WorkWhile is on a mission to help the 83 million Americans who work hourly wage jobs earn a better living and live better lives. WorkWhile hires the best hourly workers and matches them with shifts that fit their skills, schedule, and location. Employers get access to a quality workforce, while employees get stable income and unmatched perks like next-day pay.
Our business is scaling rapidly across three distinct pillars:
- Workforce Marketplace: Our core, high-growth marketplace that intelligently matches labor supply and demand in real-time.
- Newday (SaaS): A "Bloomberg Terminal of Labor," our B2B SaaS platform that provides enterprise customers a single pane of glass to manage their entire internal and external workforce.
- WorkWhile Wallet (FinTech): A neo-banking solution for the working class, designed to protect earnings, reduce debt servicing, and provide a full suite of financial services.
About the role
We are looking for a strategic, analytical, and results-driven leader to join us as our Director of Strategic Finance & FP&A. This is a pivotal role that will serve as the financial backbone for our high-growth, complex business. Reporting directly to the CFO, you will be a key architect of our financial future. This is a highly visible, "player-coach" role that combines deep technical modeling with high-level strategic partnership. You will build the financial framework that guides executive decision-making, leads our annual planning, and supports future capital raises.The ideal candidate is a first-principles thinker who thrives in a fast-paced environment, can seamlessly navigate the unit economics of a marketplace, a SaaS business, and a FinTech platform, and is passionate about building a best-in-class finance function.
What you get to do every day
- Financial Modeling & Strategy:
- Develop, own, and maintain the company’s three-statement, consolidated long-range financial model.
- Build and refine sophisticated, driver-based unit economic models for our distinct business lines, including Marketplace (LTV/CAC, fill rate), SaaS (ARR, NRR, logo churn), and FinTech (interchange, loss rates).
- Model complex scenarios to support strategic, "what-if" analysis for new initiatives, GTM strategies, and resource allocation.
- Business Planning & Forecasting:
- Lead the end-to-end annual operating plan (AOP) and budgeting process, partnering with department heads to set ambitious but achievable targets.
- Drive the monthly and quarterly rolling forecast, analyzing performance against plan, and delivering actionable insights and variance analysis to the leadership team.
- Fundraising & Investor Relations:
- Serve as a key partner to the CFO in all capital-raising activities (equity and debt).
- Own the investor-facing financial model, manage the data room, and lead the financial diligence process.
- Prepare compelling materials for the Board of Directors, investors, and banking partners, including robust equity and cap table modeling.
- Executive & Cross-Functional Partnership:
- Act as a trusted strategic advisor to the executive leadership team, providing financial rigor and data-driven recommendations on key decisions.
- RevOps: Partner with Sales and Revenue Operations to design, model, and analyze the effectiveness of GTM strategies and sales compensation plans.
- Product: Collaborate with the Product organization on pricing and packaging strategies for our Newday and Wallet products, modeling the P&L and unit economic impact of new constructs.
- Data: Work with our data teams to define and align on key business metrics and ensure data integrity across all financial reporting.
What you bring to the role
- Experience: 8-10+ years of progressive experience in a strategic finance role, with a background in investment banking, private equity, venture capital, or a high-growth technology company.
- Modeling Expertise: Expert-level financial modeling skills (P&L, balance sheet, cash flow) with a proven ability to build complex, scalable, and driver-based models from the ground up.
- Fundraising Track Record: Demonstrable experience supporting successful fundraising (equity and/or debt) and managing investor diligence.
- Strategic Acumen: A "first-principles" thinker who can translate complex business models and operational data into a clear financial narrative and strategic insights.
- Communication: Excellent communication and presentation skills, with a proven ability to influence senior executives and build strong cross-functional relationships.
- Leadership: A "player-coach" mentality with experience managing and mentoring high-performing individuals (or a strong desire to do so).
- Education: Bachelor’s degree in Finance, Economics, Accounting, or a related field.
Bonus Points
- MBA, CFA, or CPA is a strong plus.
- Complex Model Experience: Direct experience in a multi-product or multi-business-model environment (e.g., Marketplace + SaaS, or FinTech).
- Systems & Data: High proficiency with data analysis and BI tools (e.g., Metabase, Tableau, Power BI) and a working knowledge of SQL.
- Start-up DNA: You are highly adaptable, thrive in a fast-paced and ambiguous environment, and have a proactive, "get-it-done" attitude.
Benefits & Perks
- Remote flexibility plus a hub in San Francisco for connection, collaboration and culture.
- Work in a tech-forward environment where your ideas for automation, simplification and transformation will be heard and acted on.In-person company offsites
- Medical, dental, & vision coverage
- Flexible time off
- 401(k) with employer match
- WFH stipend to support your home office needs
WorkWhile is an Equal Opportunity Employer. Women, minorities, individuals with disabilities and protected veterans are encouraged to apply. WorkWhile has a diverse, mission-driven, and supportive culture—we look for people who want to take ownership, are energized by ambiguity, and strive to make a lasting impact. If this resonates with you, we’d love to chat!
