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Chief of Staff

Pie Insurance

Pie Insurance

People & HR, Operations
United States
Posted on Saturday, May 13, 2023
Pie's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance.
Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.

As Pie’s Chief of Staff to the CEO, you’ll report directly to our CEO and work closely with him in addition to our President and senior leadership team. You will work to drive business initiatives forward, streamline cross functional communication and objectives, and have a direct impact on Pie’s efficiency and productivity. This is a high visibility role and your executive presence, operational excellence and strategic thinking will be a multiplier for Pie’s senior leadership team.

This role has the option to be hybrid or remote, but the Chief of Staff needs to be available to work during East Coast core business hours on a regular basis. Hybrid work locations provide team members with the flexibility of working partially from one of our Pie offices and from home. Remote team members must live and work in the United States* (*territories excluded), and have access to reliable, high-speed internet. This role will require travel to our offices and other locations in the US or abroad.

How You’ll Do It

Strategic Initiatives and Special Projects

  • Support the CEO in evaluating and researching strategic opportunities
  • Lead special projects critical to the CEO and Pie’s senior leadership team
  • Oversee regular competitive analysis and updates

Strategic Planning

  • Collaborate with the FP&A team to drive Pie’s regular planning and forecasting process
  • Partner with senior leadership to understand impact of strategic initiatives and build them into the near and long term plans
  • Organize strategic planning with Pie executives and leaders to ensure Pie effectively plans for 10, 5, 3, and 1 year time horizons
  • Hold strategic planning stakeholders accountable for deliverables and follow ups related to strategic planning

Organize and Lead Pie’s OKR process

  • Manage Pie’s OKR process with executive and leader stakeholders to ensure Pie develops annual and quarterly OKRs to achieve our vision
  • Collaborate with senior leadership to develop, monitor, and report on Pie’s quarterly and annual OKRs
  • Collaborate with Pie leaders to extend the OKR framework throughout the company with departmental and individual OKRs

Executive Operations and Internal Communications

  • Participate in all senior leadership team meetings and drive the agenda and capture/track follow ups
  • Attend senior leadership’s team meetings across the company to ensure strategic alignment across teams, raising disconnects and identifying risks
  • Collaborate with key stakeholders to drive effective All Hands meetings

Board of Directors & Investor Relations

  • Act as a project manager for Board of Director meeting preparation and slide deck completion
  • Prepare and track action items from board meetings
  • Prepare quarterly investor updates for distribution

The Right Stuff

  • 7+ years of diverse experience including strategic management consulting, investment banking, strategic business development, and/or business operations in a high growth environment
  • A Bachelor’s Degree is required. MBA, Master’s Degree, or equivalent years of experience is highly preferred
  • Proven experience organizing and collaborating with multiple teams and stakeholders at all levels to achieve cross functional goals
  • Experience planning, leading and executing strategic initiatives, leading change and facilitating strong collaboration. Must have demonstrated ability be effectively influential without having direct authority
  • Excellent project management skills and history of successful execution of project goals
  • Excellent communication skills: clear, direct and transparent oral, written and interpersonal communication skills
  • Dedicated to versatility and efficiency with an ability to act nimbly and adapt to changing priorities
  • Ability to form strong relationships across the business by demonstrating superb interpersonal awareness
  • Bias for action and calm under pressure
  • Ability to think strategically and call out potential risks and solutions by applying agile thinking
  • Some travel could be required in this position, up to 30% travel.


Base Compensation Range
$175,000$245,000 USD

Compensation & Benefits

  • Competitive cash compensation
  • A piece of the pie (in the form of equity)
  • Comprehensive health plans
  • Generous PTO
  • Future focused 401k match
  • Generous parental and caregiver leave
  • Our core values are more than just a poster on the wall; they’re tangibly reflected in our work

Our goal is to make all aspects of working with us as easy as pie. That includes our offer process. When we’ve identified a talented individual who we’d like to be a Pie-oneer , we work hard to present an equitable and fair offer. We look at the candidate’s knowledge, skills, and experience, along with their compensation expectations and align that with our company equity processes to determine our offer ranges.

Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.

Location Information

Unless otherwise specified, this role has the option to be hybrid or remote. Hybrid work locations provide team members with the flexibility of working partially from our Denver or DC office and from home. Remote team members must live and work in the United States* (*territories excluded), and have access to reliable, high-speed internet.

Additional Information

Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.

Pie Insurance participates in the E-Verify program. Please click here, here and here for more information.

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