The 6 Enduring Chapters of Every Sales Playbook

The elusive sales playbook. Every company wants one. Every VP of sales claims to have one in their pocket.

It took us 5 years to really get the Levelset sales team clicking, and even then I didn’t feel like we figured out the “playbook”. So don’t feel lost or frustrated if you haven’t quite locked in your own playbook in the first few years. 

Playbooks are a living, breathing thing that grow and evolve with the business. Your sales team may start out focus on selling to SMB, then you need to move upmarket. Or maybe your team has a Product-Led selling motion and needs to figure out how to outbound. 

There are many reasons a playbook changes over time, and that’s why your team should revisit the playbook at least once a year to make sure it represents what is happening on the sales floor.

Though your playbook will evolve, there are some chapters of your playbook that will remain constant no matter the size or scale of your business. I will call these the 6 Enduring Chapters of Every Sales Playbook.

‍Chapter 1: The Principles of Your Sales Motion

The first chapter is an opportunity to bring your new team members into your sales team culture. Start your playbook with an overview of who you are, what you do, how you do it, and where you are going as a team.

For most high-growth companies, the sales team is an amazing opportunity for each individual to achieve success for themselves: personal, professional, and financial. 

I’ve written before about creating a coaching culture and about building a culture of sales success. These are the under-currents that move your sales team in the direction you want them to go. Bring these principles to life in your sales playbook.

Here are some elements to include in the first chapter of your sales playbook:

1. Company Mission and Vision - get the team bought in on what the company is building. Start with why the company was founded and what the mission of the company is. Everything the sales team does is in service of the mission and vision. That’s the only way to create big outcomes.
2. Sales Team Core - sure, you have your company core values, but what about your team? What are the virtues to live by that guide every decision you and your team makes. Some of my favorite from the Levelset sales team were “Help First, Sell Second” or “Do the right thing”. Be deliberate about your values and your culture will follow.
3. Definitions - this is an often overlooked part of the playbook, but you have to define the terms that you use. Words have meaning and you should use them purposefully. Some terms to define for your team: Sales Qualified Opportunity, Sales Accepted Opportunity, Closed Won, Closed Lost, Effective Date, Close Date, Lead, etc.
4. Qualification Framework - Spell out the framework that you use to qualify leads. It could be BANT, or SPICED, or MEDDIC. Whichever you choose, you have to put it in black and white for your team.
5. Value Proposition - what’s the elevator pitch for your company and product? When your sales reps are at a cocktail party or meeting with a prospect at a conference, what do you want them to say? Put it in writing!
6. Tech Stack - what tools are you expecting your team to use. What is the purpose of each tool and what benefit does it have to the salesperson. You would be surprised how often reps fail to adopt a piece of technology simply because they don’t understand what it is used for.

‍Chapter 2: How to Generate Demand

Once you have your principles laid out, it’s time to instruct your team how to go and get revenue. This starts with the most important part of every selling motion: how are you generating demand for the business? Whether you are running an SDR team, or you have inbound leads, or you have a PLG motion. You need to instruct your team how they can turn leads into opportunities and real sales pipeline.

Spend the time filling out exactly how a rep can be successful in the role by generating demand for themselves. Some things to include:

1. What does a great lead look like - this is your Ideal Customer Profile. What are the firmographic and demographic details of a great prospective customer. What challenges are they currently experiencing in their work? What do they use the product to do? Tell a couple of stories about successful customers and illustrate what a great lead looks like.
2. Where to find great leads - When a new rep joins your company, they need to learn where to find new customers. Perhaps you already have great leads in your CRM. Or maybe you have ZoomInfo or Apollo for your reps. Maybe they need to use google to find leads. Wherever they may be, you need to give your reps the tools and instruction for where to find those strong-fit prospective customers.
3. How to convert great leads into opportunities - this is where it gets fun. This is where you give your reps the tools they are going to use to reach out to customers. Include your compelling prospecting emails and cold call openers. Put your most successful scripts. Include links to recorded calls where a rep can listen to previous successes. The team should have everything they need to go and start prospecting into the market.
4. Handing off an opportunity - this is most relevant if you are running an SDR team, but it can also be helpful if your AEs are sourcing their own pipeline. You have already defined your SQO and SAO requirements in the principles section of your playbook. Now it's time to show reps the exact steps to move them into the sales pipeline. 

