Around the table: a candid conversation about today’s sales realities
Recently, my team and I started talking about bringing together current clients, former clients, and trusted colleagues across B2B sales and marketing. These are people we’ve worked with or watched in action, and we often have 1:1 conversations with them about what’s working, what’s not and what’s changing.
Another big reason to get those conversations going is that we constantly get questions like, “How are your other clients tackling this?” So we decided to get a few folks in a (virtual) room and start a series of roundtable conversations. We’re calling it the Inner Circle—small, focused groups where we can trade ideas and challenges with peers.
Our first session happened a few weeks ago, and while the group was small, the insights were anything but. Here’s a quick recap of what we discussed:
Deals are stalling—and not where you think
One of the strongest themes that came up? Deals are getting stuck—but not at the top of the funnel. It’s the middle and end stages that are jamming up. Several participants noted that pipeline creation is humming along just fine. One said their SDR team built a massive pipeline over the last 18 months, but not a single deal had closed from it. Another called it “pipeline constipation”—and, unfortunately, that label stuck.
Qualification came up as a key fix—but not just qualifying in. Leaders are pushing reps to qualify out early. One participant even said they celebrate when reps disqualify deals fast, because the worst kind of deal is the one that lingers for 9–12 months before quietly dying at the finish line.
Why deals slow down
We also spent time on three factors that are dragging out sales cycles:
- More stakeholders. It’s harder than ever to build consensus. Instead of one or two key decision-makers, sellers are now navigating committees.
- Fewer in-person meetings. We used to fly out, get five people in a room, read the dynamics, and build trust. That’s harder now—but everyone agreed we need to make the effort to get our AEs in front of buyers whenever we can.
- More scrutiny. Finance, legal and InfoSec are playing a bigger role—and slowing things down.
And then there’s the internal champion problem. Several leaders said they’ve lost momentum—or entire deals—when their main contact moved on, retired, or got pushed aside. When new stakeholders step in, it can feel like you’re starting from scratch.
The takeaway? Time kills deals. But building urgency isn’t as simple as tightening your pitch. It’s about building trust and alignment across departments, personas, and time zones.
The handoff problem—and a new model
Another recurring theme: momentum stalls after the SDR handoff. Once a meeting is booked, reps often disappear—and AEs can’t always keep up.
Some teams are rethinking that model. They’re giving SDRs (or xDRs) a bigger role in account-based selling—working with AEs to maintain momentum after discovery. One CMO shared that their SDRs are responsible for re-engaging “hibernated” opportunities that have gone cold after 1–3 months. This helps uncover why deals stalled and puts prospects back into a nurturing motion—with human follow-up, not just emails.
We also discussed the challenge of incentivizing xDRs to stay involved. The outcomes they’re driving here are often less tangible than initial opportunity creation, which means comp plans need to evolve.
Methodology ≠ muscle memory
Methodologies like MEDDIC, SPICED, and Sandler were mentioned, but the consensus was clear: having a framework isn’t enough. You need to enable it—and make it feel valuable to the buyer, not just the seller.
One idea that stood out: building a mutual success plan early—before the POC even begins. It’s a roadmap that works backwards from “Closed Won,” outlines every stakeholder and milestone, and shows the value you’ll deliver—personally, professionally, and emotionally. It becomes a shared commitment. We even talked about tying each milestone to forecast stages. That’s next-level forecasting discipline.
Today’s buyer wants the ugly truth
One of the most honest and refreshing parts of the conversation came when we shifted perspectives—from sellers to buyers. Most of us are buyers too, and everyone agreed: buyers today are more skeptical, more independent and more allergic to fluff or hype.
One participant summed it up perfectly: “I don’t want to talk to your best customers. Show me your one-star reviews. I want to know what your worst days look like.”
Buyers don’t want a polished pitch—they want to know how your company handles friction, failure, and feedback. And as a group, we admitted we could all do more to show prospects why they’re making the right decision—and how our solutions will make them look like champions.
What’s next
This was just the beginning. We’ll be growing the Inner Circle slowly over the next few months, adding more voices and more perspectives. The goal isn’t to make this a massive group—it’s to keep the conversation sharp, honest, and useful for those shaping the future of B2B sales and marketing.
Huge thanks to the first group who joined. You made it valuable for everyone. And to those reading—let me know if you’d like to be part of the next one.
