Inside Sales Training: An InsideOut Approach

Inside Sales Training: An InsideOut Approach

Inside Sales Training- An InsideOut Approach

Inside sales training: it’s the first step to sales success.  

The quality of training an SDR receives will have a huge impact on their effectiveness and satisfaction. It influences everything from lead generation to velocity through the sales funnel, and even average deal size.

Effective training is the difference between high performing SDRsand reps that might struggle to rise above the noise – but what should inside sales training look like? What can aspiring SDRs expect when first learning the trade?

Firstly, there is no one-size-fits-all. If you’re being told that, you’re being sold to. Right now, we’ll cover the basics of the InsideOut sales training program, an agnostic approach which can be applied to most organizations. With some modification, of course.

What is Inside Sales Training? 

Inside sales training shares many  similarities with the more traditional approach to teaching the sales process: developing seller skills and enhancing understanding of the buyer process to drive impactful lead generation and maximize sales potential.

Where these two types of training differ is in the focus. Typical outside sales training can rely more on social skills like rapport building, need discovery, negotiations, and closing techniques. Whereas inside sales training focuses on outreach methods, data, sales tech stacks, and prospecting.

Cold Emailing

Cold Calling

Social Selling

Client Engagement

Research & Development

Building Sales Pitches

Since the pandemic-influenced shift to remote working, inside sales training has been by no means exclusive to sales newcomers. Inside sales roles are an estimated 45.5% of the United States’ 5.7 million professional sellers. More industries and businesses than ever are looking to bring their outside reps inside.

Our inside sales training groups consist of people from a variety of backgrounds, experiences and greatly different age ranges. Creating a learning environment that covers the basics while keeping sales veterans challenged can be the most challenging part. 

Again, you’re likely to find a different approach in sales teams across the globe. Here at InsideOut, we begin with a two-week process:

Week One

The First Steps


Our inside sales training begins with a week one orientation, what we call ‘umbrella training’. It’s an ‘umbrella’ as it can be applied across our portfolio of clients, whether inbound, outbound, hybrid, B2B, B2C, or B2P.

The first week is really about creating the chance for trainees to sink their teeth into everything InsideOut. From learning the company values and expectations, to the demands of the inside sales role.

Day One 

Introductions & Getting Started

The first day is all about building rapport amongst the new trainees. We give them a feel for InsideOut through a broad introduction to the company. Who we are, what we do, and what we value.

We set the expectations for growth and growth opportunity by introducing the current sales managers. The main focus for the first part of the day is to set expectations for what the company will provide to each individual, and how we take their goals seriously.

Day one also introduces the trainees to InsideOut’s tech stack. Technology, data and analytics power our work – from CRMs to cadence managers to data sources, and communication channels like Slack and email etiquette internally.

Day Two 

Day two takes a closer look at the role of an SDR and where they fit into the enterprise – alongside the problems we solve as SDRs and who we help.

This is followed by our introductory guide to outreach: ‘What is Prospecting: 101’. In this session, we explore how SDRs can identify Ideal Customer Profiles (ICPs), how to leverage BuyerDNA to craft personalized messaging, and using LinkedIn to identify intel and spark conversation.

In the afternoon, we go deeper into outreach tactics and skill sets. We pull the cover back on the approaches to engage prospective customers, be that through phone, email, or social media.

The second day is capped-off in-house with a personality assessment. We discuss how different charisma types typically communicate based on buyer demographic and data research. We’ll then assign reading around dispositions to automate the sales process and standardize data.

Day Three 

Day three focuses on the best practices for qualifying new leads and the importance of disqualifying once we have engaged the prospective buyer.

We begin by exploring how SDRs can determine fit, using the ‘Spin Selling’ methodology. This is a technique designed to close complex deals through a defined question-category flow system. Think: Situation, Problem, Implication, and Need-Payoff Questions.

Through this, we delve into the depth of what makes a qualified lead vs a non-qualified lead, but on a sophisticated level rather than a typical, one-size-fits-all basis.

