Sr. Director of Product, Bills

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2026 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team? About the role We are seeking a seasoned, entrepreneurial product leader to serve as the Head of Product for a new venture we are building. This is a pivotal, high-visibility leadership role critical to the future of Flex and we are looking for a leader with a rare combination of strategic vision, entrepreneurial grit, and proven team leadership. Reporting to the CPO and working in a close partnership with the General Manager of this new venture, you will be the single-threaded owner for the entire product function of this new business. You will have the unique opportunity to build a new product portfolio from 0-to-1, with the autonomy of a startup and the resources of an established market leader. This is not an optimization role. You are not inheriting a mature product. You will be responsible for navigating extreme ambiguity, leading a team to find product-market fit, and establishing Flex's next major revenue stream. You will be the GM's key partner in shaping the business, and you will be accountable for translating a high-level vision into a tangible, successful product. Core Responsibilities - Venture & Portfolio Strategy: Partner directly with the GM to define the multi-year business and product strategy for new ventures. Develop and manage the investment thesis, incubation framework, and portfolio strategy for new product initiatives. - Team Leadership & Development: Build, lead, and mentor a high-performing, dedicated team of senior product managers. Foster a culture of rapid experimentation, deep customer discovery, and high accountability. - Product Vision & Execution (0-to-1): Own the product lifecycle from concept to launch and scale. Translate ambiguous, high-level strategic concepts into a coherent product vision, a lean MVP, and a prioritized, metrics-driven roadmap. - Discovery & Validation Framework: Establish and lead the process for continuous customer discovery, rapid prototyping, and market validation. Ensure the team is relentlessly focused on solving the right problems and validating assumptions before scaling. - Executive Partnership & Communication: Serve as the primary product evangelist and leader for the New Ventures division. You will be responsible for communicating the product strategy, roadmap, progress, and risks effectively to the executive team and other senior stakeholders. - Business Ownership: Define and own the key product metrics for the new venture. You will hold a high degree of accountability for achieving product-market fit and early commercial targets, demonstrating a strong P&L orientation Qualifications - Extensive Leadership Experience: 10+ years in product management, with at least 4-5 years in a leadership role (Director or Sr. Director) managing other product managers. - Definitive 0-to-1 Track Record: You must have a clear, demonstrable history of leading a product organization to build and launch net-new (0-to-1) products into the market. You must be able to articulate the framework you used to navigate from ambiguity to a shipped product. - Proven Scaling Experience: Experience scaling a product from its initial concept (MVP) to a validated, growing business line (e.g., $XM in ARR, X-thousand users). - Strong Business & Commercial Acumen: Deep experience building business cases, analyzing market opportunities, and aligning product strategy directly with financial goals. P&L-awareness or direct P&L influence is strongly preferred. - Exceptional Executive Presence: Proven ability to communicate and influence at the highest levels. You must have experience presenting complex strategies, trade-offs, and results to C-level leadership. - Talent Magnet: A demonstrated ability to hire, manage, and develop senior-level product talent. - Thrives in Ambiguity: You are comfortable and effective operating with a high degree of autonomy in a fast-paced environment. Bonus Qualifications - Previous experience as a founder or co-founder. - Experience in an innovation lab, new ventures group, or "startup-within-a-company" environment. - Experience in FinTech or PropTech Compensation Flex takes a market-based approach to pay, ensuring compensation is commensurate with a candidate's experience and our internal leveling guidelines. For candidates located in our Tier 1 (NYC/Bay Area) markets, the base salary pay range for this role is below. Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside of the cities listed below, your starting pay will be adjusted to align with the market conditions of your specific geographic zone. Please speak with your recruiter for additional information regarding the specific range for your location. Tier 1 (NYC/Bay Area) $288,000 - $360,000 USD Life at Flex We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace. Offices Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program. Benefits For full-time U.S. employees we offer: - Competitive medical, dental, and vision - Company equity - 401(k) plan with company match - Unlimited paid time off + 13 company paid holidays - Parental leave - Free Flex subscription For full-time non-U.S. employees, we offer: - Competitive compensation + company equity - Unlimited PTO