How Lessonly’s Kyle Roach teaches his team to sell the dream

Collin Stewart, CEO

10 April 2019

It’s a subtle, but important nuance: sales reps don’t sell software, they sell a dream. And that dream inspires prospects to buy, well, software.

Seems like such an obvious idea when it’s spelled out, doesn’t it?

During the day-to-day routine of sales development, however, this can be a difficult thing to remember. For example: you have 65 calls to make today, and follow up with another couple dozen prospects via email. Oh, and then you have to research new prospects, make sure they’re the right fit, and get them in Salesforce for the next day. It never ends.

When you’re balancing all those requirements, it can be easy to slip into default value props. Our software does this. This innovative feature does that. How about we hop on a call and show what we’re talking about?

Sound familiar?

For Kyle Roach, Manager of Sales Development at Lessonly, those well-worn scripts were all too regular for his team about 8 or 9 months ago. So they changed things. They started selling the dream.

“Consumers buy with their gut, they want to be associated with a brand and a movement. So, we push that, we live on that, and we do it everyday. Our brand is built on that,” says Roach, on a recent edition of The Predictable Revenue Podcast.

“Initially, our SDR team was pushing features. That was a disconnect. So we aligned, got in the same boat, and started rowing.”

Establishing Lessonly’s “sell the dream” process

It all starts with a concise mission statement, says Roach. Something that sets the foundation for everything the company says, builds, and does. Luckily, Lessonly had a great mission statement: “we help employees do better work so they can live better lives.”

“For us, that meant that instead of leading with ‘we’re a training software’ we say ‘we help you do better work,’” says Roach.

For those that don’t have a mission statement quite yet, Roach says the most effective way to craft one and develop an effective true north, is to begin to ask “why?”

“I urge everyone to ask ‘why? ‘Why are we doing this?’ And, then, ask yourself – why are you doing this?’” says Roach.

“Once you’re done that, then ask your customers – ‘why did you buy from us?’ If you do that, you get a pretty good idea of your dream or mission is. Then, you brand it and push from there. Get it out in the market.”

Executing “the dream”

So…what does that mission statement look like on the ground? How does it translate to actual prospecting?

According to Roach, to begin infusing their messaging with the right tone and word choice – remember, Lessonly was used to pushing features, not “the dream” – they needed a rubric to follow to make sure they were not only overhauling all the necessary outputs, but testing different messaging options whenever possible.

The Lessonly framework:

  • Decide: decide on what you want to say. Remember, isolate your variables. The more defined your test, the clearer your results will be.
  • Document: what is the test? Who is involved? What are the key tasks and deadlines? How will we know we’ve won?
  • Deploy: put it into action! Get it out in the world. And make sure you have identified your redflags so you can iterate quickly if it fails.
  • Discuss: retro the project with everyone involved. Look at quantitative and qualitative results to determine next steps.

“When anyone starts to move from selling a movement and vision into tactics, it is easy to be ambiguous. But, we need it to penetrate everything – how we write our messaging, how we speak on the phone, and how we handle objections. Everything. Even our two directors of sales and our president use the same process. It is totally transferable to anything. It results in a better working piece of the pie, whatever it may be.” says Roach.

“So, this is the process we ran on every one of those variables. And we’re still running it.”


The Lessonly cadence

From there, the Lessonly team established a baseline cadence, through which they began communicating their new and improved messaging.

Their cadence:

  • Day 1: First email (with 20% personalization)
  • Day 2: Follow up with a “thoughts” email (this is a super simple email that simply asks “any thoughts on the email below?”), done in the morning.
  • Day 2: LinkedIn contact, done in the afternoon,
  • Day 3: Call
  • Day 5: Email (short, personalized)
  • Day 7: Demo video – generic 1-minute marketing video.
  • Day 9: Final call
  • Day 9: Apologies email (delivered in multiple-choice style)

The first email, not surprisingly, is a great example of where Lessonly SDRs would “sell the dream.” Their formula for that first email is to personalize the top 20% with any relevant anecdote they can find about the company from press releases, social media posts, or the news.

From there, they connect that anecdote to the dream Lessonly provides: helping employees do better work. Before they changed the tenor of their prospecting, this is where Lessonly reps would have gone into an ad-hoc description of the features the software has.

They employ a similar tactic on their cold calls. For example, every time a Lessonly rep calls a prospect, they open with a very clear statement about why they’re reaching out, they ask permission to proceed (never assume your prospects are okay with you just rambling on), and then proceed to inject their discussion of why Lessonly can help them.

“Before this system, SDRs ran their own cadence. To standardize that, we took the best pieces and out, put it into one cadence, and tried it. We use SalesLoft, so we’re able to insert templates to bolster our messaging with how Lessonly helps,” says Roach.

“We worked our way down this cadence and tested every piece. And we coach our team to look for a thing they can connect with the dream or the movement.”

(Editor’s note: we had wordsmith Patrick E. McLean on the pod a while back to discuss how to write concise emails that convert. You can read about our chat here, or listen to the podcast here)


The impact of this has been significant for Lessonly, both in a brand awareness capacity, and on their bottom line. People are recognizing Lessonly out on the streets, says Roach. There is no way to measure that, but it is a win for the company.

“Just by getting our SDRs talking about the movement is a huge market awareness win for us,” says Roach.

Of course, booking more meetings is a win as well – and Lessonly SDRs have been able to accomplish that in spades. Just 18 months ago, the company had 9 commercial SDRs, booking 15 meetings per week.

It was tough, admits Roach. At time, it felt like the sales development team was running in quicksand. Now, the company has 6 SDRs, and they are booking 20 meetings per week.

“Getting 5 more meetings on the books, with 3 less headcounts is really good,” says Roach.

“It’s the product of a more engaged, more focused group of reps. And that’s awesome.”

For more of Roach’s thoughts on how Lessonly “sells the dream” to their prospects – including how Lessonly aligned marketing and sales, and how that influenced how they message their values – check out the rest of his interview on The Predictable Revenue Podcast.