Alright, Sales Players, let’s talk about a major rite of passage in tech sales: your first six-figure annual contract.

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It’s one of those career milestones where everything changes.

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You stop thinking in terms of how many logos you need to make your number, and start thinking in terms of which logo could get you above quota and pay you tens of thousands in commissions.

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You stop chasing dozens of $10K deals and start hunting down the $100K-plus per year opportunities that will make you a legend at your company.

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This is when you begin to realize that a long and successful career in enterprise sales may be within your reach.

In this two-part email series, I’ll be sharing the basic frameworks I’ve used (and refined) to close the largest SaaS deals of my career.

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I'm talking about the $100K-plus contracts that actually moved the needle on quota, W2, and my long-term career growth.
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Oh, and by the way, none of this is based on theory...
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These steps come from my own experience over the years doing enterprise sales, combined with insights from some of the top performers I’ve interviewed on the podcast.
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This week, I’ll be covering the first three steps:

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Step 1: Account Targeting (Finding Sales-Market-Fit)

If you want to close big deals, you have to sell to companies that can actually spend big. Pretty obvious, right?

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Sure. Yet too many reps waste time chasing accounts that will NEVER spend close to six figures with them.
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Here’s the approach:

• Which companies in your book could reasonably spend $100K or more per year on our product?
• Do they resemble your best customers?
• What pain can you solve for them that is big enough to justify a $100K+ annual investment?

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I start by building out a short list of 20 to 30 target accounts that match our ICP and also show strong indicators: things like headcount, funding stage, tech stack, or market momentum.

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Then I look for compelling events by digging deep into earnings calls, org changes, LinkedIn job posts, anything that signals real intent or urgency.
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And most importantly, I try to uncover the personal motivators behind the buyer’s role. What’s in it for them? A promotion? A bonus? Internal political capital? Get clear on this early. It really is one of the biggest factors for getting your Champion to seek budget approval at the $100K+ per year threshold.

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Step 2: Discovery that Filters for Fit

Once I have interest from the right account, I go straight into detective mode.
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Solid discovery doesn’t just uncover pain. It helps you figure out whether the deal has a real shot of closing at six figures or more.

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Basic questions I ask:

• What is this problem costing you?
• What happens if you don’t fix it?
• Who’s involved in the decision-making?
• What does your internal buying process look like?
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I always tie it back to one or more of these outcomes:
​Increase revenue, reduce costs, or manage risk.

If your product doesn’t clearly do at least one of those, you’re unlikely to win a $100K deal.

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Step 3: Build Your Internal Deal Team

I've said it before, and I'll say it again. Big deals don’t get done in a vacuum. You need to assemble a deal team.
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That means working cross-functionally. Pull in your solutions engineer, customer success lead, implementation partner, and an internal executive sponsor for any deals with a six-figure a year potential.
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And don’t just drop a Slack channel invite and hope everyone shows up to the next call ready to go.
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You have to set expectations. Prep each team member and let them know what role they will play in making this deal happen.
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I recently wrote about How I Rally My Internal Team Around Deals and shared a simple deal doc that outlines the opportunity, timeline, key players, and potential blockers.

It keeps everyone aligned and helps leadership step in without needing to ask for context.
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The best closers I’ve worked with are elite at managing internal resources. They don’t just close. They orchestrate.

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Next week, I’ll be breaking down the final three steps in the process:

• Running a proof of concept (PoC) that actually converts
• Building trust that accelerates deals
• Structuring a proposal or offer, your buyer can’t ignore

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Until then, let me know how I can help you in your journey to closing your first (or next) $100K annual SaaS deal.