Tom Young, VP of Sales at BMC Software, joins Matt Benelli to challenge outdated assumptions about how enterprise sales should work. Drawing on decades of experience and a recent moment on the other side of a buying decision, Tom reveals how sellers often leave buyers to navigate complex purchasing decisions alone, leading to stalled deals, weak adoption, and low rep confidence. The problem isn’t buyer intent. It’s a lack of structure, coaching, and guidance.
This conversation gets tactical and strategic. Tom breaks down the myth that buyers know how to buy, why seller-led engagement models outperform passive following, and how high-performing FLMs simplify complexity through coaching, not control. CROs and sales leaders will appreciate the clear through line: when managers teach reps how to lead a buying journey, not just chase a number, sales cycles shorten, win rates improve, and performance becomes repeatable. If you’re building a scalable sales org, this is a must-listen.
The Myth CROs Can’t Afford to Believe
Enterprise buyers don’t know how to buy.
We assume they do, especially if we’re talking to a C-level stakeholder or someone who’s been around the block. But even experienced champions don’t always know who needs to be involved, how the money flows, or what internal hurdles exist. That assumption that the buyer has a process leads to reactive selling.
As Tom said, “I didn’t know who my EB really was. I didn’t know how to get it funded. I didn’t have a plan. I needed someone to guide me.”
Reps Don’t Need More Tools. They Need to Own the Engagement.
Here’s what high-performing reps and their managers do differently: they sell the engagement model, not just the product.
Tom’s best-performing sellers start their process by walking buyers through a series of steps: investigation, technical validation, internal alignment, and go-live planning. They call it what it is, a decision framework. And they get buyers to opt in. It’s not a sales cycle dictated by internal CRM stages. It’s a mutual plan to reach an outcome.
This shift has real consequences:
- Faster sales cycles
- Higher win rates
- Fewer “no decisions”
It gives buyers clarity, builds internal consensus, and gives the rep control, not in a pushy way but as a trusted guide through a complex decision.
Managers Make or Break the Model
The framing matters.
Sellers can’t do this if their managers are stuck chasing forecast updates, doing deal reviews disguised as coaching, and checking boxes in their CRM. Tom was blunt: when reps are left to figure it out on their own, deals stall. When managers coach the engagement model, not the number, performance lifts.
That means:
- One-on-ones aren’t for pipeline inspection. They’re for coaching skills that improve pipeline health.
- Mutual action plans aren’t glorified close plans. They should end with a go-live celebration, not a PO date.
- FLMs need frameworks, not “tips and tricks.” They need to know how to run a process, hold reps accountable, and develop people without micromanaging.
If that’s not happening, it’s not a problem with sales execution; it’s a problem with leadership design.
What CROs Should Be Asking
If you’re the CRO, you must institutionalize this shift. Start by asking yourself:
- Are my managers actually coaching, or just doing forecast triage?
- Can our sellers walk a buyer through the steps of an effective decision-making process?
- Do our 1:1s have structure? Are they driving skill development or just checking activity?
- Are reps learning how to sell the engagement, or just how to pitch the product?
The bottom line: your team’s performance is only as scalable as your frontline managers’ ability to coach.
Tom summed it up best: “Our job isn’t to sell the product. It’s to ensure the outcome.”
That starts by teaching your reps how to lead buyers, not chase them.
Let’s talk: www.coachem.io
