Bryan Grobstein, then-Director of Revenue Enablement and now Head of Revenue Strategy & Enablement at Lunchbox,  delivered this presentation at the Revenue Acceleration Festival in March 2021.

Enablement is one of the fastest-growing job descriptions in the world and has become even more of a priority for companies experiencing hyper-growth due to the desire to define, deliver, and document scalable revenue playbooks that will help achieve repeatable revenue and additional funding.

In this article, I’ll share my experience being part of, and leading the charge on, the implementation strategy for revenue enablement when it previously didn’t exist.

My name's Bryan Grobstein and I am the Director of Revenue Enablement for Lunchbox. I have spent my career in revenue operations and enablement working at predominantly hypergrowth companies and several early-stage startups.

All of my roles have, for all intents and purposes, been as the inaugural enablement team member. At Groupon, I joined a small team of internal transitions and promotions. And everywhere else, it's been the first and only, sometimes in perpetuity, contributor to the enablement function.

The rise of enablement

Enablement is probably one of the fastest-growing job descriptions in the revenue world. You might notice it as a trending topic on things like LinkedIn, and all of these amazing organizations like the Sales Enablement Collective popping up to support this growth.

You would have been hard-pressed to find a revenue or sales enablement function at an early stage startup five years ago. It's an arbitrary number, but at the time it was sales training and development or learning and development.

It's recently become much more of a priority for seed-funded/series-A funded companies experiencing hyper-growth.

It coincides with that desire to define, deliver, and document scalable revenue playbooks that will help achieve the repeatable revenue that warrants another round of funding, whether you're going from C to A or A to B, or the ultimate goal of an equity event or an IPO.

I'm excited to share my experience after being part of or leading the charge on the implementation strategy for revenue enablement when it previously didn't exist within the business.

The ecosystem

One important precursor to all of this is clearly delineating the revenue leadership ecosystem.

While there is a lot of grey area and overlap in the startup world in particular, the defined swimlanes are core to your team members. All team members should be cross-functional and within the revenue hierarchy, so that they understand the internal escalations, resource requests, accountability around deliverables.

The ecosystem

It reduces the redundancy and allows key stakeholders to align on programmatic solutions to common revenue problems. You never want to be in a situation where team members are working on solving the same problem and they just don't know it.

It drives greater levels of collaboration and communication as well to ensure that accountability on the deliverable is owned by the revenue executive team, the revenue ops and enablement group, or your frontline revenue leaders.

What are the differences between revenue executives, leaders, enablement, and RevOps?

This is radical candor in the spirit of transparency: I saw a similar Venn diagram at a seminar I took recently and couldn't help but steal the concept so I could communicate it to my internal teams, to explain what I do relative to my colleagues and the other leaders within the revenue organization.

Revenue executives

The sales executives, the revenue executives, whether you have a CRO, a VP of Sales, or any variation thereof. But when I say sales executive, I truly mean that executive level, potentially the C-suite even. They're the culture setters. The culture keepers might come from the bottom up.

The original presentation of this Venn diagram included the phrase "culture eats strategy for breakfast", because as much as we're all an amalgamation of the strategy, leading the charge with the revenue teams around how we are going to scale revenue in terms of having a people-driven approach to solving the problems, it's really important to have and exhibit the culture from the top down.

They determined the right vernacular, the right verbiage, the right definitions, and the ultimate blessing at the very least of the sales strategy.

Revenue leaders

The right side at the bottom, is where we have the revenue leaders. The planning, the execution, the coaching. The front-line mentor manager is extraordinarily important.

They provide things like execution, using the KPIs and the numbers and the measurement of the business, the lead, and the lag to ensure there are success metrics we can leverage for sales talent, sales coaching, and performance management.

Rev ops and enablement

Where we live, in the enablement function, can be an amalgamation of ops and enablement. It can be just RevOps that has enablement, or enablement that partners with RevOps.

It's tools and technology. Not only the sourcing, but also the implementation, the coaching, the management, and the evolution. It's also about ensuring there are job aids, resource guides, and that there is adoption and adaptation of those tools into the sales process.

Sales productivity is a huge part of what the revenue enablement and revenue operations team will do, not only as it relates to those tools and tech, but as it relates to creating structures for effective messaging, a common sales methodology as an example, and efficiencies through automation.

