The Four Pillars of Building a Successful Outbound Sales Team

How to build an outbound sales team is a nuanced question that could take a book to answer. I may even work closely with someone that’s written a notable book, or two, on the topic.

Because of the sheer scope of the issue, I decided to focus on how to build and prep an outbound team. These are critical pieces to outbound success, to be sure, but I’ve been thinking a lot about what comes after those initial steps – namely executing and measuring outbound activities. So I thought I’d write a follow up to discuss the importance of execution and measurement, and, by doing so, paint a more fulsome picture of how to build an outbound sales team.

But before we get to those new concepts, let’s review how to build and prep.

Building your team

This is a problem plenty of companies struggle with, and an issue I often discuss with clients and other entrepreneurs. The reason this is such a prevalent issue is because far too often managers try and hire experienced candidates for Sales Development Rep jobs when this is, ultimately, a junior role.

Our suggestion is to hire new college grads, or reps just a few years into their career. Sales development teaches effective tactics and great sales habits and because junior salespeople are still learning, it’s a great role to launch a career in sales.

As new team members join – and your outbound discipline starts to take shape – it’s imperative you invest in a robust onboarding process. Fundamental concepts to cover in that training period are the importance of prospecting, specialized inbound and outbound roles, what your product does, and why your customers give you money for that product.

That process should last about 3 months. I know it sounds like a long time, but you have to resist the urge to set your reps free too soon. It’s understandable to want to see returns from your new team, but the results will improve in the long run if you spend more time training. Of course, over time, you can taper off your onboarding process to regular weekly check-ins and one-on-ones.

Prepping your team

So, where should all of these ideas, questions, and theories live?

In an SDR playbook – complete with an account list, a breakdown of your internal sales process, detailed customer personas, and tailored messaging for each buyer type.

Don’t forget: each of your verticals will require unique messaging. Customers love being spoken to in their industry-specific language.

If you don’t have any of that data, don’t worry, you can gather it by interviewing your customers. You can even include your new reps in those fact-finding calls so they can hear firsthand what your current customer have to say (for those interested, we’ve compiled some effective customer interview questions here).

We’ve chatted with dozens of sales leaders that have designed comprehensive playbooks, but none more impressive than Rigor’s Business Development Manager Sarah Affleck (you can listen to our chat here, or check out her amazing onboarding playbook here).

Although her inspiring playbook is a testament to what can be done, all you need to get started is the basics: 

  • a synopsis of all the roles on the team
  • a succinct description of where your meetings / leads come from
  • qualifying questions
  • your various sales stages and the exit criteria for each stage (what it takes for each lead to move from discovery to opportunity, for instance)
  • a breakdown of the tools you use
  • any internal best practices you’ve developed


Once you have these critical pieces in places, it’s time for your reps to do the work. Pipeline doesn’t build itself, right?

But that doesn’t mean sales leaders can’t still be a valuable, supportive presence. Far from it, in fact. For example, to help your reps execute each call it’s important to help them develop a call plan.

To be clear, this isn’t developing a call script, we should never program sales people. What we, as reps and sales leaders, should aim for is consistency in our conversations – in particular the questions we ask our prospects and the desired outcome of each call. That means having different call plans for inbound and outbound prospects, and approaching discovery calls differently than follow ups.

An effective way of helping reps solidify call plans is to actually score their calls. For instance, there are fundamental elements that should be covered, or included, on every prospecting call:

  • establishing rapport
  • discovering needs / discovery
  • pitch quality
  • deal sizing – you have to understand the size of the deal you’re working
  • decision making process – who are the stakeholders, and who approves the purchase?
  • timeframe – when does the prospect want get the deal done by? And, what could get in the way?
  • mutual action plan – what are the mutually agreed upon next steps?
  • Calls that include all of the above should score well, while calls that don’t contain these core principles, should score lower (note to the sales leaders out there – score your team’s calls at random, on a weekly basis. It’s always best to hear a call that your reps don’t anticipate you’ll listen to).

The reality of sales is that rarely, if ever, do deals close after one call. We have to work for it. As such, your follow up becomes a critical piece of your sales process. You could even make a persuasive argument that the single  biggest difference between a good rep and and a mediocre one is the effectiveness (and persistence!) of their follow up.

With outbound in particular, effective follow up requires different, creative tactics. Remember, you are interrupting people’s days, so you must ensure that you are doing so in the most interesting and relevant way possible.

Here are a few different styles of follow up you can try:

Highly tailored messaging. This is based on what you learned in discovery. For example, your prospect may have told you they are hiring a new VP in Q1. So, at the end of Q1, email them and ask if they’ve made that hire yet. If yes, that could be the catalyst to get the deal done.

Content driven. This is more educational in nature and typically means you came across a blog post, case study, or report that you share with a prospect because you believe they can benefit in some way from it.

Trigger based. This is similar to a content-driven follow up, but instead of sharing a relevant blog post you read, your follow up is rooted in news shared by your prospect’s company in a press release or recent report.

Bumper message. This is very simple follow up messaging, used only to get back on your prospect’s radar, and elicit an answer from them about whether they are interested in the deal or not. For example, a bumper message can be a simple as: “hey is this still a priority for you?”


The final piece of the outbound puzzle is measurement. Your team has done a lot of work to get outbound off the ground, but without understanding its effectiveness, how do you know what to improve?

You need clarity on what is happening on your company’s pipeline – good or bad.

To get started, ensure you are tracking your inbound and outbound funnels separately, on different dashboards and with different reports. If you don’t, you run the risk making outbound (or inbound) look better than it is, which will make it very difficult to institute changes in the future.

Some of the baseline metrics you should be tracking are:

  • Activities – the calls and emails you are executing to generate meetings
  • Work-in-progress calls – the number of meetings you are booking for yourself to engage in discovery with a prospect
  • Pipeline generation – the number of meetings you are passing on to Account Executives, and the pipeline you are generating (this is a critical metric)

As for your messaging – never forget about your messaging – be sure to vary your copy from market to market and track which is more responsive. There are plenty of factors that can influence that responsiveness: for instance, if you have a strong case study for one, and not another, you will see that effect on your dashboards. So, as soon as you outline which vertical that is, put more resources into it. Double down on what is working.

After all, that’s why we measure. You want that routine feedback loop. You want to know where you’re falling short, and where you’re killing it. Because once you build, prep, and execute – you will have to constantly refine. It’s all part of building an outbound sales team.

We’ve compiled this ebook out of our Top 10 podcasts so you can take advantage of all the brilliant sales leaders and practitioners we’ve had on the show, and leverage the actionable tactics and strategies they’ve shared so you can start 2021 strong. 



We’re not just a cold calling company.

Read The Best-Selling Award-Winning Book!