Chapter 3: The Sales Process

Once an opportunity has been created, it needs to be worked. Your playbook lays out the step-by-step process to get a customer from opportunity to a closed won customer.

These are the elements of your Sales Process that should be included:

1. Sales Process Stages - possibly the most used part of every playbook, the Sales Process stages are the exact stages your team will use to move a new opportunity through the evaluation and into either Closed Won or Closed Lost. There are many free resources on building a strong sales process. Some key ingredients: make sure each stage is clearly named, defined, and associated with a step in the buyer’s evaluation process. Each stage should have an entry criteria and exit criteria. Each stage need key “gives” for the customer (like a case study or other piece of collateral) and get “gets” from the customer (like an introduction to the economic buyer or data from their ERP system).
2. How to run a discovery call - quality pipelines starts with a strong discovery process. Put your discovery on paper. Give the team your 10 best discovery questions. Link to successful discovery calls that sales reps can emulate on their own calls. Make it clear what the correct outcomes are for your discovery stage.
3. Confirming your Champion - one of the Keys to Unlock a Deal, define the “champion” for your team and illustrate why working the champion is so important. Include sample plays that you can run to qualify and confirm your champion in the deal. Differentiate the Deal Champion from the Deal Coach.
4. Creating a Closing Plan - another of the Keys to Unlock a Deal, provide a sample closing plan that the reps can use to put their opportunities on the path to success. Provide a library of potential steps that could be included in the closing plan. Give the reps a bank of collateral that they can use to support their closing process (terms, case studies, etc.)
5. Manufacturing Compelling Events - yet another of the Keys to Unlock a Deal, show your reps how to manufacture compelling events. Provide examples of time-based incentives that they can use to accelerate deal timelines. Show them the email scripts that they will use to confirm the compelling events with prospects.
6. Creating an Executive Summary - Give  the reps an example executive summary, which is a one-page guide to every deal. The sections of the executive summary are as follows: partnership summary, key stakeholders, current challenges, desired outcome, why your company is the right partner, commercial terms, expected ROI. This is the document that your champion will use to sell the deal when you aren’t allowed to be in the room.
7. How to Close a Customer Document - Another of the most-used documents on the sales floor, this document shows in excruciating detail how to close a customer in your CRM and backend system. What fields to complete, how to fill them out, how to select the right CS partner, how to book the revenue, how to get legal involved, etc. Don’t assume your reps will understand how to actually close the customer once they already have a “yes”.
8. How to give a great product demonstration - Of course you should provide your sales demo deck in your sales playbook, but you should also coach your team on how to give a great product demonstration. Most reps will run a product demo like its a product training. This is a terrible way to sell your product. Show them how to do it! Inlude links to videos of great product demonstrations.

‍Chapter 4: Setting up the customer for success

The only way to successfully scale your revenue is for your Sales and Customer Success teams to work closely together. One of the key sections in your sales playbook should teach your reps how to bring customer success into the sales. Some things to include in your playbook:

