When to hire your first AE

When to scale beyond founder led sales and how to prepare

Hi friends - Happy Sunday and Happy Mother’s Day! I’m in Naples celebrating my superwoman Mom.

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Last week we started a month long series on sales hiring decisions and considerations.

SDR - check.

This week we’re going to talk about when to hire your first AE (Account Executive) AND what to do before you hire them to maximize their chances of success (and yours).

When to hire your first AE

What is an AE?

An AE is an account executive. The best ones are ‘full cycle’ reps meaning they can do it all - beginning to end.

They are great at prospecting, running outbound to get their own meetings, AND great at sealing the deal.

When should you hire your first AE?

AFTER* you’ve found, or, have strong signs of product market fit.

If you aren’t sure if you have it, check out this very well articulated piece on levels of PMF from First Round. Using their 4 levels, I wouldn’t hire one before you’re at 2 - Developing, minimum.

And even after you hire one, I’d expect to be intimately involved in the close* until you’re at a 3 minimum, maybe a 4 (especially if you’re selling a complex product or to a complex customer - enterprise).


NO ONE. Literally no one. Is going to be a better salesperson than YOU - the founder - until you achieve some strong signs of PMF.

No else will care as much as you. No one else will know as much as you. No one will have as much passion for the problem as you. No one else will get the inherent respect you command with the prospect as the founder. No one can orchestrate the feedback loop to your product and eng team as quickly as you.

It’s all you, baby.

And the transition doesn’t happen overnight. Your best bet is to remove yourself from the sales process one layer at a time, over a long period of time. First from top of funnel, then the middle, then the bottom.

If you’re ready, what should you do before you recruit* for an AE?

This ~8 min podcast I did with Bolster is a great quick listen.

To summarize -

Step 1 - Create an Ideal Candidate Profile - like your ICP for sales but for recruiting. Recruiting and sales are soooo similar.

An ideal candidate profile might include things like:

  • Someone with enterprise* B2B sales experience - not just SMB sales. Very different.

  • Someone with software* sales experience - not services. Again, very different.

  • Someone who has sold to your buyer* before and intimately understands the unique profile of a CFO, or CPO, or Head of Data Science for example.

Get super clear on the ideal candidate profile and then be rigorous about finding the person who fits that mold.

Step 2 - Prepare strong answers to the questions the candidates (the good ones) are going to ask you.

If they are great sales people, they aren’t going to walk away from a steady income, a more predictable sales cycle, and maybe even residual commission without YOU selling them too.

A good sales rep should ask you about:

  • Where are your deals coming from now? Inbound? Outbound? Your founder network?

  • What marketing efforts are you running? What kind of investment have you made or will you be making to support their sales efforts?

  • How long is your sales cycle?

  • What is your ACV? What are you avg conversion ratios?

  • What are the biggest objections you are hearing?

  • What CRM / sales tools do you have?

Sales reps are MONEY motivated by design. They are going to aim to understand the probability that they will be able to make $$ selling for you.

If they aren’t convinced, they won’t take the job.

What should you do before you hire an AE?

Set them up for success before they start.

I see so many founders hire an AE before they have -

  • Clarity on their ICP, buyer, and positioning

  • A CRM and basic sales tools

  • A sales playbook

  • Case studies or reviews (any kind of social proof)

…among other things. These are some very basic things your sales rep is going to need to hit the ground running for you.

Most* sales reps have never had to set up a CRM, to define the ICP, build the playbook, and don’t know how to develop strong positioning.

They are great at learning the playbook…and then running the plays. You need to give them the words, tools, and assets they need to play ball.

It’s unfair to them, and to you, if you don’t properly prepare. It’s unfair to expect them to build all of these things when they’ve never done it.

And some of them might tell you they’re up for the challenge! They want to come in and build.

It’s an honorable sentiment. But 90% of them won’t do it properly, or fast enough, despite good intentions and a good effort.

And then they will burn out because they aren’t closing deals fast enough. Their ego will take a hit. And so will their bank account.

My recommendation?

Hire a fractional CRO or CMO to help you build out the basic infrastructure and the table stakes sales assets before* that first hire starts.

Bonus? It will help your recruiting efforts.

Whenever my clients have their candidates talk to me and I can reassure them that they aren’t walking into a sh*t show…it 100% increases their odds of taking the leap.

Of course this is my core business so it might sound biased…but even if you don’t hire me personally, I stand by this strategy as your best shot* at a successful founder led sales transition plan.

Want to explore your options? Check out the talent network Bolster has curated with hundreds of fractional GTM leaders.

“But why wouldn’t I just hire a VP of Sales before the AE? Skip the fractional stuff.”

I’ll be answering that question next week.

Want to learn more about how I support startups? Book a strategy call.

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That's all for now! See you next week.

With love and gratitude, 

Jess Schultz

Founder & CEO

Amplify Group