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Preparing for your first sales hire: A checklist for Founders

Preparing for your first sales hire: A checklist for Founders

Check these items off BEFORE you make that first sales hire

Jess Schultz
March 09, 2025

Hi friends - I’m back! And this week, I want to give you a checklist to follow BEFORE you make that first sales hire. Trust me, it will increase your odds of success 5x.

Before I jump into that juicy content…

Did you know I regularly host educational sessions or masterclasses? 🎓️

Yep - for VCs, accelerators, MBA programs, and any other groups looking to level up.

Here are some of the topics I’ve presented -

GTM Fundamentals for startups
Founder Led Sales & Marketing 101
How to transition out of Founder-Led Sales (successfully)
How to run effective outbound at scale
Boost inbounds by building your personal brand
How to structure and activate strategic partnerships

…to name a few. These sessions are generally 1 hr and have been reported as being very ‘practical, tactical, and actionable.’ 🙂

Feel free to reach out if your team, portfolio, or community could benefit from a session like this.

Ok, let’s get into it!

Your first sales hire checklist

Why preparation is critical

First, let’s discuss why preparation is critical—I repeat, CRITICAL—to the success of your first hire.

Most founders are pretty good sellers, even without any training, because of their industry expertise, passion, and personal interest and investment* in the outcome.

No W2 will ever care about your business and success the same way you do. Period, full stop.

That AND most* salespeople you can recruit don’t know your industry, product, or customers as intimately as you do. So, they can’t sell or win the same way you do.

Salespeople are also not magicians.

They are more like skilled captains. You are the navigator. 🚢

I recently binged the series The Last Ship, so maybe that’s why ship analogies are top of mind 😆

I asked good ole’ Google for some help articulating my point here -

So, the founder is a navigator who determines the course and provides the ‘necessary directions to reach the destination’.

And the salesperson is the captain, following the navigator’s instructions to maintain the planned course. 💡

Yet, too many of y’all are unfairly expecting the salesperson to be the navigator AND the captain…with no map and no compass. It won’t end well.

How to prepare for success

Make sure you can check off 80% of this checklist -

What ya need	Why ya need it
A clear mission, vision, and values	What do you stand for? How should they represent your company and brand in the wild? Why should they be excited to make you money?
A recording of your founder origin story	Why did you start this company, and what do you hope it will become? They should know your story as well as you do. I suggest recording it so they can listen to it multiple times to really, really know it and tell it like you do. This story is what makes you such a great salesperson—give them the same ammo.
A well-defined ICP/buyer persona	Include the names and LinkedIn profile URLs of real people who have bought from you before and fit these definitions so they know exactly what to look for.
A list of your current clients and the story	How did you win? How did you get introduced? Who was the champion? What features/products do they use? How long have they been clients? How much do they pay you (ACV)? We don’t want them calling existing clients, and it helps them with valuable storytelling in their sales process.
Competitor analysis	Who are your top competitors, and how is your product different? Who are they going to bump into? Remember - status quo is also a competitor. This includes manual processes, FTE, and spreadsheets.
A well-defined positioning document by ICP/persona	How are you truly different from the competition (including the status quo)? How does your positioning change for different buyers or use cases? Teach them how to win.
An on-demand demo recording	Again, a recording so they can watch it over and over again to understand your product and have an asset they can easily share with prospects. I don't care if it's fancy—it can be a simple Loom.
Recent sales call recordings (min of 3)	So they can hear you in action and learn from you. Bonus: If you have dozens + have been logging your sales calls and emails in a CRM, they can study and reference.
Table stakes sales collateral	At a minimum, a one-pager and a sales deck. Bonus if you have a decent proposal template or custom collateral for unique ICPs/buyer personas, too.
Table stakes sales technology	A CRM + a source for lead data (emails, numbers, etc.) and automated sequencing (e.g., HubSpot and Apollo). They need a way to find leads and their contact info + track their activity.
A list of closed lost opportunities and why you lost them	This is low-hanging fruit for them to re-engage warmer leads.
Case studies	Hopefully, at least 3 of them. This is one of the most frequently requested assets in B2B sales.
Customer reviews	Hopefully, at least 10 of them are publicly available on a well-known site like G2 or Capterra. Did you know 85% of buyers trust an online review as much as a personal recommendation?

If you don’t have 80% of that before they start…they may not be successful at all…and if they are able to figure it out anyway, I guarantee it will take them longer to deliver results for you than it otherwise would have.

Lost time, lost momentum…lost runway. No bueno.

Some related content

Hope that helps! See ya next week. 👋

Want to learn more about how I help startups increase their revenue by 150-590%? 👀

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With love and gratitude,

Jess Schultz

Founder & CEO

Amplify Group

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