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The ultimate guide to inside sales prospecting in 2020

Here is your guide to building a modern inside sales development team.

Building and maintaining a successful sales development team is a daily challenge. Between hiring, onboarding, 1on1s, and call blitzes, it can be hard to zoom out and find new ways to generate pipeline. In this guide made specifically for sales development leaders, I will walk you through the steps required to build a modern and successful sales development team.

But first, let’s cover the roadmap.

Insides sales prospecting basics

  1. What inside sales prospecting currently looks like
  2. What’s wrong with current sales development organizations

The T-shaped SDR

  1. What is a T-shaped SDR
  2. Benefits of a T-shaped SDR

How to build a T-shaped sales development team

  1. Mindset shifts
  2. Assessing your team’s core skills
  3. Assessing your team’s secondary skills
  4. Defining your metrics and goals
  5. Organizing your team’s day
  6. Getting started

What inside sales prospecting currently looks like

If you run a sales organization with 10+ employees, chances are that you have divided the work of these employees into two categories. One set of employees will focus on generating sales opportunities, they are called SDRs (Sales Development Representatives) or BDRs (Business Development Representatives). The other set of employees will focus on turning these opportunities into closed business. They are called Account Executives (AEs).

In certain sales organizations, salespeople take care of the full sales cycle. It’s often seen in early-stage startups, where resources are scarce and role specialization doesn’t make sense yet.

The main job of SDRs is to generate opportunities for the AEs. They do so by dealing with incoming requests (inbound leads) or proactively reaching out to prospects (outbound).

This job is by definition repetitive. They are often required to crunch tens of dials every day and send templated emails to prospects. The answer rate is in the low 1 figure, and rejection is permanent.

Yet this organization type works. Most successful sales development teams rely on cold calling and cold emailing because it simply works. It’s a numbers game and with enough activity, enough pipeline can be built.

But sustaining this kind of structure is becoming more challenging than ever.

What’s wrong with current sales development organizations

According to TOPO’s 2019 Sales Development Benchmark Report, only 48% of SDRs consistently reach their targets.

Problem #1: Traditional outreach channels are largely overused

When I ask prospects what tools they use for cold outreach, I get the same overwhelming answer: cold calling and cold emailing. These two channels have been used for decades but prospects have built strategies to stop being disturbed by pushy salespeople. They often do not answer an unknown number or mark you as spam as soon as the first email of your sequence lands in their mailbox.

When using an email or cold call, you use the same crowded channel as everyone else and you reduce the chance of your message being noticed.

Problem #2: Outreach relevance and personalization are declining

One problematic trend in cold outreach is the lack of personalization and relevance. How often have you received a cold email knowing it is a template? It happens to me every day.

Most SDRs use the same templates as all their colleagues. They are also built using widely known blog posts. That’s why we constantly receive messages that look similar. We often see emails with an introduction, some bullet points, and a call to action.

Our brains are pattern recognition machines. When you see a cold email with an intro, some bullet points, and a call to action, your brain immediately recognizes the pattern and dismisses the content. That’s why so many people do not even read your messages. And it’s the same with cold calls. When you ask “Is it a good time to talk?”, people know you are trying to sell them something, and they shut down.

That’s what Josh Braun calls “Being a white circle in a sea of white circles.”

A second problem is the lack of personalization, or even worse, lazy personalization. When an SDR approaches me, congratulating me for attending the same school as her, my first reflex is to shut down and dismiss this person.

And that’s a critical thing to remember. Cold outreach and prospection are marketing activities. An important aspect of marketing is to catch the attention of a target audience.

Sending cookie-cutter emails or reading cold call scripts doesn’t achieve that.

Problem #3: Most SDRs are incentivized to become AEs

I was discussing with a Head of Sales a few days ago and he shared his goal for the quarter. He told me: “My main goal for Q2 is to change the perception of the SDR job, from just being a stepping stone to becoming an AE to becoming a career path in itself.”

