Build Your B2B Sales Playbook
- Brett Sheppard
- Aug 3, 2022
- 8 min read
Updated: Jul 28, 2023

A sales playbook provides a common framework and approach for engaging with prospects and closing sales. The playbook defines your sales process and how it maps to your customer's buying process. At an early stage startup, developing and refining your sales playbook is often a team effort among the company founders, head of sales and head of marketing.
Most of the sales playbook will be unique to your company – what customer problems you’re solving, and what are your target of buyer and influencer personas. Where you can leverage from industry best practices is in your choice of sales methodology. Below are among the sales methodologies that work well at early-stage startups.
Having a written playbook helps onboard new sales hires faster. It helps provide consistency across sales teams by documenting best practices used in each sales territory that may benefit the sales teams in other regions.
I've worked with early stage startups where for every new sales hire, the CEO or VP of sales will spend a full day onboarding that new hire. It's not a scaleable, repeatable process.
“The sales playbook captures your company's knowledge about its markets, value propositions, offers, competitors, and best practices,” according to a blog by VisionEdge Marketing Founder and President Laura Patterson. Patterson recommends that a good sales playbook should contain a customer analysis and buying process, the company offer and value proposition, competitive analysis, sales methodology, and sales best practices.
According to Aberdeen, best in class companies are almost twice as likely to have sales playbooks vis-à-vis laggards. A sales playbook frees up salespeople time.
Over time, as you build out and refine your sales playbook, it should include:
Stages in the buyer’s journey
Buyer personas
Best practices around sales opportunities
Workflow between sales development reps and account executives
Repeatable winning sales processes
How to utilize sales tools in context at each stage
Both simple and complex processes
Email templates
Demo scripts
A playbook helps you disseminate the most effective techniques. If one rep has success with a specific outreach method, you can share it easily with the entire team (including salespeople based in other regions) by putting it in the playbook.
The playbook is operationalized through sales training and steps within your marketing automation and CRM software.
Rather than having each rep develop their own messaging, questions, and resources to use with prospects, give them ready-made content to use and adapt. This lets them focus on selling.
How To Write a Sales Playbook
HubSpot provides guidelines on how to write a sales playbook. The following section is adapted from “The ultimate guide to creating and using a sales playbook”.
The first step is figuring out who should be involved.
Representatives from sales are critical — ideally, the VP or Director along with several top-performing reps.
Product marketing needs a seat at the table too, since their team is well-versed in your buyer personas, product messaging, position in the market, etc.
Bring in subject matter experts as well. These people will give you the insights you need to create winning sales collateral.
If you have dedicated sales enablement, sales operations, and marketing operations teams, they should also be at these discussions.
Many experts recommend naming one person as the project manager. The PM is responsible for the timeline, content submissions, and content approval.
Next, outline your goals. Are you creating a brand-new template, expanding an existing one, or editing and updating one?
If you’re starting from scratch, consider picking a single part of the sales process. Your reps are likelier to adopt a short, focused playbook over a long, complex, multifaceted one. It’s also less overwhelming to tackle your playbook in sections rather than all at once.
Maybe your reps are struggling to identify qualified buyers. You might start with a playbook on qualification, including an easy-to-use framework, qualifying questions, and common indicators of fit.
On the other hand, if your biggest priority is improving demo quality, your first playbook should cover presentation strategies and structure, various value propositions linked to your product’s features, and sample messaging.
The third step is auditing your existing content. Your salespeople are already using email templates and sequences, calling and voicemail scripts, meeting agendas and presentation decks, customizable questions, and so on.
Don’t let these go to waste: Not only do they require less work than creating content from scratch, reps are far likelier to adopt content adapted from what they’re already comfortable with.
Sales Resources For Your Playbook
One common mistake I’ve seen at many early stage startups is to adopt a single source for a sales methodology, and say things like “We use the Challenger Sale”, without thinking through the consequences. Where this approach can fail is that it’s rare for a single sales methodology to best fit your company’s unique situation.
It's hard for a single sales methodology to fit each stage of your sales cycle to different types of customers. Moreover, many of your mid-career sales people will have already received training in multiple sales methodologies.
The best sales playbooks draw from several sources, such as one or more of the sales methodologies discussed below, and compile the key tips into your company’s sales playbook. When you create your company’s own playbook, it can be helpful to reword or leave out some of the author-specific terminology, so your team sees one cohesive playbook versus a hodgepodge of different selling acronyms and catch phrases.
Sandler Pain Questions

David Sandler observed that "People make buying decisions emotionally; they justify those decisions intellectually."
Sandler teaches us that by asking a series of probing questions, we can learn about what the prospect's real business needs are at an emotional level.
There is a similar philosophy of asking a series of "why" questions to probe into what's truly driving interest in making a change.
Products that address emotional pains are much more likely to get budgeted and purchased than ones that may represent improvements only at an intellectual level.
David Sandler's sample pain questions:
Tell me more about that ...
Can you be more specific? Give me an example.
Hong long has that been a problem?
What have you tried to do about that?
And did that work?
How much do you think that has cost you?
How do you feel about that?
Have you given up trying to deal with the problem?
MEDDIC

