Full-Time

Chief of Staff

Updated on 9/3/2026

PointOne

PointOne

11-50 employees

AI-driven timekeeping and billing for firms

No salary listed

New York, NY, USA

In Person

Category
Business & Strategy (1)

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Requirements
  • At least four years of experience in a similar Chief of Staff position driving outcomes for a venture-backed company, unless the candidate has previously been Chief of Staff at a high-growth technology company.
  • A generalist range across strategy, execution, and operational details.
  • Strong analytical and written communication skills.
  • A high degree of ownership and comfort operating autonomously in ambiguity.
  • Judgment to handle sensitive information and work closely with founders.
Responsibilities
  • Work directly with the CEO to ensure the company's most important projects are completed efficiently and effectively.
  • Own cross-functional projects end to end, filling gaps wherever the business needs it most.
  • Turn ambiguous goals into plans and then into shipped outcomes.
  • Prepare materials for the board, investors, and the team.
  • Build the operating cadence that keeps a fast-growing company aligned.
  • Own projects spanning operations, hiring, and go-to-market and carry them through to results.

PointOne provides an AI-powered platform that streamlines timekeeping and billing for law firms by automatically generating detailed time entries and narratives from lawyers’ work. It targets law firms of varying sizes and helps replace manual timekeeping with automated data capture across client matters, reducing admin work and ensuring no billable time is missed. The product works by analyzing legal tasks and activities to produce structured time entries and narrative descriptions, delivered via a subscription-based platform. It emphasizes enterprise-grade security, data encryption, and clear data ownership with customizable retention policies. The goal is to save time, improve billing accuracy, and boost profitability for law firms by making timekeeping and pre-bill review faster and more reliable.

Company Size

11-50

Company Stage

Seed

Total Funding

$3.6M

Headquarters

San Francisco, California

Founded

2023

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Simplify Jobs

Simplify's Take

What believers are saying

  • March 2026 Series A and $20 million total funding extend runway.
  • Revenue grew tenfold since July, signaling product-market fit across dozens of firms.
  • PointOne claims 6-11% more billable time daily, a direct ROI lever.

What critics are saying

  • 8VC-backed Clockify, Billables AI, and Clio compete on adjacent legal workflow automation.
  • Privacy backlash over always-on tracking and private Azure handling slows large-firm adoption.
  • If billable-hour economics shift, PointOne's revenue-capture pitch loses urgency by 2027.

What makes PointOne unique

  • PointOne passively captures lawyer activity and auto-writes compliant time entries.
  • October 2025 SurePoint partnership embeds PointOne into mid-market law-firm workflows.
  • April 2026 Minnesota Attorney General rollout proves enterprise-scale government adoption.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Meal Benefits

Company Social Events

Company Equity

Growth & Insights and Company News

Headcount

6 month growth

7%

1 year growth

-9%

2 year growth

-6%
Business Insider
Mar 23rd, 2026
AI startup PointOne raises $16M to automate lawyers' timesheets

PointOne, a legal-tech startup, has raised $16 million in a Series A round led by 8VC, with participation from Bessemer Venture Partners, General Catalyst and Y Combinator. The company has developed AI-powered software that passively tracks lawyers' computer activity to automatically complete timesheets. The startup has signed dozens of law firm clients and grew revenue tenfold since July, according to co-founder Katon Luaces. PointOne's platform runs in the background as lawyers work, filling in time entries with client information, work descriptions and legal codes. The company positions itself as capturing billable time that would otherwise go unbilled, rather than simply saving time. It encrypts sensitive data and offers firms the option to use models in a private Azure environment. PointOne has now raised $20 million in total funding.

Law360
Jul 10th, 2024
AI Billing Startup PointOne Raises $3.5M In Seed Funding

AI billing startup PointOne raises $3.5M in seed funding.

Law.com
Jul 10th, 2024
Timekeeping Startup PointOne Secures $3.5M Seed Round, Including Investment From Cooley Fund

On Wednesday, PointOne, a legal tech startup that automates legal timekeeping and billing, announced that it raised $3.5 million in a seed financing round that saw participation from Bessemer Venture Partners, General Catalyst, Y Combinator and an investment fund affiliated with law firm Cooley, among others.