Dear SaaStr: How Do I Learn to Close Big Enterprise Deals Better?
Closing high-ticket enterprise deals is a different beast compared to SMB or mid-market sales. It requires patience, strategy, and a deep understanding of the enterprise buying process.
In fact, arguably … SMB sales and enterprise sales have almost nothing in common. More on that here:
Here’s you can … learn. How to go from SMB sales to enterprise.
Here’s how to approach it:
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Map Out Stakeholders Early: Enterprise deals often involve multiple stakeholders—procurement, IT, finance, and the actual business users. Identify and map out all the key players and their motivations early in the process. Remember, the actual buyer is often not the end user, so you need to understand who holds the budget and decision-making power. Most SMB sales reps and even most founders aren’t very good at this. Learn to be good at this. Force yourself. Make sure in every Big Deal, you identify 5 stakeholders. And work with each of them.
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Build Relationships at Multiple Levels: Related to the prior point, but you have to build trust at multiple levels in big enterprise deals. Don’t just rely on one champion within the organization. Build relationships across different levels—executives, managers, and end users. Executive sponsorship on both sides is critical for pushing deals through. Yes, that can mean a lot more demos and work.
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Focus on ROI and Business Impact: Enterprises care about solving big problems. Your pitch should focus on the critical business issues they’re facing and how your solution delivers measurable ROI. Document clear business cases and tailor your proposal to their specific needs—generic pitches won’t cut it.
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Start Small, Then Expand. At Least — If There is a Clear Path to Expand: Big-ticket deals often start as smaller departmental deals. For example, a $25k pilot can grow into a $1M+ enterprise-wide contract over time. Focus on landing the logo first, then build expansion metrics into your sales comp plans to drive growth within the account. But beware of pilots that can’t go anywhere. Sometimes, you have to close the whole org, or someone bigger will go around your little pilot and close everything. Read the opportunity correctly.
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Leverage Proof of Concept (PoC) and Paid Pilots: A well-executed Paid Pilot or PoC can help you prove value and reduce buyer risk. Enterprises often hesitate to commit to large contracts upfront, so offering a short-term PoC can help you get your foot in the door and build trust. Don’t run from them. Embrace them. Get good at doing them — and knowing when to offer them, when not to do, and when to only do so when asked.
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Be Patient with Long Sales Cycles: Enterprise deals take time—sometimes 6-12 months or more. Be aggressive in moving the deal forward, but also get comfortable with the longer cycles. A great VP of Sales can help shrink this timeline, but you can’t rush enterprise decision-making. Really understand their process.
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Get on a Plane. Starting Meeting Bigger Prospects and Customers in Person: For high-ticket deals, face-to-face meetings are often essential. While Zoom works for smaller deals, in-person meetings build trust and help you close larger contracts faster. Don’t underestimate the power of showing up. And if your competitor does and you don’t, they’ll win more often. It’s not worth … not showing up.
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Make It Easy to Buy. Remember, You Are Just a Startup: Enterprises often complain about how hard it is to buy from vendors. Simplify your pricing, contracts, and approval processes. Don’t pretend you are larger than you are. Don’t hide things. The easier you make it to buy, the faster deals will close.
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Lean on Customer Success Stories: Use case studies and testimonials from similar enterprise customers to build credibility. Enterprises want to see that you’ve solved similar problems for others in their industry. Highlighting big logos you’ve worked with can make a huge difference. It really, really helps. Everyone wants to know what great tools others in the industry, and their competitors, are using.
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Charge for Value: Don’t be afraid to charge more as you add more value. Enterprises are willing to pay for solutions that solve critical problems. Position your product as a solution, not just a tool, and price it accordingly. Keep raising prices on each deal, until you get pushback. More on that here:
Enterprise sales are all about solving big problems, building trust, and playing the long game. If you can master these steps, you’ll be well on your way to closing high-ticket deals.
And finally, bring them together. Do city tours, road shows, as many and as often as you can. And dp your own customer event once a year. Your existing customers will then sell your prospects for you, if you put them together and they are happy.
A bit more here:
And a related SaaStr session here:
