Dave Lichtman

CEO and Founder , Enablematch

Interviewing for Enablement

Accelerate: In your opinion, what makes a candidate a good fit for a sales enablement role? 

Dave: It varies by level.  As an undercurrent, you’ll always want a person to be insatiably curious, sales-friendly, and metric-oriented.  

  • Junior Roles:  For a junior role like a sales enablement program manager, a good candidate will be highly organized and know how to execute.  They’ll demonstrate an ability to project manage, build content, and deliver. With that, a strong understanding of sales is important.  
  • Mid-Level Roles: As one moves up the chain, there an increasing importance on building relationships.  With a mid-level enablement professional, they’ll be partnering closely with front-line sales managers and sales leadership.  These relationships are essential to be successful, and strong candidates will have a long track record of successfully partnering with sales.  
  • Senior Roles: With the head of enablement for a company, this person must be able to build solid relationships with various stakeholders across the organization– yes, sales; but also marketing, operations, finance, etc.  One senior enablement leader told me that the main reason she as been so successful for so long at her company was from the equity she built up across her stakeholders. If a person doesn’t “play well with others,” they will continually struggle to make enablement the company-wide powerhouse it needs to be.  



Accelerate: What steps would you suggest someone take to transition into a sales enablement role for the first time? 

Dave: Fact:  Nobody plans on going into sales enablement.  We all end up there from varied backgrounds, but the most common background is in sales.  Many former sales reps looking to move into enablement struggle with the transition. But regardless of your background, before making the leap, there’s a series of questions I recommend asking yourself:

  • Do you really understand the details of the role?  (see below for more about that)
  • Can you be selfless and derive satisfaction from making others successful?  Many people– from sales in particular– are successful at being focused on his/her own territory and quota.  Some struggle putting the focus off of one’s self.
  • Can you focus on details on execution?   There’s a large project management component to successful enablement.  If you’re not a details person, think twice.   
  • Can you build relationships internally?  
  • Based on all this, Is this really what you want to do?  

So where to begin?  Start to learn about the role– do information interviews, read some books (there are many), and join groups that specialize in sales enablement (in particular Accelerate Sales and the Sales Enablement Society).  Additionally, I always say that it’s easier to transition to enablement in your existing company rather than going to a new company. At your current company, you understand the company, the products, the industry, and the sales team.  Conversely, you’re a known entity to them. Start there to transition. If not at your current company, when you look at other companies, look for places where you know some high-level leaders who can attest to your skills and help you with the transition.


Accelerate: When interviewing what questions should a candidate be asking the company about the specifics of the role? 


  • Tell me about the last big sales enablement initiative.  Why was it started, who was involved, how was it rolled out, and what happened?
  • How has the sales leadership (CRO or VP of Sales) personally been involved in the success of sales enablement.  How frequently does the sales enablement leader meet with the sales leadership team?
  • What are the next big enablement initiatives?


Accelerate: For someone looking to transition into a sales enablement role, what red flags should someone be aware of before interviewing? 

Dave: There’s a tendency to think “I got this” because you’ve sold and lived through some enablement.  Not true. There’s an entire world that exists behind the curtain that you probably weren’t privy to (strategizing, program development, pilot groups, Q&A, engagement with subject matter experts, etc.).  Before walking into an interview, I’d speak to several enablement professionals to understand their world. Learn the terminology, sketch out the motions of enablement programs, and internalize the challenges.  At a minimum, you need to know what you don’t know.


Accelerate: What is one mistake you see companies make when looking to hire on their first sales enablement role? 

Dave: There’s a tendency to promote the most successful sales rep into an enablement role with the plan to teach everyone what made him/her successful.  But that doesn’t really work. Much like how often the top sales rep makes a lousy sales manager because it’s a different skillset; the same holds true here.  If it’s the first hire, I would seek out someone who has lived through your planned growth. They’ll have a template for how to scale enablement teams (when to hire, what roles to hire, etc.).  Knowing your company (its people, its products, its industry) are all great. But knowing how to build an execute enablement programs should take priority.


Accelerate: Why do you think so many companies have problems filling sales enablement roles? 

Dave: A few reasons:  Most company’s internal recruiters don’t have a network of enablement people.  So every search starts from scratch. And, enablement people every day tell us that they hate speaking to recruiters because recruiters don’t understand their world, and they end up spending half the call explaining what their job is.  Lastly, the effectiveness of a sales enablement person comes down to *how* they do their job. And most recruiters (and even some sales leaders) don’t understand the nuances of enablement to ask the right questions to judge their strength. 


Accelerate: How did you get into sales enablement? 

Dave: Earlier in my career, I was a sales trainer.  Think traditional classroom trainer. Old school.  I was the antithesis of all the things we consider modern enablement (poor alignment with sales, no accountability to sales KPIs, etc.).  From there, I spent 9 years at Salesforce as a salesperson than a sales leader. From there, I worked for SalesHood which is a modern enablement platform. That’s where I learned how much “training” has evolved from my old job to modern enablement.  That’s where I built out my network of amazing enablement professionals and saw the huge challenge for CROs to find transformational sales enablement professionals. From that, Enablematch was born.


Accelerate: How do you see the sales enablement industry changing over the next five years?

Dave: The biggest trend you’ll see over the next few years is the consolidation of enablement vendors in the effort to make it easier for reps. There are so many vendors across the spectrum and app/login fatigue is already a challenge.  There will be M&A activity for all the providers to offer an expanded end-to-end footprint. Furthermore, AI will continue to be the buzzword; so I expect you’ll see a lot more intelligence and coaching being pushed to the reps from platforms. 


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