Sales Enablement

The Challenge: When our sales organization rolled out a new service line, the enablement approach was designed quickly but fell short of preparing reps for success. We relied heavily on virtual lecture-style sessions (about an hour each) with limited interaction. There was little time for Q&A, practice, or coaching. At the same time, reps were expected to learn: -The details of a complex new product, -How to navigate and apply a multi-page cost calculator spreadsheet, and -How to correctly enter deals into Salesforce. Because everything was introduced at once, without staged practice opportunities, reps struggled to confidently position the new offering with prospects. Reflection: This experience taught me the limits of lecture-based training for sales teams, especially when the product is complex and tied to detailed tools like cost calculators. Sales professionals need more than information — they need guided practice, coaching, and clear plays that reduce ambiguity. What I Would Do Differently: If I were leading this rollout as a Sales Enablement Manager today, I would design it as an end-to-end sales play rather than a one-off training. That would mean: 1. Defining the ICP (Ideal Customer Profile) - Pre-curated list of prospects who are most likely to benefit. 2. Building the Outreach Sequences - Pre-built email, call, and LinkedIn cadences in a sales engagement tool. - Messaging aligned with clinical/product experts and tested for clarity. 3. Providing Ready-to-Use Sales Assets -One-pagers, case studies, and ROI calculators embedded directly into sequences. 4. Creating Safe Practice Environments - Role-plays, objection-handling sessions, and sandbox versions of the cost calculator and Salesforce workflows. - Coaching sessions where reps can make mistakes and get feedback before engaging prospects. 5. Measuring Impact - Tracking pipeline growth, meeting set rates, and closed-won deals attributable to the play. - Using win/loss analysis to continuously improve the play. The Value of a Sales Play Approach: By structuring this kind of rollout as an end-to-end sales play, the enablement function not only trains reps but also directly influences revenue outcomes. Instead of focusing on “time spent in training,” we would measure success by: -The pipeline generated during the campaign, and -The closed-won deals tied to that pipeline. This approach ensures that enablement is seen not as a support function, but as a driver of measurable business impact. The e-learning example below was more typical of the ask from leadership at the time. We were asked to provide courses that described our products or customers that supplemented manager training for new reps during onboarding. This decreased ramp time for new sales reps.

This 7taps microlearning course was designed to provide just-in-time training to our sales team about the new mental health services our e-therapy company provides. The sales team had been missing opportunities to expand their pipeline due to their inexperience with our other mental health services (they instead focused on our SLP services in most calls.) Outcome: This just-in-time support improved sales associates pitches during discovery calls and led to a 25% increase in scheduled meetings with account executives.

Challenge: Our organization was rolling out Outreach.io as a new tool for prospecting. Our entire team needed to be trained and needed a sandbox to practice developing their skills before applying what they learned with customers. Solution: I developed this Articulate Storyline program to provide additional practice and evaluate the overall readiness of each sales team member as the final step in our certification program. This led to partial automation of our onboarding of new reps, faster ramp time, and better use of Outreach by all sales reps.