How to Hire Your First Two Salespeople

Sujan Patel is the founder of Mailshake, a sales engagement software used by 38,000 sales and marketing professionals. He has over 15 years of marketing experience and has led the digital marketing strategy for companies like Salesforce, Mint, Intuit and many other Fortune 500 caliber companies.
  • August 12, 2020

Sales managers often bemoan the Pareto principle.

Also known as the “law of the vital few”, its applications are wide-ranging, but in the context of sales it suggests that 20% of salespeople make 80% of sales.

It might not be literally accurate for every organization, but it’s broadly true. That’s because the top performers keep hustling to close deals even after their poorer-performing peers have given up.

Naturally, it’s super important for startups to work with those top performers. They have a crucial role to play in building your revenue early on and scaling your business.

I spoke to Justin Welsh, Founder of The Official Justin, to find out how startups should go about hiring their first two salespeople:

1. How Do You Get Ready to Hire Your First Salesperson? [0:38]

When looking for your first salesperson, Justin emphasizes the importance of building what he calls a “salesperson persona.” This entails thinking about what you’re selling and what a salesperson within your organization needs to embody – not every salesperson is suited to every type of sales job.

When he was at PatientPop, a healthcare technology platform, he was looking for salespeople with the following attributes:

  • 2-5 years of sales experience
  • Average contract value of $5-15k
  • Someone who had moved a lot of units, quickly

“When someone didn’t meet one of those criteria, I would take the interview and try to learn if I made a mistake. But if they met none of them, it’s just not a good spend of my time early on,” says Justin.

2. Why Do You Recommend Hiring Two Salespeople? [2:17]

Say you’ve hired a great salesperson. They’ve got a fantastic track record and wowed you in their interview.

But they’re just not bringing in the numbers. That must be your problem, right? Maybe your product doesn’t have market fit, or it’s priced too high.

Or alternatively – maybe you hired the wrong person. You just can’t know for sure.

That’s one of the reasons Justin recommends starting out by hiring two salespeople rather than one. It goes some way to removing potential false positives and negatives from your results.

What’s more, two heads are better than one when it comes to camaraderie. As Justin explains: “They can work together, learn objection handling, tweak the pitch, stay late in the office talking about how to get better at this job. That was how I was as a sales guy early in my career.”

3. How Does Company Culture Fit Into Your Hiring Process? [4:11]

We’ve all heard and read plenty about hiring on culture as well as skills and experience. But what exactly does that mean, and why is it so important?

To Justin, culture is the way you pursue your company objectives on a daily basis. It needs to be defined early on – don’t just leave it to develop by chance. To understand your culture, you first need to define:

  • What is your mission?
  • What is your vision?
  • What are the values you live by every single day?

Hire people who align with your culture and they won’t just treat it like any other job – they’ll be committed to your success. “You get involved early on and you’re really proud of what you’re building, not just proud of the paycheck you’re bringing home every week,” says Justin.

Culture doesn’t just exist company-wide – there are departmental cultures, too. “You have a company culture, but you also have a sales culture. You have a customer success culture and a marketing culture,” Justin explains.

“But the mission, vision, and values are the common thread, the stitching that puts all of those departments together so you have a cohesive vision for your company and a cohesive hiring strategy across your business.”

4. Do Your Early Sales Hires Need Different Characteristics to Later Hires? [6:40]

You want to hire the best salespeople at every stage of your business growth. But your first few sales hires will need different characteristics to those you hire down the line, because they’ll have a lot more responsibilities. They need to figure out the fundamentals and foundations of selling your product, from the messaging they use to the collateral that supports it.

“Not everyone has that, and you really need that in your first sales hire,” says Justin.

“The worst thing you can do is hire someone who comes from a really big organization and is used to having unlimited resources and marketing materials and fancy slicks. They get there and they’re like ‘hey, where is all that stuff?’ It’s not there in an early business.”

So how do you find people with the right characteristics? Justin says it’s all a matter of experience: “Show me an environment you’ve been in that’s like this business that I’m interviewing you for, and show me how you thrived.

“If somebody can do that, you’re starting to find what I call your ‘purple squirrel’ – that guy or gal who is an excellent salesperson, but also curious and creative as hell, has leadership skills, everything that you look for in that first sales hire.”

5. How Do You Find Top Performers? [9:55]

Of course, you’re not the only business looking for great salespeople – everyone else is, too. So how do you attract the best?

Part of it is down to brand building. Find people with big networks, create content that features them, and promote it via social. “It’s a great way to get your name and face out there and your business name, and people will start being interested in that,” says Justin.

He also recommends a more direct approach: the forced referral, a method popularized by HubSpot’s former Chief Revenue Officer, Mark Roberge.

It’s simple. Once you have a couple salespeople on your team, book a meeting with them and scroll through their LinkedIn connections. Ask them to pick out the 20 best salespeople they know – and tell them to introduce you.

Justin explains: “That was a way we uncovered some really unique top performers who I think otherwise might not have been interested in a 15-person startup in LA at that time.”

Are you searching for your first sales hire? What sort of characteristics and skills are you targeting? And how do you plan to find them? Let me know in the comments below:

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