Senior Director, Strategy & Operations (Housing)

Flex•New York, NY

23h•$264,000 - $330,000•Hybrid

About The Position

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. Flex enables its users to pay rent throughout the month on a schedule that better fits their finances and budget. The Strategy & Operations team is the "API" through which company strategy, operating rigor, and ways of working are translated into execution across Flex. As Senior Director of Strategy & Operations for the Housing division, this role serves as the most senior embedded operator within one of Flex's most strategically critical business units. This role is distinct in its mandate: it is not a team builder or central function leader, but a hands-on, high-ownership strategic operator embedded in the Housing division, working as the primary S&O interface between Housing and the Revenue organization. This individual will own the most complex, highest-stakes initiatives at the intersection of property partnerships, consumer growth, and cross-functional execution — including standing up Flex's efforts to leverage its property network to drive consumer awareness and adoption at scale. The role reports to the Chief Business Officer and works in close partnership with the GM of Housing and the Revenue leadership team. This is a hybrid position with on-site expectations of 3 days per week in our New York Headquarters. For candidates outside of the NY/NJ/SF area, relocation assistance may be available.

Requirements

12+ years of professional experience, with a track record spanning management consulting and/or senior strategy, biz ops, or chief of staff roles at high-growth companies
Deep experience at the intersection of partnerships, go-to-market, or consumer growth - you understand how to build and operationalize a business motion that bridges supply-side assets and demand-side goals
Exceptional conceptual thinker who moves fluidly across levels of abstraction—from strategic framing to execution mechanics—without losing altitude
Proven ability to lead high-stakes cross-functional work at scale, with the credibility and interpersonal skill to align senior stakeholders across organizational boundaries
Comfortable operating in ambiguity and partial information - you structure complex problems quickly, move with urgency, and revise as you learn
Superior written and verbal communicator - your memos are clear and well-argued, your verbal communication is confident and direct
Advanced financial modeling and quantitative analysis skills; fluent in the numbers behind a growth business
Strong bias for action, high bar for your own work product, and obsessive attention to detail
AI-first in how you work - you default to AI tools to accelerate research, analysis, synthesis, and communication, and you have a demonstrated track record of meaningfully changing how a team operates through applied AI adoption
NYC-based and comfortable working from our Flatiron office 3+ days per week

Nice To Haves

Experience in fintech, lending, consumer payments, or proptech
Prior experience at a top-tier consultancy
Familiarity with the operational rhythms of a growth stage company
Experience building or scaling a partnerships-led or property network-driven growth motion

Responsibilities

Serve as the primary strategic and operational interface between the Housing division and the Revenue organization, ensuring tight alignment on goals, priorities, and execution
Own the top-down strategic framing and operating model for better aligning Flex’s sales motion to revenue-driving outcomes, optimizing the company's partner relationships into a scalable engine for increasing renter awareness and adoption
Define and drive the go-to-market playbook for leveraging Housing partnerships to reach consumers at the right time and place, working cross-functionally with Revenue, Marketing, and Product to bring it to life
Build and manage the operating mechanisms—frameworks, cadences, data infrastructure, decision rights—that enable Housing and Revenue to execute together with speed and clarity
Serve as a trusted thought partner to the GM of Housing and Revenue leadership on their highest-stakes challenges
Proactively identify operational gaps and build the systems to close them before they become bottlenecks