Discover sales playbook insights from 3 sales leaders

Discover sales playbook insights from 3 sales leaders

The sales landscape is always one of rapid adjustment. As markets, trends, and new tools continue to develop, sales methods evolve right alongside them. And we bet you’re always looking to reinforce your competitive advantage.

Well, having a sales playbook is essential to growing and scaling your sales efforts to maintain that advantage.

But how do you make a sales playbook?

To extract some key sales strategy insights, we did some digging to see what 3 sales management experts highlighted as they developed their winning sales playbooks.

These insights are from:

  • Tito Borht
    CEO/CRO, Altisales \

  • Stephanie Glenn
    VP of Commercial Sales, Salesforce

  • Russ Armstrong
    Head of Business Development / VP Strategy, Boast AI \

So, how do they do it?

Well, after spending the time analyzing their sales playbook talks for you, we identified six common themes:

Change Your Sales Approach As You Grow

While some techniques may be evergreen, adaptability should be a primary focus for any sales team. As you grow and expand, you’ll begin to notice distinct shifts in the effectiveness of your sales strategies.

You should be asking yourself questions like:

What works at the enterprise level? What is worth keeping from the SMB level? And what needs to change completely to allow you to thrive?

As explained by Tito, at less than half a million in revenue, your tactics may include calling friends and family or relying on personal connections to make a good impression.

Do things that don't scale

Obviously, this is unsustainable as a larger business, but that doesn’t mean old data or techniques are obsolete.

If the same style of pitch works for a fortune 500 and a mom and pop shop, find out what it is about your pitch that resonates so strongly across prospects

Manage Your Sales Team

Communication among the sales team should be frequent and informative.

Every team member should understand their role and responsibilities within the greater scheme and a uniform sales culture should be cultivated to ensure that everyone is on the same page.

How does culture get captured in your playbooks?

First, your entire sales team needs to know the ins and outs, the nitty gritty details of your product (or products and services) and how it measures up against competitors.

This includes features as well as shortfalls (we call them product gaps), which will enable you to give prospects accurate and detailed information about the current and future development of your product. It’s all about setting the right expectations.

On the culture side of thing, for example, if punctuality is a priority for your company, emphasize that heavily and ensure that it becomes an ingrained part of the habits of the team.

Building strong habits and a company identity and culture will present a polished and professional appearance to potential buyers – your future customers.

Sales Design in your Sales Playbook

A super-star culture vs. a science culture: Russ discusses the difference and explains how a science culture develops more repeatable results with less stress.

Company culture can develop in two ways:

The superstar culture emphasizes specific top performers in the business and relies on them to do the heavy lifting and act as role models.

This is a high stress, high risk style of operating that lacks safety measures and contingencies if the superstar fails to perform as desired.

The science culture on the other hand focuses on provable, repeatable results meant to ensure that long term, sustainable strategies are utilized throughout the sales process, regardless of individual performance.

The science culture’s adaptability and reliance on proven success make it the far more attractive option to any company that uses their data effectively.

Use data as your guide to documenting your proven sales process

All three sales experts emphasize data driven adaptability as being crucial to a successful sales force.

Tito in particular emphasizes the laborious process of recording your interactions, templates, and strategies to collect as much actionable data as possible.


Tracking your results with each engagement can provide insight into the exact point where your messaging breaks down or fails to engage a customer or buyer.

There’s a lot of discovery to this part of the process, so trial and error is unfortunately the reality for a lot of startups and growth businesses. Significant expansion into new product areas and launching new services means repeating the discovery process, so it’s even more critical to have past successes and a systematic approach captured as part of your playbook.

And the tedious work of maintaining detailed records of call strategies and language will pay off when you can interpret that data to optimize your messaging in the future.

But there’s a catch.

The data cannot all be taken at face value. Tito cautions that metrics in isolation can be misleading.

Measure what's working and what's not

Measuring the sales process

Tito illustrates this perfectly when examining outbound emails:

Out of these two templates what are we seeing?

Template #1 has a 24% open rate and a 6.76% reply rate

Template #2 has a 28% open rate and a 9% reply rate

If you were to just stop there… most people would tell me “just start using template 2 what do you mean?”

But here’s the key: Sentiment

You can start using something called Outreach Sentiment. For every reply you get, you can mark what percentage of those replies are positive, meaning it’s getting you a meeting, how many are neutral, which I’d consider “no thank you, bye”, and how many are negative. Which is like “I’m annoyed, go to hell!”

