Driving Sales Enablement That Delivers: A Conversation with Tom Kiernan

In the latest episode of Sales with ASLAN, global sales enablement veteran Tom Kiernan joined hosts and long-time friends Tom and Tab for a deep dive into what separates high-performing sales enablement programs from the rest. With a career spanning more than 15 years, including leading enablement strategy at Visible Alpha through its acquisition by S&P Global, Tom K brings unique clarity to a misunderstood role.

These takeaways could transform your approach if you're in sales leadership, enablement, or want to accelerate your team's performance.

Watch the 50 minute episode below:

1. Sales Enablement Starts with Leadership 

“If enablement isn’t embedded at the top — with the CRO, sales, and client success it becomes disconnected from what really matters: results.” – Tom Kiernan

One of TK’s key themes was that sales enablement can’t live in a silo. It must be tied to the executive vision and synced across departments. And the research further highlights this as a priority. According to the 2024 Sales Enablement Landscape Report, only about half of respondents said they felt aligned with leadership teams.

ASLAN’s strategic sales training methodology starts with leadership buy-in, ensuring top-down alignment and adoption from day one.

2. Measure What Matters: Outcomes, Not Activities

“It’s not about how many trainings reps go through it’s about whether those skills show up in the conversation, and whether that moves the needle.” – TK

Rather than measuring vague competencies, TK promotes outcome-based sales enablement metrics, specifically those tied to business results like trial-to-close velocity and customer retention. Using AI-powered conversation intelligence platforms (like Gong or Chorus), sales teams can capture real behaviors and build targeted scorecards.

According to Forrester, organizations that adopt conversation intelligence tools see up to a 20% boost in rep productivity and almost a 25% improvement in pipeline conversion.

3. Use AI to Power Precision Coaching

TK’s teams leverage AI to identify coaching opportunities at scale, not just random call reviews, but actual moments tied to sales KPIs.

This is where ASLAN+ shines.

ASLAN+, our new AI-powered sales enablement platform, delivers real-time coaching, bite-sized training, and interactive role-plays all embedded in the daily workflow. It allows teams to close gaps instantly and reinforce what great selling sounds like, not just what it looks like on paper.

4. Change Management is Non-Negotiable

“You can’t just drop a new playbook and expect people to change. You have to manage the transition and understand where your team actually is today.” – TK

Tom K emphasizes objectively assessing current skill levels before introducing change. ASLAN’s Other-Centered® Selling Assessment provides a diagnostic snapshot of current selling behaviors and benchmarks them against top-performing reps, helping leaders focus on real development needs.

Final Thoughts

Modern sales enablement is not about content. It’s about connection, tying learning to live deals, linking behaviors to business outcomes, and aligning with leadership to drive sustainable change.

As Tom K summed up:

“The only enablement worth doing is the kind that impacts pipeline velocity, win rate, and customer outcomes. Everything else is noise.”

If you’re ready to turn sales enablement into a growth engine, Sales with ASLAN is your go-to resource, and ASLAN+ is your in-the-moment, AI-powered solution.

Listen or watch the full episode now

Available on Spotify, Apple Podcasts, YouTube, or wherever you get your podcasts.

Learn more about how ASLAN+ can transform your team’s sales performance at [ASLANtraining.com].

Catch up on all the latest Sales with ASLAN podcasts to learn how to stand out after the shortlist here. And for more detailed strategies and insights, check out the ASLAN blog.

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Want to learn more from Tom Kiernan? You can follow him on LinkedIn