The Future of Flexible Work: Why the Contractor Experience Matters

We surveyed 500+ finance, HR, and Ops leaders to learn how they are hiring, managing, and preparing for professional and gig workers in the next 3 years.

In this session, you'll learn how to:

→ Identify the #1 contractor complaint and how to fix it

→ Cut support tickets in half with a self-service portal

→ Navigate the biggest onboarding bottlenecks

The contractor management gap is bigger than you think:

→ 95% of organizations manage contractors across 3+

→ 69% of contractors cite payment speed as their #1 complaint

→ Only 20% of HR leaders say they're very confident managing contractors

Save Your Spot for the Live Discussion

Join us on April 22nd, 2026 at 1:00 PM ET.

Meet the speakers

Don Weinstein

Advisor & Investor, Former CPO & CTO, ADP

Don Weinstein is a strategic advisor, venture investor and corporate board member as well as an experienced Fortune 500 Corporate Officer. He currently serves on the board of several PE and VC-backed portfolio companies, while also advising funds on potential investments, including business, technology and operational diligence.

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Previously, as ADP’s Chief Product and Technology officer, he worked closely with ADP’s Board and CEO on transforming the technology organization into an agile, product-led team delivering the next generation of cloud native SaaS products. Prior to that, he served as ADP’s Chief Strategy Officer where he oversaw all aspects of corporate strategy and M&A.

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Prior to joining ADP, Don held senior technology and strategy roles within IBM Corporate Strategy and PwC Strategy and Change Consulting. He began his career with GE as an Edison Engineer.

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Don holds a bachelor’s degree in engineering from Rutgers University, a master’s degree in engineering from Drexel University, and an MBA from New York University’s Stern School of Business.

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Greg Franczyk

Co-Founder & CTO, Wingspan

With over a decade of experience leading engineering teams at companies like Google and The Washington Post, Greg Franczyk understands how scalable systems break—and how to rebuild them. He’ll use that lens to unpack what finance and ops teams should expect as flexible work continues to reshape processes in 2026.

Sara Strope

Wingspan

Sara is a customer-led CMO focused on helping B2B companies accelerate growth from acquisition through retention and expansion.

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Sara's B2B marketing experience spans venture-backed startups (TaxJar, QuotaPath) to global, publicly-traded companies (IBM, Vimeo). She has a proven track record of bringing new products to market, building high performing teams, and leading through transformation.

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