Chris Oliver
Senior Enablement Leader
Senior Enablement Leader
I build enablement systems and A.I. workflows that show up in the metrics.... not just the training completion reports.
Most enablement programs get forgotten by Friday. I build systems that show up in the metrics Monday morning, connecting learning strategy directly to revenue, ramp, and retention. With 10+ years in Tech and enterprise environments I specialize in Sales Enablement, Learning & Development, and GTM readiness.
In addition, I use the most recent innovations in A.I. to increase productivity speed and content creation.
A.I. Powered Enablement Tools
Simulations and Interactive Learning
The Coaching Room puts you in the chair of a frontline sales manager with four underperforming reps and limited time. Each rep has a different root cause: confidence erosion, a process gap, a broken territory, or no real problem at all. Your job is to figure out which is which, run a realistic coaching conversation, choose the right manager action, and live with the outcome two weeks later.
Live Enablement Experiences
Sales Training Programs
New Hire Onboarding equips new reps with the core skills, knowledge, and confidence they need to ramp quickly through a streamlined, modern learning experience. Built as a blended journey of LMS modules, live training, assessments, and real-world practice, the program eliminates outdated duplication, focuses on essential selling behaviors, and guides learners toward a clear, standardized certification.
Discovery 201 elevates reps from order-takers to strategic advisors by teaching them how to uncover true business pain and steer conversations with intent. This training sharpens narrative control, deepens qualification, and drives higher-quality pipeline.
Result: 90% average post-training assessment score.
Winning the Customer teaches agents how to build trust quickly, guide clients with confidence, and create momentum that leads to strategy sessions and mutual agreements. This program elevates first-tour interactions into high-value customer experiences that drive re-engagement and competitive offers.
Momentum Matters transforms reps from reactive responders into proactive value-creators through a structured four-part learning experience. Each activity builds on the last by helping sellers spot reactive habits, understand customer expectations, deliver differentiated value, and then put it all together in scenario-based roleplays that re-enforce proactive selling.