GTM Fireside Chat: How the New Gen Buys (and Why You’re Doing It Wrong)
Today’s buyers aren’t following yesterday’s playbook, and if you’re still selling like they are, you’re already behind.
This fireside chat dives into how the next generation of customers, especially in B2B SaaS, makes decisions, evaluates products, and engages with vendors. Spoiler: it’s not through long email chains, clunky demos, or 15-slide decks.
We’ll explore what modern buyers expect, what’s broken in traditional GTM motions, and how startups can adapt quickly. Whether you’re building your first sales motion or scaling a repeatable revenue engine, you’ll walk away with tactical insights and a refreshed mindset for selling to a new era of decision-makers.
Date: August 27, 2025
Time: 10 AM to 12 PM (fireside chat followed by a networking brunch)
Location: SVB Cafe (Linkedin Building, 17th Floor Cafe)
Speakers:
Bill Macaitis, CMO
Bill offers board advisory services where he shares his cumulative go-to-market knowledge leading marketing for the three of the fastest growing SaaS companies in history: Slack (CRO/CMO), Zendesk (CMO) and Salesforce (SVP Marketing). He took both Zendesk and Slack to IPO.
Doug Bell
Doug is the co-host of The Cannonball GTM Livestream and a Partner/Fractional CMO at Chief Outsiders. He helps SaaS companies accelerate growth through practical, AI-enhanced marketing strategies that actually work. At Chief Outsiders, Doug works directly with CEOs and leadership teams to establish clear go-to-market strategies, create compelling positioning, and build demand generation engines that deliver measurable results. His approach combines 20+ years of SaaS marketing leadership with the real-time innovation happening at the intersection of AI and marketing.
Moderated by:
Jon Festejo, CEO and Co-founder, Salesbricks
Jon has worked closely with early-stage founders on pricing strategies and the quote-to-cash process, and has seen common mistakes that can hold companies back. He will be dedicating one day each month to share key dos and don’ts, and help you avoid these pitfalls.
This event is co-hosted by SVB