How to hire your first salesperson (part 2)
The detailed step by step playbook in recruiting
Hey 👋 I’m Nate! Every week I write about the strategies for building a sales engine at companies both big & small. My goal is to provide leaders with actionable insights rooted in examples so that you can apply them to your own company. Please send me questions on the topic and I’ll do my best to provide direct advice and/or cover in an upcoming newsletter.
In last week’s post, we went through part 1 of how to hire your first salesperson. We covered items 1-4 below and in part 2, we’ll cover 5-7. Enjoy!
Writing the job description
Building your candidate funnel
Phone screen
“On-Site”
Pop quiz
Final presentation
References & backchannels
How to close
Final presentation
The last step is the most important because it combines several elements together at once in a challenging format: selling skills, preparation, team dynamic, and coachability. The structure that we found best in evaluating candidates was tasking them with learning part of our product and then having them pitch it to us in a mock presentation format. Here’s how this looked:
We would provide them with a scenario that was similar to something they would face as a full-time sales rep
We would make an account in our sandbox so that the candidate could familiarize themselves with the product and practice
We sent over industry and company-specific information to help them with their pitch
One person on the team (not the hiring manager) would be a resource for them to ask questions as they prepared over a 1-week time period
Big lesson: The reason that you want a candidate to learn your product and industry is because you already do. You want to be more knowledgable so that you can steer the mock scenario. Letting the candidate pitch the product for their own company relinquishes control and won’t allow you to properly evaluate someone.
Your goal is to test their ability to pitch well, work with your team, and gather enough data points in 1 week to make your decision. This presentation is a big ask. Some people have declined to do it because it’s a challenge, but the reality is that it’s a critical component of the process. The best people always step up.
Let’s walk through this presentation from start to finish:
After the on-site, send over the mock pitch, sandbox credentials, and clear expectations for the presentation.
Call the candidate and walk them through everything (10 min). Remind them that you want them to be successful and for this to go well. You want to hire them, and everything you’re providing them should enable you to do that.
Assign them someone else on the team who they can ask product related questions to. The goal here isn’t just to help them, it’s also to see how they fit in with more of your team. This additional exposure to other teammates will provide more feedback on what it’s like to work with this person. The candidate should be clear that it’s expected they proactively set aside time with your teammate.
If this step isn’t completed at least 2 days before the final presentation, call the candidate and cancel - they have already failed to follow easy instructions and it’s not worth wasting your time further.
As the week progresses, call the candidate to check in. See if you can answer any questions and check in on their preparation. Ask them to walk you through their outline for the meeting. This is another great lens to understanding how you might work together and how prepared they are. You’d be shocked how many people simply want to “wing it”…that’s not something you want to hear about at this stage.
When they get to the actual presentation, make sure you start the meeting by giving them the opportunity to ask any clarifying or outstanding questions. This shouldn’t take more than 5 minutes. Then you’re going to want to jump into the mock scenario and “get into role” so that you can see their pitch. This usually works best if you have 2-3 people from your side so that you can play off each other and see how the candidate handles pitching an entire team, but it can be done with just one person too.
Unlike the “pop quiz” in the previous interview, you’re looking to see a much more polished and prepared salesperson in this meeting. There are several key items you want to see them absolutely nail:
Organized and well-structured meeting agenda that they can stick to (even when you try to throw them off).
An air of formality where they’re understanding everyone’s roles, what is important to each stakeholder, and who is the decision maker.
Strong ability to do thoughtful discovery and understand how they are creating business value in their pitch. Because of the time & resources they’ve been given for this step, this component should stand out the most.
Impressive knowledge of the product. It won’t match yours of course, but it should impress you how much they’re able to pick up in a week and what they can infer from limited data.
Dynamic control of the meeting resulting from great listening. You should see what happens when they start covering something that you tell them isn’t important - do they keep going or ask why and then move on? Their ability to switch gears on the fly will help them be successful.
Comfort with saying “I don’t know” about something related to the product or business. This is a big test because the reality is that they won’t know everything, and it’s an immediate fail if they make the answer up instead (this happens more than you’d think). It’s always ok to tell a prospect that you’ll do some digging for the answer and get back to them, but lying or creating unrealistic expectations is a recipe for disaster.
