Bryan Grobstein
Table of Contents

Bryan Grobstein heads Enablement & Strategy at AnyRoad, a company that combines end-to-end event management with rich feedback and analytics to measure the impact of your experiential marketing strategies.

In the interview, Bryan talks about how enablement can be a changemaker but needs both top-down support from leadership and bottom-up support from reps to be truly effective.

(‍This conversation has been edited for length and clarity.)

Elevating enablement with the C-suite

The way you go about elevating the role of enablement will depend on a number of factors, such as the size of the organization, maturity level, and other such variables. 

In this context, I focus on the binary of depth and breadth in your skillset or job description. 

Specialists focus on depth. How skilled or invested they are in terms of the typical deliverables or KPIs of the enablement function? 

Breadth is thinking about how your expertise, either historical or within the current organization, can apply to other functions when you are not carrying a quota or generating revenue. 

For example, consider how sales enablement can interlock with product marketing. Or working with channel partnerships or integrated partnerships to find ways to generate revenue outside traditional go-to-market motions. 

Also, it's important to evaluate revenue operations or strategy by directly looking at current trends. Tools for data visualization and business intelligence can help chart new directions. What can we do differently from before?

Enablement needs to be a changemaker and develop a kind of business plan. There's a gap in what we're doing today. Here's where that gap is. And here is a strategy to fill that gap.

Let data guide your actions


As an enablement professional, you're closely tied to the folks in the field. This allows you to be a conduit or the voice that advocates and champions various causes based on what you see and hear. 

For instance, conversational intelligence tools allow you to understand what your teams are saying, what they're hearing, their challenges, and so on. Not just in their day-to-day job but how easily they overcome challenges regarding product and feature requests. 

Some organizations that find their sweet spot with ICP and target personas often go deep into those and find a lot of success. But, as the market saturates, they hit a tapering effect. It’s time to change direction. 

What is a different persona we can go after based on designation and skin in the game relative to the problems we solve? What other segments, industries, or geographies can we focus on? How can we assess these metrics? 

As an enabler, you're facilitating inbound BDRs with visibility into the types of businesses coming through the inbound funnel and their associated trends. You’re also seeing current trends when looking at opportunity creation and their different sources, whether BDR sourced, inbound, AE sourced, or channel partner sourced. 

As you identify these trends, you may see that only 5% of the pipeline is associated with a specific cohort. Could it be 10% or 15%? Here are the questions to ask:

  1. What's the serviceable market within that category?
  2. How do we experiment with existing messaging, content, and collaterals in that category? 
  3. How much do we have to iterate on that messaging, content, and collaterals? 
  4. What would be the social proof we could use to create that relatability? 
  5. We do great work for ‘X,’ where can we go next based on whatever is adjacent or intersecting with that? 

Enablement is uniquely positioned to help move opportunities forward in this way.


Enablement is selling internally

If you’re an enabler who does GTM enablement or revenue enablement, your audience is not just sales or people who are KPI-driven or have quotas or targets. 

People outside that world often see enablement materials as having a sales bias. They might think it’s a sales presentation, not applicable to their day-to-day responsibilities. It’s your job as an enabler to sell them your recommendations or initiatives. 

Sales skills are people skills. 

Enablement needs to manage people and sell internally. For instance, if someone manages a team of 12 and you're trying to get them to adopt a new concept, use a new tool, or get behind a specific goal. All you’re doing is selling—that's the whole job.

How to unlock rep adoption

Change management is complex, no matter who the end-user is or how exciting an initiative is. If it's not in the top three things that your sellers (or whoever you are targeting) are focused on at any given time, it is unlikely to be a priority for them. Here’s what you can do instead.

