Associate Director, Workforce Management

We’re looking for an analytical and strategic leader to build the forecasting and capacity engine behind Lemonade’s AI-first Customer Operations. As our Associate Director of Workforce Planning & Analysis, you’ll translate automation, product changes, and volume trends into clear staffing plans, financial impact, and operational decisions across CX, Claims, and Underwriting.

You’ll partner closely with senior leaders in Operations, Product, Analytics, and Finance to model how automation affects workload, build multi-scenario forecasts, and ensure we operate as leanly and efficiently as possible—without compromising customer experience. This role is ideal for someone with a strong background in operational analytics, financial modeling, and/or workforce planning, who thrives in ambiguous, fast-moving environments and wants to shape how a hybrid human + AI workforce scales. You will report to the Director of Operations in the centralized Customer Operations enablement team, as well as manage a WFM team of Workforce Analysts.

In this role you'll

• Build and continuously refine forecasting and capacity models that incorporate volume trends, automation impact, and operational goals across CX, Claims, and Underwriting

• Partner closely with Product, Talent Acquisition, Analytics, and Finance to translate automation and product changes into clear staffing, budget, and operational decisions

• Lead multi-scenario planning using advanced analytical techniques, predictive modeling, and data science best practices to support long-term workforce and financial decisions

• Provide clear, data-driven recommendations to senior operational leaders, helping them make bold staffing decisions while protecting customer experience and team health

• Evolve WFM tools, processes, and planning cadences, driving improvements in forecast accuracy, model quality, and reporting standards

• Build strong cross-functional relationships and act as a trusted partner who brings clarity, insight, and strategic thinking to complex operational problems

• Lead and develop a high-performing WFM team, raising the bar on analytics, communication, and operational rigor

What you'll need

• 6+ years of experience in workforce planning, operational analytics, FP&A, or strategic operations

• Strong analytical and modeling skills, with the ability to synthesize complex data into actionable insights

• Demonstrated experience influencing senior stakeholders through clear communication, data narratives, and strategic recommendations

• Ability to thrive in a fast-moving, ambiguous environment and build structure where it doesn’t exist

• Bachelors degree or equivalent professional experience

• SQL strongly preferred, along with proficiency in BI tools (e.g., Looker) and advanced Google Sheets / Excel

• Experience managing or leading a WFM or Analyst team is a plus

• Ability to work and manage in a remote environment

• Enthusiasm about learning and adapting to the exciting world of AI – a commitment to exploring this field is a fundamental part of our culture

*Please note that we are unable to sponsor applicants for work visas

Unfortunately, we cannot consider applicants from these states; Colorado, California, Montana, Hawaii, New Mexico and Puerto Rico.

Lemonade's US base salary range for this full-time position is $140,000 - $157,500 plus equity + benefits. Our salary ranges are determined by role, level, and location. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Speak to your recruiter to hear more about the specific salary range for your preferred location.

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