Confidence in closing and setting next steps. Some of the best salespeople will set the stage for this early in the meeting with an upfront contract (“Can we agree that if we like what we see here today that your team would be willing to test the product and potentially buy?”). Others will make the ask at the end, and both will be able to get through some light objections to ensure the deal moves forward. The key is that they need to leverage the business value they’ve built through the course of the meeting to get past any objections. The better they do with their discovery, the easier the objection handling will be and vice versa.
Once the presentation ends, we would always give feedback. We never told the candidate explicitly if we were going to extend the offer - this was simply a time for everyone on our side to chime in with their candid thoughts. Regardless of your decision, it’s always helpful to provide constructive feedback.
After the candidate departed, the group that was in the presentation would find 5-10 minutes to discuss. Your goal is to have everyone in agreement, especially for the first hire. You all want to be blown away with each component and feel like they will be able to hit the ground running. As your sales org grows, there will be opportunities to work with candidates who do a good (but not great) job and have them present again with the feedback you’ve given them. But for the first hire, you want to be amazed at the performance and chomping at the bit to bring them on to the team.
References and backchannels
Your goal with references should be right in line with how you’ve done them in the past for many other roles: verifying the things you already know about the candidate and getting a better sense of what it’s like to work with them. You want to talk with at least 2 references and 1 must be a former manager. Employ the same tactics here that you would with other roles, and then layer on some of the following sales-specific themes:
Ask for 1-2 examples of specific deals and why they stood out as impressive
Find out how the candidate handled a deal that went sideways
Learn what they did to help other team members - especially those who were at the bottom of the leaderboard for the quarter
Understand what best practices they used to stand out on the team and which of those were deployed to the group
Ask about the areas they need to improve or get better on
This is the critical question. It’s the reference’s opportunity to say something negative. People can be honest to a fault, and something might come out here that isn’t great. If that’s the case, you need to dig in and get more information to decide if it’s a deal breaker or not.
Overall, references should be very positive because the person has agreed to do them on behalf of the candidate and knows the drill. On the other hand, backchannels are an amazing way to get unfiltered feedback. I find these to be the most impactful because the reviewer doesn’t owe the candidate anything. There’s two quick ways to backchannel:
Send the candidate’s LinkedIn profile around to the team and see if anyone is a 1st or 2nd degree connection. For any 2nd degrees, have that employee reach out and ask them how closely they know/worked together.
If you can figure out who their 1st or 2nd skip-level manager was at any role, you could reach out cold for the reference. You’d be shocked how many people will reply.
A quick housekeeping item: never ever backchannel to a contact at the candidate’s current company. Seems silly to bring up, but I’ve seen people do it and everything blows up. It’s bad.
How to close
Competition for talent has been fierce the last 10+ years, and with economic changes at the start of 2023, the landscape might finally be changing. It will make closing candidates slightly easier, but the reality is that there will always be a strong market for the best people.
There’s no reason to go through all the typical suggestions for how you should pitch your company to candidates. If you’ve gotten this far, you know how to do that. However, there are certain selling points that will speak to your ideal candidate:
Stock: In most sales roles, stock grants are typically very small. Your ideal candidate has been an IC for several years and the majority of their earnings have been through salary + commissions…not stock. Putting a meaningful amount of stock in front of them is a big deal - both from a signaling perspective (how much you care about them and this role) and the potential for their bank account. Lean into this selling point.
Product feedback: Most companies have a pretty terrible feedback loop between sales and product. Sales makes product requests on behalf of customers and because there are so many, the vast majority fall on deaf ears. But at a super early stage company, not only is that feedback hyper critical, it’s also digestible and it’s an opportunity to build a culture around sales working in harmony with product.
Process impact: Since you’re going from a sales team of 1 to 2, there is likely very little process. And the person you’re hiring should have a lot of experience building and participating in processes that they’ve seen work (or fail). Coming in early stage will give them the opportunity to implement some of the best practices. It’s also an opportunity to prove that they can do more than simply manage a pipeline, which leads to the final selling point.
Upward mobility: Growth within the company is always going to be appealing for the right person. The reason it’s particularly meaningful for salespeople is that without the right timing, it can take years to get the level of autonomy you’re going to offer them in months. Their success can catapult their career faster than either of you imagined.
Beyond the close
Hiring a great candidate is just the first inning of a very long game, but it’s so important to get right. Take your time with each step of this process and don’t compromise.
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