B2B Sales Module #6: Scaling to $5M+ with a team

People who are “naturals” at sales tend to build shitty sales organizations.

They rely on innate abilities instead of learning to build systems + hire people that outgrow them.

Today we break past that limitation.

As a reminder, I’m spending 6 days giving you the 101 version of what we teach in our B2B Sales Accelerator.

• B2B Accelerator Pillar #1: Booking Meetings, The Only Metric That Matters
  Book meetings that lead to real revenue
  

• B2B Accelerator Pillar #2: Defining (+ refining) your ideal customer profile
  Find customers who can’t wait to work with you
  

• B2B Accelerator Pillar #3: Creating a Killer Offer
  Create an offer so good, it sells for you.
  

• B2B Accelerator Pillar #4: Mastering your sales calls 
  Mastering sales calls—even if selling feels uncomfortable
  

• B2B Accelerator Pillar #5: Creating your sales system
  Building a repeatable system you can scale
  

• B2B Accelerator Pillar #6: Hiring a salesperson to scale to $5M+
  Making key hires that take your business to $5M+ 

Yesterday we covered building your sales system. Today? We're talking about scaling it with a team.

In year 1 at GrowthAssistant, we hit what most would call the bootstrapper's dream:

• $200K MRR

• Minimal overhead

• High profit

From the outside, it looked perfect. 

But GA’s CEO Adriane saw something different: Risk masquerading as safety. 

Running lean felt safe. But relying on Adriane + I for sales? 

That was actually dangerous.

After a short discussion, we re-framed hiring a potential salesperson as an investment. 

We thought about it like this…

Maximum Downside:

• 3 months' salary = $25,000

• If it didn't work out, we'd revert back

• Total risk: $25K

Potential Upside:

• Base case: Maintain current trajectory

• Bear case: They cover their salary

• Bull case: $500K+ additional ARR

The result? That $25K "bet" helped us scale to $10M ARR.

When You Build a Real Sales Team, Three Things Happen:

1. Your revenue becomes predictable - because it's not tied to your personal energy

2. Your business becomes sellable - because it runs without you

3. Your growth accelerates - because you have multiple people driving revenue

The mistake most founders make:

They start from the top down. They hire a salesperson first and then look to support them by hiring staff.

The last position you should hire is the salesperson.

We had contractors taking a tremendous amount of work off my and Adriane’s plates before we started our sales hire discussion.

If we didn’t do that, our new hire would just get bogged down in low-value work.

In the Accelerator, we teach members how to hire junior folks and task them with low-risk work: finding prospects, following up after a sales call, etc.

And then, after we’ve worked with them to build an infrastructure for sales, how to make their first actual sales hire.

You'll learn exactly how to:

• Create a sales playbook that turns average hires into top performers

• Structure compensation packages that drive massive results

• Build a 90-day onboarding system that gets new hires closing fast

• Know exactly when to make your first hire (and how to make it successful)

Tomorrow, I'm hosting a free workshop where I'll show you our sales system in action - the same one that's generated over $20M across our portfolio companies.

(We don’t plan to have a recording, so register to learn live.)

This is your last chance to join us before applications open for our next Accelerator cohort.

See you live tomorrow!

jesse

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