• Sales Assembly

How Lessonly's Unique Onboarding Leads to Quicker Speed to Productivity


Lessonly is a company dedicated to helping employees around the world do better work. The belief that employees flourish when they are shown that their productivity and development are valued is evident in Lessonly’s stellar onboarding program. Their structured program helps reduce the time to productivity for new sales reps. This quicker speed to productivity means that new reps are contributing to the company goals and growth faster than reps at many other companies.

We sat down with Lessonly’s CSO Justin Fite, Director of Sales Enablement Bryan Naas, Sales Director Matt Lubbers, Account Executive Brad Martin, and Sales Development Representative Erica Raeber to learn more about their unique approach to onboarding.

Sales Assembly: What is it that makes Lessonly’s onboarding program so successful?

Matt Lubbers, Sales Director: The primary reason we excel with onboarding is because we’ve made the conscious decision to put emphasis on it. Creating a repeatable process, giving the team a place to refer back to content when needed, and automating it all through our tool has proven to help us ramp up our team members within six weeks.

Bryan Naas, Director of Sales Enablement: Lessonly is best at onboarding because of our coordination between consuming learning content and real-world practice scenarios that help accelerate our team’s time to productivity. We start every program, onboarding included, by focusing on the business impact we want to drive.

Erica Raeber, Sales Development Representative: We practice what we preach everyday. We are a company that focuses on the learner and supports his or her learning in the workplace. What is so unique about our platform is that I get to use Lessonly everyday to learn, practice, and perform and it makes me a better salesperson.

Sales Assembly: What are the top three best practices that make Lessonly so great at onboarding?

Justin Fite, CSO: 1 - Realize that the learner will move quicker than most companies realize and trust in the material determines effectiveness of ramping or training efforts. 2 - Build a manageable assessment framework for ramping, with both subjective and objective measures, so progress is clear to managers. 3 - Realize that ‘ramping’ is what all sales resources should be doing all the time. Continuous training best matches the reality of our business and most businesses.

Brad Martin, Account Executive: 1 - Continuous learning. We are always iterating on our training and tweaking our approach to be the most impactful. 2 - Practice. Having the ability to practice in areas where you struggle to turn your weaknesses into strengths. 3 - Feedback. Receiving feedback from peers and managers on your craft, iron sharpening iron, to help us be the best we can at our jobs.

Bryan: 1 - It starts with a maniacal focus on planning to ensure we are enabling the right skill and competencies to meet the business impact we want to drive. 2 - Using Lessonly’s democratized content creation tools, we leverage the entire team to build all the right content that is needed. 3 - We have a clearly defined set of metrics that we track on a monthly basis to ensure each ramping rep is progressing toward goal.

Sales Assembly: How do you measure the success of your onboarding program?

Bryan: We measure success in two phases - first, we track time to productivity and progression to quota as our top line metrics. Below that, we track 10 data points on a monthly basis that allow us to predict success or failure and adjust the learning or coaching of each rep in real time and ensure their success.

Sales Assembly: What techniques have you seen be most impactful as you’ve onboarded new sales people?

Matt: The thing we we feel is most important is documenting each element you’re teaching so that: 1 - the rep can refer back as needed, 2 - it’s consistently repeated as new hires are brought on, 3 - the instructor/manager/enabler doesn’t continuously get asked questions.

Brad: Having a structured learning path. Knowing that you have a structured learning path that will lead you to productivity gives you confidence that the business is investing in making sure you are successful in your role.

Sales Assembly: How does Lessonly’s onboarding program directly impact the overall success of the company?

Erica: Great onboarding helps because from day one at Lessonly you feel a part of the team. When the company makes it a focus, everyone prospers. I can’t imagine having started at Lessonly and not having developed a plan of action.

Matt: It’s all about speed to productivity. Getting a rep ‘ready’ within four to six weeks means, for us, they can be at max productivity within 6 months.

Bryan: Our quality onboarding program helps reduce the time to productivity for each of our new sales reps. This reduced time means they are contributing ARR faster and contributing to our company goals and growth.

Justin: Predictable contribution from sales is essential for smooth growth. For a company growing over 100% YoY, the better we can plan contribution, the more efficient for our model (CAC). Also important is the impact of a smooth ramp to maintaining a clear, supportive culture for our team.


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