What makes a great sales playbook?

This week Harry Stebbings interviewed Matt Rosenberg, Chief Revenue Officer at Grammarly on 20Sales, his sales focused spin off from the popular 20VC podcast.

Prior to Grammarly Matt led sales at Compass and Eventbrite - and has led the transformation from PLG to an Enterprise sales model at both Grammarly and Eventbrite.

In the interview (which I encourage you to watch or listen to - link at the bottom of this post) Harry asks Matt,

“How do you define a sales playbook?”

A playbook is simply a set of repeatable processes that lead to the best possible outcome
— Matt Rosenberg

Matt goes on to say that a playbook has a time and a place - it is not defined by the individual.

You must be wary of the new VP Sales that arrives with the playbook we ran at <other tech co>.

The best leaders are able to define new playbooks on the fly depending on the product, the market, the evolution of technology.

For the rest of this post I’ll help you dig beneath the word and define how you build and run a playbook, or sales play.

I also want to add that a lot of my thinking is defined by my time at Highspot where guiding sellers with effective sales plays is a key part of the product offering.

What is a sales playbook?

Matt talks about a playbook - and this is derived from the world of sport, where a physical book would be used to describe the particular ‘plays’ that the team would take in any situation.

Source: https://www.flickr.com/photos/marada/6039505049

The coach would teach the team about different plays in training, and then call out which play would be enacted in a particular scenario.

This translated to the world of business where a thick binder of sales plays was recorded.

Say this.

Then say that.

If the customer says this, show them that.

And the seller would haul this binder around in the back seat of their car - and maybe open it once in a while.

Today playbooks and sales plays have moved on with technology.

Good sales plays are built around the seller

Serve the seller - a sales person is focused on exceeding their target. If a seller doesn’t immediately see how a sales play is going to help them win, and show them how to win, it will be disregarded.

In the flow of work - sellers are experiencing tech overload, so the sales play can’t be on the virtual back seat of the car, it needs to be exposed in the system they are already working in - typically their CRM

Bite-sized elements - think of your GPS directions on a long drive. You don’t care about the turn you’ll take in an hour - you just need to know about the road you are on now and the next turn coming up. Same with plays - give the seller what the need to know for the immediate next step.

Specific assets - great plays provide sellers with multiple assets in different formats. A graphic, a video, a demo, a talk track, questions to ask, delivered at the point of need depending on the individual opportunity.

Real examples - nothing helps bring a story to life better than hearing how a specific line of questioning or a talk track landed with a customer and how that customer responded. Sales plays that show call recordings, meeting transcripts and customer feedback helps a seller to understand how this play can impact their own ability to win.

How should I structure a sales play?

At Highspot they provide a very structured approach to a sales play.

By structuring the content in this seller-centric way, it leads the seller through the process neatly, and they can access what they want quickly as they prepare for a call or meeting.

The real work goes into creating the right type of content to help your sellers to learn in a way that resonates and sticks.

In the learning pyramid below you have the passive teaching methods on top, and the participatory teaching methods on the bottom.

The percentage describes the typical retention rates for each method.

Contrast that university lecture where you drifted off to sleep (5%) with your first driving lesson (75%).

It can be tempting to load your sales play up with recorded video (lecture), documentation (reading), and product walkthroughs (demonstration).

Instead, ttry and include methods for discussion in team meetings, practice pitches (everyone loves roleplay!) or by asking your AEs to teach your SDRs or vice versa.

Break your content down

An easy technique to help with this is to break down large format content into micro content.

  • Use single slides or images instead of full decks

  • Use call snippets of max 2 minutes instead of full one hour meetings

  • Micro video instead of 90 minute webinars

  • Micro-training instead of a full course

  • “Record yourself” instead of a full certification

This kind of multi-media micro-content served up at the point of need based on the specific opportunity is far more engaging.

Think web design rather than Sharepoint folder.

What behaviour do you want to change?

There are two main types of playbook:

Sales Kits: these are collections of content around a specific topic or audience.

Think of a sales kit for a particular persona like the CFO, or a sales kit for your new ACME product - a central place to find the relevant content.

Drive seller behaviour: these are based around a strategic initiative such as cross-selling or a competitive swap out.

Be specific about what you want the seller to do differently as a result of this play.

Measure the success of your plays

There is no point launching playbooks if you can’t measure if they are working.

I’m a big fan of the OKR framework - but which ever goal setting model you use, your sales plays must be linked to a corporate objective.

Objective:

We are a multi-product company

Key Results:

50% of our customers have bought our new ACME product

50% of sellers have sold ACME to at least one customer

KPI:

% of customers with ACME

% of sellers that have sold ACME

Initiative:

Launch an ACME sales play

Launching the sales play is an initiative that supports the two Key Results.

And if we achieve the two Key Results we will by default be able to say we are a multi-product company.

If you cannot define the high level objective, or how you will know when you have reached it - then your sales play is an orphan headed for the virtual back seat of the car.

How do you launch a playbook?

Follow a plan as you launch your playbooks.

By focusing on the outcome first, and the intended change in seller behaviour, you will find it much easier to build engaging and effective content to help your sellers to win.

Good luck, speak to your sellers, and build a playbook that helps them to be successful.

In the meantime, check out the full interview between Matt and Harry here:


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