Anthony Kappus
GM & COO @ Upwork
About
GM and COO of Upwork (NASDAQ: UPWK), the world’s largest AI + human-powered work marketplace. We connect millions of independent professionals with businesses of every size—from startups to the Fortune 100—to solve their hardest problems.At Upwork I'm responsible for our $4B human+AI powered work marketplace. I also work marketing, communications, legal, payments and trust and safety. Before joining Upwork, I spent over a decade building Redfin in a range of executive roles spanning digital revenue, legal, and corporate development. During that time, Redfin grew from $125M to $1.9B in revenue and from 800 to more than 6,000 employees. I led the negotiation of Redfin’s $2.4B sale to Rocket Mortgage, which closed in July 2025.
United States
Seattle
Computer Software
Executive Management, Trademarks, Recruiting, Bankruptcy Law, Initial Public Offerings (IPO), Acquisitions, Real Estate, Litigation, Venture Capital, Cross-border Transactions, Finance, Labor and Employment Law, Securities Offerings, Joint Ventures, Licensing, Privacy Law, Corporate Governance, Corporate Law, Mergers & Acquisitions (M&A), Venture Financing
Experience
GM & COO
Upwork
Chief Operating Officer
Upwork
Chief of Digital Revenue and Chief Legal Officer
Redfin
Seattle, Washington, United States
I led Redfin’s digital revenue, corporate development and legal teams
Chief Legal Officer
Redfin
Greater Seattle Area
Senior Counsel
Redfin
Tech and VC Practice
DLA Piper
Greater Seattle Area
Education
Haskayne School of Business
University of Calgary
Business
Anthony Kappus's Contact Information
Phone
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