Deputy Chief of Staff, FreeWill
$110-130k
+ Stock options
More information about location
Tech to make charitable donations easier for donors
Be an early applicant
Tech to make charitable donations easier for donors
201-500 employees
Be an early applicant
$110-130k
+ Stock options
More information about location
201-500 employees
Company mission
To make estate planning warm, intuitive, and totally free.
Role
Who you are
- 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
- 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
What the job involves
- 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
- 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
Application process
- 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)
Our take
Estate planning has long been seen as a complex, intimidating, and costly process, resulting in a significant number of adults in the US, approximately 70%, not having a will. FreeWill, however, aims to change this perception by offering a user-friendly tool that enables anyone to create these crucial documents.
By leveraging FreeWill, individuals can take control of their end-of-life planning and ensure that their assets are distributed according to their wishes. The platform guides users through the necessary steps, helping them name beneficiaries, designate asset distribution, and appoint executors to manage their estates. The company also sets itself apart with its Crypto for Charity platform. By including options on digital currencies, FreeWill makes it easier for Crypto and NFT users to make tax-advantaged donations as well.
FreeWill's no-cost estate planning tools are made possible through the support of nonprofit organizations, allowing individuals to create their wills and leave a gift for a cause they care about. By integrating charitable giving into the estate planning process, FreeWill encourages individuals to consider philanthropy as part of their end-of-life plans. With over $7.8B+ committed to nonprofit organizations to date, the company's dedication to supporting charitable causes and the significant impact individuals can make through their estate planning choices is truly evident.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
-12% employee growth in 12 months
Company
Funding (1 round)
Mar 2022
$30m
SERIES B
Total funding: $30m
Company benefits
- Medical, dental, and vision coverage
- Unlimited PTO
- Flexible work hours
- Paid parental leave
- (Virtual) Team events
- Professional development
- Monthly co-working reimbursement
Company HQ
Hell's Kitchen, New York, NY
Leadership
Jennifer Xia Spradling
(Co-Founder & Co-CEO)Graduated from Stanford University with a Masters in Business Administration. Previously worked as an Advisor at Paribus, a Private Equity Associate at Bain Capital and as a Business Analyst at McKinsey & Company.
Patrick Schmitt
(Co-Founder & Co-CEO)Graduated from Stanford University with a Masters in Business Administration. Previously the VP of Marketing at Farmingo and the Head of Innovation at Change.org.
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