How to do sales enablement that doesn’t suck [2024 edition]

Al Sargent
14 min readMar 28, 2024

If you’re in B2B sales, you’ve probably suffered through sales training sessions that were downright awful. Too long. Irrelevant content. Death by PowerPoint.

And if you’re in product marketing or product management, you’ve probably delivered at least one such session in your career. Standing in front of a bored, apathetic whose silence speaks volumes. I know I have.

It doesn’t have to be that way.

Here are some ideas on how you can deliver sales enablement that actually helps your sales team hit their goals:

  1. Build excitement for Customer Zero
  2. Weekly demos
  3. Give SDRs the broader context
  4. Align with sales leadership
  5. Frequent enablement sessions
  6. Per-team sessions
  7. ABQ: Always be quizzing
  8. Make it fun
  9. Make it easy to pattern-match
  10. Reduce seek time
  11. Continually survey sales
  12. Use call recordings

Let’s dive into each one of these.

Build excitement for “Customer Zero”

The wrong way: Too often, product marketing focuses on simply throwing content “over the fence” to sales, merely informing them as opposed to exciting them.

The right way: I always stress to my product marketing team that they should think of the sales team as “Customer 0”, your very first buyer. If you can’t get them excited, they won’t sell your new product or feature.

Like a lot of these suggestions, it seems obvious. But I often don’t see product marketers step up and get the sales team excited.

Short weekly Demos

The wrong way: Demos come after a product launch, are heavily produced, and too long. As a result, too much time passes post-launch to build excitement for the sales team.

The right way: Every week, after your sales all-hands (or your company all-hands, if you’re small), have your product and engineering teams give demos of new products, features, and capabilities. 10–15 minutes is typically enough to cover what’s new. This will get Customer Zero — sales — excited about what’s coming. For product marketers, the recordings of these weekly demos will provide a significant body of material to create a more polished launch video.

Clear instructions for SDRs

The wrong way:

Product marketing often creates one-size-fits-all content for all types of sales team members. But general guidance that works for seasoned account execs doesn’t work for a new SDR (sales development rep) fresh out of college.

The right way:

Sales development is a numbers game: emails per day, meetings per week, qualified leads per month, and so on. Efficiency rules.

I often hear from SDR managers that their team needs step-by-step discussion guides and clear lead qualification guidelines. These help new SDRs ramp quickly, so give them that.

Eventually, they’ll improvise, but early on, they need recipes.

Ecosystem context

The wrong way:

When delivering sales enablement for a new product or feature, product marketers dive straight into their value props, without any background explanation for a non-technical sales audience. This leaves sales confused — the exact opposite of the excitement you want to build.

Here’s an example.

I once worked for a software monitoring company that checked whether applications and their underlying cloud infrastructure were up and running. We released a new extension that could monitor Kubernetes.

The wrong way would be to jump right into covering what new monitoring metrics the new extension provided, without explaining what Kubernetes actually is.

The right way:

Provide just enough context for the sales team to confidently discuss a new product or capability.

Crafting this is an art. You don’t want to take a trip down memory lane, filled with pointless details.

On the other hand, historical background is relevant if it connects to sales situations today.

Back to the Kubernetes example: What worked was explaining Kubernetes to the sales team in simple terms related to sales qualification.

The explanation went like this:

  • Kubernetes manages a group of cloud servers.
  • You typically need a group of servers when you need to scale up to handle a lot of users. Lots of users = important app.
  • So, Kubernetes is an indicator of an important app.
  • So, when a customer mentions Kubernetes, qualify up.

Be sure to cover lingo. For example, Kubernetes is often shortened to k8s.

Explain adjacent technologies. For instance, we mentioned that Kubernetes is provided by the big three cloud providers (Amazon, Google, Microsoft) as well as smaller ones, so for qualification purposes, don’t bother asking what cloud provider they use.

In tech, there are lots of foundational technologies. Your job as a product marketer is to give your SDRs just enough background to speak coherently to a customer.

