Every B2B SaaS company Bill Macaitis advises tells him the same story: great product, happy customers, but dozens of competitors doing the same thing.
Bill Macaitis knows what it takes to break through the noise. As the former growth leader at Slack, Zendesk, and Salesforce, he's seen what separates winners from the rest. His verdict on 2026: the old playbook is dead, and the companies clinging to it are about to get crushed by a wave of lean, AI-powered competitors.
If people don’t know you, everything else gets harder: growth slows, sales cycles lengthen, deals shrink.
AI has lowered the barrier to entry, and funding continues to pour into similar products. Feature advantages vanish quickly. Pricing advantages vanish even faster. Brand is the one thing competitors can’t instantly duplicate.
Yet many B2B companies still treat brand as optional. They don’t measure it. They don’t budget for it. And they wonder why their pipeline feels unpredictable.
When Macaitis joined Slack as CMO with just 50 people, the first thing he did was start tracking brand metrics monthly: aided recall, unaided recall, sentiment, share of voice. Just having the data and graphs gave him ammunition to fight for budget and prove impact.
The insight most marketers underestimate: brand quality directly affects sales velocity. Deals move faster when prospects already trust you. They move slower when your brand is unknown.
The smart play? Run brand campaigns in specific cities while keeping sister cities as control groups. Measure the lift in pipeline, deal size, and velocity.
For many SaaS companies, the real problem begins on the pricing page. High-friction entry points push prospects away before they ever experience the product.
The question Macaitis asks: How do we get our product into as many hands as possible?
The answer often hurts - give away way more than feels comfortable.
"Every free user is a person on my marketing team," Macaitis explains. If you have 5 million free users, you have 5 million marketers spreading the word, bringing the product into new organizations, educating the market.
Slack gave away their core product for free. Then they charged for enterprise requirements - not features. Single sign-on, compliance exports, provisioning and deprovisioning. Things IT departments needed, not users. The users were already hooked. The sale became about upgrading, not convincing.
The second shift: from per-user to outcome-based pricing. Per-user pricing made sense when software replaced people. Now AI makes each user 10x more productive. Charging per seat becomes absurd when one person does the work of ten.
Customer support companies now charge per ticket resolved. AI platforms charge for tokens consumed. This isn't just a pricing tweak - it's a realignment with value. Customers pay for what they get, not what they might use.
Companies confident in their product's value will thrive. Those clinging to guaranteed per-seat revenue will lose to competitors who bet on themselves.
Product-led growth terrifies sales teams. They think it means fewer commissions, smaller deals, or no jobs. They're completely wrong.
Selling to a company already using your product is infinitely easier than cold outreach. Macaitis has run sales teams. He knows the difference between grinding through rejections and expanding active users.
The winning model for 2026 is product-led sales: let users in free, track product-qualified leads, then deploy sales to expand. Free users already in the product become qualified leads based on usage patterns and company firmographics. Sales focuses on expansion, not education.
In this model, sales teams spend less time cold-prospecting and more time expanding accounts with proven engagement and internal champions.
Companies that treat PLG and sales as mutually exclusive strategies will lose to those that integrate both.
B2B marketers are stuck in an old playbook: white papers, analyst relations, events. Meanwhile, buyers are on their phones scrolling LinkedIn, TikTok, Instagram, YouTube, and X.
"Put your marketing where the eyeballs are," Macaitis says. Social, mobile, and increasingly video - that's where the attention is. Not on your blog that nobody visits.
The opportunity is massive because so few B2B companies are doing this. Unlike SEM where you compete with 100 bidders, social and video channels for B2B remain relatively untapped. The targeting has become incredibly precise too - you can reach specific individuals at target accounts, not just spray and pray.
The pushback is always the same: "But we're a serious company. We can't be on TikTok. That's not professional."
Macaitis has heard this objection at Salesforce, Zendesk, and Slack - every time they moved upmarket from SMB to enterprise. His response is simple: buyers are still people.
When you have 20 competitors who all look the same, talk the same, and show up in the same channels, it's nearly impossible to stand out. People develop deep affinity for brands that feel different - that talk differently, look differently, and show up in unexpected places.
The risk-averse playbook is the riskiest playbook now. Create content that makes people laugh. Show up on channels your competitors ignore. Talk like humans talk.
The companies that win won't be the ones playing it safe. They'll be the ones that stopped trying to fit in.
Companies are hitting millions in ARR with five people. Building in months what used to take years. Operating at one-hundredth the cost of traditional SaaS companies.
These aren't anomalies. They're the new normal. AI-native competitors don't need 500-person engineering teams or massive sales floors. Some don't even charge upfront - they just take a cut of the outcomes they deliver.
"This is a huge tidal wave that's coming right now," Macaitis warns. The funding is massive. The builders are smart. The technology enables them to move at speeds traditional companies can't match.
Responding to this shift requires more than adding an AI feature. It requires rethinking your operating model, pricing, and go-to-market strategy to stay competitive in a faster environment.
The comfortable middle is disappearing. On one side, AI-native startups will offer your functionality at a fraction of your price. On the other, established players with strong brands will lock in enterprise accounts.
The companies that survive won't be the ones with the best features or the biggest sales teams. They'll be the ones who build brands people recognize, remove friction from their products, combine PLG with sales, shift to outcome-based pricing, embrace AI tools, stand out from the crowd, and operate with the efficiency of their AI-native competitors.
The playbook Macaitis lays out isn't complex. But it requires abandoning everything that worked for the last decade. For many B2B SaaS companies, that will be the hardest part.
The question isn't whether to change. It's whether you'll change fast enough to matter.
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/
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01:48 - Brand is your only real moat
04:15 - Measure brand so finance believes it
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
25:10 - Shift pricing to usage/outcomes/freemium
28:34 - Product-led sales makes deals easier
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.
