Full-Time

Staff Product Manager

Posted on 3/15/2025

Pilot

Pilot

201-500 employees

Outsourced bookkeeping, tax, and CFO services

Compensation Overview

$231k - $313k/yr

+ Equity + 401(k) match + Health benefits

San Francisco, CA, USA

In Person

Category
Product (2)
,
Required Skills
Amplitude
Product Management
Looker
Data Analysis
Requirements
  • A substantive track record of shipping product that demonstrably moves the needle
  • 7+ years building products that customers love, especially in B2B
  • Outstanding analytical, problem-solving, and decision-making skills
  • An exceptional ability to learn complex things, and then explain them simply
Responsibilities
  • Drive an area of Pilot’s product and be responsible for that product delivering substantial impact for both our customers and our business
  • Talk to customers, understand their problems, and turn those insights into great solutions
  • Work closely with our engineers and designers to build and ship new features
  • Make smart decisions about what to build next based on customer feedback and data
  • Keep an eye on whether what we're building is actually helping customers
  • Be an ambassador for your products who keeps our teams and customers excited about what we’re shipping
Desired Qualifications
  • Experience as an entrepreneur running a business yourself
  • A background in finance or accounting

Pilot provides outsourced financial management for startups and small businesses. It handles core back-office tasks—bookkeeping, tax preparation, and CFO-level financial guidance—through a subscription-based service, giving clients ongoing access to a team of finance experts who manage their numbers and strategic planning. The product works by offering tiered service levels tied to client size, with recurring fees for ongoing support rather than one-off projects. Pilot differentiates itself by specializing in early-stage and small companies, delivering a dedicated finance function with scalable expertise, backed by substantial funding from investors such as Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock. The company’s goal is to let business owners focus on growth by providing professional, reliable financial management and predictable costs through a repeatable service model.

Company Size

201-500

Company Stage

Series C

Total Funding

$158.3M

Headquarters

San Francisco, California

Founded

2016

Simplify Jobs

Simplify's Take

What believers are saying

  • Gartner forecasts 40% enterprise AI agent adoption by end-2026 boosts demand.
  • 58% small businesses report positive AI impact with 38% cost reductions.
  • $250K Growth Fund announced February 2026 enhances Pilot's SMB brand loyalty.

What critics are saying

  • Xero's April 2026 Xero OS captures Pilot's SMB market share in 6-12 months.
  • Local Partner Program since December 2025 diverts customers to cheaper bookkeepers.
  • Profit Leap's AI CFO bot undercuts Pilot's pricing within 12-18 months.

What makes Pilot unique

  • Pilot launched world's first fully autonomous AI Accountant in February 2026.
  • Pilot's platform uses human-tagged dataset for unmatched transaction automation.
  • Pilot combines AI bookkeeping with U.S.-based expert verification for accuracy.

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Benefits

We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers

The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).

Flexible vacation/time-off policy

All federal holidays are observed

Competitive benefits package including wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway

Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks

401(k) plan

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

1%

2 year growth

0%
Benzinga
Feb 24th, 2026
Pilot launches $250K fund for small businesses with free AI bookkeeping and growth grants

Pilot, an AI-powered accounting solutions provider, has launched a $250,000 Small Business Growth Fund in partnership with Hello Alice to support 18 small business owners. The fund will distribute one $50,000 grant, two $25,000 grants and 15 $10,000 grants to businesses investing in operations, expansion or financial infrastructure. Recipients will also receive one year of free Pilot bookkeeping services, including access to its AI Accountant, which autonomously handles the entire bookkeeping process from onboarding to final financial statements. The initiative addresses a structural gap in financing access, as many profitable small businesses struggle to secure capital despite strong performance. Applications are open from 24 February to 31 March 2026, with recipients to be announced on 5 May 2026. The programme aims to support SMBs facing tightened credit standards and rising interest rates.

