Managing and scaling an outbound sales team

If outbound sales works for your company and product, it can be a powerful way to grow your business.

Outbound sales is low cost, forecastable, relevant to almost any industry, from tech sales to small local businesses, and most importantly, almost infinitely scalable. Meaning that because you aren’t relying on inbound leads, you have the entire universe of prospects to call on. So once you nail your process and ensure that it’s ROI positive, you can grow a long way.

Managing and scaling an outbound sales team

However, outbound has its challenges. Anytime you need to scale an organization of people; chaos can ensue if you aren’t careful. This guide will help you know when to scale, how to hire, and how to train and develop your growing outbound sales team.

Before you scale

Just because you raised funding, you launched a product, or your CEO told you ‘it’s time to scale,’ doesn’t mean you’re ready to scale up your outbound sales team. Here are a few things you need to make sure you’ve checked the boxes on before you scale up the team.

1. A repeatable process

When you started out, the founder or head of sales probably did most of the sales, and then hired at least 2 reps to figure out the sales process. If you’re still ‘figuring it out,’ you should not try to scale.

You don’t need to have everything calibrated to a T, but you should have a somewhat repeatable process that entry to mid-level sales rep can follow and get results.

2. Baseline metrics

How do you know if your repeatable process is working? The metrics.

There are 4 main types of metrics that you need:

  • Activity metrics

Measuring dials per day or talk time ensures your reps are putting in the effort.

  • Efficiency metrics

Conversion rate is probably the most common and ensures your reps are efficient and not wasting leads.

  • Overall performance metrics

Total revenue booked, for example, lets you know the overall performance of each rep.

  • Quality metrics

It’s important to measure things like customer retention to ensure your rep isn’t selling customers things they don’t need.

3. Enough work to do

If you’re bringing on another sales rep, you must have at least enough work for them to do. At a bare minimum, you need enough leads in the sales pipeline for them to work. Otherwise, you’ll be taking leads away from existing reps, and they won’t be happy.

4. Technology and systems

Your first couple reps might be able to work off an Excel spreadsheet, a cheap CRM, or Salesforce without proper implementation. But are your systems and technology operating smoothly enough where your reps can just ‘sell’ and not worry about navigating hacked-together systems?

You need to think about things such as call routing, lead distribution, and reporting. It might be time to hire a CRM consultant to ensure everything is ready to manage an actual team.

5. Make sure your process is optimized

Your sales process doesn’t have to be fully optimized (and probably never will be), but you should make sure the process is optimized enough so that there’s no low hanging fruit on the table.

You might think the best way to increase your conversion rate or sales efficiency is to hire more reps and let them compete. While this is partially true, they will be following the process that you created. If your process is extremely sub-optimal, every rep will learn suboptimally and will need to adjust later on once you discover this.

It’s much easier to optimize the process when you only have a handful of reps.

If you’re unsure of whether your process is optimized or not, there are many ways to find out. You can spend some time as a rep, bring in outside consultants or advisors, or benchmark against with other comparable companies in your industry.

Hiring: the omnichannel sales funnel

Hiring well is the most important part of scaling an outbound sales team. Of course, most companies don’t place nearly as much emphasis as they should on it.

When you’re scaling, you need a process for sourcing and interviewing.


Typically, a sales leader should spend 25-50% of her time hiring reps. You should be sourcing candidates by the following means:

  • Relationship building: your network, and the network of your employees, investors, and advisors
  • Outbound: reaching out to people cold via Linkedin
  • Inbound: allowing people to find you via job boards.

Potential hires from relationships will be the highest quality on average, followed by outbound, followed by inbound.


For most prospects, you will want to start out with a 15-minute phone screen. The exception is that you received a personal intro from a friend who you trust — in this case, it may be worth a longer phone call or coffee meeting. Not only have they been ‘pre-screened,’ but you want to show that you value the introducer’s relationship and recommendation.

Treat your phone screens as the qualifying stage of your sale — you need to see if there’s any chance they will be a fit.

