Revenue Operations

Hiring a Revenue Operations Professional: Enablement

Welcome to the fifth article in a multi-part series that will help you find the perfect fit for your revenue operations team. Because revenue operations often spans technical system administration, data analytics, enablement, process management, and project management, we’ll break down the different functions to cover them in more detail.


While it is possible to find someone who can pull off all of these functions, we feel obligated to point out that placing the burden of managing all of these components on one human will not set them up for success. A team of one may save you money in the short term but consider a plan to scale the team before your workhorse shows signs of burnout absolutely essential.


In my experience, startups tend to build out client-facing organizations, then add systems support and analysts. Enablement is typically (but not always) handled “in-house” by customer-facing leadership. Sales managers teach their preferred sales methodologies, customer success documents their repeated issues and shares them, and marketing has people who specialize in various channels.


The end result is many people mirroring different “best practices” that have worked well for those managers in past positions, not necessarily the best fit for your organization in its current state.


There are many benefits to having an enablement team, and among them are:

  • A deeper understanding of adult learning theory
  • You have another set of eyes monitoring performance and morale
  • Best practices are objectively identified and rolled out across teams
  • Go to market motions become more efficient 

What Makes a Good Enablement Professional?

The best enablement director I’ve ever worked with started out as a college professor. She had years of teaching adults under her belt before deciding to pursue a more lucrative income.


This professional not only understood learning theory. She knew salespeople were already overwhelmed. She monitored people’s performance, shadowed salespeople on countless calls, reviewed tech to organize and automatically serve content, and became a trusted voice for customer-facing roles.


She was a purple unicorn.


While enablement professionals don’t have to be tenured professors to make a huge impact on a company, they need exceptional emotional intelligence, a knack for technology, and a mind for numbers. Communication and collaboration are the names of the game.

What Kind of Experience Is Needed?

If you have a large company, finding a person who has worked in an enablement field for at least five years and has a proven track record of improving efficiency is a great way to start building out an organization. They’ll likely need content writers and a creative designer to generate the amount of collateral you need to keep your go-to-market engine running as smoothly as possible.


If you’re just forming the department, it’s best to start with someone with a few years of experience and hire more inexperienced professionals to support them.


Many enablement professionals get their start as a subject matter expert or managing and training a customer-facing team. I’ve watched team members gravitate toward an enablement role naturally. They’re often the person on the team who gets frustrated by repetitive issues and solves them through documentation, training, and technology.


If you’re recruiting an in-house subject matter expert, make sure their communication skills are on point and that they’re interested in learning more about adult learning theory. Someone who hates public speaking and isn’t data-driven will be a poor fit.

Hiring an Enablement Professional

The Job Requirements

An enablement professional must have a sharp eye for opportunities for improvement with the finesse to make people feel like changing how they do things was really their idea all along. They should also be comfortable speaking in front of large crowds and can capture and hold their audience’s attention—which means they need to be able to read a room.


The enablement professional:

  • Is an excellent verbal and written communicator who lives for order and keeping things as simple as possible
  • Comfortable speaking in front of large groups in-person and remotely
  • Technology savvy—picks up product details quickly 
  • Has experience with HighSpot, Showpad, Seismic, Guru, LevelJump, Klue, DealHub.io, or other similar content management and learning management systems
  • Is an artist when it comes to presenting and has expertise with PowerPoint, Google Slides, or similar presentation software
  • Is skilled at developing and monitoring metrics that prove an increased efficiency in the go-to-market motion
  • Develops metrics to monitor employee progress and escalates to management when necessary
  • A true collaborator who knows when to bring in subject matter experts to uplevel content
  • Experience with MEDDIC or Sandler, deep knowledge of Challenger-based methodologies, and knows of SPIN, BANT, or NEAT methodology
  • Familiar with the latest customer success methodologies and has experience overseeing a knowledge base
  • Has a passion for process improvement and helping others succeed


Big Bonus Points:

  • Sales Enablement Certification
  • A Master’s in Adult Education or Adult Learning
  • A Certification in College Instruction
  • Graduate of the Challenger Development Program, SPIN Selling, or Full MEDDIC or higher courses
  • Obtained a Silver-tier or higher of Sandler Training

The Questions

Q: What is the first thing you want to do to determine our organization’s largest enablement need?

