Scaling a sales team in a mid-market B2B SaaS company isn’t rocket science—it’s harder. You’re trying to build the perfect engine while driving 100 mph down a highway that’s constantly shifting lanes. One wrong move and you’re off the road. In my decade of experience scaling teams across all the lovely, fun departments like New Business Sales, Customer Success, and even Billing (yes, that’s as glamorous as it sounds), I’ve noticed that companies often trip over the same hurdles. Let’s dive into the top five mistakes you might be making when scaling your sales team and, more importantly, how to avoid them.

1. Failing to Define Clear Roles and Responsibilities

Let’s start with a classic: the jack-of-all-trades sales rep. In the early days of your startup, your salespeople might have worn multiple hats—sometimes all at once. But as you scale, this approach leads to chaos. You end up with a team where everyone’s doing everything, but no one’s doing anything well.

Here’s the kicker: unclear roles lead to confusion, dropped balls, and a lot of finger-pointing. Salespeople are either stepping on each other’s toes or letting leads fall through the cracks because “that wasn’t my job.”

The Fix: Before you bring on new team members, map out exactly what each role should accomplish. Are they focused on hunting new business, farming existing accounts, or a bit of both? Who handles the renewals? Who’s in charge of upselling? Define these roles clearly and communicate them with the entire team. Trust me, when everyone knows their lane, your sales process becomes a well-oiled machine.

2. Ignoring Data in the Hiring Process

“I’ve got a good feeling about this one.” If you’ve ever said that during a hiring decision, it’s time for an intervention. Too many companies rely on gut feelings when hiring, ignoring the mountains of data at their disposal.

This is especially true for mid-market companies that think they can still operate like a scrappy startup. But scaling means being intentional—about everything. And hiring is no exception.

The Fix: Use data to inform your hiring decisions. Start by defining what success looks like in your current sales environment. What traits and skills do your top performers share? Use assessments, track records, and behavioral interviews to ensure your candidates fit the profile. You’re not hiring just to fill seats—you’re hiring to build a team that will drive growth.

3. Overcomplicating the Sales Process

You know the saying, “Keep it simple, stupid”? It’s advice more sales leaders should heed. As companies grow, the sales process often becomes a labyrinth of unnecessary steps, approvals, and check-ins. This complexity slows down your sales cycle and frustrates your team. Worse, it confuses your prospects, leading to lost deals.

The Fix: Simplify, simplify, simplify. Go through your sales process with a fine-tooth comb and strip out anything that doesn’t add value. Are there redundant steps? Do you really need three layers of approval before sending out a contract? Streamline your process to make it as efficient as possible. Remember, the faster your reps can move, the more deals they’ll close.

4. Neglecting Continuous Training

Your sales team is your frontline, and like any elite force, they need constant training to stay sharp. Unfortunately, many companies treat sales training like a box-checking exercise—something to be done once and then forgotten.

But here’s the thing: the B2B SaaS landscape changes faster than a toddler’s mood. New competitors, new features, new sales techniques—they all require your team to be on their A-game.

The Fix: Make continuous training a priority. Regularly update your team on the latest industry trends, product developments, and sales strategies. Bring in external experts if necessary. And don’t forget to invest in soft skills training—things like negotiation, empathy, and active listening. A well-trained team is a confident team, and confidence closes deals.

5. Focusing Too Much on Acquisition, Not Enough on Retention

Ah, the thrill of the chase! Many sales teams are so focused on acquiring new customers that they neglect the ones they already have. But in the B2B SaaS world, where customer lifetime value is everything, retention should be just as important—if not more so—than acquisition.

Letting existing customers slip through the cracks is like trying to fill a leaky bucket. Sure, you’re adding new customers, but if your churn rate is high, you’re not really growing.

The Fix: Shift some of your focus (and resources) from acquisition to retention. Build a dedicated customer success team if you haven’t already. Develop a playbook for customer engagement that starts the moment a deal closes. The goal is to ensure that your customers see continuous value from your product. Happy customers are more likely to renew, refer others, and maybe even upgrade.

Wrap Up

Scaling a sales team isn’t easy, but it’s not impossible either. By avoiding these common pitfalls, you’ll set your team—and your company—on the path to sustained growth. Remember, clarity in roles, data-driven hiring, a simplified sales process, continuous training, and a focus on retention are your keys to success. Ignore them at your peril.

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