This listing pays about $225,000 a year. Across 59 open chief of staff listings that state pay, the middle half runs $155,000 to $225,000 and the median is $183,000. That is inside the middle half of those listings, 23% above the median.

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About the job

About Freehand

Freehand (freehand.ai http://freehand.ai) is building autonomous AI agents for enterprise spend management, replacing internal and outsourced (BPO) headcount and shared service centres with "AI Employees" across procure-to-pay and order-to-cash workflows, selling to Global 2000 CFOs.

Freehand counts Apple, Meta, J&J, Pfizer, Cardinal Health, Dunkin', and Samsara among its customers. We're now scaling the team across GTM, product, and operations.

The Role

We're hiring two Founder's Office roles to take on the highest-leverage strategic projects across the company: fundraising, board and investor comms, org design, key customer expansions, revenue operations, cost optimization, and special initiatives that don't yet have an owner. You'll work directly with the CEO and leadership team, with end-to-end ownership of workstreams that shape how Freehand scales. This is a front-row seat to building a category-defining enterprise AI company in San Francisco.

How we think about the business

Freehand, like any business, runs on five pipelines: capital, talent, sales, implementations, and product. Each has its own throughput, conversion, and cycle time, and each both constrains and feeds the others, and the overall business. The Chief of Staff / Strategic Finance role is to make those interactions legible, financially, operationally, and visually, and to actively de-bottleneck them.

What you'll do

- Build the top-down financial model of the business as the intersecting output of the five pipelines, and decompose it into functional models for sales, implementations, product, talent, and capital

- Identify the dynamic binding constraint in each pipeline and at the company level; quantify the cost of each bottleneck and the ROI of unblocking it

- Stand up dashboards for each pipeline and a consolidated business view, leading indicators, throughput, conversion, cycle time, unit economics

- Partner with each function head to set weekly, monthly and quarterly goals tied to the model, and drive a prioritized list of debottlenecking initiatives across the company

- Run weekly functional reviews and fortnightly business reviews alongside the CEO

- Own strategic initiatives across customer expansion, pricing, org design, and cost optimization, and other high-leverage problems that don't yet have an owner

- Run board meetings end-to-end: materials, narrative, follow-ups, investor materials, modeling, process management

Ideal background

- CS undergrad from top tier college in India (IIT/NIT) or the US (Ivy League school); MBA from HBS, Wharton, or Stanford

- At least 2-4 years in investment banking or private equity

- At least 2-4 years in an operating role (BizOps / Strategic Finance) at a consumer tech or B2B software company

- Founder or very early-stage startup experience is a strong plus

- Proven track record of hands on financial modelling across GTM, product, tech and ops; comfortable moving between board-level strategy, management decision making and hands-on functional execution

Working at Freehand

We proudly offer the following Benefits to all our full-time employees:

- Take what you need Vacation Policy

- Monthly home-internet costs

- Full health coverage (with multiple gold-standard carriers across medical, dental & vision)

- Life Insurance and Disability benefits

- HSA/FSA Access

- 401(k) with a 4% Employer Match

Equal Opportunity

Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of it, apply anyway. We care more about your willingness to learn & take initiative than whether your resume maps perfectly to every line.