How to Scale Your Sales Team For Easier Enterprise Selling

Apr 12, 2021
Mohammed Shehu

Booking more business than you can handle is both a dream and a nightmare for many sales leaders. Having nailed product-market fit, settled on a cadence, and built a high-performing sales machine, you might realize that you need more hands on deck to handle all that new business.

Scaling a sales team is all about leveraging your existing strengths and talents and keeping everyone on track through relevant KPIs. But ramping up your sales ops is a lot harder than you think.

Between trying to maintain (or even increase) quota requirements and keeping hiring costs down, sales leaders struggle with balancing pipeline growth against the financial and structural implications of scaling an outbound sales operation.

A good sales team can be a huge asset to your business, but scale it up too quickly or on shaky ground and you could quickly lose any momentum you’ve gained. This article will guide you through the right way to scale up a sales organization by suggesting solutions to your most likely challenges.

Top challenges in scaling a sales team

Enterprise sales are hard enough as it is, but scaling a sales team in the wrong way can compound that headache. Here are the common challenges that sales leaders typically face:

  1. Having the wrong skills on the team
  2. Poor onboarding for new hires
  3. Using the wrong tools
  4. Not getting buy-in for internal sales processes
  5. Hiring too quickly

Let’s explore each of them in turn.

#1: Having the wrong skills on the team

As your B2B sales team first started growing, the first few reps were likely hired by trying to strike a balance between cost, skills, and potential revenue per sales role. This probably led to a less than desirable mix of experienced and junior talent on the same team.

As you scale up, you’ll need a team that can work faster and close deals more effectively. This might mean upskilling the under-performing reps and bringing on fresh talent to bolster your ranks. There are many skills to look for when hiring a sales rep — we’ll cover the full list in a future article — but some of the main ones include:

  1. Relationship-building: Being able to quickly establish rapport with clients.
  2. Active listening: Fully concentrating, understanding, and responding to what is being said in order to uncover pain points and offer tailored solutions.
  3. Tech-savvy: Knowing how to use different tools to accomplish key goals within the sales cycle.

Another common mistake is sales leaders hiring for a job description instead of company culture fit. A new hire needs to be the right fit for your team and be able to both adapt to your existing sales process and suggest improvements to it.

Hiring for culture fit ensures that your established processes are implemented without a hitch — a boon for any sales leader trying to get from $1m to $10m ARR. But the hiring process opens up another can of worms:

#2: Poor onboarding for new hires

New hires typically wrangle with questions such as:

  • What should I say to prospects?
  • How do I respond in this instance?
  • How do I address competitor offerings?
  • What’s the best way to negotiate this deal?
  • How are things done here, and what do I need to know?

Because of this, a great onboarding process can mean the difference between a new hire’s success or failure.

An intentional onboarding process that facilitates team integration is non-negotiable.

As a sales manager, there are a few ways to improve your onboarding process and set up your sales team for success. Here are 4 that are guaranteed to make an impact:

  1. Letting reps view a full sales cycle
  2. Letting reps learn on demand
  3. Letting reps demo sooner
  4. Setting and tracking the right metrics

2.1 Let reps view a full sales cycle

While some organizations limit new hire onboarding to call shadowing, it’s essential to give new reps access to the entire activity map of your sales cycle. This helps them understand your team’s sales strategy, buyer context, average sales cycle duration, and the right plays to make at different times.

At each stage of the sales funnel, new reps should know what sales success looks like: good lead generation, good discovery calls, good objective handling, etc. This is where it pays to have a dedicated library of winning sales activity from previous reps, which brings us to the next point:

2.2 Let reps learn on-demand

The biggest obstacle to a call shadowing program is coordination. You need to arrange for the new rep, the experienced salesperson, and the client to all be available at the same time — which can be a logistical thorn.

A better option is to let reps learn on-demand — accessing your repository of previous calls, sales enablement content, and sales playbook. We’ve covered many of these before, but here are some key items you’ll need to provide to help new reps hit the ground running:

  1. Sales talk tracks, to know what to say over the phone.
  2. Product sheets, to have on-hand information about each offering.
  3. Competitor comparisons, to know how your offering differs from the rest.

Yes, compiling all of this takes time and effort, but you can crowdsource most of it from your current talent. Your best reps typically have market knowledge and know how to handle common objections, do discovery calls, stage demos, etc. Instilling a culture of documenting sales activity quickly expands your knowledge base and helps you design a scalable sales process.

2.3 Let reps demo sooner

All the onboarding and training in the world won’t help if your new rep doesn’t actually put it into practice. The best way to learn is to teach, and doing demos early forces sales reps to learn the ins and outs of the product, know how to qualify leads, improve the conversion rate, and increase sales efficiency — especially if your team deals with SaaS sales.

2.4 Set and track the right metrics

Data is a sales manager’s best friend - but data hitched to the wrong metrics is just a pretty graph on a dashboard. To counter this, every sales team needs a North Star metric - the one KPI by which all sales activity is measured.

This metric could be the number of demos hosted, deals closed, churn rate, usage rate, or any other vital metric. New reps need to be single-mindedly obsessed with and assessed along this North Star metric to ensure they are delivering according to the company’s priorities.

