Deputy Chief of Staff

Summary

Join FreeWill, an award-winning social-good startup, as their Deputy Chief of Staff! This high-impact role requires a fast-paced, high-ambiguity environment expert who can build AI solutions, optimize systems, run critical meetings, and drive new initiatives. Reporting to the Chief of Staff, you will be a key leader across many work streams, owning the internal AI roadmap from day one. FreeWill offers a competitive salary ($110K-$130K) with multiple compensation package options and excellent benefits. The ideal candidate is a top problem-solver with a proven track record of impact, a growth mindset, and a relentless work ethic. This is a remote-first position, open to candidates in most US states.

Requirements

• 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

Responsibilities

• 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
• 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
• 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

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