Strategic Sales Enablement: Advanced Tips to Uplevel Your Program & Drive Real Results

Whether you run a one-person sales enablement program or are part of a team, the sheer scope of the job can be overwhelming.

I hear you.

Which is why we’ve put together this guide on sales enablement, focusing on the three primary parts of the job: strategy, execution, and governance.

Let’s get to it, shall we?

Sales Enablement Strategy: Always Start Here

Everything in business starts with strategy (or should!). Success depends on understanding your objectives, both for the organization and the people you support.

Don’t forget you’re in the “people business”

It’s easy to get mired in the projects and pressures of the job. Especially when the job covers so much territory. But it’s important to remember why the sales enablement role exists — to help your salespeople succeed.

As Roderick Jefferson says,

There are 4 Ps to ensure sales enablement success: PEOPLE, PURPOSE, PROGRAMS, & PLATFORMS. Never forget that we’re in the “people business”!

While our success is deeply rooted in ensuring that we are partnering with all of the company’s business units to decrease time-to-revenue and increase seller productivity… NEVER forget it all begins and ends with people!

We often get lost in products, processes, programs, etc., and the “human element” around how a company fits into their prospect’s or customer’s journey gets lost in the mix.

RELATED: Demystifying Sales Enablement: What It Is, Why It Matters, And How To Do It Right

Get buy-in from the top and the bottom

Now here’s where it can get challenging: you serve the revenue-producing employees, sure, but you do it to help your executive team achieve their goals. That means you need to align both up and down — understanding the problems of people at every level and finding ways to help them all reach their goals.

Mark Eckstein, Revenue Enablement Manager at Bizzabo, explains it like this: You need to understand the challenge or problem that management wants you to solve. Then you need to speak to the employees and understand the problems they face.

From those conversations, you can identify the divergence between management and employees — which will help you make recommendations and set priorities.

For employees, what are some easy wins? Start with these projects, so you can build credibility with them.

Give reps some assignments and tasks they’ll be excited about. Start by making their life easier so they are willing to give you their time in the future.

Whitney Sieck, Director of Revenue Enablement with Greenhouse Software, agreed that you need to meet the company where they are.

She recommends a programmatic approach, working with the existing sales operating rhythm instead of creating additional work streams for enablement initiatives.

Analytical and consultative skills go far in establishing an enablement function. Be sure to collect a healthy mix of qualitative and quantitative data in order to drive stakeholder alignment in decision making. Create an enablement maturity model to help the team understand current state and a roadmap for continuous iteration and optimization.

How do you do this? It really depends on your organization. Every company has unique challenges and goals, so you need to think outside the box.

Sales enablement best practices will get you started, but you need to be able to think strategically.

Stephanie Middaugh, Sr. Sales Enablement Manager at Divvy, says it well:

Do what’s right for your business. Every business will require something a little different from Enablement and a great enablement leader will be able to mold their previous experiences into a strategy and framework that will work for you business, leadership, and customer-facing reps.

She should know. Her company is a player in a new industry and is in hyper-growth mode. Her experience from SaaS companies, while still applicable, hasn’t been 100% transferrable. She had to leap-frog off of that prior experience while thinking outside of the box to understand how to make her reps and company successful.

Set priorities based on the org’s strategic objectives

You may feel torn between organizational initiatives and the needs of individuals. Remember, when the organization succeeds, so does every individual who works there.

So when you’re facing competing priorities, top-level goals should win. Marcela Pineros, Global Sales Enablement Leader at New Relic, stresses this point:

Make sure you’re aligned to the company’s business-critical expectations and current goals. Whatever those key goals / initiatives are, stay tuned in to them.

Beyond that, there are different ways you can approach enablement.

As long as you keep one eye on those business-critical goals, Mark Eckstein recommends setting priorities by looking for a healthy middle ground. For example, if new ARR is the metric that his work is being measured against, he looks for specific areas that will push that needle, taking into account the needs of the sales team.

Marcela doesn’t necessarily look for a middle ground. For her, it’s more about validating that the project will move the needle on your goals:

  1. Does it align with the organization’s key strategic priority?
  2. Will it make the biggest possible impact on that priority?

She says you may need to say no to initiatives that don’t align. Of course, you’ll need executive air cover to make those kinds of calls, but it helps you stay on track, pushing the initiatives your executive team cares about most.

RELATED: Sales Training is Only One-Third of What You Need to Be Doing for Sales Enablement

Define in advance what success looks like

Devin Daniels says, before kicking off any project or initiative, you need to define what success will look like and identify any leading indicators to measure your progress along the way. Be sure all relevant stakeholders and leadership have bought into this definition.

