Complete Inside Sales Strategy Guide

Complete Inside Sales Strategy Guide

Inside sales is a science. Whether you’re just starting out or a seasoned seller, there’s always more to learn.

The industry is constantly evolving, growing at a rate 15 times faster than outside sales.

Why? New technologies keep popping up to help companies 1.) automate their processes and 2.) better understand prospect behaviors.

This guide will give you the background you need to truly understand inside sales.

mailProspecting campaigns in your inboxPersonal, multi-channel inside sales touches including calls, InMail, and email

What Is Inside Sales? The Definition You Need

Inside sales is a type of selling that relies on technology to sell products or services remotely.

As inside sales tools continue to adapt, the B2B sales process becomes easier. You can put your outreach on autopilot and focus on reporting to help you make decisions.

All in all, inside sales is the future.

Inside Sales vs. Outside Sales: The Key Differences

So, why is inside sales growing so quickly compared to outside sales?

It all comes down to time and money.

According to the Harvard Business Review, inside sales costs 40-90% less to bring in new customers than outside sales.

In outside sales, you have to travel to meet prospects and customers. This means paying for transportation, meals, and hotels. Not to mention the time you’re wasting while traveling.

Inside sales reps are able to complete their tasks remotely while staying in the same place.

So, what’s the sweet spot? Instead of putting it as inside vs. outside sales, use both together. This is known as a hybrid model.

For example: Some companies will use Sales Development Representatives to do cold outreach and book meetings while having outside sales reps take it from there to make the sale.

So, What Are Some Inside Sales Jobs?

We pulled a list of Yesware users who have “inside sales” in their job title and this is what we found:

inside sales

Note: There are even more people who work in inside sales but do not have the keyword “inside sales” in their title (think Account Executives or SDRs).

How To Put Your Prospect Front-And-Center With 8 Actions

1. Thoroughly Understand Your Product or Service

If you’re pitching your product or service and don’t know what you’re talking about, your prospect will see right through you.

How can they trust you to be an expert when you can’t answer simple questions or if you stretch the truth and make promises you can’t follow through on.

Don’t do this. To convince your prospect you’re worth their time, you need to have the confidence and knowledge to sell your product effectively.

How to do this:

  1. Take the extra effort and meet with different departments (product, marketing, engineering) to understand their perspectives of the product.
  2. Meet with more experienced sales reps on your team to do role-playing exercises where they can throw prospect FAQs your way.

This will help increase your confidence so you can sell smarter.

2. Build a Profile of Your Ideal Customer and Their Pain Points

How to do this: The Director of Enterprise Sales at has a few suggestions for understanding your ideal customer and their pain points.

Two questions to ask when building a profile of your ideal customer:

  1. What’s the ideal use case?
  2. Have they used similar tools in the past? If so, which?

Three questions to understand their needs:

  1. What’s the specific goal your ideal customer wants to achieve?
  2. How will they measure these goals internally?
  3. What are the needs of the individual, the team, and the company?

Here is an Ideal Customer Profile template to save for later.

3. Use Customizable Templates to Personalize Your Outreach in Seconds

When you live inside your inbox, you tend to use the same emails over and over again.

Using email templates makes this a hell of a lot easier.


Instead of taking ten minutes out of your day to find an old email and sub in your new information, save the email (with placeholders) into a custom library that lives in your inbox.

Sales Engagement Data Trends for Sales Managers to Know Going Into 2022Looking at hundreds of millions of tracked email activity over the past year, this ebook is filled with our top studies & findings to help your sales team accelerate results in 2022.

4. Don’t Just Send Cold Email—Build Rapport

Just because you’re not meeting face-to-face doesn’t mean you get to stop being personal.

As humans, we love personalization. In fact, the sound of hearing our own name brings us joy.

Instead of sounding robotic, show them that you’ve taken the time to get to know them.

How to do this: Build trust with your prospect by:

  • Researching their likes, dislikes, and pain points. Hint: Here’s a free research template to plug prospect info into.
  • Making your cold email all about your prospect. After all, you’re asking for their time to read your email — the last thing you want to do is bore them to tears.

Have a prospect who’s interested in sports? Use this template:

Subject Line: The {!player} of {!industry/market niche}

Hi {!First Name}, 

I see that you’re a {!team} fan, so you must be excited about {!player} {!player’s achievement}.

As {!company} continues to scale, your {!department} team needs {!pain point that you solve for} just as {!how same point applies to team}. We’re the {!player} of {!industry/market niche}…{!funny comparison}.