FinTech Magazine
Dec 9th, 2025
Pilot Launches Local Partner Program to Empower Bookkeepers and Strengthen Small Businesses Nationwide

Pilot launches Local Partner Program to empower bookkeepers and strengthen small businesses nationwide. New Initiative Provides Bookkeepers with the AI-powered Technology and Personalized Services to Serve Clients More Efficiently, Supporting SMBs and Local Communities Across the United States SAN FRANCISCO, Dec. 09, 2025 (GLOBE NEWSWIRE) - Pilot, the leader in AI-powered bookkeeping and advisory solutions for SMBs and startups, today announced the launch of the Pilot Local Partner Program. The new program provides independent bookkeepers and accounting firms with access to cutting-edge software and automation capabilities, personalized advisory services and sales enablement tools to scale their organizations and support small businesses within their communities. "Small businesses make up more than half of the private sector, yet many struggle in their first five years because they lack the financial visibility and support needed to make the decisions that help them thrive," said Jessica McKellar, founder and CEO of Pilot. "Local accounting and bookkeeping firms are the partners who show up, who understand the stakes, and who help entrepreneurs turn hard work into lasting progress. They're the quiet champions of small businesses everywhere. With the Pilot Local Partner Program, our goal is to equip these advisors with the tools and services they need so they can lift up the businesses in their own backyards and build lasting relationships with the talented, passionate, and caring business owners who make up the fabric of their communities." The Local Partner Program extends Pilot's proven AI-powered platform to independent bookkeepers and accountants nationwide, enabling them to deliver automated bookkeeping and personalized advisory services to their clients. In addition to access to its platform and processes, Pilot empowers its local partners by connecting them directly with pre-qualified prospects to grow their business and establish new revenue streams. Leveraging its existing sales and marketing channels, Pilot manages the lead generation process and matches bookkeepers with customers based on specialties and location. This allows Pilot partners to operate more efficiently, increase productivity and dedicate more time to servicing their clients strategically. "Our relationship with Pilot is a true partnership, and they are committed to our team's success as well as that of our clients," said Abel Castaneda, Founder and CEO at Apex Advantage Bookkeeping. "This new program allows us to utilize an industry-standard platform and collaborate with a team of experts to scale our business, better serve our customers and strengthen our relationships within the community. With the combination of our expertise and Pilot's best-in-class technology, we are a stronger business that delivers more value to our customers." Pilot provides its customers and partners with a scalable platform and high-quality accounting and advisory services. The company's advanced technology automates most bookkeeping tasks, from onboarding to generating real-time, tax- or-loan ready financials, based on each customer's unique business model and preferences with minimal human intervention. Pilot's AI capabilities, including its 24/7 financial chat advisor, are underpinned by the industry's most comprehensive transaction-level dataset, which is verified by its team of U.S.-based accounting experts. The unmatched volume and accuracy of Pilot's proprietary data enable enhanced automation for real-time financial insights and allows independent accountants and bookkeepers to focus on higher-value advisory services. The Local Partner Program is now available to accounting firms across select cities, with plans for nationwide expansion in the coming year. For more information on the Pilot Local Partner Program or to join, visit: https://pilot.com/local-partners About Pilot Pilot transforms bookkeeping and advisory for SMBs and startups by combining advanced AI automation with human expertise. The Pilot platform leverages a massive, high-quality, human-tagged dataset of financial transactions to deliver unmatched automation, benchmarking, and actionable insights at scale - all verified by US-based bookkeeping experts and customers. With headquarters in San Francisco and Nashville, and backed by leading investors including Sequoia, Index Ventures, Stripe, and Bezos Expeditions, Pilot is building the future of accounting - empowering both customers and local partners. Learn more at https://pilot.com. Media Contact: Geoff Lopes Marketbridge for Pilot [email protected]

Montana Associated Technology Roundtable
May 16th, 2024
Pilot and Zendesk Pitch Deck Teardown!

Zendesk has partnered with Pilot to spill the tea about perfect pitches.

Travel And Tour World
May 2nd, 2024
Pilot and Flying J Gear Up for Tourist Season with Over 10,000 New Job Openings in North America

Additionally, Pilot recently introduced an upgraded mobile app, facilitating seamless access to company updates, documents, training materials, and resources for team members.

Tanahun Taranga News
Dec 24th, 2023
Lawyer claims Jimmy Haslam admitted bribery charges during recent testimony

And it underscores the fact that, as Pilot lawyers acknowledged in a previous hearing, federal prosecutors are investigating bribery allegations.

INACTIVE