As the co-founder of Sales Assembly, Matt Green spends his days talking to revenue leaders at companies like G2, Sprout Social, and ActiveCampaign, helping them train their teams and solve the problems that don’t show up in LinkedIn posts.
By now, Matt’s seen what’s working — and what’s not — across hundreds of revenue teams. We sat down with him to get the inside scoop on the sales skills that are most in-demand with sales leaders right now and where he’s seeing the most demand for training.
Top takeaways
➣ Today’s sales teams need to get better at two things: framing business value for different stakeholders and writing business cases that actually persuade.
➣ In-person selling is back. Storytelling is the skill that sets top reps apart.
➣ The most effective sales training is live, peer-driven, and reinforced, so reps actually apply what they learn.
➣ The biggest challenge for new sales leaders? Stepping out of the friend zone and having hard conversations.
➣ Many of the ‘new’ sales trends are a return to fundamentals — cold calling and in-person events are making a strong comeback.
In this edition
The biggest skill gaps Matt is seeing right now
Sales Assembly doesn’t offer role-based training. They’ve found that salespeople need the same set of skills, whether they’re a founder, an AE, or a BDR. Things like:
Running effective discovery
Driving urgency
Building multithreaded relationships
Here’s what Matt sees as the most common gaps holding teams back right now:
Helping buyer champions navigate internal conversations
Many B2B sales teams are struggling to adjust to how B2B buying actually works today, says Matt.
“Every purchasing decision is going to be made when you’re not in the room.”
Sales reps need to figure out how to influence the internal conversations that happen between calls. That comes down to two key skills, Matt explains:
Value articulation
Buying is a team sport now. You need to win over your champion, and they need to win over their CFO. That means sales teams have to get good at “articulating value to two different audiences with two different motivations, two different sets of priorities.”
Your job isn’t just to convince the champion that your product is valuable. It’s to arm them with a clear, compelling case they can take upstairs.
Writing skills
Today’s sales professionals need to be able to write, says Matt. You need to be able to become an “eloquent but succinct writer,” who can send a persuasive email and put together the kind of business case that a CFO will actually read.
In-person sales
Face-to-face selling is making a comeback — but not all reps are ready for it.
Many newer reps came up during lockdowns and never got comfortable with face-to-face meetings. “There’s just all of this anxiety,” says Matt. “You want me to sit down at a dinner for 90 minutes with people I’ve never met? I do 25-minute Zoom calls.”
Matt’s advice? Focus on storytelling.
“If I could recommend that you hone in and try to improve on one skill, it would be storytelling.”
Being able to tell a great story puts the salesperson in command of the room.
Matt Green, co-founder of Sales Assembly
The right way to train salespeople
Matt’s seen what works (and what doesn’t) when it comes to sales training. His playbook is simple:
Make it live. “I’m a big believer in live training,” he says. “It tends to lead to better learning outcomes. And that’s what’s most important, right?”
Make it collaborative. Peer learning boosts engagement and buy-in. When veteran reps can swap ideas with peers from other respected companies, they’re more likely to stay open to new approaches.
Make it stick. Sales Assembly builds in Day 7 and Day 30 check-ins to make sure reps are actually applying what they learned. Training shouldn’t just sound good — it should show up in the work.
What great sales leaders do differently
Training builds the foundation, but stepping into leadership is a whole different skill set.
Matt sees a lot of first-time managers struggle with the mindset shift. They want to hold people accountable and still be everyone’s buddy. But leadership comes with a higher level of responsibility — not just to your team, but to the business.
“It’s about really stepping out of that friend zone mindset and saying, ’Okay. I'm a leader. Here's the enormous sense of responsibility and therefore accountability that I have right now.’"
Often, organizations focus on hard skills when upskilling salespeople into leadership roles — accurate forecasting, deal coaching, and so on.
But the top skill that new sales leaders should work on? Having difficult conversations.
“If two people on your team are up for promotion, only one of them is going to get it. How do you have that conversation with the second person?”
Matt’s advice is to skip the “shit sandwich”. Instead, be direct and to the point. Start tough conversations with the phrase “I owe it to you to be honest about this.” Because you do.
The trends sales leaders are talking about behind the scenes
Some of the biggest shifts in sales right now aren’t all over LinkedIn, but they’re definitely showing up in leadership conversations.
Here’s what Matt’s hearing behind closed doors:
AI as augmentation, not replacement
Things have, thankfully, moved on from the “AI will replace SDRs” conversation. Now the discussion has become more nuanced, focusing on how to “repurpose the SDR function and make it more efficient by layering AI on top.” It’s less about replacement, more about rethinking team structure.
In-person sales is back
Matt reports more sales teams investing heavily in trade shows, road shows, and smaller events. It’s a “way to break through the noise” created by AI sales tools, he explains.
Cold calling is (somehow) in vogue again.
Believe it or not, good, old-fashioned cold calling is having a moment.
“It’s becoming much more effective than it was previously.”
New game, same rules
Sales might be evolving fast, but according to Matt, the fundamentals still win. Train your reps to write like a human, tell a good story, and survive a dinner with strangers. And maybe — just maybe — pick up the phone.
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