{!First Name}, I’d love (if possible) to be referred to the best person on your {!department} team to introduce {!Your Company} as a mean to hit your {!goal}.


Hungry for more?

5. Stop Wasting Time Logging Info to CRM With a Salesforce Sync That Does It for You

A recent study showed that sales reps were spending an average of 4 hours per week updating Salesforce. The worst part? They only updated 40 percent of the total data they were supposed to upload.

The teams that are ahead of the game use automation instead. Salesforce Sync logs your emails, attachments, calls, and meetings to your Salesforce record in real-time.

Not only that, but a bi-directional Salesforce sidebar lives in reps’ inboxes to 1.) pull in contact activity so they have the right context when they send an email, and 2.) create new tasks or edit contact info based on email replies.

Here’s what Yesware user Courteney McDonnell, Director of Customer Engagement at Placester had to say about Salesforce Sync:

Yesware has easily saved each CSM 30 minutes each day. Before Yesware, we had to bounce between Salesforce, Google Sheets, and a customer’s account just to identify which would be most relevant. Yesware’s Salesforce sync reduces the number of clicks we need to review a customer account and send up-to-date information.

databaseSkip the manual data entryAdd Salesforce to your Outlook or Gmail inbox

6. Keep Tabs on Your Competition

Your competitor should be your biggest motivator.

It’s a complicated relationship: You have the same goals for your customers, but you’re stuck going head-to-head to prove your worth.

To better understand your competition, keep tabs on them.

How to do this:

  • Set up Google alerts for competitor news to understand where they are headed and what kind of improvements their product/service will have.
  • Follow them on Twitter for big announcements, content posts, and to track their customer’s complaints. Hint: You can even use a tool like Tweetdeck to track when a competitor is mentioned by customers having service issues — there’s no better time to slide in with an alternative product.

Here’s a template for cold email heroes:

Subject Line: {!Pain point}? We can fix that

Hi {!First Name},

We’ve been hearing from several existing {!Competitor}’s customers that they’ve been experiencing significant application performance issues recently. We can imagine that your team would be getting frustrated if that’s also happening at {!Company}.

We’ve developed our solution to support leading enterprises such as {!Customer 1}, {!Customer 2}, and {!Customer 3} with stability, security, and reliability in mind so you won’t have these problems with {!Your Company}.

Are you available early next week to discuss why companies like {!Customer 4}, {!Customer 5}, and {!Customer 6} moved from {!Competitor} to [!Your Company} this year? If not, please let us know when’s best to reconnect.


Here’s a doc with the templates — for easy copying.

7. Step out of Your Element and Social Sell Like a Boss

Can I let you in on a secret? Social selling works.

According to a study, LinkedIn InMail’s response rate is 3x higher than a regular email.

If you want to social sell like a pro, you’re going to need to make connections that catch your recipients’ attention instead of annoying them.

Here’s how to spark a connection with LinkedIn InMail:

  1. Do your research: Just like your average cold email, you’ll want to understand their pain points, needs, likes/dislikes.
  2. Use your personal selling skills: Before pressing send, ask yourself: If I were the person receiving this email, would I say “yes” to this request?

Here’s a LinkedIn InMail template that warms up a cold connection:

Subject Line: {!How You’ll Solve Pain Point} 

Hi {!First Name},

{!Positive Connection To Their Company}.

Working at {!Their Company} you must experience {!Pain point} quite often.

At {!Your Company}, we help our customers {!How You Solve Pain Points} and have achieved great results. {!Fact or Statistic About Your Company}.

I’d love to chat more with you. Does this sound like something you might be interested in?

Talk soon,

{!Your Name}

mailSave top-performing emails as templatesNever write the same email twice with Yesware

8. Persistence Pays Off: The Importance of the Follow-Up Email

Sending follow-up emails can feel awkward. You’re intruding back into someone’s space after an immediate rejection, hoping for something better.

But taking the minute to not skip this step puts you ahead of the game.

Yesware data shows that 70% of unanswered sales email chains stop after the first attempt. This means when you do follow up, you stand out as someone who cares to keep trying.

If you don’t receive that first reply back, try again.

How to do this: Yesware’s Campaigns lets you send automated email campaigns based on your recipient’s engagement.

So you can send emails (to up to 200 people at once) without relying on your own memory.


Inside sales is constantly growing thanks to the productivity software that puts your work on autopilot and helps you understand the prospect’s behavior.

When you have the right tools and data, you can sell smarter (no matter where you are) and keep your customers happy.

Tip: Nail your sales process this year — sales process mapping guide for 2021.

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