When you start looking at that data, we know that the first template, despite the lower open rate and lower reply rate, 19 emails out of the 50 replies were positive and this is telling me that out of the 3000 delivered, every 158 emails I send, I get somebody to take a meeting with me.

In the second example, despite the higher open rate and reply rate, I’m only getting one (meeting) every 394 emails.

So we can’t just base our decisions off of open and reply rate. If we want to get really scientific, really want to build a world class team, we have got to start looking at the percentage of positive replies.

For this example, a high number of open responses isn’t worth much if they are overwhelmingly negative, and a low number of open responses with enthusiastic, high priority targets can be a boon.

When collecting data effectively, you can determine whether quality or quantity of interactions are your goal, and then act on it.

Data collection can occur before you even make contact. If you notice specific activity on your website, that information can help to identify ideal clients.

Russ suggests using specific signal metrics to prioritize prospects: e.g. if someone has downloaded three whitepapers multiple times then consider adding them to your email list.

Closed-won favors the prepared

It may seem obvious, but adequate preparation every time, all the time, is one of the cornerstones of a successful campaign.

One great way to be prepared is to get your sales content organized and ready for prospecting. Try Content Camel for FREE.

What are the key elements of being prepared? Here’s what you’ll need to capture in your winning playbook:

  1. Understand your ideal customer profile
  2. Understand your competition
  3. Understand the key pain points
  4. Start early
  5. Communicate all of this to your team

At Content Camel, we’ve written a lot about these elements of winning sales strategies. Let’s break them down!

1. Ideal Customer Profiles

How do you choose which companies to target?

An Ideal Customer Profile (ICP) documents which companies get the greatest value from your product. These customers may have high retention rates, act as champions for your brand, or simply be a high volume customer.

Some considerations include the account size, revenue, and location of a company, but it’s encouraged to adapt your own metrics to get the most accurate results. An ICP, for example, might be made up of an audience that converts to a sale the most quickly.

We’ve created an in-depth article and template for creating Ideal Customer Profiles and Buyer Personas which will help you to identify priority targets.

Ideal Customer Profile Template

Win with our ICP template

Getting a documented version of your ICPs will help you to structure your pitch to appeal to the needs of your best buyers, accelerate your sales process, and increase your win rate.

2. Understand your competition

Understand your competitors and what niche you fill; what would take your place if your company stopped existing today?

A great way to truly understand your competition and communicate this to your sales team is to create competitor battle cards.

These can be used to break down the differences between your offering and theirs, and the recommended approaches to positioning against them. Making sure your team is equipped with positioning for all your main competitors is critical for a complete sales playbook.

Hubspot has a battle card template and a deep dive.

3. Understand customer pain points

Demonstrating the pain points in your prospect’s process (current state) without your service/product is more effective than just listing the virtues of your product or service.

A good sales strategy will have your sales team working to build urgency, communicate the cost of inaction, and demonstrate the value of your solution (and how you do it better).

Defining triggers and pain points gets added to your playbook. And is part of the foundation of your sales content used through the buyer’s journey.

Check out our article on structuring a successful Sales Content Strategy from initial contact to converting prospects to closed won deals. It’s a great deep dive on amplifying those pain points 👍.

4. Start early

Stephanie heavily advocates for in-depth client research before ever even reaching out to a potential customer.

She describes Salesforce’s tactic of beginning their territory management process 5 months before the beginning of the fiscal year.

Smarter territory management

Those months of diligence paint a vivid picture of the opportunity and allow your sales team to be ahead of the curve as they plan their engagement strategies for the coming year.

Before you make the call and kickoff your campaigns, you’ll want to:

Perfect Your Pitch

Messaging templates can be thought of as a race car, and the optimization process is the pit crew working feverishly to get the car back on the road.

Failing or suboptimal parts get replaced to improve efficiency and keep things running smoothly.

A poorly chosen word or phrase can be as devastating to your interaction as a blown tire, so make sure you’re always working with updated templates and positioning to have the most positive impact.

Don’t worry, we have you covered here, too:

Messaging Template

Read our article for an in-depth look at messaging templates and to grab a free template.

When calling and emailing, make sure to clearly demonstrate the benefits of your product or service in your pitch – not just the capabilities. This Value Proposition should be as clear and direct as possible for the sake of your prospect.