Sales intelligence through distilling of the information that comes from some of the systems and tools. For example:

  • What are your conversions from outbound cold calls to first contact?
  • From contact to set?
  • From set to held?

Utilizing those metrics to have a prescriptive learning experience will help fill those skill gaps and drive more success metrics.

A cross-functional approach

This is a Venn diagram, they're intersecting circles because there has to be a collaborative approach a cross-functional approach, even though they're within the same business unit, to ensure long-term sustainable, repeatable success.

Revenue operations & enablement: connective tissue

I'll dig into a lot of these a lot deeper later but ultimately, I want to focus your attention on the revenue operations and enablement.

It is truly the connective tissue, it is what brings all of this together within revenue and also connects us with other business units like marketing, product, finance, and a variety of other things.

As a sales enablement professional, as a revenue enablement professional, it's fundamentally about creating the space for a growth mindset and the evolution of a living and breathing playbook or revenue playbook

Your desired outcome is both bi-directional, through these circles and outside of these circles, and reciprocal, it's give to get. It's not only a sales tactic, but it's an internal communication tool as well.

That being said, jumping into the connective tissue, there needs to be top-down advocacy for revenue programs from those revenue executives I already mentioned, along with a concerted voice from every thought leader.

Building partnerships

The only way you get buy-in from those frontline team members is when everyone is on the same page and that page is within a playbook. Enablement can influence the initial trajectory of the go-to-market process. But the ultimate outcome is mitigated by the coaching across the entire buyer’s journey.

While enablement plays a role in that and creating things like rubrics and scorecards and providing tools within potentially a learning management system to execute that coaching, a lot of the coaching comes from the frontline sales managers, the revenue management team. There needs to be cross-functional alignment across the entire ecosystem.

Connective tissue


To kick off these partnerships and that alignment, I typically conduct discovery conversations, meetings, focus groups, doing my own research, and due diligence to ultimately come to, if you need something you are familiar with, like a SWOT analysis.

Strengths that we have, weaknesses we need to address, opportunities for growth and adjustment, incremental change. These really help us determine the priorities for the implementation of a sustainable enablement program.

Something to anticipate when having these conversations is a potential, but often typical, lack of continuity in the responses you're getting, and the information you're distilling.

Feedback & requests

Bottoms up feedback, what you hear from your SDRs, AEs, technical sales reps, and sales engineers is what you need need for two categories of learning.

  1. Product education, particularly when you're talking about SaaS sales, solutions that are highly technical.
  2. Systems skill gaps. What I mean by that is the ability to effectively navigate your salesforce instance, to better understand the implications of the bi-directional sync and API integration of your different sales tools.

Mastering those can be a force multiplier within your revenue organization, and they know it. And there's a degree of confidence in their sales acumen that has them focusing their attention on building the skills around products and systems.

The top-down request or guidance around priorities is often oriented towards:

  1. Process
  2. Sales-readiness.

Have a buyer-centric, value-driven sales methodology that's guided and not about feature function. Be mindful of the competitive landscape.

Four buckets of learning

So all things being equal, there are four buckets of learning that help the team members understand how symbiotic the relationship is between these requests and that you can't have one without the other.

Stories sell

I find that win stories, post mortems, and peer-to-peer learning are the most effective ways to drive adoption of the core competencies and align around the change you are going to bring to the table as the inaugural enablement professional.

It's our job to give these subject matter experts, and when I say that I truly mean your SDRs within the organization that are on the front line talking to prospects, first. They're at the tip of the spear and they have a lot of value as it relates to enabling the remainder of the team.

Their voice is as important, if not more important (controversial statement), than the VP of Sales. We need to give them that voice and space I mentioned earlier to socialize their wins, their losses, the opportunities that we have with our organization to be more competitive in the space

Those narratives translate to repeatable revenue for the whole team. Because stories sell not only as it relates to our customer interactions, but stories sell as it relates to our internal buy-in to the organizational trajectory.

Cultivate relationships

I strongly believe in cultivating those relationships with your SDR team and SDR leadership, with your account executives and account executive hierarchy, both presale (demand generation, prospecting, and landing), and post-sale. It's super important to the revenue playbook.

  • Who is doing the implementation?
  • Who is doing the onboarding?
  • Who is doing the account management to expand and retain?

