John Spottiswood

Chief Operating Officer Jerry

As the Chief Operating Officer at Jerry, John Spottiswood executes business strategy and operations for Jerry. John leads teams, including marketing, product development, partnerships, administration and customer experience, while actively expanding service offerings into new categories of fintech and related automotive services.

John brings to Jerry 25 years of deep experience in building operations teams and generating growth and revenue at technology startups including Match, LendingClub, DemandTec, QuinStreet, and Inflection, where he held executive leadership positions.

John holds a bachelor’s degree in economics and Japanese from the University of California, Los Angeles, and a master’s degree in business administration, with distinction, from Harvard Business School.

Education

MBA (with distinction), Harvard Business School
BA (Economics & Japanese), University of California

Expertise

Business development
Growth marketing
Hiring and team building
SEM, SEO, and email marketing

Transforming Modern Insurance Models with Data and AI

9:50 AM Keynote: The Next Level of Agentic Service: Lessons from Jerry’s AI Journey

AI has already transformed customer service—but what does it take to reach the next level? In this session, John Spottiswood, COO of Jerry, the country’s leading automated insurance brokerage, shares how his team moved beyond traditional chatbot architecture by implementing MCP framework to power a new generation of AI-driven service. After reaching a performance plateau with an earlier multi-agent system, Jerry reimagined its AI approach—giving its service agents secure API access to real data and introducing an orchestrator model that determines which tools to use and how to synthesize responses. The result: faster, more accurate customer interactions, improved satisfaction, and meaningful cost efficiencies. We will unpack what made this leap possible—highlighting the importance of data quality, orchestration strategy, and building systems that pull the right information at the right time.

Check out the incredible speaker line-up to see who will be joining John.

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