Senior Penetration Tester

OpenKrill; United States; Remote; USD 101,000 - 129,000; Full time

Benefits offered by this job

Medical

Dental

Vision

Flexible time off

Parental leave

RRSP match

Wellness reimbursement

Volunteering days

Professional development budget

Charitable donation match

Job summary

Forward Financing, a fintech company, is seeking a Senior Penetration Tester to uncover vulnerabilities in our software and AI‑assisted systems. You will help shape how we test software that AI helped write, with testing moving as fast as AI.

You’ll work across core systems, APIs, and AWS infrastructure to improve security. You will bring hands‑on pentesting and code review skills, define AI pentesting approaches, and communicate risk to engineers for timely remediation.

Qualifications

• 5+ years in application security, offensive security, or product security.
• Hands-on pentesting and code-review depth across web apps, APIs, and AWS.
• Interest in AI to solve problems in testing and security workflows.

Responsibilities

• Conduct manual penetration tests across systems and AI-enabled components.
• Define how to pentest AI, including testing LLM apps and agent-generated code.
• Triage findings from SAST tools and fix real vulnerabilities.

Skills

Application security

Offensive security

Code review

AI/LLM testing

Secure SDLC

Hacker mindset

Security communications

Education

Bachelor's degree in Computer Science or equivalent

Tools

AWS

SAST tools

Job description

Forward Financing is a financial technology company based in Boston, Massachusetts with team members throughout the United States, Dominican Republic, and Canada. The company is on a mission to unlock the capital that fuels small businesses across America. Recognized as a Best Place to Work by Built In Boston and certified as a Great Place To Work®, Forward is investing in its employees, technology, and customer experience – with long‑term success in mind every step of the way.

As a Senior Penetration Tester, you'll find the vulnerabilities in Forward Financing's software before an attacker does. You'll pentest our core systems along with the AI systems and agents our engineers are shipping, and help shape how we test software that AI helped write. Our engineering organization is moving fast with AI, and our security testing needs to move at the same pace.

In this role you will:

• Conduct manual penetration tests against each of our systems, and build the AI‑assisted tooling and automation that extends how much ground those tests can cover.
• Help define how we pentest AI. Bring us new ideas for testing LLM applications, agents, and agent‑generated code, and build the ones that work into our regular testing.
• Triage findings from our SAST tools, fix the vulnerabilities that are real, and tune the rules that produce false positives.
• Perform secure code review across web applications, APIs, and AWS infrastructure.
• Build tooling and security services within the Forward application stack, including AI‑assisted tooling that speeds up the security team's own work.
• Support the test‑to‑production review process so AI‑built work is security‑reviewed before promotion.
• Explain risk to engineers in enough detail that they can prioritize and fix what you found.

Why you should apply:

• Shape a growing function: Our security program is early enough that your work sets the standard. You'll have influence over how we test, what tooling we build, and how we secure AI‑built software.
• Mission driven company: Forward is a trusted source of fast, flexible funding for small businesses that have often been underserved by traditional financing options. When you join the team, you will help ensure all small businesses have access to the financial support they need to succeed.
• Flexibility is a top priority: Our employees are empowered to choose where they want to work (whether that’s from home, in the office, or a combination of both) with flexible hours.

ROLE REQUIREMENTS:

• 5+ years in application security, offensive security, or product security.
• Hands‑on pentesting and code‑review depth across web applications, APIs, and cloud infrastructure (AWS).
• A hacker mentality. You're curious about how systems break, and you keep pulling on threads after the scanner comes back clean.
• Interest in using AI to solve problems, whether that's in your own workflow or in the systems you're testing.
• Understanding of AI/LLM attack surface: prompt injection, insecure agent tool use, and vulnerabilities characteristic of AI‑generated code.
• Experience with modern programming languages such as Ruby, Python, TypeScript, or Go, and with secure SDLC practices.
• Ability to communicate risk and priorities to other security and software engineers.
• Typically has a Bachelor's Degree in Computer Science or equivalent technical degree, or equivalent industry experience.

NICE TO HAVE:

• Experience pentesting or red‑team­ing LLM applications and agentic systems.
• OSCP/OSWE or comparable offensive certifications.
• Experience contributing to bug‑bounty or external testing programs.
• Background in fintech or other regulated environments.

COMPENSATION:

Annual Targeted Salary: $143,000-$183,000 CAD

Annual Target Bonus: 10%

At Forward Financing, we're committed to fair and transparent compensation. We believe in providing a compensation package that recognizes your skills, experience, and the unique value you bring to our team. We take a market‑based approach to pay, regularly reviewing benchmark data to ensure our compensation remains competitive, equitable, and aligned with our performance‑driven culture.

Final offers are determined by a variety of factors, including the candidate's qualifications, relevant experience, specific skills, and internal equity. This approach ensures that our compensation is competitive and equitable. Your recruiter will provide specific details on the expected base and variable earnings as it pertains to this specific role. This position is to fill an existing vacancy.

TOTAL REWARDS:

• medical
• dental
• vision
• a flexible time‑off policy
• paid parental leave
• RRSP match
• wellness reimbursement
• volunteering days
• annual professional development budget
• charitable donation match

Forward is proud to be a remote‑first company, keeping workplace flexibility a top priority for our employees. As a business, we are focused on impact; we are more concerned with your contributions to the success of the company than where you get your work done. To help facilitate in‑person collaboration, employees are welcome to work from one of our premiere office locations.

When we aren’t collaborating to drive business and support our customers, we’re finding virtual and in‑person ways to get to know our colleagues, celebrate team wins, and have fun together!

OUR CULTURE: THE FORWARD COMPASS

The Forward Compass is the standard we hold for ourselves and one another—guiding how we lead, collaborate, and show up every day to move in the same direction.

• Back the Builders: We are wired to fuel customer progress, not just provide support.
• Rooted in People: We create an environment that balances deep connection with the extreme ownership and honesty required to reach our highest potential.
• Flying V: We move through coordinated effort with speed and urgency to achieve what no individual could do alone.
• Always Forward, Never Finished: We pursue growth with a relentless drive that keeps us ahead of the competition.

About Us:

Forward Financing is a fintech company based in Boston, Massachusetts with team members throughout the United States, Dominican Republic, and Canada. The company is on a mission to unlock the capital that fuels small businesses across America. Whether facing challenges accessing traditional financing or simply needing a convenient, flexible solution, Forward is committed to funding more of the millions of small businesses nationwide. By simplifying the requirements, streamlining the process, and using advanced proprietary technology, Forward is often able to deliver approvals within hours and funds that same day – giving more businesses the financial opportunity they need to thrive. Plus, with their dedicated teams and award‑winning service, customers get personalized support when they need it most.

Since 2012, Forward has expanded access to capital by providing over $4.8 billion in funding to more than 92,000 small businesses. The company is A+ rated by the Better Business Bureau with an Excellent / 4.7 stars rating on Trustpilot.com http://Trustpilot.com. Recognized as a Best Place to Work by Built In Boston and certified as a Great Place To Work®, Forward is dedicated to empowering both its team and the customers they serve, helping them succeed and thrive.

EQUAL OPPORTUNITY EMPLOYMENT INFORMATION

It is the policy of Forward Financing to ensure equal employment opportunity without discrimination or harassment on the basis of race, religion, national origin, status, age, sex, sexual orientation, gender identity or expression, marital or domestic/civil partnership status, disability, veteran status, genetic information, or any other basis protected by law. We welcome and encourage applications from people with disabilities. Please let us know should