What Great SaaS CEOs Do Differently in 2026
Written by Dave Bailey
Written by Dave Bailey, Jun 05, 2026
Is the SaaS Apocalypse real?
I recently got a group of my enterprise SaaS CEOs together to discuss what’s working in GTM.
Surprisingly, they’d each had some of their strongest quarters ever.
While this doesn’t mean growing a SaaS company is easy, but it does suggest the SaaS apocalypse narrative is too simplistic.
If you’re running an enterprise SaaS company, here are a few of my takeaways from that session.
1. The Standard Playbook is Alive, but the Bar Keeps Getting Higher.
If you’re still using a combination of outbound, webinars, case studies, pilots, SEO, partner channels, and in-person meetings . . . good! This playbook still works, but the quality standard needed to stand out is getting higher.
Ask yourself: what does a 6- or 7-star experience look like for each of these elements? Then make it happen.
2. Your Pipeline is Limited by the Strength of your Offer.
Outbound is still key to growing your pipeline, but unless you can lead with a killer offer, this channel won’t deliver. If your offer is vague, it won’t cut through.
Ask yourself: what is the sharpest pain point your competitors can’t help with, and your unique feature that resolves it.
3. The Founder-led Sales Phase is Lasting Longer.
A lot of founders are frustrated by how long they are needed to support in sales. I’d treat this as just one of those things that’s annoying but true, and get on with it.
Ask yourself: what is the highest leverage way you can support your sales team on the most important deals.
4. Technical Sales is the New Relationship Holder.
Traditionally, the sales team thought of themselves as the trusted advisor, bringing in technical sales as a human FAQ. But increasingly customers want sales engineers, solutions architects, and forward-deployed engineers who can design the pilot, answer hard questions, and get the product live.
Ask yourself: what is the profile of someone who can 'wow' your customer, and how can you get them in front of customers faster.
5. AI Can’t Fix Poor Relationships.
Even if AI can do things traditional software can’t, the bottleneck to sales often isn’t technical, it’s internal debate and conflict inside your client’s organisation. If tech and compliance don’t get on, that can become a blocker for you.
Ask yourself: how can your presence bring different stakeholders together in a way that creates alignment?
6. Customers Expect You to Be Even Faster.
It’s always been a good idea to follow up immediately. But in an AI world, if you don’t do this, your competitors will. And it’s not just follow ups: pilots, technical validation, and proof-of-value deployments are ripe for streamlining so clients can "see it work" faster.
Ask yourself: if you truly prioritised speed in your sales and deployment, what would you have to do differently?
If you’re running an enterprise SaaS business, I hope one or other of these will help you raise your game so you can continue growing.
Related Reading:
- How to Scale Sales at Your Startup
- What Founders Can Learn from Outbound Sales Teams
- 4 Pricing Techniques to Find The Right Price for Your Product
Originally published on June 5th, 2026