This sentence summarizes the current incentive for SDRs. Their goal is to bite the bullet for a few months and get promoted to Account Executive as soon as possible. The average tenure for an SDR is 15 months.

I find that pretty long when you know what the job entails. If I was an SDR, I’d do everything possible to become an AE or change jobs.

But the good news is that it can change. Meet the T-shaped SDR.

What is a T-shaped SDR

The best way to understand what a T-shaped SDR looks like is to look at the illustration below.

T-shaped SDR

As you can see, the T-shaped SDR has a vast range of skills. Some of these skills are very developed, we call them core skills. The vast majority of skills are not as developed, they are secondary skills.

If you look at the illustration above, you can see that the T-shaped SDR is proficient in 3 key categories (in turquoise), Network building, Outreaching, and Content building. These 3 categories include a set of domains (in red) and specific skills (in blue).

As you go deeper into the level of knowledge, you see that a T-shaped SDR has a general understanding of domains like lead sourcing, cold calling, or design. Going even deeper, you observe specific skills like lead generation, scraping, or objection handling. In this example, pitching and objection handling are two core skills. It means this SDR has a strong focus and expertise in these two areas. All other areas are also developed, but not as much. They are secondary skills.

Now let’s study each bloc in detail.

The central bloc is comprised of the outreaching category, with specific domains and skills, as shown below.

T-shape core bloc

The two secondary blocs include network building and content building categories, as well as specific domains and skills.

T-shaped secondary blocs

Keep in mind that this illustration is just an example. A junior SMB SDR will typically have core skills like pitching and objection handling, where a senior Enterprise SDR may have core skills in account research and account networking.

Being a T-shaped SDR means that you have a broad knowledge covering a wide range of sales development tactics, with in-depth knowledge in one or two specific areas.

The benefits of a T-shaped SDR

What’s the point of building a T-shaped sales development team?

I see a few key benefits, based on the current situation of sales development in B2B sales organizations.

Benefit #1: It allows you to start more conversations

A T-shaped SDR will be able to start more genuine conversations with prospects, using a creative and relevant approach. Take two SDRs. Your standard SDR, relying on cold calling and cold emailing as only channels to outreach. This SDR will perform tens of dials every day and send templated emails, with minimal answer rates and booking rates.

Your T-shaped will take a totally different approach. Using her copywriting skills, she will send a non-threatening LinkedIn invitation to a prospect, following up with a personalized LinkedIn voicemail. She will then use her scraping skills to find secondary contacts and share a slide deck she built to provide value to the prospect.

Which one of these two SDRs will start more conversations?

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Benefit #2: It makes the job more diversified

Your traditional SDR’s job is pretty repetitive. Find a hundred leads, cold call them, send templated emails, book a few discovery calls or demos, and repeat.

OK, I may oversimplify here. But ask any SDR about his job and he will tell you it’s a pretty repetitive one.

One the other hand, the T-shaped SDR will develop strategies and tactics to start conversations and generate opportunities. The best way to do so is to be creative and relevant. It means being able to use a vast array of tools and tactics to grab the attention of a prospect and make them stop in the course of their days.

It is not rare to see a T-shaped SDR quickly building a landing page using Unbounce, creating a slide deck with Powerpoint, or recycling a company page LinkedIn post to share it with more context to his audience.

As a T-shaped SDR, you are not expected to hit the phone all day long, you are expected to start more conversations and generate opportunities. And cold calling is just one aspect of it.

Benefit #3: It develops a wide range of useful skills

The SDR job is an entry-level position. Most SDRs are graduate and belong to the millennial generation or gen Z. For them, money is not the strongest motivator. They are interested in personal growth and development.

Knowing this, do you think cold calling tens of prospects every day to make money is really a strong motivator?

I don’t.

Instead, if you can train them, mentor them, and help them develop a wide range of business skills, chances are that you will attract SDRs for something else than just a pay check.

