Bloomberg Businessweek Podcast Summary

Episode: Upwork Rolls Into the Human + AI Era

Hosts: Carol Massar, Tim Stenovec
Guest: Erica Gesserit (CFO, Upwork)
Date: November 25, 2025

Overview

This episode explores how Upwork, a leading online freelance marketplace, is leveraging artificial intelligence (AI) to drive growth, improve job matching, and respond to shifts in the labor market. Carol Massar and the Bloomberg team interview Erica Gesserit, CFO of Upwork, to discuss the company’s recent investor guidance, impact of AI on job matching and client demand, and broader implications for the workforce.

Key Discussion Points & Insights

Upwork’s 2025 Performance & Outlook

• Strong Results and Positive Guidance
  • Upwork’s shares rose 5.5% following fiscal guidance for 2026 and 2028.
  • The company projected a 7–9% CAGR in Gross Services Volume (GSV) and 13–15% revenue growth, with a 20% CAGR in adjusted EBITDA through 2028.
  • Recent growth came ahead of schedule:
    • “At the end of 2024, we told our investors that we would … take a year and really reinvest in our company and rebuild Upwork. … We would return to GSB and revenue growth in 2026. Well, we did that two quarters early.” — Erica Gesserit [02:29]

Sources of Growth

• AI as a Growth Engine

  • AI is a key area where Upwork expects outsized benefits.
  • Despite fears AI would hurt their business, Upwork is a "true beneficiary"—with $300M in annualized GSB from the AI category, growing over 50% year over year.
    • “Whereas we are truly a beneficiary of AI. We now see about annualized volume of $300 million in GSB from the category on our platform and that is accelerating.” — Erica Gesserit [02:29]

• Expansion with SMBs and Enterprise

  • Upwork is targeting deeper relationships with both small & medium businesses (SMBs) and large enterprises for future growth.
  • “One is AI, one is SMB, expanding our relationships with SMB, and one is the outsized opportunity that we have with large enterprise.” — Erica Gesserit [02:29]

AI's Impact on Job Matching and Talent Discovery

• Reducing Friction in Hiring
  • Upwork’s new AI tools automate the job post and proposal process for both clients and talent, resulting in faster and more successful matches.
    • “Now AI does all of that for both our clients and our talent and it’s making them find each other faster and … get them done.” — Erica Gesserit [04:07]
• UMA: AI-Powered Recruiting
  • UMA, Upwork’s AI companion/recruiter, searches the platform’s 18 million-strong talent base to identify the best matches.
  • “Now we’re seeing fill rates much higher using … the AI recruiter than with a human recruiter.” — Erica Gesserit [05:10]

Why the AI Recruiter Outperforms

• Superior Data Utilization
  • Upwork’s decade-plus dataset on jobs, skills, and outcomes gives AI models an edge.
    • “We have one of the best data sets honestly on the planet. … The recruiter, the AI recruiter is much better at scanning across all of this data than a human can be.” — Erica Gesserit [05:43]

Market Dynamics and Demand Drivers

• Client Demand Trends
  • While the freelance market, especially SMB demand, has been flat due to macroeconomic pressures (inflation, interest rates), Upwork is gaining market share within a challenging landscape.
    • “The last few years have been, as we all know, tough on the job market. … Upwork was relatively flat … but still relatively flat. And it’s really these investments that we’ve made in AI, we’re actually seeing both the category itself increase and that is really accelerating.” — Erica Gesserit [04:07]
  • Upwork remains valuable for SMBs seeking affordable, high-quality, on-demand talent.

AI and the Future of Work

• Humans + AI vs. Humans
  • Gesserit predicts AI will not replace humans, but humans with AI will outperform those without:
    • “Humans with AI will replace humans without AI.” — Erica Gesserit [07:36]
  • AI is automating simple, repetitive tasks, but most complex and high-value work still require human involvement.
  • The volume of low-dollar jobs (under $300) has declined (from 5% to 3.5% of activity in two years), but AI-related work commands higher spend—about three times the platform average.
    • “AI jobs on our platform, clients who engage in AI work spend about three times what our normal kind of platform work does. … That work is more complex. It requires humans and humans using AI agents, but it requires humans in the loop.” — Erica Gesserit [07:36]

Notable Quotes & Memorable Moments

• On Upwork’s AI Edge:
  • “We have one of the best data sets honestly on the planet. … The AI recruiter is much better at scanning across all of this data than a human can be.” — Erica Gesserit [05:43]
• On Reframing AI’s Role:
  • “Humans with AI will replace humans without AI.” — Erica Gesserit [07:36]
• On What Makes the Matches Work:
  • “Our companion on our site is now recruiting talent. … UMA goes out within our 18 million strong talent base and identifies the right talent for that job.” — Erica Gesserit [05:10]

Timestamps for Key Segments

• 01:22–02:04: Upwork’s market performance and investor expectations
• 02:04–03:44: Erica Gesserit interview begins — focus on AI, SMB, enterprise, and growth drivers
• 03:44–04:07: Overview of Upwork’s two-sided marketplace
• 04:07–05:04: AI’s role in the hiring process and friction reduction
• 05:04–05:43: UMA, AI recruiter, and higher fill rates
• 05:43–06:40: Superior data as a competitive advantage for matching talent
• 06:40–07:32: SMB client demand and macroeconomic impacts
• 07:32–08:40: AI’s impact on the workforce—humans + AI, spending patterns, and ‘humans in the loop’

Conclusion

This episode dives deeply into Upwork’s transition into the AI era, emphasizing its proactive embrace of AI to enhance the marketplace experience and redefine the modern workforce. Upwork’s leadership sees AI not as a threat but as an enabler of higher-value work, empowering both companies and talent. The conversation provides forward-looking insights into how AI will shape the interplay between human skill and technological progress in the labor market.