Navigating Financial Services and Compliance in Modern Business

In this episode, CJ is joined by Kapil Agrawal, CFO at Outschool, former CFO of Poshmark, and former Global Head of Pricing and Finance Business Partner at Uber. Kapil shares insights on Uber's pricing strategies and the use of promotions to drive customer growth. He discusses the multiple North Star metrics used at Uber before explaining his role in changing the company’s take rate. He also talks about his role at Poshmark and how he raised the company’s gross margin. The conversation explores the advantages and challenges of marketplace models versus subscription models and highlights the potential of combining both. Also covered is the significance of high-quality decision-making as a leader and the role of hard work in achieving this.

—

SPONSORS:

MUFG is the largest bank in Japan and a global banking powerhouse with a focus on empowering Growth and Middle Market stage companies in North America and Europe. MUFG provides comprehensive banking services for VC-backed, PE-backed, and public companies with revenues starting at $40M. The bank combines its global capabilities with deep operational understanding to help companies accelerate their growth trajectory. Contact group head Bob Blee at bblee@us.mufg.jp to find out more.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics.

Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how.

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo.

Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:

(0:00) Preview and Intro

(02:50) Sponsor – MUFG | Brex | Vanta

(07:15) Discounting and Promotions at Uber

(09:26) Pros and Cons of Acquiring Customers with Promotions

(13:48) How Uber Determined the Promotion Term of Nine Months

(14:33) Promotional Launch Strategies Across Different Uber Platforms

(17:49) Sponsor – Tropic | RightRev | Planful

(21:10) The Multiple North Star Metrics at Uber

(24:31) Retention for Drivers Versus Passengers

(25:25) Tackling the Competition for Drivers

(27:20) Changing Uber’s Take Rate

(31:55) Raising the Gross Margins at Poshmark

(37:53) Moving from Buyer and Seller Cohorts to User Cohorts

(39:20) Poshmark’s Take Rate

(42:46) Intro to Outschool

(43:20) Transaction-Based Models Versus Subscription-Based Models

(45:04) The Role of Capital Allocation

(47:22) Combining Transaction-Based and Subscription-Based Models

(49:45) Being Judged on the Quality of Your Decisions

(54:00) Hiring: Generalists Versus Specialists

(56:06) Long-Ass Lightning Round: A Price Cut Regret

(57:34) Advice to Younger Self

(58:44) Finance Software Stack

(59:28) Craziest Expense Story