PEO Medical Underwriting Lead G&A San Francisco, CA

Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system.

Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365—all within 90 seconds.

Based in San Francisco, CA, Rippling has raised $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America's best startup employers by Forbes.

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Rippling PEO co-employs tens of thousands of worksite employees, and many of our clients join Rippling PEO for its top-notch benefits offerings. As we've scaled, managing our book of business has grown increasingly complex and the stakes have never been higher – medical costs continue to trend upward, and competitors are struggling to manage their portfolios effectively.

This is a pivotal moment for Rippling PEO, and we're hiring our first dedicated in-house Medical Underwriting Lead to meet it. Until now, we've relied on third-party partners to own our underwriting strategy; we're ready to have expertise in-house. You'll own the underwriting policies that govern our thousands of RPEO clients, lead the annual renewal process, and directly shape how we price and win new business.

This is a role with real financial accountability and the autonomy to build something that doesn't fully exist yet at Rippling.

You’ll partner closely with Aetna, Kaiser, HUB, and internal teams across Sales, Account Management, and Finance, but ultimately, the underwriting strategy is yours to define and defend.

• Drive achievement of business goals through articulation and application of sophisticated underwriting policies, initiatives, and long-term vision.
• Proactively identify, analyze, and mitigate complex risks that could materially affect financial results, driving sound, unbiased, and strategically informed actions.
• Serve as a subject matter expert and partner with our 3rd party underwriters, sales teams, Account Management teams, and other departments on the principles and practices of new business underwriting and rating.
• Own and maintain the underwriting guidelines that govern automation and decision frameworks.
• Architect and lead high-impact, cross-functional strategic projects, fostering robust partnerships across the organization (ex: Deal Desk).
• Execute the annual renewal process and refine renewal approach.
• Work directly with all Rippling PEO brokers, benefits partners, and key PEO partners to best serve our shared members.
• Use data to drive fact-based decision-making to optimize our PEO benefits offering and plan performance.
• Autonomously execute special projects related to PEO benefits and managing our book of PEO customers.
• Serve as a Rippling PEO benefits expert to support internal and external teams.

• A minimum of 8+ years of strategic financial underwriting experience, demonstrating deep mastery and extensive insurance industry knowledge, including determining pricing and developing action plans to manage risks and changes during a policy period.
• Proven track record of successfully leading and influencing large-scale, strategic cross-functional projects with significant organizational impact.
• Skilled in generating and formatting accurate reporting, as well as experience in analyzing and interpreting data to support strategic decision-making.
• Knowledge of other benefit programs (life, dental, medical, etc.) and pricing of related benefits is a plus.
• A resourceful self-starter with excellent organizational and time management skills.
• Ability to execute with conviction and good judgment with limited guidance; require minimal direction in an ambiguous context to take action and then adapt quickly.
• E…