It’s easy for enablement teams to become a catch-all for new projects, and even easier to start a project without fully asking yourself, “How are we going to know if we’re successful?”

Creating a shared definition of success with your stakeholders ensures there are no points of contention or confusion when the project wraps up, and it provides you with a constant North Star throughout.

It’s also important to identify any leading indicators, because that gives you a way to track progress during the project, rather than having to wait until it’s completed to understand whether it was successful.

For instance, do your top one-percenters perform better in onboarding? Or do they have a book of business when they start?

Become a strategic partner

Saying no may seem like a hard line to draw. But it supports a key best practice, and that’s to be seen as a strategic partner.

As Marcela says,

Training is typically seen as a money pit, but in reality, it can help the company make money. You need to see yourself as a contributor to the company’s bottom line. It’s a new mindset, but it’s key to creating a successful sales enablement program.

You need to come to the table with solutions. Think in terms of how you can contribute from a people side, and what you can do to open doors and facilitate growth.

Chad Dyar, Head of Field Ops and Enablement at Hearsay Systems, adds that Enablement needs an end-to-end plan for initiatives that require collaboration, process, technology, and training, and also for those that change management skills.

When Enablement owns one piece, it’s easy for things to get deprioritized or go off the rails, but when it has the lead — whether it’s for onboarding, coaching, content, or any other change requiring a behavioral shift — there is a much higher probability of a successful launch.

Enablement needs to be that kind of a strategic partner, and that requires a seat at the leadership table. Otherwise, it becomes a function dedicated to fire fighting instead of driving strategic growth and cultural change.


Enabling a revenue team requires insights into the overall challenges, priorities, and personalities of the revenue organization. Often Enablement becomes an isolated order-taker, managing what Chad calls the “feel-good queue” of projects.

Feel-good projects don’t have a strong ROI but seem like the right thing to do. When Enablement is tied to the leadership of the revenue organization and is measured on the same goals as the rest of the revenue organization’s leaders, it becomes easier to prioritize projects as well as measure their impact overall.

Hire a diverse team for enablement

As you can see, sales enablement covers a lot of ground. You’ve got to deliver on a wide range of initiatives and projects.

That’s why Chad recommends hiring a diverse team of problem solvers who are willing to get their hands dirty.

Look for people with a background in sales, marketing, customer service, training, analytics, and operations. Then, when you scale your team, you have a brilliant chemistry set of problem-solving talent that can conceive, build, and measure a solution for any task they are assigned.

Sales Enablement Execution

Execution is about the psychology of education, instructional design, thinking through the information and skills that need to be transmitted, and finding the best way to do it.

While most people understand this, when executed, it often ends up devolving into a strategy of bringing people on-site and talking at them for 6 hours.

That doesn’t win friends in any situation, but now, when workers are remote, tolerance is much lower for this approach.

Your remote workers have far too many distractions. Like this man, a subject matter expert being interviewed in his home:

Think about all the distractions you deal with when working from home: pets, children, partners, and roommates. Not to mention the normal flow of work emails and messages.

Marcela makes a good point:

We need to draw from the best practices we know from ages ago, then capture attention and engage with relevant ideas. These are going to be more effective today — especially when you’re working with a remote team.

Start with knowledge management

Marcela believes (depending on how large the company is) you should start with knowledge management. Ideally, you want to capture the lessons learned from the field, review and harness them, then crowdsource the best resources — sharing them across the organization — so everyone can benefit from them.

As the program gets bigger, though, content itself can become a problem. Marcela advises figuring out the best vehicles for getting the content out to people from Day 1. Create systems and processes that scale, so as your program grows, you’re able to manage the growing amounts of content you’ll produce.

How do you scale your program? Here are a few ideas…

Build great relationships with potential stakeholders

It’s hard being an army of one. Mark Eckstein is a one-man team supporting 40 on the sales side and 15 in customer success — and every new hire goes through 2-week or 1-month training.

There’s no way he can run all the sessions himself. So he relies heavily on subject matter experts throughout the organization.

He recommends building trust by building relationship with them before you need to call on them.

Build trust with your experts. They need to understand that you’ll help make them successful. To do that, you need to make small investments.

Set the stage for what enablement is, and assure them you won’t create more work for them, that partnering together will actually make their life easier.

Invest in your trainers

Not all managers are good at coaching. Because of that, you should also develop programs that enable your managers. Basically, coach managers to coach.

