BILL’s CPO on Creating a Financial Platform

August 27, 2026

AI Summary

5 min read

Mike Cherry, Chief Product Officer of Bill, opened the episode with a personal detail: his grandfather owned a bowling alley in the 80s and 90s, and watching him run it gave Cherry an early, visceral sense of what small business owners struggle with. Decades later, after product leadership roles at Square and Gusto, Cherry joined Bill because he believes that sophisticated financial management is one of the major reasons businesses succeed or fail — and that AI is an extreme talent for the financial domain in particular.

The Platform Thesis: One Plus One Equals Three

Bill started as a powerhouse in accounts payable automation and has expanded through building and acquiring — notably the Divvy acquisition for spend and expense management — into a multi-product financial platform. The core logic is that a business managing all of its money-out operations (AP, spend, expense, procurement) on a single platform makes better decisions because those decisions are informed by a wider context of financial activity. Cherry describes this as a "one plus one equals three" dynamic: each additional product a customer adopts delivers cumulative value.

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What you'll learn

1 (00:18) **Introduction & Guest Background** - Host Niritz Patel introduces Mike Cherry, CPO of Bill, and Mike shares his career journey from engineer to product leader at Square, Gusto, and now Bill.
2 (03:10) **Bill’s Platform Evolution: From AP to a Financial Ecosystem** - Mike describes Bill’s growth from a single AP automation product to a multi-product platform through building and acquiring.
3 (06:14) **How AI is Reinventing Financial Workflows** - Mike outlines the first wave of AI’s impact: accelerating menial financial tasks with high accuracy.
4 (08:02) **Unlocking Financial Intelligence Through Data & Context** - Mike explains how Bill’s vast data—over a trillion dollars in payments and 500,000 businesses—enables smarter financial intelligence.
5 (10:05) **End-to-End Platform vs. Best-of-Breed: The SMB Preference** - Mike discusses how small businesses are increasingly choosing to consolidate around trusted platforms rather than stitching together point solutions.
6 (12:05) **Will AI Consolidate or Expand the Competitive Landscape?** - Mike sees a growing number of AI upstarts but believes trust will be the deciding factor for SMBs in financial management.
7 (13:25) **Positioning in the Fragmented Payment Landscape** - Mike explains Bill’s strategy to marry payments and financial services directly within the workflow.

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Show Notes

Reducing inefficiencies across financial services, automating workflows and maximizing available cash flow for small- and medium-sized businesses (SMBs) is central to BILL’s mission. On this episode of Tech Disruptors, the company’s chief product officer, Mike Cieri, joins Bloomberg Intelligence analyst Niraj Patel to discuss the creation of a future financial platform that covers payments, spending and expenses, accounts payable, financial planning and analysis and more. He explains how BILL is leveraging AI across its portfolio, which serves close to 500,000 SMBs, and talks about the fragmented payments landscape, customer priorities and the company’s transaction agents.