Business is like the world itself: it never stops evolving, it’s super-competitive, and ruthless, to say the least.

You need to make sure your sales reps are equipped for what’s around the corner; if you fail to do so, you’re begging to fall flat on your face.

Like a knight in shining armor, you - as a product marketer - can give your sales teams the confidence they need to tackle the toughest of challenges, with the help of sales enablement sessions.

What are sales enablement sessions?

Sales enablement is the process of ensuring sales reps have the resources they need to secure more deals for your company. Materials may include content, tools, knowledge, and information to ensure they can sell the product or service to prospects in a more effective way.

The process is a crucial part of any product marketing project; it’s the point in which the key components align and your blood, sweat, and tears pays dividends.

Sales enablement sessions are the ideal opportunity to put the sales reps on your team in the right frame of mind and reps should be encouraged to ask questions to establish a firm understanding of areas including:

  • How your product works,
  • How to position your product,
  • Your USPs (unique-selling-points),
  • Rival products.

The key takeaways for a sales enablement session are by no means set in stone, and will be determined by the timing of when an event is taking place.

For example, if it’s in the run-up to a new product launch, the emphasis should be on elements such as pricing, methods your reps can use to sell it, etc. On the other hand, if the session is taking place following the overhaul of a product, the focus should be on repositioning, while events on new personas need to focus on the characteristics of the new personas.

When a product marketer takes the time to plan in-depth sales enablement sessions and provide their team with high-quality materials, this equips a sales rep with the quintessential skill sets to interact with prospects effectively.

And, as we all know, a confident sales rep is an effective sales rep.

How to plan your sessions

So, you may now know what sales enablement sessions are, but what do you need to consider when you’re planning your sessions?

Set goals

When planning your sales enablement sessions, always have one thing firmly in your sights: the goal. It’s part and parcel of product marketing to set measurable goals, and this ought to be the case when you’re getting ready to launch your sales enablement sessions.

Apologies for sounding like a broken record, but as we’ve said many times, focusing on goals you can’t measure simply doesn’t make sense. You need to be able to assess:

  1. What went well so you can continue to implement this in future practice, and
  2. What didn’t work, so you don’t make the same mistakes.

In the same way a high-school teacher sets learning objectives for their students, do exactly the same for your sales reps.

Consider what you want them to take away when they’ve finished with the session and conduct the acid test; if they pay the utmost attention to the content and engage with activities, yet fail to learn something tangible, then it’s been a fruitless exercise and it’s time to go back to the drawing board.

Consider your audience

Warning: Product marketing cliche incoming. 🚨

A master should be led by the protegee, not the other way around, and this is applicable throughout the world of product marketing.

Suffice to say, PMMs needn’t buck the trend when it comes to planning sales enablement sessions.

Look at things from the perspective of the attendee, as this will be crucial when you’re planning your session. For instance, how much experience will your reps need for the content to make sense? This will influence the goals you set for your session, and outline the parameters for what constitutes success when you’re analyzing your results.

Think about constraints

It’s fair to say some things aren’t always plain sailing, and you’ll need to plan ahead and think about potential constraints when you’re planning your sales enablement session.

While there’s no doubting the benefits the end result can bring, there are bumps in the road you may encounter when you’re planning a sales enablement session, including:

  • Juggling multiple projects,
  • Tight time constraints,
  • Aligning your deadline with other teams, to coincide with sales updates, etc.

Establish your budget

While it’d be nice, product marketing teams aren’t provided with a bottomless pit of money to work with. A set budget is put in place and you’ll have to work within a certain set of parameters to accomplish your goals.

The way you plan your sales enablement sessions will have an impact on how you choose to plan your session. For example, if you have some cash at your disposal, you could invest in resources to improve the interactivity for the attendees. On the other hand, if you’re working with your hands tied, you’ll have to be a little more industrious and innovative to achieve the desired effect.