In the same way, your subject matter experts aren’t going to be professional teachers. You need to work with them to help them be comfortable organizing and presenting their expertise.

Also, they may not realize that trainees will grade their training sessions. A simple but thoughtful gesture, according to Mark Eckstein, is to make sure instructors know what they’ll be graded on.

Recommended Reading: Design for How People Learn book, by Julie Dirksen

Experiment constantly with short feedback loops

Mark Eckstein recommends not falling in love with your initiatives or programs. They won’t all work, and there’s no way to know until you test them.

The key, he says, is short feedback loops. That way, if something isn’t working after the second cohort, you can quickly pivot and update your programs.

In fact, he has about a 50% new program for each cohort. Every training session has small turnarounds based on the feedback loops he’s built into his workflow. As questions come up, he makes changes on the fly before the next cohort.

Another way to build feedback loops into your workflow (especially if you’ve got a large team), is to assign a liaison to each function or group within your organization.

Marcela Pineros takes this approach, providing a conduit to each group through a point-person on her team. She explains,

They’re the brokers. They’re the feedback loop for my team. That makes it easier for me because they regularly meet and have discussions. I can easily keep tabs on best practices and integrate them into our program.”

Of course, that’s harder to manage as a one-person shop, which is why it’s so important to set priorities that align with the organization’s strategic focus.

Less is more when it comes to content

When it comes to sales enablement content, every expert I spoke with agreed on this point: Less is more.

Mark Eckstein recommends short snippets of content in multiple versions or teaching styles. The idea is to identify your sales story as told by different best sellers as quickly as possible.

Think of these as knowledge slices.

I take live calls from all the top salespeople across the organization, each selling to different sales stages. I’ll cut their conversation into snippets. After I’m done, I’ll end up with 400 of these knowledge slices. They’re just two minutes on average.

So I may have, say, 14 examples of different salespeople talking about integrations.

This way, reps can watch how each rep sells across personas, company sizes, sales stages, and how they talk pre-pipeline, during negotiation, and after the close. Listening to these snippets one right after another, it’s easy to see how they each handle it.

You can expect each call recording to give you 20 or so snippets. Then you need to organize them so it’s easy for sales reps to find the examples they need when they need them.

They’re going to listen to the rep’s voice, and how the prospect asks certain questions. This helps reps understand the trends, as well as how prospects are evaluating the product.

Classes should also be short. Think 8-minutes max for each video. You can make them with tools like Gong or Chorus. But it may be smarter to create them yourself.

Mark says he likes to own the content, which doesn’t happen when you’re leaning too heavily on any one tool. His goal is to make sales enablement content available to everyone on the team, regardless of whether they’ve got a seat on [your preferred tool].

Leigh Smith agrees that bite-sized, interactive chunks of content work best — they’re easiest to digest and retain. He also recommends that you leave your reps with something at the end of the session that they can refer back to. It could be something as simple as conversation starters for a cold calling session.

Develop content for different learning styles

Everyone has a different learning style — whether visual, audio, or tactile — so you need to develop content for every type of learner.

That’s a given, right?

Well, Leigh Smith takes that one step further. He believes each session you deliver needs to be available in several different formats. He wants his presenters to be keenly aware of their audience and be agile enough to adapt their points to that audience.

That means if you are delivering a PowerPoint presentation, you may have only one person in the room who’s engaged. It’s important to be prepared to deliver the most critical pieces of information in that session in multiple ways — because it’s the only way to ensure you get your message across to everyone on your team.

That’s one reason Leigh doesn’t do training for huge groups. He believes the most effective way to deliver coaching/training is in small groups in which you can go at a slower pace. He recommends using the pace that’s dictated by whatever team you’re working with.

Better still, group team members by how they learn and split up your training so you can deliver the training in the way they learn best. That way you can be sure each group is engaged in what you’re delivering.

Develop champions and success stories

As humans, we resist change, especially if we’ve been doing something one way for years. Breaking bad habits takes continuous education and positive reinforcement.

That’s why Leigh Smith says it’s not enough just to deliver the training. You have to prove that it works. To do that, leverage success stories and develop champions that you’ve identified within your own sales team.

Sometimes the quickest way to get people to buy into your sales philosophy is to find two or three champions who start outperforming everyone else. Once that happens, the rest of the team will sit up and take notice of what you’re saying.

Get buy-in from sales managers and reps

Robert M. Peterson, Ph.D. suggests creating unique programs, like “Monday Is Deal Day!” To make this work, create a mandatory field in the CRM where reps describe their wins and why they think they won it. The largest deals will then get featured in the weekly communication for the entire revenue-generating org.