Benefit #4: It helps increase the tenure of an SDR

Following benefit #3, a T-shaped SDR will stay in this job longer. When your job requires you to learn how to cold call, build landing pages, map accounts, and develop partnerships, you’ll need more than just a few months to become proficient. This makes the job a lot more diverse and interesting.

Benefit #5: It allows for a different career path

The current SDR career path is pretty standard. The logical step after SDR is Account Executive. Even during the recruitment process, most SDRs are promised a quota-carrying position within 9 months.

This dynamic makes the position of SDR pretty challenging to sustain on a long term basis. And what happens to SDRs who do not want to be promoted to an Account Executive position?

As a T-shaped SDR, you can build a different career path. Imagine the possibilities offered by the vast amount of skills you develop. For example, an SDR with copywriting as a core skill could develop in this role and build a career training SDRs on copywriting.

The career opportunities are more diverse, which can be a good retention argument for an employer.

Mindset shifts

Building a T-shaped sales development team requires a few mindset shifts. Experienced sales development leaders may have a tough time understanding a few key concepts, as they directly contradict business development practices that are commonly accepted.

Shift #1: It’s not just a numbers game

That’s the first thing I heard about sales. At the time, I was studying at HEC Montréal and we had a class about sales management. The teacher told us that sales was purely a numbers game.

And it’s partially true. Sales is a numbers game. The more calls, emails, and touchpoints you perform, the more answers you will get. I’ve also experienced that strategy with great success when I was working at Applause.

But things have changed. Buyers are tired of receiving the same templated emails. They receive tons of them every day, and their brains are trained to ignore them.

What if you could send a fraction of the emails you send, to get the same results?

Shift #2: If you hire humans to do what a robot could do, hire the robot instead

We all heard AI is coming for our jobs. If you think about how most sales organizations function, 80% of the job could be done by robots. Most SDRs are sending automated sequences, with dynamic fields. They don’t even personalize their messaging to their Ideal Customer Profiles (ICP).

Think about it. What are your SDRs doing that a robot couldn’t do? Finding leads and emails? You can use Hunter and automate that part. Sending templated emails? You can use Salesloft or Outreach for that.

The only thing that cannot (yet) be automated is cold calling. If you use scripts, I guess you will soon be able to use Alexa to do some cold calls.

And instead of hiring 10 SDRs, you’ll be able to hire 1 nifty campaign manager and an army of robots and scripts.

As exciting as it sounds for your balance sheet, this will not happen. The job of the SDR is to start conversations and build business opportunities. You should focus on providing sales enablement tools so they can automate repetitive tasks and focus on the human part of the conversation. I’m talking about discovery skills, empathetic listening, or objection handling.

Shift #3: Diversification of tasks does not always reduce productivity

This one sounds counterintuitive. In general, when you reduce the diversity of a job, you make it more productive. That’s the underlying concept of Taylorism and what you see in factories.

I won’t do an economic course here. But a sales floor is not a factory.

Moreover, the job of an SDR is extremely unproductive by nature. In what other profession do you see someone doing a hundred calls to book one meeting? Most of the time spent building messages, pitching or any sales activity will not yield any results. The average win rate of a deal is around 20%. It means that 80% of the deals generated do not close.

And this comes from various reasons, the main one being that sales is about dealing with humans. And humans are unpredictable.

The approach with a T-shaped SDR is different. By diversifying the skills developed by an SDR, you give her a set of tools she can use to be more relevant and creative. I’ve seen fantastic results using LinkedIn voicemails or curating content about sales on LinkedIn.

More skills mean more tools and a lot more resources to start conversations.

Shift #4: What worked yesterday won’t work today. What works today won’t work tomorrow

In sales development, new tools and tactics get old pretty fast. If you find a kickass email subject line, you can be sure that it will stop working if you do not update it after a while.

Prospection is a bit like military technology. When you develop a tactic, strategy, or technology, the opponent is surprised at the beginning and you win. But soon enough, a counter technology is developed and your secret weapon doesn’t work anymore.

