Enablement Strategist

Services United States Indianapolis, Indiana


Enablement Strategist

About Lessonly

Lessonly is the powerfully simple training solution that empowers people to learn, practice, and perform like never before. Our mission is to help teams around the globe do better work and live better lives with world-class training and enablement.

Why Lessonly? 

We exist to help people do better work and live better lives. It’s our company mission, and we’re committed to bringing it to life on our team and around the globe. To make this happen though, we need humble, hungry, and people-smart leaders to join our llama pack. We’re looking for people like you.

If you’re ready to build a career you love, Lessonly could be the place for you. Here, each llama is truly valued. We get to experience career clarity, camaraderie, and progress in work and life together, and it’s its own kind of magic. We’re excited to review your application and learn more about who you are and what you’d bring to our pack.

Position Summary

Customers invest in Lessonly to transform the way that learning and enablement happens inside their organizations via a best-in-class training software. However, many of them desire an extra set of hands to launch faster, think more strategically, and deliver more to their teams than they otherwise could under their own power. 

Enter the Lessonly services team, which partners with our customers to design training programs, develop training content, and optimize their accounts in a way that ensures a higher overall likelihood of achieving their business outcomes. 

The Enablement Strategist is an advisor to customers and serves as the extension of each customer’s team working to make Lessonly a success. By developing intimate knowledge of their customers’ businesses, enablement goals, and operations, the Enablement Strategist will leverage their breadth of experience and consummate Lessonly understanding to provide strategies and recommendations to customers, so they can reach their desired results efficiently, and with velocity. 

Success in this role looks like assisting each customer to fully utilize their investment to its maximum potential while delighting internal and external stakeholders with service that exceeds expectations. 

Core Responsibilities:

  • Consult customers on enablement strategy, particularly pertaining to the use of Lessonly
  • Provide tailored enablement program recommendations based on intimate knowledge of a customer’s organization and use case
  • Partner with Account Managers and customer Program Owners to prioritize initiatives to optimize Lessonly’s efficacy/ROI
  • Influence through showing enablement value and create opportunity for the expansion of Lessonly in to multiple teams within an organization
  • Manage initiatives/projects and engage necessary internal and external stakeholders - potentially with multiple customer teams
  • Ensure that all initiatives/projects are delivered on time and within scope

Additional Responsibilities:

  • Engage in training and professional development
  • Perform research to ensure the appropriate guidance for customer solutions
  • Ideate and communicate opportunities for Services continuous improvement
  • Track billable time and communicate utilization to customers


  • Customer-facing experience required
  • Project management experience required
  • 3-5 years experience preferred
  • Training/Enablement, Consulting, Sales Enablement, or Customer Service experience preferred
  • Experience with using Lessonly preferred
  • Ambitious, results and achievement oriented, while still remaining disciplined with facts and accuracy
  • Inquisitive problem solver, critical thinker
  • Ability to influence
  • Quickly adapts to change and thrives under pressure

Lessonly Benefits

  • Health Insurance - Medical, vision, dental, and life plans available.
  • Disability Insurance - Short-term and long-term coverage.
  • Paid Parental Leave - Because time with your new baby llama is important.
  • Unlimited PTO - We believe in making time for life, so we like to keep this benefit simple. 
  • 401k Plan - Save and prepare for the future with us.
  • Equity - When we win as a team, you should win, too. 
  • Flexibility - What works best for you, works for us—whether that means you’re in the office, at a coffee shop, or at your kitchen table. We have llamas working in Indy and across the U.S. We also provide everyone with a tech stipend to keep their tech rocking and rolling smoothly.
  • Work Happier - Our community is one of recognition and fun. From company-wide shoutouts to dogs in the office to our vibrant Slack workspace, we’re constantly collaborating and celebrating together. 
  • Make Indy Brighter - Every year, we select four organizations that serve kids in Indianapolis and dedicate our time, money, and talent to them. Making time to volunteer and give back to our community matters.
  • Professional Development - We learn from experts, community leaders, and each other constantly. From Mass Classes and workshops to company events and daily conversations, we’re always growing.
  • Accessibility - We’re conveniently located in the Monon16 neighborhood, right by the Monon Trail and the Red Line if you prefer to run, walk, bike, or bus to work. 
  • Self-Care - We have in-house yoga, ping-pong, two Peletons, a meditation room, a library for silent work, a mother’s room, wellness groups, and more because we’re humans first and llamas second.

Lessonly is an Equal Opportunity Employer, we do not discriminate against any protected class including, race, color, religion, sex, national origin, sexual orientation, gender identity, genetic information, disability or protected veteran status. Lessonly will provide reasonable accommodation to qualified individuals with disabilities. Please contact [email protected] if you require a reasonable accommodation to apply for a job.