Chief of Staff

Summary

Join FreeWill, an award-winning social-good startup, as their Chief of Staff! This senior, strategic role bridges departments, ensuring smooth strategy implementation. You will manage OKRs, oversee executive reporting, and facilitate key meetings. As a trusted advisor, you'll align organizational functions with strategic goals. The compensation is between $120K and $180K, depending on experience. FreeWill offers excellent benefits and a remote-first work environment (excluding AL, CO, and LA). Apply via the Careers page on our website.

Requirements

• Experience as a management consultant, chief of staff, or senior manager within a fast-paced, dynamic organization
• Strong facilitation skills: Ability to design, lead, and run a variety of meetings – including 1:1 discussions with senior leadership, executive team meetings or other offsites. Excel at structuring agendas to focus on outcomes, managing discussions to stay on track, and driving alignment among diverse stakeholders
• Strong communication skills: Exceptional communicator capable of translating complex ideas into clear, concise messaging – whether writing executive summaries, delivering presentations, or facilitating team discussions, knack for adjusting communication style to suit the context and audience
• Strong analytical skills / ability to dive into data: Adept at analyzing data sets to uncover actionable insights. Experience working with quantitative and qualitative data with the ability to synthesize in such a way to inform strategic decision-making
• Seeing the bigger picture and strategic mindset: Critical and strategic thinker who identifies patterns, opportunities, and risks – always looking to position the company for future success
• Curiosity: Maintain a constant sense of curiosity, always asking questions and seeking to understand how things work. Approach challenges or feedback with an open mind, eager to learn from every situation
• Indexing to action: Bias towards moving forward, ensuring that plans quickly translate into meaningful progress – moving initiatives forward while keeping an eye to iterative improvements
• Strong relationship skills and very high EQ : Excel at building trust with a wide range of personalities across all levels of the organization. Ability to understand and navigate different dynamics to foster a collaborative work environment while maintaining confidentiality and professionalism
• Calm under pressure: Composed and focused even in high-pressure situations – solving problems quickly and keeping individuals focused on solutions
• Growth mindset - low ego: Approach every situation with humility, always open to learning new skills and evolving approaches. Comfortable being out of a comfort zone and embracing challenges as opportunities for growth

Responsibilities

• Accelerate strategic initiatives
• Unblock efforts – primarily between the R&D + revenue-facing sides of the business – to ensure efficient product launches and strategy execution
• Maintain strong relationships and timely communication across the organization to prevent silos and expedite decision making
• Increase alignment across the organization
• Own Objectives + Key Results (OKRs) for the company, including the planning process
• Act as “sherpa” ensuring that there is progress on company strategy – inclusive of providing project management and regular updates to the executive team, as well as the broader team
• Maximize the power of data to inform decisions at the executive level
• Work with the business operations team to analyze data + write summarized reports for use in executive decision making
• Run Quarterly Business Reviews (QBRs) + Annual Business Reviews (ABRs) for the executive team – with smaller readouts for specific teams (Operations, Product, PS Innovation)
• Be a versatile asset to pinch hit on core company needs
• Take point on initiatives or projects that will help the company + don’t cleanly fall within one other department (i.e., cross-functional items)
• Take on any ad hoc projects to increase internal efficiency + effectiveness or propel FreeWill forward
• Boost the impact of Senior Leadership
• Facilitate the Executive Offsites – including planning + executing bi-annual exec offsites, and smaller leadership offsites (e.g. GTM leaders)
• Ensure all executives are aligned to the same north stars
• Own the agenda for Department Heads + Revenue Leadership to maximize executive time; provide a summary of discussions + action items resulting from meetings with ownership of follow-up
• Own the shell of board meeting decks – inclusive of initiating creation each quarter and ensuring proper analyses are tagged with an owner, completed, and reviewed by co-CEOs
• Act with a high level of integrity + professionalism
• Carry confidentiality in dealing with sensitive business or organizational issues
• Leverage a neutral position at FreeWill by being a candid contributor on strategic decisions to be made by various levels of the business

Benefits

• Work from home
• Unlimited PTO
• Flexible hours
• Competitive salary
• Commuter benefits
• Company stock options
• 401k
• Medical/Dental/Vision (some single coverage medical plans are 100% employer paid, subsidized rates for spousal, parent-child, and family coverage)
• Short-term and long-term disability insurance
• Life and AD&D insurance
• Free One Medical membership
• Paid parental leave for all parents
• Regular (virtual) team events
• $250 monthly co-working budget which can be used for local co-working spaces
• $300 annual budget to outfit your home office or cover utility bills
• $1,000 referral bonuses for growing our FreeWill community
• $1,000 annual professional development budget