Hey, 👋 Scott from The Sales Mastermind here.

Today’s edition only takes 3 minutes.

The first hire in any function is always the hardest you'll make for that function.

That holds doubly true for sales, as the job is inherently not within the seller's control (buyers decide when and from whom they buy).

So far this year, I have hired eight sellers to join founder-led sales org. And I have seen consistent near-errors to avoid when hiring your first seller:

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Wrong Experience

Being a successful first sales hire is radically different from being a successful seller in a team of three or more, and it's worlds away from selling with a well-established brand behind you.

Imagine a Microsoft sales representative cold calling versus a cold call from a no-name Microsoft integrator, such as "Steve's IT." One call gets answered, and the seller has instant credibility. The other gets a lot of "Who?" and the buyers hang up.

Your first hire is a generalist as well as a seller; they need to be able to solve problems and find a way despite a lack of structure, support, or institutional knowledge.

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Hiring to a Deadline

Founders love deadlines, but I've never seen a deadline help when it comes to your first seller.

The first seller is a unicorn (they're mythically rare).

A hiring deadline means you'll hire the best available at the time you set the deadline. That person almost certainly will not be the unicorn you need.

Instead, keep interviewing until you find the right person. It might take 10 interviews, it might take 30.

It's better to wait an extra month or three for the right person than to waste six months and $100,000 on the wrong hire. Take your time, and you will find them eventually.

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Lack of Leads

This is a controversial one; you need to provide your first seller with inbound leads.

It's hard enough to learn to sell something that has never been sold by a non-founder before (see newsletter 46 for why founders sell differently), and expecting the seller to learn how to generate leads will break them.

If not inbound leads, at the very least, you need a proven system to generate leads. For example, a proven cold call script with documentation on how to find the right leads and what success looks like - ideally, you also have a dozen or more call recordings of successful cold calls. 

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Slow to Start

The person you hire needs to start selling ASAP, ideally within the first five days of onboarding. Waiting too long sets up the wrong behaviour.

If you have inbound leads, have them do the legwork of qualifying the lead and setting up sales calls for you to run while they shadow.

If you don't have inbound leads, have them cold call or DM on LinkedIn or attend a networking event.

Any longer than five days, and you're setting the wrong expectations.

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No Onboarding Plan

Once you have found your unicorn, the worst thing that can happen is a lack of preparation before they join.

Always have a documented onboarding plan, with objectives for the first five, 30, 60, and 90 days (if you're interested, I can share the onboarding template I use for clients; reply to the email, and I'll send it over).

High-level example:

• Day one - set up tools
• Day two - review ICP documents and case studies and learn the product
• Day three - watch 5+ sales call recordings and document two learnings from each recording
• Day four - get inbound leads to begin qualifying and booking sales calls for the founder
• Day five - catch up on any of the above, plus reach out to 4-5 key team members they need to know (other founders, head of product, head of marketing, etc)
• First 30 days - qualify and shadow the sales process
• First 60 days - learn to run the sales process themself (with you shadowing)
• First 90 days - run the process without you and close their first deal

An indicator of a strong first hire is if they challenge your onboarding plan based on the order, structure, or lack of something in the first day or two. An indicator of a weak first hire is if they challenge the onboarding plan after 2 weeks or more.

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Bonus

With your first sales hire, it's hard to truly know if they'll be successful within the first few months. But it is often clear if they are struggling in the first month.

And if they're struggling, give them a chance or two, but no more than a month of leeway before moving them on and starting the hiring process from scratch.

If you can afford it (meaning at least 6 months' salary for each in the bank and 20+ leads per seller), start with two and within 3-4 months, either:

• Both will succeed, and you're on your way to the moon
• Both will fail, and you'll know your process is fundamentally broken
• One will succeed, and one will fail, and you can learn from both outcomes

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If you're considering hiring your first sales representative and want them to succeed, reply "hiring", and I'll help you lay the groundwork before you waste six months and 100k hiring the wrong person.

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Until next week,
Scott Cowley

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