MEDDIC is a sales methodology based on qualification for complex enterprise B2B sales environments.
Metrics: Measure the potential gain leading to the economic benefit of your solution vs. competition.
Economic Buyer: Identify and meet the person who has the ultimate word to release funds to purchase.
Decision Process: Know and Influence the process defined by the client to make purchase decision.
Decision Criteria: Know and Influence the criteria defined by the client to make purchase decision.
Identify Pain: Identify and Analyze the pains which require your solution to be relieved.
Champion: Identify, Qualify, Develop and Test your Champion or your Internal Seller.
Neil Rackham SPIN Selling
Neil Rackham takes Sandler's pain questions a step further, and identifies four types of questions that salespeople should ask prospects. Open-ended questions are often more valuable than closed yes or no questions.
Situation questions aim to understand a prospect’s current situation
Problem questions get to the heart of the prospect’s issue
Implication questions probe the prospect to think about the consequences of not solving the problem
Need-payoff questions prompt the prospect to consider how the situation would change if their problem was solved

SPIN selling techniques work well for major account sales, where you want to have an ongoing relationship with the customer, and talk with multiple buying centers and influencers in the customer's organization. In large accounts, the old adage is still true to "always be closing", but the context is different and more nuanced. The larger the decision, the less effective traditional closing techniques will be.
Rackham defines the stages of a successful sales call as the preliminaries, investigating, demonstrating capability and obtaining commitment. Of these, investigating is the most important step. Commitment can represent attending a product demo or giving access to a higher-level decision maker. At that stage of the conversation, check that the key concerns are covered, summarize the benefits, and propose a commitment.
Matthew Dixon and Brent Adamson Challenger Sale
The Challenger Sale methodology works well when you are selling into mainstream organizations or late adopters, who need prodding to consider a new approach. It also fits well for the 80 percent of buyers who primarily look to avoid pain. It’s less suited for the 20 percent of buyers who are more proactive in looking to create new value.
Dixon and Adamson group every B2B salesperson into one of five personas: relationship builders, hard workers, lone wolves, reactive problem solvers, and challengers. According to their research, salespeople are almost evenly distributed among these profiles. However, the most successful by far were the challengers.
Challengers follow a teach-tailor-take control process. First, they teach their prospects, not about the product or service in question, but about larger business problems, new ideas, and astute insights. Next, they tailor their communications to their prospect. Lastly, they take control of the sale by not being afraid to push back on their customer, and focusing more on the end goal rather than being liked.
Skip Miller Proactive Selling
Skip Miller teaches us to think about a sale from the buyer's perspective. Successful salespeople think like a customer, and by being proactive to think one step ahead, can control the buy/sell process. Great salespeople do not have great answers, they have great questions. They qualify from a buyer's perspective early and often.
Miller takes the traditional 5-step selling process that is captured in most customer relationship management (CRM) software, and adds insights about how the buyer perceives each stage. How you prepare for a validation process will determine how successfully the prospect takes ownership.
I first learned from Skip when in the early days at Tableau we leveraged his sales training and incorporated it into our sales playbook. Skip has a good summary of his sales methodology here.

Solution Selling
There are many good reference books and sales guides that teach us how to take a solution approach for business to business (B2B) sales. For an early-stage startup, it can be difficult to talk about having a "solution", when in fact you are offering more of a point product or tool. Solution selling still offers important insights, by reminding us to think about how what we're selling fits in with what the buyer already has today or plans to invest in the future.
Fortune 500 companies and government agencies have complex enterprise architectures. It's important to explain how your offering fits as seamlessly as possible with what the buyer already has today, and offers incremental approaches for adoption versus a large-scale rip-and-replace of large legacy systems.
Jill Konrath SNAP Selling
Konrath's work addresses the problem that many B2B buyers are waiting later in the decision-making process to contact a salesperson, preferring to do their own research first. At the same time, they may be too busy to dissect complexity.
She groups her advice under four areas:
Keep It Simple: Your sales team needs to make it incredibly easy for prospects to change their current habits and adopt what you're selling.
Be iNvaluable: Modern buyers are overwhelmed. Salespeople need to be unique experts who stand out and showcase value.
Always Align: Selling today includes aligning business objections with core beliefs. It's about making people want to work with you.
Raise Priorities: Frazzled buyers have a priority list. Sellers need to focus on what the prospect is focused on to win deals. This goes back to the old adage that what you are selling should address one of the organization's top 3 business priorities.
Gap Selling by Keenan
The idea that modern selling is a matter of solving problems for your customers isn’t novel. That’s a mindset that many of us carry. But Keenan’s central argument in his new book is that these gaps are often hidden, even from customers themselves.
“The worst thing in the world you can do at the beginning of a sale is take your buyer’s word for granted or sell to a need,” he writes in Gap Selling. “I know it’s what we’ve been taught to do but a need assumes the customers know what they want, and that’s a bad assumption. Sure they think they know what their problem is, but what if they’re wrong?”
This is where Keenan’s methodology really focuses: working with customers to help them recognize their true gaps, and using these revelations to propel deals forward.

Shut Up and Listen
"Shut up and listen" is my own mental approach for what I tell myself before talking with prospects and customers. From my experience, the best salespeople listen far more than they talk. When I go into a B2B CxO customer meeting, I personally remind myself to “shut up and listen”. This is my own mental shorthand to remind myself what the prospect or customer has to say about their business needs is far more important than what I have to say about the product or its features.
What methodologies does your B2B sales team use?
Brett
Great cheat sheet...saving. Thanks!