Category Archives: SaaS

When a company is transitioning from founder-led sales (FLS) to sales-led sales (SLS), you hear the word “playbook” a lot. For early-stage companies, this rubs me the wrong way because when I hear playbook, it conjures up an image of:

• A large sales enablement team
• A hefty three-ring binder full of paper (or its digital equivalent)
• A lot of templates (which perhaps commit the cardinal sin of the template leading the content)
• A formal onboarding program that teaches playbook contents
• And perhaps a formal sales process (e.g., MEDDIC) or methodology

That’s all great when you’re $100M+ in ARR and you’re trying to institutionalize a model that you know works — from repeated experience with scores of reps over many quarters. But for an early-stage company with less than a dozen reps and that’s still highly dependent on the founder(s) to sell software, it’s overkill.

So when these companies say they need a playbook my retort is, “no you don’t — you don’t need a playbook; you just need a handful of plays.”

What is a Playbook?

While the term gets bandied about, few seem to define it. Many companies will tell you how to make a sales playbook. For example, Pipedrive does so in a not-so-mere 4,500 words. But if the how-to-make-one guide is nine, single-spaced pages, then how big are the playbooks themselves? Usually, big. Per Pipedrive:

A sales playbook is a document that outlines your sales processes, procedures, and best practices. By following the strategies in a playbook, sales reps can increase their productivity, improve their win rates and drive revenue growth for the company. Sales playbooks typically include […] target customer profiles, stages of the sales process, how to handle customer objections, sales methodologies, sales tools and technologies, key performance indicators (KPIs), and strategic objectives.

Pipedrive’s how-to guide is a fine piece of work. It’s just way too heavy for early-stage startups. These startups can’t make large playbooks, nor should they. They don’t have the resources to build them, but far more importantly, they don’t know what to say — they simply don’t have enough experience to know what works across a wide range of buyers and situations. Sure, you can pay an intern to fill in templates, but you don’t have quality content.

That said, what’s my definition of a playbook?

A playbook is a collection of plays.

What is a Play?

My definition begs the question: what, then, is a play? So let’s define that, too.

A play is a series of steps to make in a given situation to help you win a deal.

The keywords are:

• Steps: the things that the sales team needs to do. While different team members may do different things at different times, the quarterback of the deal is always the seller.
• Situation: the situation for which the play is designed. For example, you might have play for leaving a deal that you don’t think is qualified (the Polite Walk Away) or for saving a deal you know you’re losing (the Hail Mary).
• Win: the purpose of the play is to win the deal. As James Mason said of lawyers in The Verdict, “you’re not paid to do your best, you’re paid to win.” The same is true is in sales. The purpose of the play is to win.

An Example Play

Because I find the notion of play still somewhat amorphous, I’ll provide a concrete example.

Situation. You sell BI tools. You are competing against a hot competitor with a slick user interface that’s generally preferred by end-users to your own. One feature, in particular, gets audible wows when demoed. Your product and engineering team has recently released a similar but inferior version of that feature to help. Because the competitor knows they will win in end-user demos, they encourage selection committees to “let the users decide” by having a large end-user demo near the conclusion of the selection process. Your competitor calls their play the “End Run” because they’re running around the IT group charged with the selection to the end-users.

Steps. You take the following steps in this situation.

• Build or re-use the slickest available demo of the product that you can find.
• Request an end-user demo session for your company, too, justified by basic process fairness.
• Demonstrate the “wow” feature several times. Know that you are likely to still lose with the end-users, but that’s not the point. You are trying to minimize the perceived gap and convince the end-users that — even if they don’t see your solution as “best” — that it’s certainly “good enough” to get the job done.
• Call a meeting with the IT team to discuss security and administration. Convince them of the importance of security and the cost of administration. Show that your product, rightfully, is superior in both these areas.
• Get IT to reframe the end-user vote as “input” (versus “selection”) and that they should ask the end-users two questions: which is your preferred solution and can both solutions do the job?
• Win the deal when IT selects your product based on security and adminstration with the end-users’ consent that your solution is good enough to do the job.

That is a play. It’s not complicated. It’s easily taught. You can and should build tools to support its execution — e.g., the wow demo and a security and adminstration white paper.

Plays Are Applied Marketing

Are plays marketing or sales? While plays are always executed by sales, I think of building plays as applied marketing. We start with what we know about the customer and market. We add what we know about the competition — both in terms of product strengths/weaknesses and common sales tactics. Then we apply that knowledge into making a play (i.e., a series of steps) to beat them.

What Plays Do You Need?

I tihnk most startups need 3 or 4 plays, each of which can be described in less than a page (if not a single paragraph):

• Replicate success. This is your primary play. If you have a few big insurance companies using your product for use-case X, then you need a play for replicating that. Who to call. What to ask. What to say. How to tell the story of your existing references. How to overcome objections. How to close.
• Replace BigCo. If you have newer, better, faster, cheaper technology than an established (now “legacy”) vendor, you need a play for how to replace them. Who to call. What to ask. What to say. How to qualify. How to win. When to give up.
• Beat archrival startup. If you have a head-to-head startup rival, you’ll need a play for how to beat them. This is usually a mix of product differentiators tied to use-cases combined with vision/roadmap to address objections along with strong messaging on safety, company/investor quality, and early market leadership.
• Polite walk alway. As an early-stage startup you should walk away from plenty of deals, so you should get good at it. The deals you qualify out today are next year’s opportunities so treat them well and get good at slow nurture.