Account execs, or AEs, typically have at least a few years under their belt. It’s a stressful job. When AEs join a company, they are on a timeline to start pulling in revenue. Then every quarter after that, they need to hit their sales quota.

Obvious, right? But I’ve seen a lot of product marketers don’t seem to share that same urgency. Even though their job is ultimately the same as the AEs — pull in revenue — albeit by equipping multiple AEs.

There’s a long list of deliverables that AEs need. Pitch decks, customer stories, competitive analysis, objection handling, pricing/packaging guides, ROI, demos, and more.

A product marketer can’t deliver all this at once. The key is prioritization.

For example, I like to a have a regular meeting with sales leadership to review and update sales content calendar, covering how I and/or my product marketing team sequence the sales enablement content we provide, and when can we deliver it. To keep timing realistic, we factor in other demands on our time, such as product launches and marketing events. I find it best to hold this meeting every couple of weeks.

Sales engineers, or SEs, are your technical sales team members, often paired with multiple account execs. They possess a unique blend of technical skills and communications abilities, and thus are typically in short supply. They probably understand the product’s functionality and technical underpinnings better than you do — make sure they know you know that — and emphasize how you can help them hone their “elevator pitch” of their product’s high-level value propositions, customer stories, and how to weave them into their product demos.

Align with sales leadership

The wrong way: Product marketing comes up with sales enablement topics in a vacuum. Typically this is based on whatever new products, features, or capabilities the product team is launching. Often this is useful, but can miss important topics unrelated to product functionality, such as a tough competitor or confusing pricing.

The right way: Have regular meetings with sales leadership— I find every other week is usually the right frequency — to determine sales enablement topics. The meeting should include whoever leads sales operations (including enablement and certification) as well as the head of sales (if a smaller company) or a couple of their trusted direct reports (if a larger company).

The goal of this meeting should be to align on the sales enablement calendar. This should include topics driven by product updates (new products/features), competitive topics, demand-generation (campaigns), and updates to pricing/packaging. It can also include “redos” — topics that were previously covered, but didn’t quite land.

These topics should fit into your sales enablement cadence, which we cover below.

Frequent enablement sessions

The wrong way: Too often, product marketing only delivers sales enablement at annual sales kickoffs. I can’t tell you how many times I, as a product marketer, have been given a slot on day two or three to train the sales team on my product. The sales team is bored out of their mind, suffering from information overload, and hung over.

How can you make anything stick in this situation?

Of course, product marketing should present at sales kickoffs, but you need other sessions where you have their full attention. Here’s how.

The right way: Hook into your sales team’s existing meeting cadence. Ask your sales leadership to carve out a portion of their weekly sales team meeting for a short, 10–15 minute timeslot focused on sales enablement.

Why does this work?

  • Bite-sized. Product marketing delivers sales enablement content in small chunks. The sessions are too short for anyone to tune out.
  • Crisp. Product marketing is forced to deliver short, compelling messaging — mirroring what sales needs to do in their customer meetings.
  • Accountability. Sales leadership is present, so everyone’s motivated to pay attention.
  • Timely. If your product team — or a competitor — has shipped a new version/capability/feature, you can explain it to the sales team within a week.

What if you have a bigger launch? Break up the content across multiple weeks. Maybe focus on customer pain points on week one, followed by new features, then pricing/packaging, and so on.

Per-team sessions

The wrong way: only presenting a one-size-fits-all session to the entire sales team. These sessions are necessary, but often not sufficient.

The right way: Work with sales leadership to set up multiple weekly enablement sessions tailored for specific sales teams. Some common patterns:

  • One session for your North American sales team, another for Europe, and a third for Asia; different teams may have differing concerns, and time zones may make it hard for everyone to attend a single session.
  • Present in the weekly SDR meeting, since they might have questions they’d be embarrassed to ask in a global sales meeting.
  • Present in the weekly sales engineering meeting, since SEs often want to go much deeper than AEs and SDRs. If you go to that depth with AEs and SDRs present, they’ll tune out and get frustrated. So, give the SEs their own session where they can deep-dive to their heart’s content. Embrace these sessions, since SEs are often deeply analytical and a great source of input to harden your messaging.