The same holds true in sales development. Right now, video prospecting is all the rage. Give it a few months and people will be tired of it.

If you develop a kickass cold outreach sequence, it will become antiquated. If you enable creativity and resourcefulness with your reps, they’ll keep adapting and developing new ways to start conversations.

Assessing your team’s core skills

T-shape core bloc

As we can see in the illustration above, a T-shaped SDR has 1 to 2 core skills. One important step in determining your team members’ T-shape profile is to identify which skills these are.

Your team’s core skills can only be under the outreaching category. A T-shaped SDR has to have outreach skills and a focus on starting conversations with strangers. If their domain of interest is in product development and they have no specific skills in cold outreach, they will not suddenly become good T-shaped SDRs.

Here is the list of core T-shaped SDR domains and skills:

  • Cold calling (domain)
  • Cold emailing (domain)
  • Social selling (domain)
  • Rapport building (skill)
  • Discovery (skill)
  • Pitching (skill)
  • Objection handling (skill)
  • Referral prospecting (skill)
  • Setting next steps (skill)
T-shape core bloc

To give you an example, my two core skills are discovery and rapport building. I have a deep understanding of these two skills. I know many strategies, tactics, and techniques to use. I am familiar with all other skills, but not as proficient.

Here are the steps to help your SDRs find their core skills:

  1. Share the T-shaped Canva with your team
  2. In the list of skills listed above, they have to select 1 or 2 core skills (blue), based on their natural interest
  3. Once their skills are clear, they can define 2 domains (red)

Assessing your team’s secondary skills

Now that you know what your team’s core skills are, you can start defining your team’s secondary skills. In that case, it is also important to keep in mind that they cannot pick random skills. For example, being able to use Excel to build pivot tables is not a necessary skill.

Secondary skills are categorized in two buckets, network building, and content building.

Here is a list of domains and skills related to network building:

  • Lead sourcing (domain)
  • Account Mapping (domain)
  • Automation (skill)
  • Lead generation (skill)
  • Scraping (skill)
  • Account research (skill)
  • Account networking (skill)
T-shape network bloc

Here is a list of domains and skills related to content building:

  • Copywriting (domain)
  • Design (domain)
  • Distribution (domain)
  • Storytelling (skill)
  • Templating (skill)
  • Creative thinking (skill)
  • Landing page building (skill)
  • Demand generation (skill)
  • Content curation
  • Growth hacking (skill)
T-shape content bloc

Here are the steps to find your core skills:

  1. Have your team go back to the T-shape Canva
  2. In the list of skills listed above, they have to select 4 secondary skills (turquoise) for network building and 4 skills for content building, based on their natural interest
  3. Once their skills are clear, they can define 2 domains (red) for network building and 2 for content building

Note that you can develop a more granular aspect of your domains and skills. This example is based on a simple canvas, to help you get a simple understanding of the T-shaped SDR concept.

Defining your T-shaped SDR team metrics and goals

Now that you have a clear understanding of your team’s T-shape profile, it’s time to set your metrics and goals.

The T-shaped SDR is still an SDR. Her main goal should be to create opportunities.

Below are metrics you can track for each category.

1. Outreaching

These metrics are pretty traditional. They are typically tracked in conventional sales development organizations.

  • Quantitative
    • #dials
    • #emails sent
    • #social touchpoints
    • #leads touched
    • #demos booked
    • #discovery booked
  • Qualitative
    • #touchpoints per lead
    • #touchpoints per discovery/demo booked
    • Answer rate
    • Booking rate

2. Network building

Network building metrics are centered on the number of connections and leads an SDR can add.

  • Quantitative
    • #leads scraped
    • #LinkedIn invitations sent
    • #LinkedIn invitations accepted
    • #automation scripts launched
    • #accounts mapped
    • #referral discovery booked
  • Qualitative
    • LinkedIn invitation acceptance rate

3. Content building

Content building metrics are focused on design and distribution of marketing content.