Why it’s asked: I prefer to work with an enablement professional who values input from every level of the organization. I don’t want to hear that their only approach is to get opinions from the C-Suite and upper leadership because they aren’t always the most objective. Talking to people on the frontlines will often uncover product issues or inefficiencies upper management may not even be aware of (or be concerned about).

Example Answer: I think it makes sense to start with interviewing management, but ultimately, I’ve found that people in sales, marketing, and customer success have more intimate knowledge of what is and isn’t working. Usually, if multiple people say there’s a problem with an aspect of the product, it’s worth digging into. Sometimes it’s a historical problem that has been patched, if there’s a functional workaround, or if the product team is aware of it and has a fix on the immediate road map. People also tend to be more candid about interdepartmental tensions, which helps me understand where we have problems during handoffs between teams.


Q: Which sales method would you suggest we use for a simple sale cycle that spans only a few weeks?

Why it’s asked: Some methodologies lend themselves better to complex sales cycles, while others are meant to quickly qualify a prospect. If someone suggests Challenger or MEDDIC here, they aren’t familiar with the tactic (unless they have a very abbreviated version they developed and provide ample explanation).

Example Answer: I would suggest SPIN, BANT, or NEAT methodology here. Here are a few examples of qualifying questions at each step...


Q: What kind of sales methodology would you recommend for a six-month sales cycle?

Why it’s asked: Again, this is just to confirm they know their stuff. It’s an easy verification.

Example Answer:  There are several methods that could work depending on how technically complex the sale is. MEDDIC, Sandler, or a form of Challenger solution selling could be a good fit.


Q: Do you have a preferred pitch format?

Why it’s asked: I’m looking for specifics here. Are there certain people you follow? Do you prefer a deck, or do you prefer a more question-based approach? Why? There isn’t one right answer, but I want a clear reason for whichever methodology the enablement professional prefers.

Example Answer: Discovery is everything. I want to make sure the sales team understands the issue that the prospect is trying to solve, what kind of pain that issue is causing (Lost revenue? Lost productivity?), and what is motivating them to change now. While we like to think we’re all rational decision-makers, the inverse is true. We are emotional beings who rationalize our decisions, which is why it’s so important to nail down the profile of your prospect before you jump into a canned deck like a robot. It makes the prospect feel like you actually care about them, and I’ve found they’re twice as likely to be open to a second call.


Q: What are the key considerations when creating content for a knowledge base?

Why it’s asked: The first thing I want to hear from my perspective employee is “audience.” I want them to understand how critical it is to know who they’re supporting with the knowledge base before we dive into best practices.

Example Answer: Is this for a customer audience? Or internal knowledge base? How realistic is it for customers to resolve their own issues (How technical is the product and the buyer? Are we talking coding updates or UI clicks?)?


Q: Have you improved go-to-market efficiency in your past positions, and which metrics did you use to measure your progress?

Why it’s asked: Proving value is, unfortunately, a fundamental need for any role. If the enablement professional is focused on marketing, I expect them to look at lead volume, conversion rates, and pipeline generated. If they’re focused on sales, we want them to look at sales stage conversion rates, time to productivity from date of hire, and percent of sales force achieving quota. Customer success enablement should be looking at ticket volumes, which tier of support is involved in what volume of cases, and customer churn metrics.

Example Answer: In my last sales organization, we decreased the average time to productivity from six months to three months. We did this in three ways. We developed a hiring profile, we developed metrics to determine productivity early in the game, and we provided more specific product training. We focused on key objections instead of the features that internally we thought were cool. It was critical to focus on what our targets cared about, even if it wasn’t as sexy.


Q: What kind of metrics do you watch to gauge sales engagement?

Why it’s asked: I want to know if my enablement professional has a method they’ve seen work in the past for identifying sales reps who are going to churn.

Example Answer: Each company is slightly different, but we found at my last company that looking at a variety of pipeline, quote activity, and meeting metrics helped build a reliable picture. We knew that if people weren’t generating quotes, pipeline, or setting meetings were on their way out of the organization. An abnormally high number of quotes signaled a problem understanding the customer’s needs. Low pipeline generation either indicated the territory was very green, or the salesperson wasn’t balancing a need to keep their pipeline healthy while trying to close.

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