Lead Application Security Engineer

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 Team Lead, AppSec, you'll take the reins of Forward's application and product security program at a pivotal moment, as we scale our use of AI to build software faster than ever. You'll lead a team of senior engineers, modernize how we pentest and remediate vulnerabilities, and make sure security keeps pace with an engineering organization that increasingly builds with, and builds, AI agents. In this role you will: Lead application and product security across Forward-built, third-party, and AI-built software. Evolve the pentest program: aggressively security-test and remediate existing software, then continuously test net-new agents and the software agents create. Proactively build and integrate AI solutions within the appsec function. Own remediation workflows and vulnerability management with Engineering, including pre-production vs. post-production gap analysis. Partner with other teams to build controls to contain external exposure: network allowlists, egress proxy, and proxy-level DLP. Support the test-to-production review process so AI-built work is security-reviewed before promotion. Grow and develop a team of senior engineers; set quality and coverage standards for offensive testing. Build and maintain security services within the Forward application stack. Why you should apply: Shape a growing function: This is a high-visibility leadership role at a pivotal moment for Forward's security program. You'll have the mandate and support to build the team, tools, and processes needed to secure AI-built software from the ground up. 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: Typically has 7 or more years in application security, offensive security, or product security, including team leadership. Hands-on pentesting and code-review depth across web applications, APIs, and cloud infrastructure (AWS). Experience building or scaling a security testing program — scoping, tooling, cadence, and remediation SLAs. 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, or Go, and with secure SDLC practices. Ability to communicate risk and priorities crisply to engineers and executives. Typically has a Bachelor's Degree in Computer Science or equivalent technical degree, or equivalent industry experience. It would be nice if you also had: Experience pentesting or red-teaming LLM applications and agentic systems. OSCP/OSWE or comparable offensive certifications. Experience running bug-bounty or external testing programs. Background in fintech or other regulated environments. Compensation: Annual Targeted Salary: $175,000-$200,000 CAD Annual Target Bonus: 12% 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: Additionally, we offer a comprehensive total rewards package, including but not limited to: medical, dental, vision, a flexible time-off policy, paid parental leave, RRSP match, wellness reimbursement, volunteering days, annual professional development budget, and 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!