Sales Tools that Actually Matter: Building your Playbook

Creating sales tools doesn’t need to be a complex process, but it should be streamlined. Whether you have 5 reps or 15,000 reps, alignment is key to your success.

To reach quotas, marketing targets, and pipeline goals, each member of the team must be able to represent your brand and solution from Day 1. Companies use our templates to target the right deals and use the best messaging to:

  • Increase close rate and  win rate
  • Reduce ramp time for new reps
  • Reduce time managers spend onboarding new team members
  • Increase collaboration between sales and marketing

Many small companies struggle to create tools for salespeople because everyone is focused on closing deals, promoting the brand, and demand generation. Don’t make your sales team wait for what they need or spend their time reinventing the wheel by creating content other reps have already built. Increase rep productivity by putting the information they need at their fingertips.

Creating sales tools doesn’t need to be held up by lack of design or headcount dedicated to sales tools. Gather information from the sellers themselves and make sure that it is shared across the team and continues to help in future cycles.

We’ve taken the methodology we’ve used with companies that have anywhere from 10 to over 10,000 customers and created free sales playbook guides that you can use to document your sales process, create buyer personas, discovery guides, demo scripts, competitive intelligence, proof of concept guides, sample proposals, and business case templates.

Here are the steps we take to launch a sales playbook from scratch:

1. Determine who should create & approve content

This should be a partnership between sales and either product marketing, sales enablement, or another trusted person who can get things done in the organization has empowered to create resources.

Create a committee of people who will fill the following roles:

  • Subject matter experts who will provide inputs and examples of existing content
  • Project manager who will manage the timeline
  • Content reviews and final approver (might vary by content type)
  • Content architect who will lead discovery of what is needed by the reviewers and approvers, gather content from subject matter experts, and edit the content into the final format

2. Prioritize content creation by figuring out what content is most needed

The content architect will speak with sales leadership, managers, and individual contributors about the key challenges sales is facing. Look at the stages of your sales cycle and determine what guidance a rep needs to do his or her job at each stage. Analyze deal data that exists to determine where in the sales cycle reps are getting stuck and why deals are being lost or going cold.  You’ll probably hear some trends during your conversations and analysis. When we go through this process with customers, we often hear the following:

  • Chasing deals that are a bad fit → We prioritize creating a selling guide
  • Not enough pipeline generated → We prioritize creating prospecting tools including territory plan templates, email templates, and buyer personas
  • Low win rates against competition → We prioritize creating competitive playbooks
  • Deals that are stuck and taking too long to close or pushing out → We prioritize creating evaluation plan tools reps can use to with customers

3. Start creating content!

Inventory what already exists

Once you have prioritized the content that you need, identify your subject matter experts.  Likely, salespeople have taken it upon themselves to create content to help themselves and their team — it’s in email, decks, and shared via word-of-mouth. Don’t recreate the wheel! Figure out what is out there and how it needs to be updated to be rolled out to the broader team. The more you can leverage existing content, the more buy-in you will get from the sales team. These are great inputs for what the sales team needs. You will probably find some inconsistencies and some inaccuracies. This is normal and part of moving from an oral culture, where everything is shared by word of mouth, to a recorded culture, where you write down specific recommendations.

Next, gather insights from subject matter experts on past deals, wins, and losses, and again, you will see trends emerge. Get specifics on what worked and what didn’t. For example, with qualification and discovery:

  • What contracting emails do they send to attendees before and after meetings?
  • How do they structure qualification and discovery?
  • How do you kick off the call?
  • What questions do they ask with different buyers/stakeholders (or for different solutions)?
  • In what order?
  • How do the answers impact what you ask next?
  • What questions do they ask to uncover who a competitor might be?

Besides the obvious “what other options are you looking at?” the best reps ask questions whose answers signal which competitor might be in the deal.

For example, Your competitor is great at search engine optimization and

You ask: How important is search engine optimization? How are you handling it today? And they are very focused on that functionality, assume that competitors will be in the deal and plan to deposition against them.  

  • What metrics do they capture?
  • How do they divide internal roles between people on the call?
  • How do they ensure they have the right people on the call from the customer side?
  • What do you ask to drive towards a customized demonstration and business case?
  • How do you use the information you gather to build your presentation/demonstration?
  • What do you use in the business case?
  • How do you summarize during the call?
  • How do you set up the next steps?

Make sure you get feedback from multiple reps in multiple business segments and geographies to see what trends and best practices emerge.

4. Ok, so what is this content supposed to look like?

We found it is most helpful to create tactical content that maps to the sales process, as well as providing a very prescriptive approach. For example, for competition, we outline the questions to ask in discovery to uncover competitors and then how to tie that to elements to highlight during a demo to set competitive traps.

We know from experience that reps will deviate from what we prescribe, but we can outline what has been most successful, so reps who are new have a clear understanding of what makes a strong pitch. For each of the guides we created, we have an example of what the content can look like.

5. Review the Content

Once the content has been created, you should have a plan for the sales leadership to validate and sign-off on what is created.  

    • Include leaders of each sales team. This can be the manager or top performer(s) that the manager appoints.
    • The head of sales should review all of the content before it is launched. Ideally, he or she should review a draft of each asset, if time allows.
    • It is also great to have a representative from product marketing to help. Although they may not have the bandwidth to produce the content, it is ideal to engage them in the review process so that they also have ownership and can provide additional insight that aligns the assets with the overall marketing strategy.

When the sign-off process is in place, it creates a roll-out plan. Gain agreement on the review process and signoff before you start creating content so that you agree with the executive sponsors (the sales leadership in this case) at the outset of the project.

6. Roll it out!

Create a timeline to launch (typically 6-8 weeks from the identification of the need to launch), have executive sponsors tease the reps with the fact that the playbook asset is coming, that they may be asked for input, and when they can expect to start using it. During a monthly recap call or regular training call, introduce it, pair it with an exercise to practice using it, and then send it out to the whole team.

Where should this content live?

This content should live where your reps do. Within our customer base, some clients use sales playbook tools like Veelo, Seesmic or Qvidian, many of which are built into Playbook tools are great because they can present the information to the reps based on the type of opportunity, the location in the sales cycle, and the relevant competition.

Others use simple content management tools like Atlassian’s Confluence or Google Sites to cut down on cost. Overall, our recommendation is that you put the information where your team is — if they live in Salesforce, put it in Salesforce (or in a tool that integrates); if they live in a different internal tool, put it there.

7. Measure results, gather feedback and revise

The best sales playbooks are continually evolving as the market landscape and your product change over time. See the impact your content is having on sales cycle length, win rates, close rates, and new-hire ramp time, and identify places where you still need help. Get reps to share what they like and don’t like about what you created through a survey and casual feedback requests. Replicate what’s working and revise what could be better. Set a schedule to regularly refresh all of the content so it doesn’t go stale and reps continue to rely on it as a go-to source for information.

Happy selling!


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