Hiring Your First AE: Perspectives from a serial ‘first-AE.’

In a recent podcast with Jonny Price, co-founder of WeFunder, we got to talking about the personal qualities we thought best defined a successful salesperson.

Intelligence, curiosity, tenacity, and attitude were highlighted as key traits.

This post isn't about those qualities.

This post is about the qualities I’ve found to be determinants of success specifically for early AEs at startups.

As a startup founder, these are the qualities you should be looking for in your first AE(s).

Mastery of the Sales Cycle

This isn’t controversial: you want someone who's successfully led a full sales cycle in the past.

No learning on the job here. You can’t afford a slow-start.

Product, competition, value props– they’ll learn those, because you'll teach them.

But the basic blocking and tackling of an effective sales motion– frameworks, deal rigor, etc.– should come with the package.

Tip: This is easy to filter for as you’re recruiting candidates, but pay close attention to their history with deal sizes and cycle times. A mismatch here can be dangerous. If you’re targeting enterprise (high ACVs), someone who’s only sold to startups or mid-market might not transition smoothly, and vice versa.

“And in this corner, the Challenger…”

There’s a zillion sales frameworks out there. Sandler, MEDDICC, SNAP – there’s simply no shortage.

I’m a big fan of the Challenger method because among many things, it recommends gearing yourself toward teaching customers something new; challenging them on some aspect of their business. Hence the name.

And while I could talk all day about the merits of one approach over the other, this is not the place for that.

AEs that challenge customers are great. AEs that challenge customers and internal teams are better.

Here’s why.

Sales are the eyes and ears of the customer, and you need a voice that can resonate across your organizational lines to move a product forward. For example:

Your AEs should be providing real-time feedback to Product; helping validate / invalidate the GTM hypotheses you’re testing.

They should be providing customer feedback to marketing; what messaging is resonating? What messaging isn’t?

Customer success– what issues are surfacing during onboarding? How do these issues affect the sales process?

AEs are your front line. You need them adept at crossing organizational lines.

Tip: This is a little more complex to filter for, but you can get strong signals from references and can drill down on this with candidates during the interview process.

Ownership Mentality

I’ve consistently observed that AEs who possess an intrinsic 'ownership' mentality rise to the top (likely true for all positions in early-stage startups, fwiw).

Why?

They’re inherently willing to step outside their job description to get things done.

This is someone who naturally can think about the bigger picture, can anticipate issues that are coming down the pike, and can proactively work to address them.

Doesn’t that sound like a business owner?

Tip: Some of the best AEs I know were previous business owners or startup founders, so this is relatively easy to filter for. As you’re sourcing candidates, index on former founders or business owners, or employees with extensive startup experience.

Make Mutual Learning a Priority

I think it’s important to look for someone you can learn from.

Automating sales processes. Navigating negotiations. Handling objections. Forecasting pipeline and revenue.

These are just a few examples, and it doesn’t have to be specific to sales. There's a wealth of knowledge and experience to be potentially gained from an AE worth his or her salt.

Second, that person should have a demonstrated ability to learn new things.

A CS major that’s successfully pivoted to a career in sales is a great example. This is someone with a desire and demonstrable ability to evolve, to grow.

The gist is you’re up-leveling each other in a reciprocal way. It’s win-win.

Tip: To identify this trait, examine their career trajectory for evidence of continuous learning and growth. Their LinkedIn profile will do some of the lifting (i.e. they do or they don’t have a history of growing into new areas), but you can drill further down during the interview process by asking a simple question:

“Can you teach me something I don’t know?”

It takes a village

Final note: the elite AEs I’ve had the privilege of working with check most if not all the boxes above.

But the best– the very best– check an additional box: the ability to create, engage, and nurture a community.

They engage in thought leadership; they contribute to relevant social conversations; they moderate or contribute to online forums regularly– you get the picture.

And they're not just present where your customers are, they actively engage in the spaces frequented by your potential customers– Product Hunt, Stack Overflow, Reddit, Capterra, G2, etc.

Most importantly, they excel at converting their audience into a community.

Filtering for community engagement chops is a little less straightforward. Look for indicators of community involvement, content creation, and social media activity.

Conclusion

In summary, hiring your first AEs is not just about finding people who are “good at sales.” The qualities we've explored here are– in my humble experience– the foundational attributes that enable account executives to truly excel in a dynamic and often unstructured environment.

These are the qualities that fuel the adaptability, collaboration, and accountability you need from your AEs so that they can help you drive your company forward.