Always be quizzing

The wrong way: Product marketing often delivers sales enablement as a series of slides, followed by Q&A at the end. There’s no way to check in with the sales team to ensure that what you’re saying actually sticks.

The right way: With apologies to Alex Baldwin from Glengarry Glen Ross, Always Be Quizzing in your sales enablement sessions. Don’t let more than 3–4 slides pass without presenting a quiz on what you just covered, and ask the sales audience to respond.

Glengarry Glen Ross

You can start with more basic questions and then work up to more difficult ones later. At the end, you can present a case study of 1–2 paragraphs that really get the audience thinking.

For smaller, in-person groups, the quiz can be simply a slide that shows the correct answer in a build. For larger and/or remote groups, you can use a tool like Crowdpurr or Kahoot to enable the entire audience to answer, display a leaderboard, and give a prize to the winners, such as a gift card you can email right after the sales enablement session. Salespeople are competitive — often they did sports in school — and I’m always impressed with how these kinds of contests get everyone listening and engaged.

Crowdpurr

Make it fun

The wrong way: At in-person sales kickoff events, by the time product marketing delivers their sales enablement on day two or three, the audience (sales) is bored, overloaded with information, tired, and sometimes hungover. Against this backdrop, product marketing “phones it in” and delivers a boring slide deck that most audience members can’t remember by day’s end.

The right way: Your audience has been sitting for hours, maybe days, silently listening. Salespeople are extroverts — they love to talk — and often were athletes in school, so this is not exactly fun. Look for ways to get them on their feet and talking. Some ideas:

  • Throwable prizes. Quiz the sales team (as explained above) but make the prizes something you can throw to the winners. One year, presenting to a few hundred sales reps in a meeting room, we did limited-edition t-shirts with custom designs for our products — something you’d want to wear on the weekends. Each time someone won a quiz, we’d huck a shirt to them.
  • Group case study. Craft a complex sales scenario that takes a few paragraphs to explain. Ensure there’s no single right answer. Break the audience into small groups, perhaps folks that don’t often work together, like an SDR from one geo, an AE from another, and an SE from a third. Have them work on a plan for the strategy they’d use to win the deal, including prospecting (SDR), pitch/proposal (AE), and demo/RFP (SE), then present to the audience. Of course, have everyone vote on the winner and give them a cool prize.
  • Whiteboard tournament. Often with technical products, whiteboarding is an effective way to pitch prospects. The energy in the room is better, since the salesperson comes across more like an artist, crafting a piece customized for the prospect. One year at a major cloud vendor with several thousand salespeople, we held a “whiteboard tournament”. We had several breakout rooms of maybe 100 people each, who learned the step-by-step of how to draw the whiteboard, and would present to everyone else in the room. The winner of each room was voted on, and graduated to the next level. Eventually, the top five presented to thousands of their peers, with the South Korean team, who delivered the whiteboard pitch in their own language, impressing the crowd and winning at the end of the day.

Make it easy to pattern-match

The wrong way: Product marketing explains value propositions in the abstract. For example, they might write, “our software is available both on-premises and as a cloud service on major CSPs”. Salespeople are left to translate how to use this information in their customer meetings.

The right way: In every sales enablement session, make it super-obvious what you’re asking the sales team to do. Include a discussion guide that explicitly describes how sales explain the new product, feature, capability, or objection handling you’re teaching.

I find it helpful to put this into a table with three columns:

  • Ask /Listen for— What the salesperson should ask, if it hasn’t already come up in the conversation.
  • If This — The pattern to look for, such as a customer requirement, pain point, a technology used, etc.
  • Then That — What the salesperson should say, show, or use (slides, demo, other sales tool).

