Want to W2 $1M? Sell AI, Not SaaS

Once upon a time, W2-ing a million dollars in sales was a mythical benchmark. A unicorn-level achievement. Reserved for CROs, founders, or the early days of high-flying IPOs. But today, thanks to AI, that ceiling is being shattered. Not through equity. Not through stock options. But through cold, hard W2 cash.

So, how do you actually do it?

Here’s the blunt truth: If you're trying to W2 $1M selling traditional SaaS at a Series D company with 45 reps on the leaderboard... you're in the wrong arena.

Here’s what the new $1M W2 playbook looks like:

1. Sell AI Infrastructure or High-Impact AI Workflow Tools

Not just "SaaS with AI sprinkled in."

You want:

• AI infra (think: compute, data, LLM integrations, fine-tuning platforms)

• Deep workflow tools that solve a hair-on-fire problem, especially in high-cost areas like healthcare, finance, or enterprise security

• Examples: Selling a platform that eliminates 80% of a radiologist’s manual review, or an AI compliance engine that scans millions of financial transactions in real-time to detect fraud and automate 90% of regulatory reporting for global banks.

These deals are big. Budgets are getting allocated. And when you’re selling mission-critical tech, discounts don’t get demanded.

It's important to understand the difference between "SaaS" AND "AI" due to the fact that they are often intertwined. 

• “SaaS” implies traditional software (think: CRM, project management, HR tools) — mature, crowded markets with lots of reps and limited upside per deal.

• “AI” in this context means next-generation platforms that automate high-cost, high-value workflows, especially where the ROI is immediate and quantifiable.

2. Join a Company at the Right Stage

Target companies that are:

• Post-Seed or Series A (with traction)

• Under 30 employees

• Sub-5 sales reps (or ideally, you’re the first or second)

Why? Because at this stage:

• You can own huge territories

• You set the initial pricing motions

• You close whales without red tape

• Founders are still in the deals with you

3. Understand the TAM (Total Addressable Market)

Ask:

• Is this a $10B+ problem?

• Do budgets for this already exist?

• Will the buyer lose their job if they don’t solve it?

Bad TAM: A niche tool for HR onboarding compliance.

Great TAM: Selling secure AI tooling into cloud infrastructure teams at Fortune 100s.

If you want a $1M W2, your deals need to be big, urgent, and scalable.

4. Inspect the Sales Team Composition

Before joining:

• How many reps are already there?

• What’s the average quota?

• What’s the highest earner making in cash?

• Are reps getting inbound, or is it all outbound?

If the top rep made $400K last year, that tells you everything.

You want to hear things like:

• "We have one rep doing $2.5M in bookings off 20 accounts."

• "The CEO still closes the biggest deals, but we need someone to take over."

• "Our win rate is above 40% when we get to pilot."

5. Accelerator Structure is Everything

Ask these questions early:

• What’s the base/OTE split?

• At what % of quota do accelerators kick in?

• Are they uncapped?

• Do they stack or reset each quarter?

Example of a $1M-friendly comp plan:

• $150K base / $150K OTE

• Quota = $1.2M

• 10% commission on everything over $1.2M

• Accelerators = 15% at $2M, 20% at $3M+

• Uncapped

If you can close $5M+ in a year (which is entirely possible with $250K+ ACVs), you’re there.

TL;DR: Where $1M W2s Happen

• You’re early (but not too early)

• You’re in AI infrastructure or a high-urgency workflow AI

• You’re in the room with the buyer

• You’re selling $100K+ deals

• You’re on a comp plan built for speed and scale

Most reps won’t get there; the stars need to align, but if you use this framework to find the right company at the right stage with the right product and TAM, it's now possible in the age of AI.