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Director, Strategy and Operations

San Francisco, CA +2

We'd love to hear from you if you like:

  • Scaling a business that has traction (40X revenue growth in 4 years | #1 rated app in the insurance comparison category)
  • Working directly with a founder/CEO and with seasoned leaders who have scaled companies like Robinhood, Amazon, LinkedIn, Wayfair, SoFi, Microsoft, etc.
  • Solving complex problems in a huge market ($2T market size)
  • Making a big impact with a Forbes Top Startup Employer

We are looking for a Director, Strategy and Operations to work directly with our founder/CEO and partner closely with our executive team. You will act as an extension of our CEO and own a variety of projects ranging from solving operational issues, driving alignment and execution on critical initiatives, increasing his efficiency by helping him prioritize his most important meetings and communications, making decisions on his behalf, and keeping our teams accountable. You will foster trust and credibility with the rest of the executive team as the CEO’s closest proxy and advisor. Your main objective will be to identify and remove bottlenecks for our CEO and partner closely with him to scale our business. 

As a Director, Strategy and Operations you will have a unique opportunity to view and understand a company’s day-to-day challenges and priorities from the vantage point of a CEO. You will be exposed to every function at Jerry (product, operations, finance, engineering, data, marketing, etc) and learn how to execute big-picture strategies and navigate the intricacies of a complex business. A successful Director, Strategy and Operations will likely go on to lead a function here or elsewhere. If you’re looking for an opportunity to greatly accelerate your career trajectory, we’d love to hear from you.

What we are looking for:

  • Structured problem-solver: You’re a logical thinker and make decisions based on data, but also have good instincts when data is limited.
  • Owner: No challenge is too complex, no issue is too hard.
  • Tenacious: You’re comfortable navigating high-stakes, conflict-laden situations, and can act quickly and decisively with diplomacy and tact.
  • Extremely organized: You balance a packed schedule, an endless to-do list, and never let anything drop.
  • Strong communicator: You communicate effectively to a wide range of audiences (from senior executives to entry-level employees) and can masterfully tailor your approach to suit the circumstances. 

Ideal profile:

  • 7+ years of experience; ideally a mix of management consulting, venture capital, or private equity, and product, business operations, strategy or growth
  • Bachelor's degree in a STEM, economics, or related discipline
  • Must be located in the San Francisco Bay area or willing to relocate (you will be working on-site at our Palo Alto office)

Jerry is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. 

Jerry is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at

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