The Enterprise Expansion Strategy
A tactical guide to expanding your footprint within enterprise accounts.
DEAR STAGE 2: We started selling into mid-market companies, but as our product has matured, we’re moving upmarket to enterprise and we see an opportunity to expand our footprint within these larger accounts. In some cases, we didn’t engage the right senior decision-makers the first time around, or our champion has left. How do we navigate this land and expand motion without risking the relationships we already have? ~ENTERPRISE AMBITIONS
DEAR ENTERPRISE AMBITIONS: You’re in a great spot. Expanding within existing customers is one of the highest-leverage plays in enterprise sales, but it’s a delicate balance. You need to navigate internal politics, ensure your initial champion doesn’t feel bypassed or neglected, and make a compelling case for why a broader rollout or deeper engagement is worth their time and advocacy.
I got advice from Stage 2 LPs, Andrew Ettinger (Founder and CEO of Game Plan Partners) and Layne Devereaux (Senior Enterprise AE at Workday), who have spent years selling and expanding inside large accounts. Here’s what they had to say:
Step 1: Don’t Assume Your Existing Champion Has (Enough) Influence
Just because you closed the deal through a champion doesn’t mean they were the ultimate decision-maker—or that they still hold influence.
Find the Economic Buyer – Who actually owns the budget and strategic vision? If you sold to a functional team (e.g., HR, IT, or Finance), but the real buying power sits with the CFO, CIO, or COO, it’s time to identify the new stakeholders and map out their relationships.
Test Your Champion’s Strength – If your existing contact can’t get you a meeting with an executive, they may not have the pull OR you might not be bringing them a compelling enough business case. As Andrew put it, “A good champion loves taking you to executives because it makes them look good.” If they hesitate or push back, ask yourself why.
Use the Right Entry Point – If your champion lacks influence at the top, start looking for new angles. Work with your internal customer success team to identify product power users who may have a vested interest in expansion.
Step 2: Reframe the Conversation Around Business Outcomes
Your initial sale may have been driven by a tactical need, but expanding requires you to align with bigger business goals.
Shift the Messaging – Mid-level buyers care about usability, process improvements, and team efficiency. The C-suite? They care about business risk, cost savings, and revenue impact. “The C-suite doesn’t care what you do—they care about business outcomes,” Andrew emphasized.
Ask the Right Questions – Instead of pitching features, lead with strategic impact and make sure you have a perspective on each of these questions too!
“Since implementing [Product], how have your key business metrics changed?”
“What are the company’s biggest initiatives this year? Where do we align?”
“How has leadership’s perception of [this function] changed since our partnership began?”
Showcase Hard Numbers – If you can tie your product to financial impact, you’ll have a much easier time justifying expansion. This might come in the form of time savings (but quantify it!), cost savings (replacing other software or FTEs), or in driving top line growth.
Step 3: Play the Long Game—But Make the First Move Now
The biggest risk in expansion sales? Waiting too long. Here are a few situations you might face where you want to be proactive:
If Your Champion Leaves, Act Fast – Their replacement will likely want to make their mark, which means reassessing existing vendors. Get ahead of it by reaching out early and re-establishing your value.
Executive Engagement – If you didn’t engage executives the first time around, don’t wait until renewal to fix it. Find ways now to keep leadership informed and engaged This can come in the form of impact update emails, a quarterly business review, etc…
Use Customer Success as a Trojan Horse – CS teams are already interacting with users. Leverage them to gather insights, surface expansion opportunities, and facilitate executive introductions.
Step 4: Make Multi-Threading a Habit, Not an Afterthought
Enterprise deals don’t happen in silos. If your only contact at an account leaves, you shouldn’t be scrambling—you should already have other relationships in place.
Don’t Just Sell—Solve Problems – Engage multiple stakeholders by helping different teams win. The more people who rely on your product, the harder it is to rip out.
Create an Internal Champion Network – Your champion may move on, but if you’ve built relationships across departments, the account stays stable.
Normalize C-Suite Engagement – If your team isn’t comfortable selling to executives, make it a priority. Land-and-expand deals live or die based on whether you can articulate strategic business value.
Just remember, expansion doesn’t happen by chance. The companies that do it best treat it as a structured, repeatable process.
Until next week!