That tells you who is performing well and what they’re doing that’s different. It also gives you success stories that validate what your sales enablement programs.

Think of yourself as an information broker

As a trainer, you’re actually an information broker. That’s how Mark Eckstein views it, and it’s the secret sauce to his programs.

As an information broker, he recommends:

  • Stay in the forums. Soak up all sales/marketing chatter. Take time to read all Slack channels, so you can see trends, challenges, and successes.
  • Go to all standups and forecast meetings. If you can target where reps are getting frustrated, you can provide workable solutions much earlier.
  • Look for what’s going on outside the structured chain. Soak up everything going on in the customer success org, so you can see the communication channels for getting things done and alleviating frustration.
  • Send templates to employees outside the sales team. You never know what will be relevant to other teams. Scale out to what will be successful across the org.

Tanya Smallwood has a similar approach. To stay informed, she says, Sales Enablement needs a seat at the table where marketing and sales decisions get made.

Sometimes that means you just insert yourself into those conversations whether you were invited or not. Taking all the marketing data, messaging, tools, and content and turning that into usable, consumable assets that sales teams can easily leverage during onboarding and in sales cycles — that’s what success looks like.

Marcela Pineros says the thing she hears most in her org is, “I need your help getting the word out about [an idea]” or “Can you help amplify [a piece of information].” This is a struggle for every information broker. The New York Times struggles with it too, she says.

How do you do it?

Realize that people will self-select the topics they’re interested in. The misconception is that we should push everything to everyone. That’s just noise. Create categories for the information. Make sure it’s easy to pull out or find the information people want and need. And make sure you maintain one version of each asset, so it can be kept updated and accurate.

Be aware, no tool does this for you. Which is why Marcela relies on Google Drive for organizing content. While there’s no easy solution, she’s found a system that’s effective and efficient.

Sales Enablement Governance

Governance is about how you’re demonstrating what you’re achieving. It’s also about how you’re updating content on a regular cadence, so it’s always fresh and relevant.

Issues you deal with in governance include:

  • Tracking
  • Coding in HTML
  • Link rot

Marcela Pineros emphasizes that as a company grows, it becomes more and more difficult to govern all your links and connections to other data sources. It’s vitally important to set yourself up for success. You want to set up systems and processes that aren’t manual or ad hoc.

Create scalable systems and structures

There are some terrific sales enablement tools, vendors, and partners. But once you lock into one, it’s hard to change.

That’s why Marcela recommends Google Drive as an agnostic content repository. It’s locked down, and sharing rights are carefully controlled. Everyone can view a resource, but only document owners can edit them. Then, you only have to keep one asset updated.

Within your training, always link back to the original document, so you don’t have duplicates that need to be maintained and updated on a regular basis.

Ryan Donohue adds that tools are only good for automating a perfected process:

Enable reps with processes that allow for creative and innovative authenticity, so they can help you perfect your processes. This gives execs the proper data points to seek out tools to yield greater results.

Every objective needs to have a measurable goal

How do you demonstrate your value to the organization? You need to be tracking outcomes — specifically, the outcomes that prove you’re meeting your organization’s goals.

RELATED: Measuring Sales Enablement: The Metrics You Need to Assess Success

As we mentioned above, you need to know what you’re measuring before you ever kick off a project. The challenge is figuring out what’s measurable.

Mark Eckstein says, when it comes to evaluating reps, you can only really track their activity: open opportunities, pipeline to date, etc.

Sales reps often have 150 activities a week. You need to know how they’re performing against those activities. It’s a good idea to create a template to measure their performance. Then share it with the entire team, so they know what they’re being measured on — and how they compare to other reps. That sets expectations and keeps everyone informed on the progress they’re making.

Think in terms of the Employee Lifetime Value. As Mark Eckstein says,

Everything we do adds to the full value of the employee. And if they know that’s our aim, they enjoy the experience more. It all boils down to clear communication. That, and reducing barriers to your reps achieving their numbers.

Getting a Handle on Sales Enablement

Sales Enablement is such a broad field, when I asked SE pros to share their best tip, I got some blank stares. There’s so much they could share with me, they didn’t know where to start.

But a strong sales enablement program can really be grouped into three areas of focus: strategy, execution, and governance. Breaking it down like this gets you to the essence of what this function needs to do well.

That makes it a lot easier to understand the scope of the job and what it takes to drive real results for your organization.

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