Tackling the Goliath: How AI Is Reshaping Venture Capital
Co-hosted with the Massachusetts AI Coalition, we invite you to a no-holds-barred discussion on the impact of AI on venture capital.
For the first time in the industry's history, venture capital is confronting a technology that is both its biggest investment opportunity and a force capable of fundamentally changing how venture itself operates. From sourcing and diligence to portfolio support and fund management, AI is rewriting the rules in real time. This panel turns the lens toward the firms themselves and how VCs are rewiring their internal processes, workflows, and decision-making from the inside out.
Join leading investors and operators as they separate signal from noise and tackle the question on everyone's mind: Is AI simply the next great investment wave or is it transforming venture capital itself?
Agenda
8:30 AM: Arrival & networking over breakfast
9:00 AM: Panel discussion
9:45 AM: Closing networking
Panelists:
Kent Bennet, Partner @ Bessemer Venture
Kent Bennett is a partner in Bessemer’s Boston office focusing on B2B application software and consumer “earthquakes.” Before his career in venture capital, Kent was a creative executive for an entertainment production company, where he developed and sold original material including a network television pilot and a feature film. He began his career with Bain & Co., where he worked on projects in industries spanning IT, retail, consumer products, healthcare, and biotech.
Giuseppe Stuto, Founder & Managing Partner @ Offscript VC
Giuseppe is a first-generation Italian-American entrepreneur raised in a blue-collar immigrant household that taught him hustle and resilience early. He co-founded Fam (originally SmackHigh), a group video chat app that grew to 7M+ users and was acquired by DraftKings, then became an executive at deep tech AI company Pison Technologies while angel investing in 30+ startups. In 2021, he co-founded 186 Ventures, an oversubscribed $37M fund where he's led all 29 investments and built one of Boston's most vibrant founder communities. His conviction: early-stage venture isn't about chasing themes — it's about understanding how founders see the world, and it works best when it's founder-led, not investor-driven.
Steve Bay, General Partner @ Taihill Venture
Steve is the Vice President of Cybersecurity at CoreTelligent, with deep expertise in information security, cyber threat intelligence, compliance, and risk. He is also the author of the newly released AI Acceptable Use Policy for VC Firms. An experienced security executive, Steve previously served as CISO at NuVasive, led the Threat Reconnaissance Unit at Security On-Demand, and built security programs for Fortune 500 companies as a Senior Lead Technologist at Booz Allen, with deep experience across financial services, retail, and healthcare.
Jingjing Chai, General Partner @ Taihill Venture (Moderator)
Jingjing is the General Partner of Taihill Venture, an early stage Venture Capital fund investing in deep tech startups globally. She has 10+ years of experience in deep tech venture investments and technology transfer. Investor in companies including Xtalpi, Deep Principle, Aheadform, Bot Auto, Axoft, etc. Jingjing obtained master degree from Harvard University and bachelor degree from Nanjing University.
Breakfast Co-Host
Massachusetts AI Coalition: The AI revolution is transforming every industry. Massachusetts has an opportunity to lead this transformation in our areas of strength, from healthcare and education to robotics, life sciences, clean energy, defense and beyond. No other region rallies together the way we do in Boston. Our mission is to empower our community of founders, operators, students, researchers, investors, and supporters to come together IRL to educate, connect, and build the future. Learn more about the coalition here.
Breakfast Sponsor
Comerica Bank (division of Fifth Third Bank): With over 30 years of experience dedicated to growth businesses, Comerica Bank's Technology and Life Sciences Division is one of the nation’s leading techology banking practices. Comerica’s specialized coverage provides comprehensive banking and credit solutions to sponsor-backed companies at any stage of their life cycle. Veteran bankers leverage their extensive industry experience, deep relationships with sponsors, and high-touch customer service, to unlock growth across the full spectrum of business maturity. Learn more here.
By registering for this event you grant the NEVCA permission to photograph and use my other media such as film and quotations, on promotional material and content.
About the Host:
The New England Venture Capital Association (NEVCA) is the representative body of New England’s VC community. Our mandate is simple and urgent: strengthen, connect, and advocate for the region’s venture ecosystem so New England remains a leading place to build and scale high‑impact companies.
Professional Advisors:
Benchmark Strategies, CBIZ, Cooley, Coretelligent, Hughes Marino, Silicon Valley Bank
Aspen HR, Citrin Cooperman, Scratch Marketing & Media, Trident Trust
Alliant, Banc of California, Comerica Bank, Customers Bank, Deloitte, Embedded Counsel, IDA Ireland, Invest in Türkiye, Nutter, The Open Accelerator