Sales Playbook value proposition

Simple and direct language that tells your target what they need to know right away

Consider the difference between “ridesharing marketplace” and “get a ride in 4 minutes or less”.

Oh, and overly formal language can hold your back, while conversational, relatable language can help to make your pitch and product more grounded. It really all just needs to reflect the attitude and perspectives of your buyers and it’s worth capturing in your playbook the actual words and phrases your prospects are using.

By aligning your tone and language with the culture of the target company, you demonstrate the natural fit the two could be if they’d purchase your product / service.

When communicating, follow ups and confirmations are important but it is critical to not flood inboxes and erode email confidence in your company. The last thing any sales team needs is to have their emails flagged as spam.

Tito recommends booking a meeting as soon as possible to maintain the contact’s interest.

If you’ve booked more than a few days away he encourages that a reminder email be sent the day before, and a courtesy email linking to the meeting be sent a few minutes before it’s scheduled to begin.

Having these standard approaches documented for the team – expectations around follow up time, and process around meeting reminders – are examples of good ways to align all sales team members. And ramp new reps quickly.

Data-driven sales

We’ve talked a bit about data collection, but what do you do once you have it?

Relying on information can still present some pitfalls if you don’t fully understand or properly apply that info.

Statistics can be an attractive and informative tool for a sales team but without proper context they can easily lead you astray.

Tito claims that the differences between companies are too extreme to use stats to predict engagement outcomes.

And, he highlights that an email can fail for reasons wholly out of your control.

Many businesses shift projects and priorities frequently, and you could simply have the bad luck of reaching out during a busy period.

So now you may now be asking: How do I use stats effectively?

Stephanie cited a study showing “391% higher odds of closing a deal if you engage with a customer in the first minute.”

Is this too good to be true?

In defence of Stephanie’s statistic, they don’t treat data like it exists in a vacuum.

She explains that the early contact can still be extremely effective even if the prospective lead is unsure or unready to make a purchase.

Thanks to the prep work, their sales development representatives (SDR’s) are ready to put the prospect on a journey in order to maintain contact and encourage future business through a drip campaign.

The information collected gives SDR’s an edge in maintaining client interest by knowing what they want and what’s next.

If you didn’t sell them because your product or service doesn’t have a feature they consider critical, let them know when you’re introducing that feature and provide development updates to maintain interest.

Tito and Russ both favour a more binary get-in, get-out approach, with Russ expressing that “time kills all deals”.

Remember: Don’t burn potential contacts just because you failed to close a deal.

Stephanie’s strategy gets the most out of each engagement by moving past an initial failure.

Her team can then begin setting up the would-be client as a new contact, or use them to help inform on how to improve going forward based on what part of the product or pitch failed to hook them.

All this subjective win/loss analysis and info gets funneled back into your playbooks as stories and anecdotes both for use in training an open opportunities.

Sales playbook tips: key takeaways

What does this all mean?

The world of an AE, SDR, and all reps is constantly changing, but after 400 years Sir Francis Bacon’s words are still true: “knowledge is power”.

Starting with a flexible, tenacious approach can quickly yield results as you experiment with different prospects and companies. It is crucial to record successes AND failures to get a full picture of your process.

Understanding your own company and product are key steps to uncovering the rest of the information. Knowing what you do and how you do it can provide insight into who and where your products are needed most, and can open the door to the other data collection methods mentioned.

Clear communication across the company and sales team will keep everyone at the forefront of your sales strategies, allow rapid responses to any problems, and project an image of consistency and professionalism.

Getting an early start on client research provides plenty of time to structure and modify your strategies before you ever do any outreach.

Giving your team the insights into target companies enables them to craft well-curated plays that can adapt and improve in real time.

If these plays fail to close a deal, your contact can still be an asset in the future if you can stay engaged with them. They can provide an insider perspective on the industry, and even become a point of contact for future clients to learn about your company.

The more useful information you can provide to your sales team, the better equipped they will be in every engagement. A flood of numbers and statistics are no good, you need to articulate the data in actionable ways, such as counting for positive responses rather than any response at all.

Above all – keep updating! As the landscape of sales keeps changing, your team needs to be ready to shift with the times and trends. Robust and comprehensive feedback should be used as the framework for your strategies, but you will still need to modify your messaging, target area, or prospect priorities as time goes on to have the best impression on every contact and set your company apart as an industry leader.

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