Sydney Sloan was previously the CMO at G2, Drata, and Salesloft, prior to which she spent 16 years at Adobe in a variety of marketing leadership roles. She is currently an advisor at G2 and Executive in Residence at Scale Venture Partners, working with early-stage founders on go-to-market strategy.
In this episode, we talk about her biggest lessons, how buyer behavior has fundamentally changed, why brand matters more than ever, and what the 2026 marketing playbook actually looks like.
Listen on: YouTube, Spotify or Apple Podcast
We discuss:
Why this is the biggest transformation in 30 years of B2B marketing
Buyer research shifted from 29% to 50% on AI chatbots in 4 months, and what that means for you AEO strategy
Why you probably don't need marketing automation the way you used to
“Human in the loop” vs “human in the lead”
How to build brand in 2026 - and why it matters more than ever
The Show-Up-Bigger-Than-You-Are playbook
Reorganizing GTM teams around outcomes, not functions
The advice Sydney would give herself before her first CMO role
Connect with Sydney:
LinkedIn: https://www.linkedin.com/in/sydsloan/
Scale Venture Partners: https://www.scalevp.com/
Connect with Finn:
Project 33: https://www.project33.io/
My personal takeaways:
1. The shift to AI search is happening faster than we think. Internal G2 data showed that in April 2025, 29% of buyers said they started their research in of of the AI chatbots. By August that number hit 50%, just four months later. In 2026, every company needs to focus on their AEO strategy making sure their brand is the citation source LLMs use.
2. Marketing automation as we know it is dead. Companies need to capture high-intent signals using tools like Clay or Common Room, and immediately deploy AI agents to act on them. Speed is the new currency.
3. Show up bigger than you are. Sydney got this advice from the CMOs of Okta and Snyk, and used it to scale Drata and Salesloft. You don’t need a massive budget, you need one anchor event or one bold move. At Drata, they bought out every ad space for two blocks around Moscone Center for RSA Conference so attendees couldn’t miss them. At Salesloft, they bought a billboard on Highway 101, but the ROI didn’t come from the traffic driving by, it came from leveraging photos of it online. Big one-off events, if properly leveraged, signal momentum to investors, customers and potential employees.
4. We’re entering the “Rick Rubin Economy”, because AI lowers the barrier to entry for content and code, so the only differentiator is taste. You can’t prompt your way to good taste. We need to hire for context and judgment, or leverage advisory boards of influencers who actually understand the market. AI provides the speed, but humans provide the creative direction that determines if anyone actually cares.
5. Do we need GTM Architects? Everyone is rushing to hire GTM Engineers and build AI workflows, but in software development, you need engineers and architects. They work at different levels of abstraction. Software Engineers build and maintain software, Software Architects design the system as a whole. We need this for GTM. You need someone to map the strategy, choose the agentic platforms, and decide *what* to automate before you build it. Sydney said she sees this as a separate role, likely sitting in RevOps, not something for the CMO.
6. The biggest mistake new CMOs make is obsessing over their domain of the marketing department. Sydney’s advice for someone stepping into a C-level role for the first time: Spend your first 90 days building deep relationships with your peers - the CFO, CRO, CEO. If you don’t understand the business context and have alignment with your peers, the best marketing strategy in the world won’t save you.
