A year ago, I wouldn't have written this blog. A year ago, AI in Sales was still mostly a coffee chat conversation: kinda' interesting, speculative and safely "somewhere" in the future. While I've been an active AI user at Tufts for 3 or 4 years, it's been not so much in our consulting work until January 2025, but now I use AI tools as frequently as I'm on LinkedIn every day. Bottom line is that my buddy Claude and I talk all the time especially in the interpretation of our own internal Hubspot data for our own business, and, most importantly working directly with our customers in architecting and building new sales processes and tools.
AI is not in the future anymore.
Gartner just published a guide for Chief Sales Officers that should be required reading for every sales leader running a B2B business in 2026. I'll save you the Gartner subscription price and give you what matters...translated into plain English and connected to the one thing that should be on every sales leader's mind right now: You're already deep into your Q2 plans, and the clock is running!
Here's the deal. If you make meaningful changes to how your team sells in Q2...right now, this month...you'll start seeing the results in Q3, and you'll fully capture major improvements in Q4. Wait until Q3 to get serious, and Q4 becomes a scramble. Wait until Q4, and you're writing a 2027 plan explaining why you missed your 2026 revenue plan...and, of course, explaining to your partner, why you missed your bonus.
So what changes should you actually make?
Stop the Random Acts of AI
Gartner found that 87% of sales leaders report pressure from the top to integrate AI. That's essentially everyone. Yet one in three CSOs admit their GenAI investments have failed to deliver the expected impact.
Why? Because they're doing what I call random acts of AI: a tool here, a chatbot there, a pilot that nobody followed up on. It's all just activity without architecture. It would be like rebuilding your kitchen without a plan, a cabinet guy and an electrician.
The fix isn't more AI tools. It's the discipline about where you deploy them. Map your AE's highest-drag activities: account prioritization, research, first-draft outreach...and target AI there first. That's where time gets wasted and where AI delivers the fastest return. Start with two or three use cases, measure them every single week without excuses, scale what works and get rid of what does not.
Treat AI Like a Teammate, Not a Tool
This is the mindset shift that separates the leaders who will win in Q3 and Q4 from those who won't.
Gartner's data is eye-opening: Sellers who develop genuine AI-partnership skills are 3.7 times more likely to hit quota. Not 10% more likely....3.7 times.
What does that look like in practice? AI handles the research, the first draft of messaging, the account scoring on opens and site browsing and the drafts of the second and third outreaches. Your AE handles the judgment, the relationship, the tailoring so that it becomes a clear division of labor. One system, not twelve tabs open across three platforms, and most importantly...especially using Hubspot's mantra: "One Single Source of Truth".
This isn't that complicated. But it requires you to get very comfortable, to define it, to train yourself and your sales team in it, and reinforce it all the time such that it becomes religion.
Existing Customers Are Your Q3 and Q4 Gold Mine
Gartner also found that 74% of B2B sales leaders say closing new deals has become significantly harder. No surprise to me on that point! If that sounds familiar to you, here's the redirect: you already know that your existing customer base is sitting there with expansion potential that you or your team haven't fully mapped.
According to this Gartner article, companies that simplify seller roles and deploy AI for market insight are 1.7 times more likely to achieve profitable growth from existing customers. That's not a small edge. That's a structural advantage!
My Q2 Action List
Here's what I'm working on right now:
- Audit where I and my partners are actually spending our time. My own audit which I did last weekend for my Q1 time was not at all what I expected and was a harsh wakeup call. Did we have a good quarter? Sure. Could I have been more productive? Claude's interpretation was "a lot", but more importantly, he provided me with strong recommendations and not just criticism!
- Picking two AI use cases and running a real pilot with measurements on territory management.
- Training everyone on actual AI collaboration, not on the software.
By 2027, Gartner projects that 95% of seller tasks will involve AI in some meaningful way. They say that by 2030, 70% of routine sales tasks will be automated entirely. I highly respect Gartner, but personally, I feel that these numbers are way too conservative and would switch 2030 to 95% in 2028.
Have a great weekend!. I need to jump in the car right now to get to Tufts' for the finals of our live competition of our Annual New Ventures Competition at the Derby Entrepreneurship Center...always an extraordinary and inspiring event!
Have a great weekend!
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Jack is a salesguy, sales manager and sales mentor. He's the founder of the Derby Entrepreneurship Center at Tufts University, Managing Partner of Derby Management, a firm deep into the science of architecting and building sales processes and tech tools, and author of numerous resources for sales professionals and entrepreneurs.
Now's THE Time to dive into your Sales planning for what lies ahead in 2026!
Think about taking a full day in April or May to commit to updating your Sales Playbook for the balance of 2026. Just connect with me at jack@derbymanagement.com, or give me a call, and we can discuss a few ideas.
"Writing the Winning Sales Plan"
"Writing the Winning Business Plan"
www.derbymanagement.com
Derby Entrepreneurship Center at Tufts.
