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5 Mistakes Sales Leaders Make When Scaling their Team

Michelle Pietsch

Jun 22, 2022

Michelle Pietsch

In my decade of leading high-performing sales teams, I’ve seen this lesson play out first-hand: scaling the sales function is a crucial step for fast-growing SaaS companies.

Yet it all depends on the stage you’re in. The needs of a late-stage startup with a well-defined sales function differ vastly from a fast-growing, pre-seed company.

Let’s say your early-stage company receives Series A funding. The board immediately says, “Go hire 20 people!” As a sales leader, you need to pause here. Understand your go-to-market approach and what customers like and don’t like about your product. Become the seller before you hire.

On the other hand, if you’re a Series C company with a well-established sales function, place your focus on training vs. hiring. Make sure the onboarding process is clear and that your sellers understand their expectations every single day, so they can come out of the gate hot. 

The size and stage of your company make a big difference in how you scale. Yet even with this understanding, sales leaders make five common mistakes when trying to grow their teams. 

The best sales leaders know how to steer around these scaling pitfalls. Let’s learn about each one and how to properly scale your sales team for the greatest impact — while avoiding high turnover and revenue loss. 

Start with your Foundation

While scaling is a necessary focus for fast-growing companies, it’s not the end-all, be-all solution. Far from it. 

Though sales teams face pressure (from both themselves and leadership) to push the growth envelope, scaling too fast leads to unsavory outcomes.

If you’re laser-focused on scaling, you risk hiring sellers who don’t align with your core persona and high turnover. (The average tenure of sellers is 18 months, with three spent onboarding. Not a great ROI on your hiring.)  

You need to start with your foundation: learning the ins and outs of your product and your sales team’s day-to-day experience.

Here are the tried-and-true steps to take as you decide when and how to scale your sales team.

Vet the data

The board says you need to hire 10 people, and fast. Yet you know each rep isn’t getting two leads per week. Hiring on more reps wouldn’t be a sound business decision at this point.

Before you add more sellers to the mix, dive into your data. Depending on which data points you have access to, it’s important to decide when to scale and when not to scale based on this information.

The data will help you understand your company positioning. What’s your go-to-market strategy? How many leads are you getting, and what are you spending to acquire them? Are demos leading to conversions?

With a solid understanding of how your product is positioned in the market, it’ll be that much easier to really sell. When this happens, you’ll understand the core persona of the sales talent you want to hire.

Focus on onboarding 

When you don’t set your sellers up for success, they’re going to fail. As a sales leader, your job is to remove as much noise as possible for your incoming reps. If you don’t do that, you’ll see constant churn on the team. 

Reps will either make the decision to leave the company, or you’ll make that choice for them. If you just hired five reps, but you lost two, now you have to make up for it. At this point, you’re not scaling; you’re just at status quo.

To remedy this, look to your onboarding stage. Determine inconsistencies in your existing process, and how you can improve them. Cater your onboarding to the specific role. Like understanding how to ramp on a Business Development Representative (BDR) over an Account Executive (AE). 

Make sure you include a solid day-in-the-life process and consistent coaching to enable your reps and keep them engaged. The smoother their onboarding process, the better their initial ramping will be — and the more successful they’ll be in the long run.

Put yourself in your sellers’ shoes

As a sales leader, you need to understand the contribution each role makes to the team’s goals. 

To do this, start by understanding your reps’ day-to-day experience:

  • What tools do they use?
  • How much time are they spending in meetings, training, and on non-revenue-generating activities?
  • What does their pipeline look like? 
  • How long does it take to create a sequence? 
  • What are the main inconsistencies in their processes? 

When you do this, you move closer to understanding when it’s time to scale and if more enablement is needed along the way.

Sales Leaders: Avoid these 5 Mistakes as you Scale

Scaling sales doesn’t always mean scaling the size of your sales team

While many companies need more reps to help them meet larger revenue goals, it’s a common mistake to think the only way to inject some life into sales figures is to throw more reps at the problem

Unless you’re already a Series C company with well-defined processes, it might be worth considering the talent you already have — and arming them with better systems, tools, and processes. 

Building on a less-than-ideal foundation doesn’t set you up for successful scaling. I often see sales leaders make these five mistakes when scaling their teams — in considering them, you can make strong business decisions and scale when the time is right. 

1. Rushing the hiring process

Your company recently raised a round of funding. Suddenly, you’re under pressure: the board, the C-suite, and other decision makers are pushing you to expand the sales team. 

The constant pressure of, “Hire, hire, hire!” is more costly long-term than waiting to hire the right person. As you’re setting your sales team up for success, slow things down to make sure the potential reps you’re eyeing are actually good fits.