  • Quantitative
    • #LinkedIn posts created
    • #reactions on a LinkedIn post
    • #comments on a LinkedIn post
    • #shares of a LinkedIn post
    • #profile views
    • #discovery/demos booked from a post
  • Qualitative
    • post engagement (reactions + comments + shares/post view)
    • #discovery/demo per post

Need help understanding which metric to choose?

As you can see, there are tons of metrics you can implement to track the progress of your T-shaped SDR team. Keep in mind that their goal should always be to generate opportunities by starting conversations with prospects.

Organizing your team’s day

With all these domains and skills to focus on, it can be challenging to organize your team’s day in an effective manner.

Here are some tips to help you get started:

Tip #1: Time block and organize team sessions

With diverse areas of focus, it can be easy to lose productivity without a good structure. That’s why I suggest to time block and organize team sessions. For example, your SDRs could block the slot between 09:30 and 10:00 to browse LinkedIn and post thoughtful comments. You can also block two hours every Friday morning to build content for the following week, with your team. You can see my calendar for an example of time block.

Calendar illustration

Tip #2: Use automation to build your team’s network

This step is extremely important to save your team’s time. Depending on the structure and instrumentation of your company, you will have automation and sales enablement tools available. Make sure your team is regularly trained and uses these tools to automate tasks like scraping LinkedIn profiles, sending connections requests, or sending email templates.

Don’t know which automation tool to use for your sales organization?

Tip #3: Develop inspiration habits

As the content building part of the T-shaped SDR requires inspiration, it is important to develop healthy inspiration habits. I suggest following thought-leaders in your industry to get a good understanding of recent trends. This will allow you to share content with your team and feed your team sessions.You can also use tools like FeedlyTrello or Pocket to get inspiration and capture it on the go.

Tip #4: Keep your priorities in check

This point is crucial. Switching from a traditional SDR role, where the job requires doing 2 or 3 repetitive tasks, your team will experience a lot of temptations. For example, if one of your SDRs has a strong preference for content building and connecting on LinkedIn, he may forget to do cold calls or build his network.

Make sure to keep your team’s priorities in check and remember that starting conversations and generating opportunities is what matters most. In most cases, your team is anyways compensated for discovery or demos booked, not for creating a viral LinkedIn post.

Getting started

Now that you have a good understanding of the challenges of inside sales prospection and the T-shaped SDR concept, it’s time to get started. If you have followed this article, you should have all the basic requirements to have your team building its network, build content, and outreach prospects.

There are other important aspects to cover, like optimizing your team’s LinkedIn profile for outreach or understanding the learning curve of a T-shaped SDR. If you want to discuss these options and how to do it, you can book a call with me.

And, whenever you’re ready… here are 3 ways I can help you crush your sales targets:

1. [NEW] Join the T-shaped Sales Community

The T-shaped Sales Community is for salespeople in tech. We produce tactical content, share opportunities, and shine a light on those who make sales happen. Join here.

2. Join the T-shaped Sales Development Accelerator

Ditch the old sales development playbook and learn the skills that will make you successful in tomorrow’s sales environment​. Signup today.

3. Work with me privately

If you’d like to work directly with me to take over the leaderboard, just book a call here. Tell me a little about what you’re selling and what you’d like to work on together, and I’ll get you all the details!

About the Author

My name is Thibaut Souyris. I’m the CEO & Founder of SalesLabs. I train and coach B2B sales teams to start more conversations.

I am the Co-host of The B2B Sales Podcast and I’m regularly invited to speak at events with Hubspot, Pipedrive or Techstars.

You can read and hear my opinion and ideas on various podcasts and blogs, including Sales Hacker, G2 and Demodesk.

I have helped 100+ SDRs and BDRs build cold outreach sequences and I work with companies like Shopify, Personio, or Hubspot.

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