Here’s a quick example:

Suppose your sales team’s North Star metric is the number of demos hosted. This means that a sales rep collecting 1,000 business emails a week on LinkedIn isn’t really pushing the needle unless those emails result in more demos booked.

By aligning all sales activity to your North Star metric, you ensure that they optimize for impact rather than just the illusion of activity.

With that said, it helps to set realistic quotas. There is likely to be a “buffer period” between when a new hire comes on board and when they start performing at their best — and this period can take anywhere from a few weeks to a couple of months. Assigning new reps high quotas too soon can demoralize them and lower team morale when targets aren’t achieved. To counter this, try to balance your company’s pressing growth needs against the necessarily patient onboarding process.

#3: Using the wrong tools

In previous articles, we’ve covered why manual tasks in enterprise sales result in harder, longer, and less effective processes. From lead generation to contact management and outbound marketing, any serious salesperson needs the right tools to close deals faster and more profitably.

This need becomes magnified when scaling a sales team to 30, 50, or more reps - where speed and efficiency matter greatly.

The martech landscape has evolved over the past 9 years, with more tools arriving to help sales teams improve the way they find, nurture, and close new prospects.

Many of these improvements have been baked into CRMs, meeting lifecycle management tools, onboarding platforms, and more. As a sales leader, empowering your team with the right tools means you get to do less hand-holding and they get to do more selling.

In a previous piece, we covered what to look for in a CRM in-depth; but in essence, you should look for a CRM tool that will:

  • Let you manage your leads and contacts
  • Enhance your pipeline management and reporting
  • Enable sales automation and communication
  • Integrate with other marketing and sales management tools you use; and
  • Come with stellar customer support — because you’ll need it.

Beyond just getting a CRM, it helps to consider the full sales and marketing tech stack and assess which tools would help your reps do their jobs better. These include lead generation tools, meeting lifecycle management tools, sales enablement hubs, and sales coordination tools - like Momentum.

Why that last one? Because as you scale your team, having the right information at your fingertips during an important call becomes table stakes. The right tool can help a rep get up to speed quickly before and during a call. Here’s what that looks like:

Sales coordination becomes more important as you shift your focus to larger accounts, so secure your sales success with the right tools to close deals every time.

#4: Not getting buy-in for internal sales processes

Scaling a sales team requires not only the right structures and processes but also the flexibility to make decisions quickly. A centralized sales process might be useful — necessary even — in the early days of an enterprise sales team. After you reach a certain size, however, that controlled process needs to become more decentralized — and there’s a good reason for this.

At 5-10 reps, for example, it’s easy enough to get a handle on where each sale is in the buying cycle and what each rep is doing to close it. However, at 50-100 reps, this process quickly becomes cumbersome.

A sales manager needs to be able to make time-sensitive decisions on the frontline without having to engage in back-and-forth approval processes with higher-ups.

This, again, is where processes and playbooks come in. When you have a solid process to follow for each phase of the buying cycle, it becomes easier for sales managers and their reps to do what needs to be done — within protocol — to close the sale.

#5: Hiring too quickly

It’s great to experience rapid growth, but there are certain financial, structural, and cultural costs to growing too quickly. This presents a compelling case for staggering the hiring process according to your team’s needs. Let’s look at some arguments in favor of this:

  1. Financially speaking, hiring too quickly can lead to taking on more overhead than is currently feasible. As any sales leader knows, each new hire costs more than just their sales compensation. The cost of training, onboarding, and equipment all extend well beyond what you pay them — and it takes time before each new hire begins to pay for themselves.
  2. Structurally speaking, scaling up your team should be tied to business needs such as new geographies you are expanding into, new client types you’re taking on, and specific processes you are implementing. This alignment ensures you are hiring the right people for the right jobs at the right time.

Also from a structural perspective, new reps need to be clued into internal processes, aided with sales enablement content, and coached or mentored to bring out the sales superstar in them. This takes time and effort, both of which can be diluted in the midst of a hiring spree where reps aren’t getting as much support as they need.

  1. I’ll explain the cultural aspect with an example. A family barbecue is an enjoyable experience because you know everyone by name; are familiar with their histories, strengths, and weaknesses; and can relate to them on a deeper level. By contrast, Coachella is you standing in a crowd full of strangers whose only similarity is that they also came to get knackered and watch famous people perform on stage. It’s hardly the right platform to form long-lasting relationships.

All of this is to say that it takes time — lots of it — for each new hire to properly integrate into your team and soak up your sales culture. You can reduce this time-to-integration by hiring in small batches and tracking the progress of new reps as you go along. You can also reduce the TTI by pairing new hires with seasoned reps and providing plenty of coaching.

What you should not do is bring on 20+ new reps at a time - that’s a recipe for chaos.

Staggering your hiring process gives you the time and breathing space to grow your team optimally. It’s better to grow slow and steady than to attempt damage control after an aggressive hiring spree.


Attempting enterprise sales requires a high-performing sales team that’s equipped with the right tools, processes, and internal support to get things done. Sales leaders should therefore work on improving the onboarding process, hiring for the right skills and culture fit, setting and tracking the right metrics, instilling a culture of documenting processes, and expanding at a controlled rate.

Beyond this, sales leaders should invest in the right tools to power sales enablement and coordination. Momentum helps high-performing sales teams to quickly access the data they need to close more deals. Get a demo of Momentum’s sales coordination platform today.

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