Director of Revenue Enablement

Website Lessonly

Say so long to so-so training


Please Note: For the health and safety of our employees, Lessonly’s physical office is currently closed due to the COVID-19 Pandemic. All of our employees are working remotely and we are re-evaluating the opening date of our office on an ongoing basis.

This position may work in the Lessonly office in Indianapolis, IN or remotely from any of the following states: Illinois, Indiana, Michigan, Ohio, 

Position Summary:

The learning software needs of progressive companies have shifted from centralized, compliance-based training technology to a modern, team-oriented learning solution where speed-to-market and speed-to-impact is essential to meet aggressive business growth. Lessonly’s integrated learning solution and expertise makes us a market leader for companies that recognize this fact and are ready to commit to growth and development.

We are adding people to our team who are attracted to a fast-growing software company, a rich employee culture, want to grow their career and have a blast doing it. Lessonly prioritizes our customers’ success, our company’s growth and employee happiness!

We are looking for a Director of Revenue Enablement to join our team. In this highly-visible role, you will partner with revenue leadership across pre- and post-sales to develop the strategy, resources, tools, processes and training necessary to help our selling teams effectively support and position the value of Lessonly to our largest customers and prospects. This role will work across departments to build supporting content and programs to enable the revenue teams to have consistent, effective and engaging conversations with customers at each stage of the customer lifecycle, while helping to improve efficiency and effectiveness of our selling organization.


  • Partner with revenue leadership across pre-sales (SDR and AE) and post-sales (AM and Services) as well as Sales Support (Solution Consultants and Technical Adoption Managers) to develop strategies and objectives that lead to the success of each individual and the team as a whole
  • Track metrics to identify trends, anticipate development needs, and proactively execute programs that accelerate growth
  • Build and coach your team, who is currently focused on specific areas of the business, and coach them to drive momentum and achieve revenue goals.
  • Work with internal stakeholders to create resources including playbooks, templates, kill-sheets, sales training programs and other assets, including product enablement, as required
  • Develop training programs for new products, marketing programs, and technology that reinforce processes and methodology, drive adoption and promote best practices
  • Monitor skill development for revenue teams
  • Manage individual development plans for the enablement team
  • Work closely with leadership and Sales Operations to monitor productivity, establish metrics, consistently evaluate tech stack budget and decisions, and execute objectives related to team success
  • Partner with the Head of Revenue Effectiveness to scale strategic enablement programs

The Qualities:

We are seeking a person who is a go-getter, who thinks strategically and at the same time can get tactical. This is a person that can be a true partner to our selling organization and has a proven track record in supporting a fast growing team. They need to be comfortable working in teams, engaging with executives, and finding creative solutions when there are limited resources. Successful candidates will have a minimum of 6 years experience in training and enablement with a preference toward SaaS experience, especially in the “start-up to scale-up” phase. Minimum 3 years of experience with maintaining and coaching teams.

Other qualities in our preferred candidate:

  • Strategic thinker that can take broad visions and concepts and develop scalable and structured plans, actions and measures and then execute those plans
  • Experience in rolling out sales methodology (Value Selling preferred)
  • Has previously participated in and helped to drive annual sales kickoff events
  • Excellent communications skills including, presenting, editing, and writing with attention to detail required
  • Proven program management and project management skills
  • Demonstrates ability to coach and lead peers to up-level performance of the team.
  • Enjoys working in a high-growth, dynamic company environment, using the broader team within Lessonly to convey value to customers
  • Flexible and adaptable to meet the needs of the changing market, our customers and our business.
  • Demonstrated ability to think strategically, and work in complex situations.
  • Naturally self-driven, results-oriented and able to work as part of a team.


  • Bachelor’s degree
  • 6+ years of working experience preferably in software/technology
  • Experience working with pre-sales and post-sales teams
  • Proficient at leveraging technology to create efficient processes
  • Ability to learn quickly and adapt

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 if you require a reasonable accommodation to apply for a job.

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