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LEARN Recap: Scaling Enablement in Hypergrowth Mode

Hypergrowth is a time of tremendous opportunity—but it’s also a time of challenges, especially when it comes to scaling successfully. At our debut virtual summit, WorkRamp LEARN, Ashton Williams, Senior Manager, Global Programs, Slack, shared four invaluable lessons for scaling enablement, offering tips and insights that organizations in any industry can implement. 

Lesson #1: Know the landscape

Whether you’re a small business that’s trying to IPO or a large business focused on maintaining an edge over your competitors, you need to thoroughly understand the landscape your organization is operating in, Ashton says. In particular, there are two questions you should be asking: 

  1. What are your organization’s long-term goals at the executive level? 
  2. How is our team going to support us in reaching these goals? 

Understanding the landscape is key to building an informed plan for growth that’s tailored to your organization’s needs. As Ashton points out, “Growth at a 50K company is different than [growth at] a startup. How you work together and what you need to know, or how you really build that enablement strategy, looks different for those different landscapes.” 

Lesson #2: Be outcome-focused

When it comes to your enablement solutions, such as courses or training programs, completion is not the same as impact—a distinction that Ashton urges organizations to keep top of mind. Instead of focusing on completion, she says, organizations will achieve better results if they focus on the long-term impact they’re trying to achieve.   

“Think more about, ‘What am I trying to do with this?’ and ‘How do I go about accomplishing that?’ as opposed to, ‘I’m going to build a course,’ or… ‘I’m going to run a training, and everyone’s going to attend,’” she suggests. 

To imagine how you might apply this approach, think about your onboarding program as an example. Are your team members simply completing the program, or are they then going on to hit their goals and drive productivity? And are those results sustained past the 30-day mark? What about the 60-day mark? “These are all indicators for whether or not the program is really preparing people for the impact and outcome that we’re trying to drive.”

Lesson #3: Don’t fly solo 

How do we best engage stakeholders?  Don’t fly solo. Ashton says, “You can move a lot quicker and build things that last longer when you involve your stakeholders.” For example, how are you going to roll out a sales methodology without involvement from your leadership? 

A vital part of doing this successfully is “knowing where your expertise stops and theirs starts,” Ashton says, who urges businesses to focus on which departments are responsible for what data. Need insights into what’s happening in the field? Look to your leadership. Into marketing? Look to your product marketing team. 

“It’s about knowing who does what,” Ashton says. “Where expertise ends and stops, and really driving accountability.” 

Read more: Data-Driven Sales Enablement: Track, Measure, Improve

Lesson #4: Automate and elevate 

“Always plan to be big,” Ashton says. “Keep the caliber high on the enablement you build, and really focus on the purpose.” 

Whether you have 1,000 employees or 10,000, utilizing automation to free up time and resources is one of the best ways to accomplish that goal.

However, using automation isn’t a free pass to set it and forget it—on the contrary, you need to continuously revisit your processes to determine what’s working, what needs to be improved, and what needs to be phased out altogether. 

This evaluation process is not only for maintaining customer trust but also for avoiding burnout on your team.

Do’s (and don’ts) to put these tips into practice

So, what are a few tips that might help us navigate the challenges that might arise? And, just as importantly, what are some myths or “dont’s” to be mindful of? Ashton offers two of each. 


  • Always remember that your stakeholders are your customers, not necessarily part of your team. Ashton has learned this from experience, reflecting on past occasions “where I have a great working relationship with my customers in the business and might not operate as professionally or organized… as I did when I first joined.” Her recommendation? Always stay on top of managing your customer relationships.
  • Understand the difference between tactical enablement and programmatic enablement. The ability to identify your organization’s long-term needs and when they arise—and being nimble between those two—is “really critical,” she says. 


  • Buy into the common myth that you must have been a seller to work in enablement. [Because] selling at another company might not actually help you sell at this company. What actually matters, then? Having empathy for the role and the challenges your customers face, along with the impact and how people buy.
  • Assume that authority automatically gives you credibility. Even if you align with other senior-level executives, don’t assume you’ll be treated as credible. You still need the data and evidence to support your ideas. 

The biggest challenge in scaling enablement (and how to overcome it) 

In Ashton’s opinion, the greatest challenge for scaling is “remembering that your content might not live a long time”—which, she adds, “can be crushing. You go to build this perfect and beautiful program or this wonderful thing that you finally aligned everyone on, and it feels like such a big win—and tomorrow, it can be out of season or no longer relevant.” 

As she reminds us, you will need to rebuild, audit, and redesign as your organization scales—and you need to be OK with that. “You’re going to scale different departments at different times and [need to consider] how to balance your resources, then remember that what’s in season today may not be tomorrow. So evergreen isn’t the goal.” 

The solution? It’s simple.

“Be agile, withstand change.” 

Read more: Strategies for Scaling Enablement and Being Customer-Centric

Looking for more actionable tips and insights from People, Revenue, and Customer Success leaders? Don’t miss WorkRamp LEARN Spring, March 23rd at 9 am PT. Get your free ticket!


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Emily Homrok

WorkRamp Contributor
Emily Homrok is a freelance copywriter with over eight years of writing experience. She graduated from Drexel University in 2011.

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