Sr. Director of Product, Bills

flex

New York, NY; San Francisco, CA · New York · Canada

Posted Aug 14, 2026

Full-time
Hybrid
Product

Job description

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

Flex is seeking an experienced product leader to serve as the Head of Product for our next product line. This is a high-visibility leadership role critical to the future of Flex. We are looking for a leader with a combination of strategic vision, builder grit, and proven team leadership.

Reporting to the CPO and working in a close partnership with the General Manager of our Bills division, you will be product owner for this rapidly growing business. Your mandate will be to scale a new product offering from early market fit to a major business line, operating with the autonomy of a startup and the resources of an established market leader.

Core Responsibilities

Product Strategy & Execution: Define the product strategy and roadmap for Bills. Own the product lifecycle from concept to launch and scale. Translate ambiguous, high-level strategic concepts into a coherent product vision and a prioritized, metrics-driven roadmap.
Discovery & Validation Framework: Establish and lead the process for continuous customer discovery, rapid prototyping, and data driven 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 owner for Bills. You will be responsible for communicating the product strategy, roadmap, progress, and risks effectively to the executive team and other senior stakeholders.
Metrics & Goal Ownership: Define and own the key product metrics for the new venture. You will hold a high degree of accountability for achieving both product and commercial targets, demonstrating a strong P&L orientation.
Team Leadership & Development: Build, lead, and mentor a high-performing, dedicated team of senior IC product managers. Foster a culture of rapid experimentation, deep customer discovery, and high accountability.

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.
Proven Track Record of Scaling Products: You have a clear, demonstrable history of leading a product team to scale early stage products from initial MVP to a validated, growing business line.
Strong 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 FinTech or PropTech
Have scaled prior new product lines within a startup or growth company

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