Top 8 Mistakes Early Stage Companies Make With Sales

Scott Leese
July 15, 2021
5 min read

Do you know what my first sales gig ever was?

I sold online lead generation tools to real estate agents and automotive dealerships.

Do you know what that experience taught me?

That sales is hard.

From tackling sales objections on calls to having to meet aggressive sales targets, selling is not for the faint of heart. That's why managing and hiring salespeople—and setting up entirely new sales teams—can be so tough.

The entirety of my career revolves around helping SaaS companies scale their sales orgs. It makes it easy to rattle off the back of my hand the mistakes that companies often make when running their sales processes for the first time.

Time for a little show-don't-tell.

Here are the top 8 mistakes that early stage companies make while setting up their sales function.

You're all over the place.

Spongebob Fire GIFs | Tenor
Source: Tenor


The very first thing that I learnt from my first job was that sticking to a process is essential to functioning as a team. Otherwise, it's impossible to share information back and forth and really land on what works best. If I do one thing and my coworker does another, it just becomes chaotic.

You need to agree on one sales process to follow. What is a sales process? A series of repeatable steps a sales team takes to move a prospect from an early stage lead to a closed customer, according to HubSpot. Your process could look like a normal 5-stage progression that most salespeople use, or something more intense like the MEDDIC sales process. The best process is the one you have.

And these processes don’t have to be limited to sales; they should live at the very core of your team. Setting up an OKR system could do wonders for your team morale, for instance, but you would need to ensure that everyone is onboard.

The biggest takeaway for me was that working as a team doesn't mean being huddled together for 8-9 hours a day. It involves a common goal that everyone works for, but with their own skill set. Any process will do as long as it gets the job done and keeps your team up and running.

You're too in love with yourself.


Source: GIPHY


Founders love talking about their product. Humans love talking about themselves. Sound familiar?

And of course, it is needed. But they tend to go into every tiny detail, which can be incredibly tiring to listen to. It's far too tedious for someone to sit through a one-sided conversation.

It's like when I have to buy a car, the salesperson wouldn't go into every little thing because they'd know what information to prioritize. Going on about all the details would just overwhelm a person with information they might not even want to know.

Bringing a salesperson onboard would require a knowledge transfer, but that would help streamline what needs to be said to whom, and what doesn't.

My good friend, Amy Volas, talked about an experience with a co-founder who simply thought sales was sleazy and manipulative. According to him, sales reps oversell the product, which creates a discrepancy in expectations.

In her words: "A situation like this is BEGGING for leadership that collaborates cross-functionally, instead of siloed departments that aren’t on the same page making the wrong assumptions." This ties in with a process that's all over the place, creating a recipe for disaster.

Shruti Kapoor over at Wingman described the process of transitioning from founder-led sales on The Sales Lift podcast here. Spoilers: Peer coaching can do wonders for the team. 

Don't hire a VP of spreadsheets.

If you've found yourself getting enamoured with people who come from big tech companies, you're not the only one. These people have built empires out of their workplaces, but they might not be the right fit for you. Especially if you're an early stage company.

So, who should you be hiring?

Getting someone who isn't afraid of rolling up their sleeves is a necessity if you're creating a sales team from scratch. It's really important to find people who value being a part of building something with you.

You need to make sure that the first sales hires have been referred to you, or have a proven record of getting things done. They have a tremendous work ethic and are very curious. They're going to ask lots of questions. They're going to try to document for you what's working and what's not working. They provide feedback about the product or about the pitch and the conversations that they're having.

But if you feel confident in hiring a senior sales leader as your very first sales hire, you have to make sure you've hired somebody who's willing to do the dirty work in the beginning.

Keep calling? Keep coaching.

A lot of companies get satisfied with their new hire's performance, and let them handle the rest. They say, "we'll just leave her alone and let her do her thing."

Now, this may be okay when things are going right. You're getting the numbers, the pipeline, the quota. But what do you do when things go wrong?

When there's no one to coach your rep, it can be hard to know where you're going wrong within your sales process, and why you're not getting through the pipeline. And honestly, if there’s no sales manager to do the coaching, it boils down to you.

You've got to get down to coaching and let your rep know where they can improve, sometimes even clear the basics of cold calling.

Not enough manpower.

Everybody underestimates how often you need to be recruiting. It’s the biggest way to miss the numbers you're aiming to hit.

The harsh truth is that the 24 hours we get in a day just isn’t enough for a sales rep, especially if you’re understaffed. Things overlap, meetings run over. You need enough people to ensure that your existing salespeople don’t burn out. In a survey conducted by PayScale, the role of sales manager was ranked as the one of the most stressful jobs, with 73 percent of respondents rating the role as "highly stressful."

PS: If you’re wondering about the state of mental health in sales, I highly recommend you check out the 2021 State of Mental Health in Sales Report by Tim Clarke at UNCrushed, Jeff Riseley at Sales Health Alliance, and Richard Harris at The Harris Consulting Group. It’s quite an eye opener.

Refit when required.

Another way to mess up is by not refitting salespeople when there is a continuous mismatch of expectations. Suppose you've done everything—from coaching to giving your rep the space to grow, but they just don't seem to be a good fit. You need to rehire in order for both of you to achieve your goals.

Pauline O’Malley says it loud and clear On The Flip Side podcast that refitting your team should be done liberally. Fire fast enough and move on, so that you both don’t waste time.

No, you don't need EVERY tool.

Having automation tools in place is essential to a team's functioning now, but it's easy to get carried away whenever a new, cool tool is available in the market. Having the right tools is critical, but too many of ‘em can throw you off balance. 

Here are my table stakes for sales teams: 

  • CRM, duh uh. But you’d be surprised at how many teams actually don’t think of it that way.  
  • Sales enablement platform for your outreach and sequences.
  • LinkedIn Sales Navigator, if you’re selling to B2B. How else will you find people!

And the last category is conversational intelligence tools like Wingman and Gong. I've got to find ways to listen to my team because we're in a remote world. I can't just sit behind my reps while they make phone calls. I've got to be able to listen to them on demand so I can share feedback and I have to find a way to do it efficiently. Do I want to sit and listen to a 45-minute phone call? No. I don't have time for that with some 250 salespeople. What I need to do is punch in and punch out at certain sections over the call and provide one or two snippets of feedback to reps and boom on to the next.

So, those are my table stakes. I don't know how I could function without those.

Some of the newest tools I’m interested in are email automation tools like Lavender, which help you write better emails a lot faster.

Don’t be THAT person.

While there are tons of ways to improve sales performance, it's important to remember that setting aggressive revenue goals can be demoralizing and also harm your rep's performance. You've got to manage your expectations first. 

It’s great to have clearly defined goals, but never let your vision get in the way of your employees’ performance.

When you hire people, your product or service goes beyond just being yours. You hire teams to get new perspectives and often, better ways of handling things. You have to consider that your vision of success should be realistic, and that can only be achieved when you have considered the capabilities of your employees.

By the way, you can listen to me speak about these sales tips and much more On The Flip Side podcast here.

Now go make some mistakes.

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