Last week, I shared the first 3 steps I use to close $100K-plus SaaS deals:

1. Target the right accounts
2. Run a tight discovery process
3. Build an internal deal team that helps you win

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If you missed that one, you can read it here.

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Today, I’m going to walk through the final 3 steps that will consistently help you take a six-figure opportunity from “interested” to “e-signed.”

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Let’s get into it...

Step 4: Design a Proof of Concept That Converts

Most big buyers don’t sign a $100K contract without trying the product first. They want to get hands-on. They want to see it working in their environment.

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This is where a strong proof of concept (POC), pilot, or trial comes into play.
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Here’s what I recommend:

• Keep it short. A few weeks or 30 days, 90 days max.
• Make it a paid POC, even if it’s minimal.
• Define what success looks like before you start.
• Set up weekly or bi-weekly check-ins.
• Align every stakeholder around the same goal.

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The best POCs aren’t just demos stretched over 30 days.

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They’re structured as mini-projects with clear checkpoints and an obvious next step.

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You want your buyer to walk away thinking, “We need this to hit our business goals.” Or "We won't be able to operate without this."

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And by the way, a well-run POC also acts as a qualification tool. If the buyer doesn’t engage or won’t commit to a short-term test, they’re probably not serious.

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Step 5: Build Trust Like a Consultant

At this point in the deal, you’re no longer just a seller. You’re an advisor. A project manager. A partner.

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Here’s what I focus on to build trust:

• Learn the buyer’s business better than your competitors
• Get on a text message basis with your champion and any other key stakeholders (harder to do with senior execs)
• Always confirm next steps
• Introduce a Mutual Action Plan early in the project

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That last one is critical. A Mutual Action Plan outlines all the steps between today and go-live. It keeps everyone on track and shows your buyer that you’ve done this before.

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I've linked a basic template example above, but if you want a more detailed version, the exact template I use for my deals over $250K/year, reply to this email or grab some time with me here.

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Enterprise buyers don’t want to be sold. They want someone who knows how to get deals over the finish line and who will operate as a project lead from discovery to go-live. Your role is to show them the way.

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Step 6: Structure an Offer They Can’t Ignore

This is where most reps freeze. The pricing conversation. I used to freeze up here, too.

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​Here’s my approach:

• Get help from your manager or a top-performing rep on your team
• Lead with value adds, not a discount
• Tie your offer to a clear timeline or buying trigger
• Make the upside obvious and measurable

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Instead of “10% off if you sign by Friday,” I prefer:
“If you move forward by July 31, we’ll include implementation support and priority onboarding.”

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This keeps the full value of the deal intact and gives your buyer something worth acting on. It also keeps your forecast honest.

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Remember, most buyers aren’t saying no to your price. They’re saying no to poor timing, unclear ROI, or lack of urgency.

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Here's a Recap of the Full Framework:

1. Target the right accounts
2. Run focused discovery
3. Build your internal deal team
4. Design a proof of concept
5. Build trust and act like a consultant
6. Craft a compelling, time-sensitive offer

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Closing Your First (or Next) $100K Deal.

If your goal is to increase your annual deal sizes, follow these steps, stay consistent, and THINK BIG!
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For years, I struggled with a fixed mindset on this and didn't believe I had what it took to close large annual SaaS agreements.

Boy, was I wrong... It took working with leaders, mentors, and coaches to help me develop the mindset, skills, and operating process that's allowed me to consistently (across multiple teams) deliver an amazing customer experience for my buyers and close deals I thought were out of reach.

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And if I can do it, so can you.

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If you want to connect with other ambitious sellers like yourself, who are working on closing bigger software deals, be sure to join us in the Sales Players Slack. You’ll find an awesome networking community, templates, feedback, and real advice.
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If you're looking for more hands-on help targeting, qualifying, managing, negotiating and closing six-figure annual SaaS deals, consider working with me 1:1. My coaching will help you pinpoint your high likelihood accounts and manage the process like a strategic advisor to your buyer, so you can consistently beat the competition, win more career-changing deals and bank bigger commission checks than you ever thought possible.
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Thanks for reading and for being part of the SP community!

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Until next week.

-Jesse