Size of the event

The size of a sales enablement session will vary from organization to organization, but it’s definitely something you need to consider to be sure you’re putting the necessary steps in place to accommodate your sales team. If the event isn’t big enough, it won’t tick all the boxes, but if it’s too large, this could be a drain on time and resources that could’ve been invested elsewhere.

Perhaps a sales enablement session needs to be held once a quarter? It may be the case you’re able to tie your event in with other quarterly events scheduled in the calendar, allowing you to kill two birds with one stone.

It can also be helpful to tie your session to existing sales meetings, in which you attend as a guest speaker. Alternatively, you can offer your services on a more regular basis, so people can book in beforehand, as opposed to heading into a session without an idea of what to expect.

This will inevitably vary depending on your set-up. If you’re launching new products every other month, you’re going to need sales enablement sessions more frequently. If you have two big launches a year, you’ll need them less frequently. It’s on you to strike the balance of not over or under-communicating.

Who should host sales enablement meetings?

It’s gonna seem like we’re sitting on the fence, but we promise we’re not bailing out and taking the easy option.

However, there’s no definitive answer for who should host sales enablement meetings. The set-up varies between different companies.

Nonetheless, we reached out to product marketers and did some digging, to see where the responsibility for sales enablement meetings fell.

We conducted a poll of 165 product marketers, in which we asked: who leads sales enablement sessions at your organization?

Our results showed 55% of respondents said product marketing orchestrate sales enablement sessions, while a further 34% indicated the process is overseen by sales enablement.

Yet irrespective of who conducts the meeting, how can you be sure you’re getting the most out of the session?

How to get the most out of your sales enablement sessions

To ensure everyone gets the most out of the time, here are some tips you can implement to boost the effectiveness of your sales enablement session:


You should collaborate with sales leadership, to ensure your message is contextualized well. It’s deemed good practice to avoid the scheduling of training events in the last month of the quarter. This time is typically devoted to closing sales opportunities, as opposed to training and development.

Craft killer content

Having decided on your goals and selected an appropriate time in the calendar, it’s time to put together your content.

Some companies have a team whose sole purpose is to focus their attention on refining resources such as scripts, battlecards, etc. that’ll be used in sales enablement sessions.

Granted, this isn’t the case every org, but this doesn’t mean you need to miss the boat. You can join forces with your stakeholders to deliver a mix of PMM deliverables and set the context for people likely to be attending your sales enablement session. Remember, when you’re liaising with stakeholders, be sure to adopt their language, and approach things from their angle.

Psst. Don’t forget, PMMs with a PMA membership can access our full-range of editable templates and frameworks to use in their everyday practice, as well as in their sales enablement sessions. 😉

People are consuming content in different ways. Therefore, where possible, convert your content into a digestible format such as a podcast, or video. This will allow them to revisit the content at a later stage and pick up on any takeaways they may have missed the first time around. On-demand platforms are also useful for people who may have missed training, with our very own PMMfixx a perfect example of this principle in action.

Never make assumptions

Never be led by the assumption your sales reps will do what you want them to do. If you don’t tell them they need to do something with a CTA, then the chances are, they won’t do what you need them to.

Want them to download something? Tell them ‘download X. Want them to use a resource in their next client meeting? Tell them ‘use X in your next client meeting’. Tie these leading/lagging indicators and metrics to the end goal.

‘Cos as we say, if it isn’t measurable, how do you know you’ve succeeded?

Select an appropriate format

You should also consider which format works best for your sales reps; there are an assortment of choices available, regularly used for adult learning.

For example, a passive classroom setting focuses primarily on information exchange. This is considered to be particularly relevant to visual and/or auditory learners, given its emphasis on using resources such as PowerPoint, as well as an emphasis on note taking.

While this method will be useful in instances where you’re revealing your insights from testing, and so forth, a workshop set-up would be considered a more suitable approach for kinaesthetic learners, who are more receptive to a more hands-on approach.

