Jobs

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!