Deputy Chief of Staff

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

About the Role

We are hiring a Deputy Chief of Staff who thrives in a fast-paced, high-ambiguity environment and knows how to make things happen. This is a high-impact, high-visibility role for someone comfortable building AI solutions, shaping and optimizing systems, running critical meetings, and jumping in to drive new initiatives – often all in the same week.

This role reports into FreeWill’s Chief of Staff and you will be the right hand to leadership across many work streams with day one impact expected by way of owning our internal AI roadmap. We are looking for someone who sees an opportunity and dives in, figures out what’s needed, and just gets things done.

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 $110K - $130K.

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.

What Sets You Apart

• Top 1% Problem Solver - Excel at breaking down complex, ambiguous challenges and crafting clear, practical paths forward - you’re the person others turn to when things get messy or stuck.
• Curiosity & Growth Mindset - A constant learner - you’re known for seeking feedback, leveling up, and a deep desire to learn and improve both the business and yourself.
• Track Record of Impact - You’ve consistently delivered results on high-stakes and high-priority initiatives; you don’t just complete tasks - you move the needle.
• Hustle - You bring urgency, ownership, and initiative. You meet challenges head on and know what it takes to drive things across the finish line with a relentless work ethic.
• Action-Oriented - You move quickly from strategy to execution - balancing big-picture thinking with hands-on implementation.

Responsibilities

This is a highly dynamic role with a wide scope - you’ll lead, build, support, and unblock across functions. No two weeks will look the same, but they will be fun. A snapshot of core responsibilities may look like:

AI & Automations

• Own and drive our internal AI roadmap – spot opportunities, prototype and build internal tools, or manage vendors
• Partner cross-functionally to streamline workflows and increase leverage through smart automations and practical AI applications in everyday operations

Operational & Strategic Support

• Optimize internal systems, tools, and processes to improve speed, clarity, and scalability
• Be the go-to problem solver – connecting dots, unblocking initiatives, and ensuring follow-through on key initiatives
• Lead key operating rhythms: run weekly leadership meetings, support QBRs and board decks, and keep priorities humming across teams

Special Projects

• Be a force multiplier - jump into high-impact projects across the business to take ownership of critical, high-leverage tasks that don’t fall neatly into one lane

Required Skills and Experience

• Experience in management consulting or BizOps at a high-growth startup
• Top-tier problem solver: Skilled at breaking down ambiguous challenges, building solutions, and driving them through to execution.
• Execution-driven: High ownership, strong follow-through, and project management chops to manage multiple priorities (adapting as needed). Keen to index to action.
• Exceptional communicator: Able to distill complex ideas into clear, tailored messaging for a variety of audiences.
• AI & automation appetite: Hands-on experience with AI tools and a desire to apply them to streamline/scale operations.
• Systems thinker: Quick to spot inefficiencies and implement lean, scalable solutions.
• Strong ability to dive into data: Structured approach in analyzing data 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. Comfort with tools such as: Excel/Google Sheets, Looker (BI tool), Salesforce/Hubspot.
• Growth mindset - low ego: Tendency to learn fast, embrace challenges as opportunities for growth, and thrive outside of comfort zones.

Hiring Process

The hiring process for this role is as follows:

• Recruiter Phone Screen (15-30 minutes)
• Hiring Manager Interview - inclusive of case question(s) (45 minutes)
• Take-Home Assessment
• Review of Take-Home Assessment with FreeWill team members (30 minutes)
• 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.

AI Policy

We are excited to engage with candidates who can demonstrate their experience and skills through their own words and work, not through AI-generated content. We want to understand your genuine interest in the company and your unique perspectives, not simply AI-driven responses. We ask that you refrain from use of AI-generated content during the hiring process which includes phone screens, video interviews, tech screens, or other assessment stages except as otherwise indicated to you by the Recruiter.

For example: Using ChatGPT to generate scripted answers to application questions or during phone screens and video interviews is strongly discouraged and will result in not moving forward in the hiring process. However, the use of an AI design tool to enhance the design of a presentation deck is permitted.

The Recruiter will be able to provide additional guidance during the hiring process if needed. If hired at FreeWill, we do encourage the use of AI in your role to build upon or enhance your skill set.

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 Alabama, Colorado, 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!