What Shopify Taught me about Sales Enablement

Becca + Ray shopify interview


I interrupt your regularly scheduled mundane scrolling with precious insights! I recently had the honor to interview Ray Owais, Retail Revenue Enablement Lead at Shopify. Shopify is the leading retail operating system for any size business that has helped 446,005 entrepreneurs sell in-person, online, social media, and even from the trunk of a car.

Like many of the pros I speak to, Ray stumbled into the sales enablement division and, as he describes it, was an “accidental enabler.” After starting his career as a high school teacher, he realized teaching wasn’t his calling; meanwhile, student loans were a monthly reminder he needed to find something else. He needed a change, so Ray took a sales position where he naturally fell into helping his peers. The gravitational pull to assist his team led him to a career in sales enablement.

Here are the takeaways from our chat in which Ray shared many reflections on the state of sales enablement.

Enablement’s role is continually evolving

Ray acknowledges that enablement is on a constant journey to be seen as a revenue multiplier and not a cost center, and I felt that in my soul! Teams all around the globe struggle with this issue over and over. I hear it firsthand, and that’s why we focus on providing teams a way to tie sales performance to your coaching, training, and go-to-market readiness programs.

“I am always constantly trying to think about the customer experience and how does that experience really becomes consistent,” Ray said. The ways consumers digest information and where they begin their journey is evolving. Sales enablement allows companies to quickly and efficiently bridge gaps. As Ray discussed, weaving the initiatives to goals can be a tough call for some teams.

Inevitably, enablement must be agile and pivot quickly to meet these needs. As such, it’s always evolving to show leaders how results come directly from their approach and solutions.

Enablement removes roadblocks within teams

Enablement can have a considerable impact on strengthening an entire team, specifically by removing departmental silos that tend to creep up over time and create roadblocks. As Ray put it, “the biggest impact sales enablement can make is to be the glue on the team.”

“be the glue on the team.”

Ray recalled hearing someone once describe the role with a made-up word “de-silofication” which just means that enablers should aspire to remove the silos in their go-to-market teams. You won’t find it in any dictionary, but he says it’s very relatable for sales enablers.

“The customer journey doesn’t stop at the sales process,” Ray pointed out (can I get an Amen?!). He also mentioned new research that shows that buyers are looking for consistency among everything else. Buyers don’t see the various departments and that’s why enablement is “democratizing success” for the entire go-to-market function.

COVID is an opportunity for enablement teams

I spoke to Ray about how the pandemic is affecting enablement teams everywhere. First and foremost, he said, leaders have had to rethink how productivity looks in this new world and reevaluate their enablement needs. There is a renewed emphasis on how teams can collaborate, and the process becomes even more critical when working from home.

Having a cadence and process in place allowed the Shopify team to pivot and embrace the opportunity Covid brought to the business, since as an ecommerce provider, Shopify has seen a significant boost during the global pandemic.

For example, Shopify has a monthly training program where week one is always assessment, and weeks two through four take trainees from the classroom to actually making calls and doing the thing they just learned. This practical application of new skills becomes muscle memory, something that has been crucial to Shopify’s success during the pandemic.

Ultimately, Covid highlights how critical the tools that enablement provides genuinely are to the team’s success. As the new normal moves forward, enablement will play a significant role in creating repeatable success in volatile environments.

Alignment with sales leadership

“The biggest thing about enablement that you have to think about is that you’re a sales leader first,” Ray said. He emphasized how enablement’s function should always be aligned with the goals of the leadership team. As he put it, “organizational strategy is the name of the game.”

"you have to think about is that you’re a sales leader first."

Unlike other areas like HR or learning and development (L&D), Ray pointed out that sales enablers go in to find the problems. Other divisions ordinarily receive the problem and devise solutions. Alas, that isn’t the life of an enabler. He describes sales enablement as being versatile, “like a Swiss Army knife.” Unique to enablers, they must align their goals with that of CROs and leadership, and then go out and proactively uncover roadblocks standing in the way of those goals or opportunities to accelerate their achievement.

Start your enablement with the outcome/metrics you want to influence

Once enablers align strategy with those of the company leaders, they must start asking, “what result is the business looking for,” Ray explained.

To determine if training impacts overall sales numbers, a clear goal or metric must be identified first.

He continues, “We cannot force buyers to buy, but there are behaviors that influence that number.” Ray says to take your goal and then ask what behavior impacts that metric and how can we influence buyers within our control.

Ray used an example at Shopify of an add-on product plagued with low sales. First, he said, they went into Gong and listened to calls. They were able to identify a very common objection and then change the core message around the product. By the team simply presenting the add-on option differently to consumers, Shopify saw a 35% increase in sales within just eight weeks.

Additionally, Ray alluded to a mystery product he doesn’t want to give away (psst, I know and it’s LevelJump) to embed milestone metrics and recognize when milestones are reached that shows learning was applied in the call. Doing so allows their team to demonstrate the effectiveness of sales enablement at Shopify.

It’s always a pleasure to hear success stories like Ray’s, especially during a pandemic.

You can see the entire interview below, and if you are looking for a way to transform your own enablement process, you may want to check out our ebook for more tips.