1. Customer Planning with Customer Success - No one likes to be surprised in business. That huge customer you have been working on? When you close them, the Customer Success team has a mountain of work to complete the implementation and make the new customer successful. Get ahead of customer surprises and bring your customer success team into the deals. Get together weekly with the customer success team to talk through key deals. Bring the Account Manager into the pre-closing call to start building a relationship. Sales and Customer Success are on the same team, so work together for the sake of making the customer successful.
2. The Handoff - What does a perfect customer handoff look like? Put it in black and white for your team. When should the sales rep engage with Customer Success? How do they communicate to CS about the customers' usage and priorities? When should the salesperson stop joining customer meetings? All of this should be in your sales playbook.
3. The First 90 days - What does success look like for the first 90 days of the customer experience? What usage metrics are good? What are the key risks that sales and CS should look out for? Create a scorecard that you can use to measure the first 90 days of every customer's experience.
4. Quarterly Business Reviews - What’s the structure of the quarterly business review? Include the key performance and usage metrics that will be covered with the customer, the purpose of measuring those metrics and how they will impact the customers’ business. Who is involved in the QBR? When should the salesperson re-engage with the customer
5. Annual Renewals - Similar to QBRs, give the team guidance on when and how they should approach the annual renewal conversation with the customer. Most teams start this conversation 90 days out from the renewal. Get your renewal process tight so the customer has a seamless transition from one year to the next
6. How to expand customer’s usage - This section could deserve a whole chapter. Define your key upsell and expansion motions that the sales team will use to increase customer spend. What is the reason for expanding spend? What’s in it for the customer? What are the exact words that a salesperson should use when approaching a customer about a renewal? Check out my thoughts on why Customer Success Should Not Carry a Quota

Chapter 5: Revenue Operations

A dry-but-necessary piece of your sales playbook, revenue operations is the oil that keeps the sales machine running smoothly. There are so many things you can include in your sales playbook, I recommend starting with the three most important:

1. Career Pathing - this section outlines the titles, roles, and responsibilities of each person on the sales team. Provide guidance on how a rep can move up in their career, how they move into leadership, how they transition outside the sales org if that’s what they want for their life and career. Career Pathing is a HUGE part of building a successful sales culture, so give it the proper attention and care.
2. Compensation - Your compensation plan should be so easy that the reps can do the math on the back of a napkin. Even if it is that easy, you should still put it in write and make it part of the playbook. Show the math for how a rep can hit 100% of their quota. Check out my essay on the Principles of Good Sales Compensation
3. Territories and Rules of Engagement - The bain of every sales leaders’ existence, Rules of Engagement. A necessary evil for every sales team, this section spells out how leads, opportunities, and customers are distributed to the team. It also outlines what happens when a salesperson breaks the rules. You have to get this stuff articulated in writing so there is consistency across the team.

Chapter 6: The Sales Operating Rhythm

If your sales team is an army, your Operating Rhythm is the drumbeat that they march to. No one likes meetings. We try to avoid them like the plague so we can spend more time on the phone with customers. But some meetings are necessary. Your operating rhythm helps your team understand the meeting cadence and the purposes for each meeting.

Here my favorite operating rhythm for a sales team:

1. Weekly 1:1 between an individual and their manager - the purpose of this meeting is for the individual. That person should come prepared to discuss what’s going well, what’s not going well, and anything else that needs to be discussed with their manager. This meeting should last no more than 30 min and the manager needs to be very present during the entire 1:1
2. Weekly sales meeting - this is a once-a-week 30 minute meeting to review performance to plan for month/quarter. It’s a time to recognize outstanding performances across the team, to highlight the bright spots and celebrate success. You can also use this meeting to announce any product updates, upcoming sales training, or anything else that might be valuable to the members of your team. Make this a fun meeting, something to look forward to! Pro tip: use this same meeting slot for your Monthly and Quarterly Kickoff Meetings.
3. Weekly Pipeline Review Meetings - This is a meeting between the manager and the individual contributors on their team. The manager should review all deals in the pipeline to form an independent assessment of how the team will perform in the month or quarter. This is the preparation meeting for the Weekly Forecast Meeting.
4. Weekly Forecast Meeting - this is a meeting between the VP of Sales or CRO and the sales managers. The sales managers come prepared to discuss their commits and best case outcomes for the month or quarter. This meeting happens at the same time every week and the agenda is run with military discipline. Check out my essay on How to Forecast Bookings.

‍Closing Out Your Sales Playbook‍

Now that you have the 6 enduring chapters of your sales playbook laid out, use the last section of the playbook to provide a directory or list of helpful resources for the people on your sales team to improve their skills.

You can include a list of sales books that you recommend, or you can provide links to YouTube videos for honing your sales skills. End your playbook in a spirit of education and encouragement. Never forget how hard it is to be a sales rep!