Vice President of Enterprise Sales

LessonlySales 6-8 Years

Job Description

Vice President of Enterprise Sales
at Lessonly
Lessonly: Vice President of Enterprise Sales

Lessonly, over the last 18 months, has made a strategic shift in its go-to-market strategy to move “upmarket.” During the first five years of our story, we focused on finding customer-facing teams (sales and customer support) with employee counts of 150 to 1,000 employees. That strategy allowed us to celebrate impressive year over year growth, reach over 2 million learners and amass over 650 customers. And in 2018, we launched our first user conference, boasting over 350 attendees in Indianapolis where we encouraged and inspired folks to "Do Better Work."

This success has allowed us an opportunity to make investments for our next phase of strategic growth and in the last 18 months with an upmarket focus, we’ve seen incredible traction. Fortune 500 customers have trusted Lessonly to help them transform training and enablement inside their organizations. With the initial traction we hoped to see, we’re looking into 2019 and expecting nearly half of new revenue to come from our Enterprise (or Upmarket) segment, and are seeking an experienced leader to drive this strategic opportunity.

Team and Go-To-Market:

The enterprise segment currently has nine Enterprise Account Executives.

In addition to the core selling team, you will have support from a Solutions Consulting function for pre-sales support on pilots, technical calls, product requests, business case design, and presentation preparation. A growing Services team supports most of our Upmarket implementations and a Senior Customer Experience team is responsible to drive upmarket accounts to key business outcomes, navigate renewals, and identify growth opportunities. Lastly, revenue operations support will drive Salesforce forecasting and operational tasks.


Proven ability to drive results and to lead Enterprise Sales teams that are navigating complex sales cycles.
A growth-stage sales leader who has shown results at SaaS companies between $10m ARR to $50m ARR, where deal sizes are at a minimum $150k with 3 to 12-month plus sales cycles.
Experience leading organizations that sell into large sales teams, customer service/call centers, or the executive level.
Must be willing to work out of the Indianapolis office or dedicate significant time to being in the office with the team.
To be successful in this opportunity, there are six key attributes the Lessonly team considers to be important:

Loves to win and has shown, through results, an ability to drive team success.
Will draw on experience to drive longer-term strategy, but is equally equipped to roll up the sleeves and get tactical.
Informing executive teams of patterns that could warrant changes in the 12 to 24-month Go To Market plan. For example, what markets should we expand to and where can we spend resources more effectively?
Updating the Enterprise Sales Methodology to improve win rates.
Working cross-functionally to drive quicker and more effective account growth.
Planning and setting Quarterly Objectives that address the highest impact projects to improve the Upmarket sales motion.
Being brought into deals as an “executive presence” to be an accelerant to the opportunity.
Being a thinking partner and co-pilot in large opportunities.
Being the best in the organization at asking great discovery questions, delivering the Lessonly value proposition, demoing the product where needed, and navigating the last 20% of a sales cycle.
Helping define differentiation strategy In a competitive situation.
Examples of being strategic include, but are not limited to:
Examples of being tactical include, but are not limited to:
Will be a proven coach who can identify patterns with Account Executives and help them become better at their craft. This means delivering clear feedback (both positive and growth opportunities) to the team and the ultimate measure of this will be if the team is improving in their enterprise sales capabilities.
Will have difficult conversations when needed, early and clearly. This could be with the enterprise team, with Conner, or with other departments.
Will be inspiring and bring energy to the day-to-day of Enterprise selling. In gaps between big deals closing, that means finding ways to celebrate progress and wins, hearing and addressing frustration, and keeping team morale high.
Will be best-in-class at hiring A+ talent ahead of schedule and manage any existing performance challenges on the team.
Lessonly benefits to help you do better work and live a better life:

Health insurance—medical, dental, vision and life. We help you stay covered.
Competitive pay, a 401k plan, and equity. Money matters and we like to think about the ways you can win as we win.
Tech Stipend. Helping you with the tech gear you need for the things you do.
Unlimited paid time off. Keeping this benefit simple so it’s simple for you to use it when you want to use it.
Parental leave. Because we think it's important to spend time with your new family.
Drinks and snacks. What’s your favorite LaCroix flavor?
Yoga, Nintendo, and Pop-a-Shot.
Free parking with downtown Indianapolis office.

Posted On

June 3, 2019