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VP Of Operations/COO

San Francisco, CA
  • Expired: March 15, 2022. Applications are no longer accepted.

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Full-time Estimated: $110,000 - $160,000 a year

  • Stock options
  • Health insurance
  • Vision insurance
  • Growing experience
  • Team management
  • Master of Business Administration
Full Job Description

SimplyInsured is on a mission to eliminate the fear from purchasing and navigating health insurance in the United States. We specifically work with small business owners who have the enormous task of purchasing the right type of insurance for their employees and their families. With more than 20,000 customers and several major partnerships including Intuit and Square, we're growing quickly and disrupting this convoluted and confusing industry by making it more transparent and fully accessible to everyone.
Our leadership team's broad experience includes founding companies; scaling successful startups like Cardpool and Domo; working in established companies like Cisco Systems, Convergys, Dell EMC, and Yahoo; consulting at Bain, McKinsey and Deloitte; and venture capital investing. We got our start in the Y-Combinator incubator, and have been funded by top tier investors at Polaris Partners, Bessemer Venture Partners, New York Life Ventures and AltaIR Capital.
We value radical transparency, feedback, bias to action, growth, and an obligation to dissent. Every opinion is respected, we hold each other to extremely high standards, we're driven by the diversity in our backgrounds, and unified by 100% alignment on our mission.
In this role, you will lead the Operations team which is responsible for customer support, revenue operations, and renewals. This role reports directly to SimplyInsured's CEO. As the leader of the Operations team, you will be responsible for delivering an amazing customer experience to small businesses at all our touch points including onboarding, through their plan, and at renewal.
As Vice President of Operations/COO, you will manage a team of approximately 60 people across the country - growing to 200+ over the next two years. You will be responsible for key customer metrics - including Customer Satisfaction (CSAT), Revenue Operations (Sales & Conversion), and Churn. You will inherit and grow a team of Director and Manager level team leaders, and be responsible for growing a team while delivering on key metrics. To be successful in this role, you must have a process-orientation, a drive for customer service, an acumen for optimization, a sales & conversion mindset, and good people management skills.
As the leader of the largest team at SimplyInsured - you will not only be responsible for delivering excellent customer experience, but also growing and mentoring a large team. A strong fit will have strong executive communication skills, experience working with the board of directors, and excellent leadership skills.

  • Undergraduate degree in any relevant field (STEM, business, economics)
  • MBA or equivalent
  • 15+ years of experience in operations, customer support, or sales operations roles
  • Experience managing a team of 50+ (with both salaried and hourly, across the US and timezones)
  • Problem solving skills to navigate complicated issues
  • Strong executive ability and leadership skills
  • High attention to detail and orientation toward building repeatable processes
  • Strong analytical skills and experience managing operational metrics
  • Expertise working cross-functionally with Revenue, Product, Finance teams
  • Familiarity with CRM and/or process automation software implementation
  • Experience in a regulated industry (e.g. finance, insurance, real estate) is a plus
  • Passion for helping people - especially when it comes to their health


  • Generous stock option packages
  • 100% Medical, Dental, and Vision Insurance coverage
  • A values-based culture that invests in employee success



San Francisco, CA
94199 USA



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