Sales Teams Need This to Close Bigger Deals
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Everyone talks about going upmarket. Getting reps to actually stay focused there is a different problem.
Most of the time it's not a capability issue. It's economics.
Larger deals in print—national accounts, complex RFPs, multi-location programs—require a lot more work. Longer cycles, more stakeholders, plant tours, technical back-and-forth, internal coordination. And the win rate is still lower than mid-market.
Your reps already know this. So they do the math.
Close a few solid mid-sized deals with a reasonable shot at winning, or spend months chasing one big opportunity that might not land? That's not a motivation problem. That's a rational response to how the system is set up.
The companies that actually move upmarket tend to get three things right:
Incentives match the risk. Comp plans account for longer cycles and lower win rates—sometimes with guarantees or adjusted structures while reps are building the pipeline.
Progress counts, not just closes. Getting a plant tour, making the final round, earning a second meeting—those are wins. If none of that shows up in how performance is measured, reps stop chasing deals that take time to develop.
Support is real. Big deals need leadership in the room, technical resources, and internal alignment. If a rep feels like they're running a national account pursuit alone, they'll stop pursuing them.
If you want the behavior to change, the environment has to make bigger deals a smart bet—not a sacrifice.
Sales Leaders: Look at your team's pipeline right now. If the deals are clustered in the same size range—month after month—ask yourself whether that's a rep problem or a system problem. Chances are, your reps are doing exactly what makes sense given how they're set up to succeed, and/or what’s in their comfort zone. Your job is to know the difference and respond accordingly.
The preceding content was provided by a contributor unaffiliated with Printing Impressions. The views expressed within may not directly reflect the thoughts or opinions of the staff of Printing Impressions. Artificial Intelligence may have been used in part to create or edit this content.
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Emily Yepes is a powerhouse sales trainer and revenue producer who lives at the intersection of sales theory and real-world execution. What sets her apart isn’t just her deep knowledge of sales doctrine —it’s that she’s still in the trenches, consistently ranking in the top 5% of over 400 Sandler sales executives worldwide. She brings that same performance-driven mindset to every training room she enters. Emily coaches the sales teams of printing and packaging industry leaders, including JS McCarthy Print+ Packaging, The Packaging School, Canadian Printing Industries Association, Norkol, ImageMark, and Sonoco on everything from prospecting and consultative selling to negotiation and account management. Her average training score? A near-perfect 4.9 out of 5—proof that her clients don’t just learn from her, they love learning from her. She doesn’t deal in hype. Emily brings a practical, psychology-based framework to sales, helping professionals rethink the way they approach buyers, conversations, and themselves. Her philosophy is clear: great salespeople aren’t born—they’re trained. With the right mindset, anyone can learn to breakdown buyer resistance and build real trust that lasts. Approachable, direct, and refreshingly honest, Emily’s training style resonates with sales teams at every level. Her sessions leave people not only inspired—but equipped to sell more and sell better.
