Moving upmarket in logistics and commerce technology.

When larger deals start exposing gaps

You may already have a few larger customers, but the team still treats each deal as a special project. Common signs include:

• Enterprise prospects like the product, then stall during integration, security, or procurement review.
• Sales qualifies accounts by revenue or order volume, with little agreement on the workflows you can support.
• Proposals depend on custom work that product or operations has not assessed.
• Larger contracts bring more revenue, but onboarding and support absorb the margin.
• Marketing attracts one type of buyer while sales is trying to close another.

I start by checking what recent opportunities and existing accounts reveal. That helps us decide whether to change targeting, improve the offer, or address delivery gaps first.

How I assess and plan the move

1. Compare the accounts you have. Review wins, losses, contract value, sales effort, onboarding, support, retention, and margin. Speak with the people selling and delivering the work.
2. Choose a specific customer profile. Define the operating problem, systems involved, buying trigger, decision makers, and requirements you meet well. Record reasons to decline or escalate an opportunity.
3. Check the promises behind the sale. Have product, operations, and customer success assess the proposed use case. Identify dependencies, capacity limits, and changes needed before launch.
4. Prepare the commercial approach. Update discovery, demonstrations, customer proof, proposals, and handoffs. Give sales a way to involve technical and delivery teams early.
5. Test and review. Pursue a limited set of suitable accounts, then compare sales effort and delivery results with the assumptions in the plan.

This combines customer targeting and commercial positioning with go-to-market strategy. The scope depends on the gaps we find.

What needs to be true before expanding

I use questions like these to assess readiness. There is no universal contract size or company stage that makes the answer yes.

If a requirement is essential and delivery is uncertain, address it before broadening the sales push. If the fit is plausible but unproven, a tightly scoped test may be the useful next step.

An example of a useful decision

Consider a commerce software company pursuing a retailer with stores, marketplaces, and direct-to-consumer orders. This is an illustrative scenario. The buyer wants order routing, inventory visibility, and a clear process for exceptions across those channels.

Before pursuing similar retailers, I would check which workflows the platform supports, how the systems exchange data, and who would own implementation. We would compare the expected contract value with integration and support effort, then define what the first account needs to demonstrate. That gives the team a basis for expanding, narrowing the target, or fixing a specific gap.

What the work can produce

Depending on the agreed scope, the work can include a target customer profile, qualification criteria, a readiness assessment, positioning and sales materials, and a plan for testing the new segment. We define owners and review the assumptions as evidence comes in.

Where responsibilities between teams are unclear, revenue function alignment can be part of the work. For more on choosing customers, read how to put an ideal customer profile to work.

Discuss the accounts you want to pursue

Bring a recent larger deal, one that stalled, and the delivery questions your team is still debating. Book a 30-minute conversation or send me the situation. We can discuss where the uncertainty sits and whether I can help.