  • Do they have the minimum required experience to do the job? If not, there’s no sense in wasting anyone’s time.
  • Are they interested in making a move? And what would make them actually take the leap?
  • What’s their current and desired compensation? This might seem awkward to ask, but if you’re too far off, simply tell them and move on.
  • Do they have any long-term incentives that would keep them at their current job? You’re likely on a tight timeline, so it’s important to know if there are bonuses, equity vesting, or other long-term incentives that would keep them from joining until a certain time.
  • Are they willing to introduce you to their current boss for a reference if an offer is conditional? As the book Top Grading points out, this question serves as a truth serum for all future interview questions.

If a candidate meets these criteria, ask a few questions about their background or ‘what if’ exercises to finish the qualification.

Here’s my favorite ‘what if’ exercise. First, ask the candidate what they do for fun. Then, ask them to sell me something related to their hobby.


Your interview process should be quick but ensure that there is a high likelihood the sales rep will be successful on the job.

Key things to discover:

  • What is the sales process at their current company?
  • What metrics have they achieved, and how do they rank among other reps?
  • Why are they looking to make a move?
  • Are they concerned about individual or team performance?
  • Are they impervious to rejection?
  • Are they ambitious, both individually and for the team?

There has been a ton written here about interviewing outbound sales reps so I won’t go into the nitty-gritty of the questions.

In an outbound role, one of the easiest ways to tell if they will be successful is to give them calls and a script to listen to and have them make some dials of their own. The best, hungriest reps will have listened to the calls several times, and while they obviously won’t be fantastic on the phones, they will be able to manage a half-decent cold call.

Things to watch out for in outbound sales hires

There are some red flags to be careful of with outbound sales reps:

Lack of respect for the customer

Many outbound sales organizations are high pressure, churn and burn operations — especially in the SMB space. Make sure your reps are making a consultative sale — not a pressure sale.

Concern for the individual over the team

Beware of things like ‘I just want to be at a place where I’m just judged on hitting my numbers.’ While this may come across as confident, you need reps that want to help others and help the company succeed.

Feeling they are too senior

Some reps may feel that they are ‘above’ an outbound sales role. They may think they deserve to be in management, and whether they do or not, they will inevitably grow sick of being an individual contributor and cause trouble. Always look for someone who is looking to punch above their weight class.

Reliance on a large brand

“Hire because they can close….Not because they are one of 4,000 reps at Salesforce that sell a product with $6,000,000,000+ in revenues, a proven brand, and huge infrastructure behind it.”

Jason Lemkin, Founder of SaaStr


As your org scales, you need to rely less on letting reps learn by osmosis and more on an organized training process.

Ideally, you bring reps on in batches and have them go through your training process together. This not only saves you or the sales trainer time, but it allows new hires to learn from each other and practice through each other.

A great deal has been written on training, but a training process, at a minimum, should include instruction on the following elements:

  1. Product — Each rep should know the ins and outs of the product, as well as the value it brings.
  2. CRM — Ensure that metrics are collected accurately and that the team is efficient by training everyone how to use your CRM properly
  3. Customer personas — Where are the typical customers, and the problem they are trying to solve?
  4. Calls — For the various types of calls – prospecting, qualifying, demo, closing – a rep should have a deep understanding of the objective of the call, the typical flow, and what the expected outcome should be.
  5. Objection handling — What the common objectives are, and how to overcome them
  6. Ride-alongs — have a rep spend a day to a week riding along with a top performing rep, learning how they handle situations. Have the trainee operate the CRM while the rep listens to calls to get them comfortable using it.
  7. Overview of the bigger picture — Every salesperson should understand what other functions do, from customer success to marketing, to engineering.

Give reps enough time for training — too little, and they will waste your precious leads.

Additionally, training and development should never end; ongoing training not only ensures each rep is improving, but that they are growing as an individual.

Here are some methods of ongoing training:

  • Regularly scheduled call reviews: Point out what the rep did well, and where they can improve. The following week, listen to calls to see if the rep improved on that feedback.
  • Batting cages: Have reps practice with each other from time to time.
  • Group training: Teach advanced concepts or use this time to help address areas all reps are weak in across the board.
  • Guest speakers: Bring in sales experts to give their tips and unfiltered stories and.
  • Field trips: Go to other companies with similar sales processes, listen to their calls, and get ideas on how you can improve.

Have you scaled an outbound sales team before? Let us know your tips in the comments.

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