  1. Involve your leadership

    Buy-in starts top-down because it's going nowhere if your leadership isn’t interested. The first thing to do is to get that buy-in and commitment from your leadership and your GTM leadership to say, “We are going to advocate, endorse, and hold people accountable.” 
  1. Identify your champions

    You need buy-in from the bottom to get the project up and running. You need to identify your champions and snipers. Your champions and top performers are those with a growth mindset. They're scrappy and will look at a new approach and say, “I have nothing to lose. I'm going to try those things and see how it goes.” 
  1. Leverage your top sellers

    When discussing the cohort of a revenue team, ask who's generating the most revenue and closing the most deals. Those are the people you need to have as part of your instructor-led training contributing to sessions on thought leadership. Pull them in beforehand and have them contribute to the content. 

If you can get people to start trying things and it works, you don't need to revisit it. The reps you train will tell their friends, who will tell their friends. That's how a trend starts. That's the goal.

Most adult educators know that less than 15% of what they present in an instructor-led classroom will be retained, and an even smaller percentage will be put into practice, making it important to identify the major priorities. 

What are the North Star changes that we're going to implement within the organization? How comfortable are we that the remainder of the list will be an afterthought? We need that clarity of thought.

Failing forward 

I am still a big proponent of failing forward, where adults learn by failing and figure out how to improve through those failures. 

A classroom session, whether virtual, live, or recorded, could be asynchronous learning where you send reps Gong calls, recorded training, quizzes, certifications, and more, to aid learning. While all of these are necessary, a better option would be:

  1. Give your reps a series of low-risk leads to call so they can figure out your pitch. Then sit down with them and go over what happened. 
  2. What did you learn? What will you do differently? 
  3. Now, ask them for the pitch they've done 15 times in front of someone who said no. 

These types of experiences create memorable and practical learnings. People with a growth mindset looking to get better will look at this methodology of teaching and growing as a way of changing their core competencies.

Being successful is about competence and confidence. Let's create a space where our reps can fail forward. Failing in these moments doesn’t impact the business much. Also, it is better if they learn from their failures than whatever benefit we would've received if they hadn't.

Creating space for learning is important

Often sales reps, CSMs, BDRs, etc., end up hyper-focused on goals, becoming outcome-oriented. There's a lot of pressure to meet goals and KPIs based on where in the customer journey you come in. This eventually turns into being unable to find the time to grow. 

A part of being in enablement is blocking the time, resources, and space necessary for learning. This could range from putting time on the calendar to sharing an article or commenting on a Gong call. 

Also, people interchange training and coaching when it should be individualized coaching. For instance, how are your reps formulating their learning objectives? Most organizations have enablement put slides together with the topic, the agenda, and the learning objectives. 

Informing your reps of the learning objective is myopic. 

We must ask them, “What do you want to take away from this learning experience? If it's nothing, log off.” It sounds cold-hearted, but we don't want to waste our time or theirs. If your reps feel they know this or it doesn’t apply to their role, it's up to them and their direct manager.

Training and enablement need to be heavily involved. Executives must be aware and contribute in some capacity, at least by providing endorsements and the core competencies of being in traditional enablement. This includes instructor-led training, deck creation, collaterals, and everything that comes with being a formal educator.

If you're not working with your audience one-on-one, it's a problem. 

The first step is intent

When people say, “I'm not good at ‘X,’ or I can be better at ‘Y,’ or I’m going to try something new,” it comes from a place of emotional vulnerability. While most people would agree there are opportunities to improve, investing in those gaps is not easy. 

Putting the time, effort, and energy into your biggest area of opportunity is hard. 

What's the number one priority for me to get better? I will change how I go about the hardest task/skill. If you can say, “I want to make a change,” then it’s just a matter of identifying that change. 

Accountability buddies, peer mentors, or coaches provide so much opportunity for a two-way street; everyone learns from everybody. For instance, the most junior person in sales can teach something to a seasoned rep with 20 years of experience, and vice versa.

In conclusion

Whether you generate revenue or not determines how valuable you are to the organization. As an enabler, you need to find a way to draw some correlation between the work you do and P&L. Be the voice that advocates and champions various causes based on what you see and hear. 

Feel free to tune in to this interview on Spotify or Apple Podcasts. If you prefer other platforms, simply click here to explore more options. Happy listening!

About the author


Bryan Grobstein

Bryan Grobstein heads Enablement & Strategy at AnyRoad.

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