Those relationships are the primary source of new-hire and continued education confidence and competence that defines your world-class enablement programs.

All of this is with the ultimate goal of immersing myself in the business to learn and diagnose, but just as important, to build the required TRUST for ongoing success.

An example of that is meeting with both Snipers and Champions before rolling anything out. Asking explicitly for support and advocacy from ICs with a lot of influence can make or break your program adoption. Who are these folks in your org and how can you make them part of the enablement experience?

That's a little bit of being on the soapbox, but let's get into the tactical things that contribute to success.

Prescriptive tools and systems

I usually will, at the outset of my tenure or support of an organization, do an assessment of the revenue tech stack.

  • What's already there?
  • What's missing?
  • What needs to be adopted more?
  • What are the usage metrics?
  • What needs to be adapted?

My favorite binary - adopt and then adapt.

  • What needs to be adapted to the workflows that are exclusive to our organization?

It's usually a collaborative effort if there is disparate functions for operations; revenue operations and revenue enablement, so everything is in alignment and there's a sync between every step of the journey where we can document, track, and report on as much of the data for our GTM function.

Common challenges

I have some pretty strong preferences based on past experiences. But it's always important to keep your ear to the ground on what is innovative, what's new, what's revolutionary, if you will, in terms of driving greater efficacy and efficiency for your organization.

It's easy to go with what you know. You've either been an administrator of a tool in past roles, or you've sourced and have relationships with a business that you've partnered with.

Instead, challenge yourself to research competitive and innovative tech

Within the first 60 days, I typically like to ensure that we have that proper license allocation, user adoption, contract terms, integrations, reducing feature redundancy, and having a prescribed workflow that's defined in the playbook with job aids and resource guides.

Areas of opportunity

This diagnosis usually helps identify areas of opportunity to improve the actual workflow the sales team and account management team are executing on a day-to-day basis.

Driving 1% greater efficiency could have a multiplier effect in terms of revenue attribution to each of those roles or steps in the journey.

I've personally seen mediocre reps, from a skill set perspective, do two times more in revenue than great reps that have been exceeding quota throughout their career but only because they've mastered the combination of Zoom info, plus outreach, plus LinkedIn Sales Navigator, plus Salesforce.

The level of efficiency you can get, throughout your day, your week, your month, will get you to that accelerator in your commission plans, to that extra layer of quota attainment in your forecast.

Key takeaway

Hypergrowth at an early stage startup cannot happen without enablement and technology tools and the automation that comes along with it.

  • Do we have what we need to scale with velocity?
  • Increasing the pace by which we achieve our goals?

Think steps ahead and make investments to ensure the revenue wins are part of a scalable playbook. Because if you're operating off of Google Sheets and Google Drive and shared things that sit on people's desktops, it's inevitably not going to scale.

The mission

The next thing is really what I hang my hat on. This is the thing I bring with me no matter where I go, as it relates to visualizing and defining my enablement brand identity.

I developed it after survey results at a former employer, Mindbody, showed the new coursework for our team members joining the organization was categorically overwhelming.

The exact definition or phrasing that was used in a lot of the survey results was "We're drinking from a firehose." We needed to make 100 hours worth of learning much more approachable.

This visual really set the stage for where a topic fits into the grand scheme of your learning experience, both as a new hire and through continued education.

The mission

Four buckets

Above, you see the four buckets; sales acumen, product mastery, industry education, and the institutional proprietary knowledge that's necessary to know what you're doing here at this business.

The mission statement is holistic in nature. But again, it's a big part of what I do, who I am as a revenue enablement professional. It has that key binary of I want people that are proven performers to come in and understand we're not going to disrupt their path to success.

Hopefully, as you brought them into the organization, they've done well before, and we want them to do the same here. We want them to take some of the guidance, the best practices, and adopt the concept and adapt it to their own style.

Intentional redundancy

When we drive home these core competencies, there is inevitably a need for intentional redundancy in the learning process.

It's perfect practice over and over again that allows many revenue professionals to better understand the small incremental changes they can make to improve performance by 1%/ 5% / 10%, even if they're already overachieving.

The learning process particularly for new hires can still be daunting because of the volume of material they have to absorb in such a short period of time. The ramp to proficiency can be three months, it can be six months, it could be nine months, depending on the deal size and complexity of the product you're selling.

