Chief of Staff

Chief of Staff

Full-time • Excellent Benefits • Work from Anywhere in the US (except AL, CO, or LA)

About FreeWill

FreeWill is an award-winning, social-good startup that has partnered with 1,800+ nonprofits who support our mission while raising more than $10B in bequests to charities since we were founded in 2017. We’ve been featured in the New York Times, Forbes, Oprah’s magazine, and our co-CEOs have even been named to Town & Country’s “Top 50 Philanthropists” list.

All of this is because we’ve figured out how to make some powerful (but complicated!) ways to donate much easier and more accessible. Our products make things easier for the donors who want to change the world and for nonprofits doing heroic work around the planet.

In the last 7 years, we’ve grown from 5 people to 200+ (all smart, tenacious, and kind), and continue to grow. We’d love to have you be a part of this adventure. In 2024, we were named a "Most Loved Workplace" by both Newsweek and Best Practice Institute; you can also check us out on Glassdoor!

About the Role

The Chief of Staff plays a pivotal role in increasing alignment and accelerating the impact of the senior leadership of the company. This is a senior, strategic role that serves as a critical bridge between departments, facilitating communication, unblocking efforts, and supporting cross-functional collaboration to ensure smooth strategy implementation.

This role will manage the company’s Objectives and Key Results (OKRs), oversee executive-level reporting, manage key weekly meetings for senior leadership (GTM, Executive), organize and facilitate Executive Offsites. As a trusted advisor, this person will ensure all functions within the organization are aligned with top-line strategic goals while developing and maintaining strong relationships across FreeWill.

FreeWill has set compensation and a non-negotiation policy for fairness reasons (we don't think that an individual's pay should be determined by how comfortable they are negotiating). As a result, we like to be transparent and up front about the compensation. When we make an offer, we provide multiple options so that employees can choose between compensation packages that prioritize salary or stock options. The offers for this role will be between $120K and $180K, depending on experience level.

If you are interested in the role, please apply via the Careers page on our website. Please do not contact Recruiters/employees by email or phone.

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

Required Skills and Experience

• 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.

Hiring Process

To apply, please submit an application here: https://grnh.se/ecbdca654us

The hiring process for this role is as follows:

• Recruiter Phone Screen (30 minutes)
• Second interview (30 minutes)
• Live Modeling Exercise and Q&A (1 hour)
• Final interviews with 3 FreeWill team members (3 separate 30 minute interviews)
• Offer (contingent on positive references)

Please note that steps in the hiring process can and may change and the Recruiter will be your point of contact in sharing any updates in terms of the process. If you are selected to move forward in this process, the Recruiter will share more details about the hiring process and interviewers. However, this is a good estimate of what you can expect. For most roles, our hiring processes take an average of 4-6 weeks.

Benefits

In addition to the immense personal and professional satisfaction you’ll gain from helping to raise $1T for high impact nonprofits in a kind and joyful work environment, full time employees at FreeWill are eligible for the following 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

Perks

• 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

FreeWill is an equal opportunity employer and we value diversity. We are committed to finding talent that is not determined on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law.

We are a remote-first company that’s able to hire in 47 states and D.C. Unfortunately, we are unable to hire in Colorado, Alabama, or Louisiana at this time. We also can’t sponsor working visas, so all applicants will need to have work authorization in the US.

Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that marginalized communities - such as women, LGBTQ+ and people of color - are less likely to apply to jobs unless they meet every single qualification. FreeWill is dedicated to building an inclusive, diverse, equitable, and accessible workplace that fosters a sense of belonging – so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings!