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The Goldilocks Rule: Making Your First Sales Hire

Oct 29, 2020
Author: Sarah Hicks

You remember Goldilocks and the Three Bears. A flaxen-haired and doe-eyed ingenue stumbles into the furry quadrupeds’ family home and samples each of their porridge, chairs, and beds. In each instance, after some grumbling at the inadequacy of the first two she tries, she settles on one bowl, one seat, and one mattress as “just right”.


Making your first sales hire as a founder is much like Goldilocks’ journey according to a recent Predictable Revenue podcast guest, Joseph Trodden – you won’t get it right the first time. In Joseph’s experience, the reasons behind that are simple.

First, entrepreneurs don’t actually know what they want. They’re looking at sales as a whole and they haven’t broken down the sales process enough to determine whether they want someone taking over lead gen, establishing partnerships, or coming up with the strategy.

Second, they don’t know their own key strengths, what specific market they’re going to target, and where exactly this new hire would operate. They therefore don’t know if they should hire someone junior to pick up the grunt work, or someone senior with more experience than them. And finally, once they’ve brought someone on, founders don’t provide their hire with the right remit. They don’t detail exactly the parameters within which they want the salesperson to operate, the sales process and its components, or the exact degree of latitude they are going to afford this person.

In every instance, expectations aren’t being properly set for this first hire, and they are destined to fail.


Figuring out the level of hire is key. To determine which gaps you need to fill, it’s as simple as deciding what you hate to do most. What do you excel at, and what is a poor use of your time?

If you hire someone senior, they can provide expertise in sales strategy, but they may not want to pick up the phone. Can your ego handle that? If you’re hiring someone junior, you need to be able to equip them adequately with tools, training, etc. It’s easy to decide to just drop someone in to take over the prospecting activities, but until that process is clearly defined and documented, someone without experience won’t be able to pick it up.

You have to understand exactly what the position is that you’re looking to fill, and be clear on what the expectations are. Joseph suggests you think in organizational terms and ask yourself these questions. What is the sales function now? What would it mean to have someone come in to take these specific things off your plate? What would that person look like? What’s the consequence of putting this person in?

Whoever you decide to bring on, make sure you are hiring for right now. You don’t want to make the mistake of bringing someone on because you think they’ll be great in 6 months. You also don’t want to make the mistake of hiring someone and promising them a role in the future that you don’t need yet. Be honest about what you want in the role and your expectations, and be transparent about projections and timeline.



The player-coach is a point of contention for many sales experts, but Joseph attests that it can be a great role depending on the stage and size of your organization.

If you have a small sales team and are looking to put someone in that management role, a player-coach might be more respected. Reps underneath this player-coach want to know that their manager can pick up the phone and actually do the job with them. But as the company grows, that manager will add more value helping other people than picking up the phone.

If you’re looking to promote someone internally to a sales manager, player-coach role, it’s important to note that the skills that make an excellent sales rep aren’t the same as those that make a great coach or manager. 


So you’ve made your first hire, and it’s working. Who do you bring on next? Joseph suggests you lean on that first hire to help you make the decision.

They add a different perspective to your own, and listening to your people’s perspectives is an essential skill you’ll need to learn as you graduate from solo-preneur to a true organization.

Ask your first hire these questions: Who should we hire? Why? What would this enable us to do? What would this enable you to do? What would the impact be across the business?


Goldilocks had a great time trying out the breakfasts, the chairs, the sleeping quarters – but as she is forced to make more and more complicated decisions about the renovations and additions being constructed on the three bears’ abode, she’s going to need some help.

In Joseph’s words, you’ll never take a business to its full potential by holding the reins everywhere. You need to do that at the start because you’re the sole point of cohesion, you have the ideas, and the people you work with are transient to properly document all your processes.

But there comes a point – Joseph’s “Inflection Point” where you need to get that stuff down, establish a culture that has meaning to you and the company, and build from there.

Here’s how to do it:

  1. Set expectations. Not trying to beat a dead horse here, but this is important.
  2. Alliance Agreements. This is a commitment Joseph designed to align any new hire with the business. Determine what this person wants in their career and life, what the business needs, and find simbiosis. You make a commitment to your employee, and they make a commitment to you.
  3. Let people fail. Empower your team to make their own decisions, don’t call every single shot. Let your people do some things you disagree with, even if they may fail, so they can learn for themselves. 


Every entrepreneur moving away from founder-led selling to building their sales team for the first time is hitting what Joseph Trodden calls the “Inflection Point”.

It’s the moment they let go of control for the first time and work towards the next level of growth. And making the first sales hire is a key piece in this puzzle. It’s something a lot of entrepreneurs get wrong the first time, often taking a route like that of Goldilocks and trying a bit of this and a bit of that before finding the right person.

But if you focus on defining which gaps you need to fill, hiring at the appropriate level, and setting clear expectations, maybe you can transition through your Inflection Point and find that “just right” hire a little bit quicker.


More blog posts for early stage founders/sales leaders:

The key to getting your first 10 customers isn’t sales – it’s product

Getting your first 100 customers with Salesflare Co-Founder Jeroen Corthout

How to build and evolve your first sales playbook with Bowery Capital’s Andrew Oddo

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