The Sales Enablement Conundrum – Does Sales Experience Make a Better Enablement Leader?
Since I began working in sales enablement back in 2006, I’ve seen this field evolve into an essential driver of sales success. However, many companies looking to build or strengthen their enablement teams still default to promoting people from sales or customer success (CS) or setting recent sales experience as a strict hiring requirement.
While sales experience undeniably brings valuable empathy and credibility, it’s not always the key to crafting an effective enablement strategy. In fact, this approach can sometimes lead to short-term, reactive tactics that lack the strategic depth required for lasting, impactful change.
At Enablementworks, we work with companies that are grappling with how to make enablement a strategic advantage.
Here are two trends I often see:
1. Promoting Sales or CS Staff to Enablement Roles : Companies frequently promote their top sellers or CS leaders into enablement roles. These individuals bring valuable insights into the day-to-day challenges of sales, which fosters empathy and trust within the team.
2. Requiring Sales Experience for Enablement Candidates : Organizations often set sales experience as a strict requirement for enablement roles, sometimes overlooking candidates with strong backgrounds in learning and development, strategy, or content creation.
While these approaches are understandable, they can sometimes lead to unintended consequences. Let’s unpack the pros and cons and consider whether sales experience should be the primary factor in enablement hiring.
Why Sales Experience Can Be a Double-Edged Sword in Enablement:
When a former sales or CS leader steps into an enablement role, they often bring real empathy and immediate relatability. Sales teams may initially find it easier to trust and work with someone who “knows the game.”
However, this direct experience can also introduce challenges:
Bias Toward Tactical Over Strategic Initiatives : Former sellers may focus on immediate wins rather than longer-term strategies. Sales enablement that lacks a strategic foundation can feel reactive—programs become “flavors of the month” without a cohesive vision or measurable impact. Difficulty Scaling Programs : Tactical approaches are great for immediate needs but fall short when building scalable frameworks for diverse teams. Sales enablement leaders need to create programs that adapt to all sales reps, not just those they can work with directly. Short-Term Thinking : While empathy and quick solutions can generate short-term satisfaction, they can’t replace a robust strategy that aligns with the company’s goals and future vision.
An effective sales enablement professional often needs skills more aligned with strategic thinking, training, content creation, and long-term vision.
Candidates without direct sales experience but with strong enablement, instructional design, or strategic backgrounds can often bring exactly what sales enablement needs to drive lasting impact:
Ability to Build Long-Term Frameworks : Those from training or enablement-specific backgrounds are skilled in creating scalable, structured programs that can be adapted across teams and geographies. Objective, Data-Driven Approach : Without the influence of personal sales experience, these professionals rely on data and objective feedback to design, measure, and iterate on their programs. Big-Picture Focus : A more detached perspective often allows non-sales professionals to understand and align enablement goals with the company’s broader strategic vision rather than fixating on quick wins.
Organizations can benefit from an inclusive approach to sales enablement hiring—one that values a mix of sales empathy and strategic enablement expertise. Here’s how:
Consider Team Structure : Blend tactical support (often brought by those with sales experience or customer success) with strategic enablement leadership who can guide vision and scalability. Seek Complementary Skills : Look for enablement candidates with strengths in learning, data analytics, and content development, even if they lack direct sales experience. Focus on Vision and Measurable Impact : Evaluate candidates on their ability to build frameworks that align with long-term goals and demonstrate their impact through data.