Winning Across the Market: Lessons from SMB, Mid-Market, and Enterprise Deals

The approach that wins an SMB deal can differ significantly from a mid-market deal, and even more so for an enterprise opportunity. At the 2026 Sandler Partners National Summit, Ben Edwards and David Povlick moderated Winning Across the Market: Lessons from SMB, Mid-Market, and Enterprise Deals, welcoming Colin Johnston, Managing Partner, Techchieva; Preet Singh, Senior Carrier Consultant, Sandler Partners; Tony Cilli, Practice Director, Intelligent Enterprise, Trace3; and Kim McRobert, Customer Advocate/Technologist, TelcoChoice.

Each panelist walked through a single deal, sharing how it was qualified, what nearly stopped it, and how it closed.

A few highlights from the discussion included:

  • SMB – Lead with Curiosity: Colin Johnston turned an owner’s “we don’t need anything” into a sale by asking about the business instead of pitching.
  • Mid-Market – Run a Real Process: Preet Singh built trust with a nonprofit through years of smaller projects, then used competing bids and contract protections to grow the account to more than a dozen solution categories.
  • Enterprise – Start with an Assessment: Tony Cilli led with a vendor-neutral assessment that kept “stay as you are” on the table, earning the trust to guide a large contact center transition.
  • Enterprise – Solve the Business Problem: Kim McRobert took carrier quoting off a client’s 80-person engineering team, building trust through thousands of quotes on a network transition that’s still underway.

The takeaway: deal size changes the stakeholders, the timeline, and the complexity, but the fundamentals hold. Find the problem first, build trust, and bring in Sandler Sales Engineering and leadership when a deal needs more support.

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The Sandler Partners National Summit

The annual Sandler Partners National Summit is the largest independent technology community channel event held each year. It brings together Partners from across the US and Canada – influential leaders, and Providers  – sharing information on solutions, selling approaches, and personal development. The atmosphere is always energetic, reinforcing the family “safe home” reputation Sandler Partners has developed over two decades. While other TSDs may focus on private equity plays, Sandler Partners continues to help solve problems that encourage trust, deeper long-term customer relationships, and ultimately success.