With AI making it easier than ever to launch startups, B2B SaaS companies are facing an unprecedented wave of competition. Bill Macaitis, former CMO of Slack and Zendesk, shares exactly what marketers need to do in 2026 to not just survive—but dominate.
Bill brings decades of experience taking companies from startup to IPO, and his perspective on what's coming is both sobering and energizing. The old B2B playbook of white papers, analyst relations, and enterprise sales cycles isn't going to cut it anymore. The companies that win will be the ones bold enough to rebuild their entire go-to-market strategy.
Key takeaways for B2B SaaS marketers:
- Why brand is your competitive moat: How to measure brand metrics (aided recall, sentiment, share of voice) and prove ROI to skeptical boards—including the hidden impact on deal velocity, deal size, and churn
- Put your marketing where the eyeballs actually are: Why B2B marketers need to stop hiding behind "serious" channels and start creating content on TikTok, YouTube, and Instagram (with tactical examples)
- The pricing revolution: Why per-user pricing is dying and how to transition to usage-based, outcome-based, or token-based models before your competitors do it first
- Product-led sales for mid-market: How to combine freemium with enterprise upsells by differentiating on compliance features (not functionality) to mine product-qualified leads
Bill also addresses the fear many B2B marketers have about being "too consumer-like" with their marketing, explaining why that risk-averse thinking is exactly what will make you invisible in an overcrowded market.
If you're planning your 2026 strategy and wondering whether to play it safe or go bold, this episode makes a compelling case for the latter.
Resources:
Follow Bill’s YouTube Channel SaaS CMO Pro: https://www.youtube.com/@SaaSCMOPro
Find Bill Macaitis on LinkedIn: https://www.linkedin.com/in/bmacaitis/
Connect with Paxton on LinkedIn: https://www.linkedin.com/in/paxtongray/
Looking for an agency that'll be worth the investment? 97th Floor creates custom, audience-first campaigns that drive pipeline and conversions. Get started here: https://97thfloor.com/lets-talk/.
About Bill Macaitis:
Bill Macaitis has led marketing and growth for the three of the fastest ever growing SaaS companies. At Slack he served as the CRO leading up the marketing, sales, success and support teams. Before that he served as the CMO of Zendesk taking the company through a successful IPO. Before that he served as SVP of Marketing for Salesforce where he helped grow revenues to $3B. Currently, Bill serves as board advisor and independent board member to aspiring unicorns and decacorns.
Timestamps:
01:48 - Brand is your only real moat
08:58 - Move B2B marketing to social + video
12:53 - Stop being boring; buyers are people
18:01 - SEO is dying; shift to AIO
21:32 - Use AI imagery when it improves UX
28:34 - Product-led sales makes deals easier
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