The categories of learning, the layers of complexity, is your responsibility to ensure they feel confident and competent in actually executing against these principles.

How do we do that?

We do that through a series of courses that are topical, kinesthetic, and practical.

The message here is that learning is not an event.

Often, enablement feels like "I identified a topic. I created coursework on that topic. I delivered it. Then I'm going to do the same thing when another learning request comes in or another fire needs to be put out in terms of skill within the business".

Impact comes from interaction and ongoing development of executing these concepts. If you've read something like Outliers by Malcolm Gladwell, he talks about 10,000 hours, it's an anecdote. If you practice anything for 10,000 hours, inevitably, you are going to master that.

The reality is it's not about just doing it for 10,000 hours, it's having the honest self-reflection and being vulnerable enough to say, "I need to do it again and again and again, and try this little thing that's different and that little thing that's different."

Building infrastructure

That's where these four steps come into play.

Building infrastructure


Naming conventions can differ throughout organizations, but prework to me is an asynchronous e-learning experience that is more of a microlearning, it's topical, it's conceptual, less than 10 minutes that they can do on their own time.


Then you bring everybody together that took that learning into a virtual or physical room to talk about those concepts and how they practically will apply them to their role and responsibility. This is where the real learning comes in.

This is where people will find the concepts resonate more, that they can steal, for lack of a better phrase, the learning from other people. The little turns of phrase, the ideas they have, the creative approach to putting those things into practice, tend to surface during these discussions.

Best practice

The best practice and certification steps are all about inspecting what we expect. These are role-plays and shadows and using conversational intelligence tools like Gong and Chorus to audit whether or not the concepts are actually coming to fruition, if you will, in prospect and customer conversations.


Certification is more of a benchmark and saying, "We are confident in your competency, and that we can say you have mastered this step or this process, this learning objective".

Sales methodology

The next big thing is in your inaugural sales enablement 90 days, I would say is implementing a sales methodology that has a brand identity, that has definitions, that is substantiated in social science and psychology is extraordinarily important. It's one of the top three things I would make sure I'm implementing at the outset.

Developing trust through buyer enablement

I have this amalgamation of all of the things I've learned from Sandler to Selling Through Curiosity to Straight Line negotiations to Challenger to Miller Heiman. All of them have influenced what I teach.

Some of it is my own, it's my style, and you very much can make it your own depending upon how the organization wants to implement sales methodology.

Some of it’s going to be off the shelf, and that's fine, too. These are all tried, true,  and tested, that you can get support from, like a franchise as an example to support your implementation of a Sandler methodology.

New hire program calendar

The last deliverable is the new-hire experience. High-velocity organizations have high-velocity hiring experiences.

New hire program calendar

My expectation is not that you're going to read this eye chart, it's more so saying you have a prescriptive experience that has that asynchronous opportunity to learn on their own but also have a guided journey through the four buckets of learning you've defined.

So they can be certifiable, in a good way, not a bad way, and feel they are prepared, confident, and ready to interact with your prospects.

Understanding the institutional knowledge of:

  • Who are our buyer personas?
  • What is the buyer's journey?
  • What systems do I use to be more efficient? And
  • What methodology do I subscribe to that is ubiquitous across the organization where my coaches, my managers, my mentors are going to use the same language so I can improve over time?

Data-driven decisions

I really, really strongly advise having some sort of way to benchmark your success. I've blacked out the names here but this is many, many years ago.

If you have a data visualization tool, if you're using Salesforce and have the right fields populated, this is a much easier exercise.

Data visualisation

But being able to see what revenue is being brought in, by whom, and how do you cohort them? By manager, by office, by segment, by territory, whatever it might be, and it helps you better understand how you are going to improve that over time and evolve your enablement programs.

This is about distilling the data - super important. Particularly as it relates to measuring the ramp to proficiency, which is likely how you're going to be measured in enablement.

Sales readiness framework

Defining your end-to-end sales process readiness framework. Again, this is something I was very fortunate to be exposed to at my time at Mindbody, where my boss showed me the sophistication and the complexity of an effective revenue organization.

Sales readiness framework

Enablement is part and parcel of this but it's not a one-person show even if you are a one-person enablement team, you've got to cross-functionally collaborate, you've got to partner with other team members.

Because you can't be the subject matter expert on everything.

Thank you.