Pie Insurance
Denver, CO

Chief of Staff

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We are an insurtech company where smart people can see the impact of their work as we tackle meaningful problems together. We work with small businesses using technology and innovation to improve how they access insurance. Like our small business clients, we are a diverse team of builders, dreamers, and entrepreneurs. So, at the heart of every decision we make is the idea that if it doesn’t serve our clients, it doesn’t serve us. 

Today, all Pie-oneers are working remotely and will continue to do so until it is safe to return to the office. As a remote team member, you will be expected to be available for meetings with team members in other time zones and have access to reliable, high-speed internet.

Our ideal candidate for this role will sit in our DC office with our CEO or in our Denver office with our President once it is safe to do so. We are open to remote candidates who are open to heavy travel (50%) when our offices reopen. We are also open to relocating within the next 12-18 months.

How You'll Do It

As Pie’s Chief of Staff, you’ll report directly to our CEO and work closely with him in addition to our President and executive 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 executive team.

Strategic Initiatives and Special Projects

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

Strategic Planning

  • Collaborate with the FP&A team to drive Pie’s regular planning and forecasting process
  • Partner with executive 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 executive leadership to develop, monitor, and report on Pie’s quarterly and annual OKRs
  • Collaborate with Pie executives and leaders to extend the OKR framework throughout the company with departmental and individual OKRs

Executive Operations and Internal Communications

  • Participate in all Executive Team meetings and drive the agenda and capture/track follow ups
  • Attend executive 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 (bizops) in a high growth environment
  • BA/BS required
  • MBA or equivalent years of experience preferred 
  • Proven experience organizing and collaborating with multiple teams and stakeholders at all levels
  • Experience planning, leading and executing strategic initiatives, leading change and promoting 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 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
  • Bias for action and calm under pressure
  • Ability to think strategically and call out potential risks and solutions

Pie Perks

  • A piece of the Pie (in the form of stock options)
  • Comprehensive health plans
  • Generous Vacation 
  • Paid sick leave 
  • Commuting allowance
  • Future focused 401k match
  • Modern office space with onsite gym
  • Our core values are more than just a poster on the wall; they’re tangibly reflected in our work and recognized with our monthly culture award. 
  • Generous parental leave

Our goal is to make all aspects of working with us as easy as Pie! That includes our offer process. When we have identified talent that is a good fit for Pie, we work hard to present an equitable and fair offer. We look at your knowledge, skills and experience that you bring, along with your compensation expectations and align that with our company equity processes to determine our offer ranges. 

We value and want to support our team members, and are proud to offer a comprehensive compensation package which includes the following:

Compensation Range for position: $150,000 - $200,000

Other Benefits: Each year Pie reviews Company performance and may grant discretionary bonuses to eligible team members.

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.

Our Achievements

Pie Insurance Named a Top Colorado Company 2020

Pie is rated Excellent by our customers on Trustpilot

Check out our great reviews from current and former employees on Glassdoor

Pie raises an additional $127M in funding

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What are Pie Insurance Perks + Benefits

Culture
Volunteer in local community
Open door policy
OKR operational model
Pair programming
Open office floor plan
Flexible work schedule
Pie provides employees with a flexible work schedule that includes Core hours.
Remote work program
Pie-oneers can work where they are most productive, whether that's in the office or from home.
Diversity
Highly diverse management team
Hiring practices that promote diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability insurance
Dental insurance
Vision insurance
Health insurance
Life insurance
Pet insurance
Mental health benefits
Financial & Retirement
401(K)
401(K) matching
Company equity
Performance bonus
Child Care & Parental Leave Benefits
Generous parental leave
We provide up to 16 weeks of parental leave for the primary caretaker. Pie also provides 16 weeks of leave for the secondary caretaker.
Family medical leave
Return-to-work program post parental leave
Vacation & Time Off Benefits
Unlimited vacation policy
Generous PTO
Generous PTO policy
Paid volunteer time
Paid holidays
Paid sick days
Office Perks
Commuter benefits
Company-sponsored outings
Free snacks and drinks
Some meals provided
Company-sponsored happy hours
Onsite office parking
We offer team members a parking subsidy.
Relocation assistance
Home-office stipend for remote employees
All Pie-oneers receive both a one time lump sum stipend when they join Pie as well as a monthly stipend to help them cover any work from home expenses like internet and phone bills.
Onsite gym
Professional Development Benefits
Lunch and learns
Promote from within
Online course subscriptions available

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