Insights Into Finance Tech and Humorous Expense Revelations

Erica Gessert, CFO of Upwork, and former Senior Vice President of Finance & Analytics at PayPal, joins CJ for this episode. They discuss Erica's experience with forecasting models at PayPal, emphasizing the need for adaptable models that change with economic conditions. Delving into her role at Upwork, Erica explains the company’s approach to customer acquisition costs, the significance of network effects in marketplace businesses, and Upwork’s take rate strategies. The conversation covers Upwork’s investment in R&D, how the company maintains platform trust in the face of bad actors, and the impact of AI. Apart from explaining how Upwork gained 20 points of EBITDA in just three quarters, Erica also sheds light on their North Star metrics, how they balance growth and profitability, their approach to M&A, and her experience reporting to Masayoshi Son during her time at Sprint.

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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. 

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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.

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TIMESTAMPS:

(00:00) Preview and Intro

(02:30) Sponsor – Planful | MUFG | Brex

(06:17) Budgeting at PayPal

(10:23) Forecasting Methodologies at PayPal

(13:15) The Impact of the Calendar on Forecasting

(15:01) Forecasting and Macroeconomic Indicators

(16:29) Planning Will Take as Long as the Time You Allot for It

(17:56) Surprising Insights About Freelancers

(19:26) Sponsor – Vanta | Tropic | RightRev

(24:55) Upwork’s Customer Acquisition Cost

(27:59) Freelancers and AI Adoption

(29:07) Network Effects in Upwork’s Model

(31:14) Upwork’s Take Rate Strategies

(34:49) R&D Investing at Upwork

(38:36) Selling Trusted Transactions

(41:12) Upwork’s North Star Metrics

(42:59) Recognising the Potential of AI

(44:05) How Upwork Gained 20 Points of EBITDA in Three Quarters

(45:29) Balancing Growth and Profitability

(46:41) Upwork’s M&A Strategy

(48:35) Long-Ass Lightning Round: A Big Career Mistake

(50:55) Reporting to Masa from SoftBank

(52:49) Advice to Younger Self

(54:18) Finance Software Stack

(54:55) Craziest Expense Story