For example, building on the example above, the discussion guide could be:

  • Ask /Listen for — where the customer deploys their software.
  • If This — AWS/Amazon Web Services
  • Then That —1) Explain that we run in 10 AWS regions [List]; 2) Explain have unified billing via AWS Marketplace; 3) Use this slide showing a map of which datacenters we run in.

Of course, you’d have additional rows of If This/Then That for other cloud providers like Azure, Google Cloud, and On-Premises.

To a knowledgeable product marketer, this approach might feel like you’re being painfully obvious. But for two of your three Customer Zero personas — the SDR and the AE — they’re often coming up to speed on the technology, and continually stressed for time, and this explicit approach makes things simpler to get things right even when moving quickly.

To be clear, this is not a mandate for how to communicate with customers. It’s only a starting point for salespeople to build upon and convert to their own communication style.

Reduce seek time

The wrong way: Sales team members, continually time-stressed, search for sales content in multiple locations, documents, and slide decks.

The right way: Continually consolidate sales enablement content so that there are fewer places to search.

  • Create a single page, such as a Google Doc, that the sales team can visit to find all their sales needs. Don’t worry about size. The document will become very long — maybe even 50 pages or more — but sales team members can search within that document to quickly access the content they need.
  • In this document, put content into an FAQ (frequently asked questions) format; the answers might link into other deliverables, but the FAQ format helps surface content in those deliverables and makes it easily discoverable.
  • Copy the discussion guides described above into this document so that they’re not tucked away in a slide deck. Wherever possible, link them together so that a salesperson has a guide of how to go from one topic to another.
  • This document should use an automatically-generated table of contents, allowing sales to click to quickly access content, rather than scrolling forever. A basic step that saves time for everyone.
  • Create a single deck of all your slide content — your elevator pitch, your customer stories, competitive slides, everything. Explain to sales that they’d never share the entire deck with a customer, but that this lets them quickly craft a deck customized to the needs of their sales situation by deleting (or hiding) slides, which is much quicker than open multiple decks and copying/pasting between them. This also avoids the glitches that can arise with different slide templates.
  • In this master deck, insert relevant tags into the comments, like #pricing, #competition, #customerstory, #industryname, or #persona, so they can easily zero on the right content for a particular sales scenario.

Continually survey sales

The wrong way: Product marketing delivers a sales enablement session, goes back to whatever they were doing, and has no idea if their session is useful or not. When it comes time for performance reviews, they don’t have proof points of how their sessions contributed to sales effectiveness.

The right way: After each sales enablement session, send out a simple survey to determine whether it worked, and how to improve. I find it helpful to have the following format:

  • How effective was the session? [Numerical score, 1–5 or 1–10]
  • What worked well?
  • What didn’t work?
  • How to improve?

That’s it. Four questions, repeated weekly or whenever you do a session.

The good news about this is that you get bad news early, so you can address it promptly, before it festers.

Review the highlights of the surveys in your regular sales enablement planning meetings that you cover with sales leadership. Use that to inform the topics and format of future sessions.

Use call recordings to track effectiveness

The wrong way: When asked how much their sales enablement content is being used, product marketing has no answer.

The right way: If your company records customer meetings using Gong or a similar tool, search the transcripts for topics that you’ve recently covered in sales enablement.

For example, when you launch a new product or feature, search for its name in the meeting transcripts every week to see how often it’s being mentioned. If it isn’t, ask why — was it your enablement session, the feature itself, the pricing, or something else?

Or if you did an enablement session on how to respond to a competitor, search for its name, review the discussion, and see if the sales team was able to successfully counter any competitive claims to arose.

Conclusion

These are some practices that I’ve found useful for delivering sales enablement sessions. Of course, there’s MUCH more that goes into preparing the content behind these sales enablement sessions, but those are topics for other blog posts.

For the other product marketers reading this — what have you found to be effective practices when training your sales team?

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Al Sargent

Occasional thoughts on tech, sailing, and San Francisco