First, take the time to understand your core persona, and how this fits into your go-to-market strategy. Determine what sales reps’ backgrounds should look like, and how you can help them succeed. 

If you say, “I want candidates to have two years of mid-market, net-new sales experience,” don’t veer away from that specific persona just to hit a hiring quota.

Why? Because It’s risky, especially if you’re in scaling mode. 

You’re going to take a chance on someone — but make sure that that chance is going to help reach your revenue target, as opposed to you spending excess time getting someone up to speed.

2. Relying on broken onboarding

A poor onboarding process not only hurts your new reps’ chances of success — it also extends ramp time. 

Sales leaders must seamlessly steward the transition from new seller to quota-hitting contributor; strong onboarding is the bridge. 

During sales onboarding, you’ll want to teach new reps: 

  • Background knowledge on the industry
  • Product features and benefits
  • A narrative that defines the selling context 

You’ll also want to give them plenty of opportunities for self-guided learning, peer mentorship, and phone-time with leads. 

3. Providing inconsistent coaching

Even if your new reps have previous experience in your industry, learning doesn’t end with onboarding — consistent coaching and training are essential to scaling your team. Without it, you’re setting reps up for failure right off the bat.

While this will look different at every company, a clear coaching mechanism should include:

  • Frequent one-on-ones
  • Pipeline reviews
  • Film and demo reviews
  • Role-playing scenarios

At Dooly, we take reps through sales calls using Gong, a tool that provides valuable insights for real-time customer scenarios and sales frameworks. 

4. Prioritizing non-selling activities

74% of reps we surveyed in 2022 agreed that too much of their time is spent on non-selling tasks, like meetings or scheduling calls. A staggering 85% said they could make more money for themselves and the company if they dedicated less time to non-revenue-generating activities. 

The problem for sales leaders? Many don’t understand just how time-consuming non-selling tasks are. Entering lead data into the CRM, cold prospecting, and sending outbound emails are all activities that quickly add up — and prevent your reps from focusing on what they do best, closing sales. 

One of my reps recently closed a massive deal on the last day of the month. The entire floor was ready to celebrate. Yet 45 minutes went by, and I thought, Why haven’t you closed it out? I wanted to see their Salesforce view and where our revenue was at. 

So I sat down next to him and watched the process we put in place to close out that deal. It took him a half hour, which is too much time. 

I immediately began to solve for: how can I condense these non-selling motions and make my sellers’ lives easier?

5. Lacking the right tools for success

When you’re hiring, every rep will have a new tool they used at their previous company that they want to bring to yours. This bloated tech stack leaves your reps with too much noise directly in front of them, distracting from actual sales activities. 

Before you add a shiny new tool for your reps, get on their level and make sure you understand what their day-to-day looks like. 

When you sit down with them to actually understand how long it takes them to send an email, schedule a call, or close out a deal, you’ll be empowered to equip them with the tools they need for the job — and cut the excess. 

(Side note: if you’re looking to close more deals and give your sellers time back in their day to actually sell, might I recommend Dooly? Top-performing sales and revenue teams trust us to help them close deals faster, gain more pipeline visibility, and get out of Salesforce. Schedule a demo today to see for yourself.) 

Scale thoughtfully—and at the right time—to watch your sales team succeed 

When scaling your sales team, adding new hires is a crucial step. But overlooking the basics, like knowing if your company is at the right stage to scale, can seriously jeopardize your efforts. 

Before you scale, go back to your foundation. Let your data lead your decisions. Equip your sellers with strong onboarding and a consistent coaching process. Put yourself in your sellers’ shoes, understanding their day-to-day and how much time they spend selling.

When you follow these steps, you’ll avoid the five mistakes sales leaders make when scaling: rushed hiring, poor onboarding, a lack of regular coaching, excessive non-selling activity, and bloated tech stacks.

Above all, get curious around when and how you should scale your sales team. Scaling is more than adding headcount. It’s making sure you have a repeatable process and your team is generating revenue.

By applying a deliberate, thoughtful approach to scaling, you’ll grow your sales team and reap the benefits along the way.

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Join the thousands of top-performing AEs who use Dooly every day to stay more organized, instantly update their pipeline, and spend more time selling instead of mindless admin work. Try Dooly free, no credit card required. Or, Request a demo to speak with a Dooly product expert right now.

Michelle Pietsch

Michelle Pietsch is the Vice President of Revenue at Dooly, the rapid-growth sales SaaS company that recently raised $80M to pioneer the connected workspace for revenue teams. Michelle has a long history of developing and scaling sales teams for fast-growing startups. Prior to joining Dooly, Michelle served as Vice President of Sales at Drift and Associate Vice President of Sales at Datadog, where she successfully grew the sales team from three reps to 300. When not focusing on building sales teams, Michelle is hanging with her family and two boys.

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