Multi-touch learning programs can also be implemented, whereby people need to complete pre-reading before they’re able to engage in tasks, or assignments are used via an eLearning platform. This method is commonly used for larger initiatives when people are breaking into new industries or creating new personas.

It’s useful to ameliorate training styles, combining elements of the aforementioned types to fine-tune and polish instructor-led training, commonly taking place within a classroom environment, or use observation methods whilst ‘on-the-job’ to ensure everyone’s well-equipped to work in the role itself.

This section ties in nicely with engagement amongst your sales folks.

Tips for getting your sales reps engaged

We all had a class in high school we hated. The teacher had zero charisma, the material was dull, and you constantly found yourself looking at the clock, wishing the hours/seconds/minutes away.

Most importantly, chances are, you learned next to nothing in these classes, right?

This is precisely why it’s essential to keep your sales reps engaged in your sessions. If they’re bored by what you’re telling them, there’s a strong likelihood what you’re saying will go in one ear, and straight out of the other.

So, you need to pull out all the stops to keep your sessions riveting, engaging, and relatable. The good news is a lot of the solutions boil down to common sense, and involve you simply asking yourself what you’d want from a session; if you find a task boring and laborious, chances are, your attendees will, too.

Encourage questions

Encourage discussion and interactivity whenever possible. Not only will this improve the atmosphere, people learn more when they’re asking questions, so don’t force people into a shell, because once they’re in there, it’s hard to convince them to reemerge. Add to that, nobody likes being talked at. Role-play is a fantastic way to bring people together and transform a robotic talk into a fun experience.

Use anecdotes

Anecdotes are also a great way to bring an idea or concept to life and make your audience sit up and take notice. Sure, you may say your product is the best thing since sliced bread, but you’re bound to sing its praises. Use active testimonials to illustrate your point. Not only will this give you credence, but the chances are they’ll relay this to prospective customers who may need a slight nudge over the line.

Embrace gamification

Gamification is also a powerful method used by sales teams, on a global scale. For example, the top weekly sales rep may be given a $100 Amazon voucher, while the second and third may get $50 and $25, respectively.

This is a common method used to drive competition, convert leads into customers, and generate revenue.

It’s human nature to have a competitive edge, and this is a trait that’s particularly common amongst sales professionals.

Use it to your advantage.

Don’t overload your sessions

You wouldn’t walk into a meeting with Hollywood executives and pitch a romantic horror movie, with a dash of comedy and a sprinkling of sci-fi.

It’d be a recipe for a disaster of astronomical proportions.

Apply the Hollywood motif to your sales enablement sessions. Don’t try and cram in a bit of product features here, benefits there, and pricing in between. If you cram too much into your sessions, this could quite easily impact the quality of your session.

You’ve got a 14-minute window before people’s attention begins to wander.

Be a good role model

You never see a game show host with a face like a bulldog chewing a wasp. They’re all smiles, and low and behold, so are the guests who are taking part.

Positive vibes are infectious; if your reps see you’re psyched about the session, chances are they’ll respond favorably. On the other hand, if your body language is far from inspiring and you emit negativity, this’ll rub off on your team, diminishing the effectiveness of your sales enablement session.

Is the sheer thought of presenting making you sweat? Follow our tips and you’ll be a-okay:

  • Do a practice run,
  • Always be prepared,
  • Use prompts as a safety blanket,
  • Assert yourself both physically and vocally,
  • Sit or stand upright and use gestures,
  • Be mindful of your facial expressions,
  • Speak confidently and loudly (without bellowing!)
  • Make eye contact,
  • Encourage audience participation,
  • Speak clearly,
  • Breathe! Take a swig of water if you need it.

And that’s a wrap on sales enablement sessions. Wanna learn even more on the subject? We’ve got your covered. There’s a whole section dedicated to sales enablement in Product Marketing Core, and tons of tried and tested templates in our membership plans.