• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
Some Fortune Crypto pricing data is provided by Binance.
The LedgerFin-tech

Stripe Backs $40 Million Investment in A.I. Accounting Service Pilot

Jeff John Roberts
By
Jeff John Roberts
Jeff John Roberts
Editor, Finance and Crypto
Down Arrow Button Icon
Jeff John Roberts
By
Jeff John Roberts
Jeff John Roberts
Editor, Finance and Crypto
Down Arrow Button Icon
April 17, 2019, 9:00 AM ET

The tech industry claims “software is eating the world” and, if that’s true, bookkeepers could be the next course. That will be case if startups like Pilot, which helps small businesses replace their accountants with an automated service, continues to get traction.

On Wednesday, Pilot announced it had raised a $40 million Series B funding round led by Index Ventures, and supported by online payments giant Stripe, which joined as a strategic investor. The startup also announced the launch of a new product called Pilot Tax, which is part of its larger ambitions to handle all of its clients back-end operations.

San Francisco-based Pilot, which launched in 2016, specializes in gathering all of the paperwork generated by a business—from sales to payroll to credit card transactions—and transferring it to commercial software like QuickBooks. This serves to move many mundane tasks off-site and, according to Pilot, allow business owners to focus on other aspects of their operations.

Pilot’s products rely on integration with QuickBooks, which is owned by software giant Intuit—and which could, in theory, regard the startup as a potential competitor. Daher, however, downplayed the potential strategic risk, saying Intuit for now likely appreciates the business Pilot is generating for it.

While Pilot relies heavily on automation to parse the paperwork, it also uses account managers (aka people) to assist its customers.

“Pilot is born out of the pain points from our previous companies,” CEO Waseem Daher told Fortune. “What is bookkeeping? It’s a series of structured data—dates, amounts, and so on—but it still involved the incredibly laborious process of people clicking around in QuickBooks.”

In his two previous ventures, which he sold to Oracle and Drobox, Daher and his team worked on automating tedious accounting procedures, which put them in position to launch Pilot.

Index Ventures partner Mark Goldberg described Pilot as a “massive platform play” since its services provide the company with a deep relationship with its clients, and an opportunity to cross-sell other products—such as the newly launched tax product.

Pilot’s competitors include Texas-based ScaleFactor, which likewise seeks to automate the backend operations of small businesses, and which is looking to expand its operations into loans.

The Series B round brings Pilot’s total funding to $59 million, and values the company at $355 million. Daher declined to provide specific revenue or profitability numbers but said Pilot is handling over $100 million in client transactions per month, and that it’s increased its revenue run rate fivefold since last year.

About the Author
Jeff John Roberts
By Jeff John RobertsEditor, Finance and Crypto
LinkedIn iconTwitter icon

Jeff John Roberts is the Finance and Crypto editor at Fortune, overseeing coverage of the blockchain and how technology is changing finance.

See full bioRight Arrow Button Icon

Latest in The Ledger

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Most Popular

placeholder alt text
Economy
'I just don't have a good feeling about this': Top economist Claudia Sahm says the economy quietly shifted and everyone's now looking at the wrong alarm
By Eleanor PringleJanuary 31, 2026
3 days ago
placeholder alt text
Future of Work
Ford CEO has 5,000 open mechanic jobs with up to 6-figure salaries from the shortage of manually skilled workers: 'We are in trouble in our country'
By Marco Quiroz-GutierrezJanuary 31, 2026
3 days ago
placeholder alt text
Success
In 2026, many employers are ditching merit-based pay bumps in favor of ‘peanut butter raises’
By Emma BurleighFebruary 2, 2026
23 hours ago
placeholder alt text
Big Tech
The Chan Zuckerberg Initiative cut 70 jobs as the Meta CEO’s philanthropy goes all in on mission to 'cure or prevent all disease'
By Sydney LakeFebruary 1, 2026
2 days ago
placeholder alt text
Personal Finance
Current price of silver as of Monday, February 2, 2026
By Joseph HostetlerFebruary 2, 2026
1 day ago
placeholder alt text
Economy
Musk’s fantasy for a future where work is optional just got more real: U.K. minister calls for universal basic income to cushion AI-related job losses
By Sasha RogelbergFebruary 1, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.


Latest in The Ledger

CommentaryEndorsements
Keeping up with the SEC: Here’s what Kim Kardashian and your financial adviser have in common
By Michael BoeseNovember 29, 2022
3 years ago
FinanceFTX
Crypto lender BlockFi files for bankruptcy after FTX implosion
By Chris MorrisNovember 28, 2022
3 years ago
The LedgerFlorida
New York bans new crypto mining power plants—for now
By The Associated PressNovember 23, 2022
3 years ago
The LedgerFTX
Sam Bankman-Fried gives most detailed explanation yet about FTX’s collapse in letter to staff while still claiming ignorance of wrongdoing
By Joanna Ossinger and BloombergNovember 22, 2022
3 years ago
The LedgerCryptocurrency
Crypto brokerage Genesis said to be warning investors it may declare bankruptcy if it can’t raise at least $1 billion
By Lydia Beyoud, Sonali Basak, Vildana Hajric, Muyao Shen and BloombergNovember 22, 2022
3 years ago
The LedgerFTX
New FTX CEO hired to clean up Sam Bankman-Fried’s mess is being paid $1,300 an hour
By Jack Schickler and CoinDeskNovember 21, 2022
3 years ago