated code.
• You write scripts and internal tools without being asked.

What Success Looks Like

• 10 days: You understand our product, architecture, dev workflow, and where our testing and security gaps actually are ranked by risk, not by visibility.
• 20 days: PR and release confidence are meaningfully higher through better automation and stronger CI checks, and engineers are noticeably faster because of your work, not slower.
• 30 days: The team has a repeatable, AI-assisted quality workflow; the end-to-end test path is solid; and we have a practical roadmap for growing our security maturity.
• Long-term: You are OLarry's trusted owner for quality systems, security readiness, and secure engineering practice; a force multiplier, not an auditor.

How We'll Evaluate You

We'll be especially excited if you can show us that you:

• Use AI tools deeply, not casually, bring examples of workflows you've built, not just tools you've tried.
• Have found real quality or security issues before customers did, and can tell the story.
• Prefer building automation over running a manual process.
• Want ownership of an area, and can point to somewhere you've taken it.

Benefits & Compensation

• Unlimited PTO.
• Stock Options.
• Healthcare Insurance - 100% coverage for the employee, 50% coverage for dependents.
• Generous revenue sharing for all new business development.
• We are committed to investing in your career by offering continuous training and support, ensuring you acquire new skills and opportunities.

We are committed to creating a diverse and inclusive workplace. We do not discriminate based on race, color, religion, gender, sexual orientation, gender identity, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state, and local laws. We are also committed to complying with the Ban the Box legislation, which prohibits employers from inquiring about an applicant's criminal background history until a conditional job offer has been made.

OLarry Core Pillars

• Owner Mindset: Think and spend like shareholders. Long‑term, frugal, fully accountable.
• Customer‑First: Start with the client, validate every idea in the market, let revenue follow.
• High-Bar Collaboration: Hire people better than ourselves and share knowledge. No silos, just collective brilliance.
• Grit & Innovation: Push through obstacles and invent better ways—experiment fast, finish strong.
• Brand Ambassadors: Grow Olarry in every interaction; selling, serving, and building trust.
• Build‑to‑Last: Make smart, long‑term choices that compound wealth and strengthen the company; never chase quick wins.