"If I were interviewing for an enablement role today and wasn't conversant on AI tools, I wouldn't bother showing up at all."
This bold statement from Dave Lichtman, CEO & Founder of Enablematch, challenges everything we think we know about hiring sales enablement leaders.
Most companies make the same costly mistake when building their sales enablement function. They assume that great enablement leaders must have extensive sales experience. They prioritize quota-carrying background over the skills that actually drive enablement success. This myth has led to countless failed hires and missed revenue targets.
But what if we've been looking at this all wrong? In this article, we'll analyze Dave's insights on identifying and developing exceptional enablement leaders. We'll explore why traditional hiring approaches fail and reveal the five core traits that separate good enablement leaders from great ones.
Before diving into what makes a great enablement leader, we need to understand when you actually need one.
According to Dave, there are clear indicators when you're not ready for an enablement leader:
When you're still figuring out your sales motion.
If you don't have a clear understanding of how deals flow through your pipeline, an enablement leader can't create structure around something that doesn't exist yet.
When you don't have predictable processes. Without repeatable systems and methodologies that work, enablement becomes a guessing game rather than a strategic function.
The sweet spot for bringing in enablement leadership comes when:
You have repeatable, winning playbooks. Your sales process works consistently, and you've identified what drives success. Now you need someone to systematize and scale these winning behaviors.
Founder-led sales is scaling to a sales team. As founders step back from direct selling and sales teams grow beyond their direct oversight, enablement becomes critical for maintaining consistency and performance.
Dave emphasizes that timing this hire correctly is crucial:
"You need to have something that works before you can enable it at scale."
Through his experience matching companies with enablement talent, Dave has identified five essential traits that predict enablement success. These traits matter more than quota attainment or years in sales.
"Sales enablement is a people business," Dave emphasizes. But this goes far beyond being friendly or personable.
Exceptional enablement leaders excel at:
Building internal capital with stakeholders. They understand that enablement success depends on buy-in from sales leadership, individual reps, marketing, product, and executive teams. They invest time in building relationships that support their initiatives.
Creating alliances across departments. Great enablement leaders operate as connectors, building bridges between often-siloed departments. They understand that effective enablement requires cross-functional collaboration.
Being a two-way conduit between leadership and field. They translate executive vision into practical reality for sales teams while also bringing field insights back to leadership. This communication bridge is essential for organizational alignment.
Navigating organizational politics. They understand how decisions get made and who influences those decisions. This political acumen helps them get their initiatives prioritized and resourced.
One of the most counterintuitive traits of great enablement leaders is their willingness to push back on requests, even from executives.
Dave illustrates this with a simple example: When given a task, bad enablement leaders say "I'm on it!" while great ones say "Let's talk about why we're doing this."
This trait manifests in several ways:
Questioning the 'why' behind requests. Before jumping into execution, they ensure the request aligns with strategic objectives and will actually drive results.
Prioritizing ruthlessly. They understand that saying yes to everything means nothing gets done well. They help organizations focus on high-impact initiatives.
Protecting their team's time and resources. They shield their teams from busywork and ensure efforts are directed toward meaningful outcomes.
Dave uses a powerful analogy: "If you say yes to everybody, you're like that lifeguard trying to save everyone - then they drown." The best enablement leaders have the confidence to push back when needed, which ultimately serves the organization better.
Curiosity trumps experience when it comes to enablement leadership. Dave explains why this trait is so valuable:
They attend QBRs willingly. Rather than viewing business reviews as obligations, curious enablement leaders see them as learning opportunities to understand business dynamics and challenges.
They study call recordings. They don't just collect data; they actively analyze sales interactions to identify patterns, best practices, and improvement opportunities.
They sit with the sales team. They spend time in the field, understanding day-to-day challenges and what sellers actually need to be successful.
They constantly learn about the product. They maintain deep product knowledge not because they're selling, but because they understand that effective enablement requires knowing what sellers are actually selling.
This curiosity-driven approach ensures enablement leaders stay connected to the reality of the sales floor rather than operating from theoretical frameworks.
Great enablement leaders operate strategically, not tactically. They understand that enablement is a business function that should drive measurable outcomes.
This business orientation includes:
Running enablement like a business. They think about ROI, resource allocation, and strategic impact rather than just executing training programs.
Focusing on clear business KPIs. They tie their efforts to metrics that matter to the business - revenue impact, deal velocity, win rates, and rep productivity.
Understanding inputs and outputs. They can articulate how their activities connect to business results and adjust their approach based on data.
Holding themselves accountable. They take ownership of outcomes and continuously evaluate and improve their impact.
Prioritizing ruthlessly. They focus on high-impact activities and say no to initiatives that don't drive meaningful results.
Dave emphasizes that these leaders are "strategic partners, not order-takers or 'training coordinators.'" They bring strategic thinking to the role rather than just executing requests.
Dave's statement about AI competency being essential for modern enablement leaders reflects the rapidly changing landscape of sales technology.
Effective enablement leaders need to:
Understand tool categories and use cases. They know what AI tools are available and how different technologies can support sales effectiveness.
Know when to use AI (and when not to). They understand the appropriate applications for AI in sales enablement and can guide organizations away from technology for technology's sake.
Have practical application knowledge. They don't just understand AI conceptually; they know how to implement and optimize AI tools for sales teams.
This AI literacy is becoming as fundamental as understanding CRM systems or sales methodologies.
Based on Dave's insights, here's how to approach enablement hiring differently:
Instead of focusing primarily on sales experience, prioritize:
Ask questions that reveal core traits:
Great enablement leaders might come from:
The key is identifying candidates with the five core traits, regardless of their specific background.
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The myth that great enablement leaders must have extensive sales experience has led countless organizations astray. While sales background can be valuable, it's not the determining factor for enablement success.
The five core traits: people skills, the ability to say no, curiosity, business acumen, and AI understanding - are far better predictors of enablement leadership success. These traits enable leaders to build internal capital, make strategic decisions, stay connected to reality, drive business impact, and remain relevant in an AI-driven world.
The future belongs to enablement leaders who can combine relationship-building skills with strategic thinking, intellectual curiosity, and technological literacy. By focusing on these traits rather than traditional sales experience, you'll build an enablement function that truly drives sales performance and business results.
In this episode of SellMeThisPen Podcast, Michael and Dave dive deep into what makes great sales enablement leaders tick. They explore the common hiring mistakes companies make, when it's actually the right time to bring in enablement, and why the most important traits for enablement success have nothing to do with carrying a quota.
Dave Lichtman is the CEO & Founder of Enablematch, where he's passionate about helping companies find enablement candidates that drive real change. With his extensive experience in the enablement space, Dave has developed unique insights into what separates good enablement leaders from great ones, making him the perfect guest to share these valuable hiring and development strategies.