This tends to involve role-playing between sales trainers and the SDR trainees to offer an authentic, simulated experience. We draw on the first-hand insight from experienced top performers with the subject matter expertise in their field.

Next up, we continue with lead qualifying and segue into objection handling. We dive deeper into the psychological reasons prospective buyers say no, how to identify a true objection vs a brush-off, and how to turn an objection into a reason to buy.

Day Four 

The fourth day of our inside sales training focuses on social selling – one of the key components in modern sales. We’ll explore optimizing LinkedIn profiles to appeal to decision-makers, practice the art of using posts and articles to generate credibility, lend authenticity to a conversation, and engage with industry leaders.

This also includes research into sparking conversation on other people’s posts and sending direct messages to decision-makers as part of the prospect outreach process.

We also practice intel gathering through Sales Navigator and LinkedIn on our own leaders, asking them to critique each reps’ emails.

This is followed by an in-depth conversation around the practice and theory of personalized messaging and how this may be leveraged to increase engagement in any written form, LinkedIn, email, or else.

We find a practical approach to be the most effective here. The trainee SDRs experiment with drafting highly personalized emails and direct messages. This builds confidence, understanding, and familiarity with this approach to customer engagement.

Day Five 

Trainees begin Friday morning by shadowing fully qualified inside sales professionals on our team, enriching their training with quality, real-working experience.

By shadowing a member of our team, the trainees see their learning in action – observing the tools and the workflow, listening to calls trying to indentify objections and buying signals, and getting to know their teammates.

In the afternoon of the last day, we try not to put any new info in the new SDRs brains. We discuss three very important items: ability, motivation, and attitude. We explore how these directly affect sales success and client relationships, and ways to continually improve all three.

We then wrap up, tie any loose ends, and make sure each sales rep knows what is expected of them, what they can expect from us, and simply, where to be on Monday morning of Week two.

Week Two 

Applying the Practice

Week two gives trainee SDRs the time to learn the sales process, the competitive landscape and tech stack for their assigned client program.

Where week one offers an overview of the SDR role, environment, and challenges, week two zooms in on our clients one by one. We teach the new sales rep how to apply the agnostic approaches precisely to their particular situation.

We’ll take a look at the typical objections. We’ll use BuyerDNA to analyze the specific buyer personas they’re targeting, and value props/talk tracks that resonate with them. We’ll also spend time exploring each client’s sales process and tech stack. 

In short, the second week is very much about applying the knowledge gained in week one to a specific client. There’s a great deal of self-study, shadowing, and one-to-ones with a manager to nurture sales confidence and develop practical learning through role playing.

What Comes Next? 

In an ideal world, the newly graduated SDR receives their credentials from the client and they get to go live in the middle of week three. We then ease off the training wheels by week four.

The truth is, inside sales training isn’t a prescribed, universal flow from coaching to call-making. Learning is highly personal and dependent on a number of factors. We’ve had fully-fledged reps with 25+ years of experience in the ranks and newcomers with zero sales experience; each of these take to the training uniquely, and we understand this.

Our sales leaders are taught to understand when a new SDR is ready to go live, with ongoing support available for those who just aren’t quite ready yet. For us, inside sales training is as much about nurturing potential as it is teaching the process.

Each trainee is fully supported from the end of the second week onwards with shadowing, role-playing, and self-study to bring them up to speed. This ensures they feel confident and capable of carrying out the SDR role to its full potential.

Do you want to get trained in inside sales and work with some of the world’s biggest companies? Submit the form below to apply.

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I bring a passion for innovation and inside sales together into the world’s first sales innovation lab, InsideOut. We help sales leaders determine and validate the best approach to acquire, grow or retain their customers within a live lab environment. Large F500 to high-growth startups can try out alternative sales methods by using our mirrored lab teams representing our client’s brand. If the new ideas work out, we develop a Live Playbook on what worked and how it worked so clients can implement the same practices.