In this episode, Ross and Andrew discuss how to drive execution excellence through adaptive enablement leadership.
Our guest for is Andrew Zinger, Senior Director, Global Sales Enablement, Fastly. Andrew is a seasoned sales enablement leader with over 20 years of experience. Before joining Fastly in 2023, he held leadership roles at top technology companies, including Figma, Dropbox, and Salesforce.
In this episode, Ross and Andrew discuss how to drive execution excellence through adaptive enablement leadership, exploring how to balance strategic direction with rallying teams around a shared vision while staying flexible to evolving organizational needs.
Listen to the episode here, and get the key takeaways from our conversation below.
“There aren’t a lot of guidebooks [to reference] when you’re promoted,” says Andrew. “There’s a struggle between asking yourself, ‘What kind of leader do I want to be?’ and ‘Am I going to be the friend that’s easygoing, or am I going to be on the opposite end of the spectrum?’ Ultimately, the key is to find a happy medium, what I call ‘the art of the possible.’”
Andrew emphasizes the importance of doing things both ethically and legally (for obvious reasons) while staying focused on reaching your goals. “The freedom is the fun part,” he explains. “But it’s also one of the primary challenges because you have to keep up with the changing landscape of how people learn.”
Everyone learns differently, which impacts how quickly team members ramp up and reach their full productivity potential. Leaders, Andrew notes, must adapt their coaching styles and resources to meet these diverse needs.
“I always say enablement is like being a street cop. You have your daily roll call and admin stuff, but you never know what’s going to come around the corner — another product launch, an initiative, or a change to a process. When this happens, you have to identify where it falls on the priority list compared to the desired outcome,” says Andrew.
To figure out the best next step, ask yourself:
The purpose of asking and answering these questions is to make sure you’re able to capture your sales reps’ attention, and keep it.
Adaptive enablement might sound like a simple idea, and in many ways, it is. But simple doesn’t always mean easy. Adaptive enablement means you’re not just receptive to change — you welcome it with open arms.
“Part of adaptive enablement means you admit when you’ve made a mistake or something isn’t working. You have to own it,” stresses Andrew. “That’s the key. I’ve had lots of failures I’ve learned from, and I’m OK with my mistakes. But I’m not OK with repeating the same mistake.”
No one is perfect, and mistakes are inevitable. More often than not, those mistakes lead to the most valuable lessons, and they teach them quickly. But when the same mistake is repeated, that’s when it becomes costly. Adaptive enablement requires a willingness to learn, iterate, dissect, and try again, over and over, until you figure out what works.
“You have to be willing to take the good with the constructive feedback and be okay with that,” Andrew explains. “But it’s also about drawing parallels to how we learn in our personal lives. Think about how you like to be sold to when you’re making a big-ticket purchase, like a new car or house. You want someone who is passionate about what they do, knowledgeable, has your best interests in mind, and comes with a perspective. They should have a track record of success that they can tell you about.”
Adaptive enablement also applies to the sales process itself. Andrew notes the importance of narrowing in on your most strategic accounts so you can really understand their industries, their challenges, and the proof points that demonstrate how your organization can help.
“It’s fun to see the light switch go off,” says Andrew. “To me, it’s a more interesting way of selling. It’s less about coming at you hard. It’s more like, ‘I’m going to be with you throughout this journey.’ And whether or not you buy today, you know that you can come to me as a trusted advisor, someone who is bought into what you’re trying to achieve and will help you solve your challenges.”
Driving meaningful change in sales organizations often hinges on the frontline managers. The reality is, no matter how strong an enablement program is, it won’t take hold without the support and engagement of the managers closest to the reps.
“We can produce the greatest content in the world, but if you don’t have people that can evangelize and make space for their teams to learn, then it’s an uphill battle . . . frontline managers have way more influence with their teams than I will ever have.”
To bridge that gap, Andrew and his team developed a program called, “License to Lead,” which is designed to equip new and experienced managers alike with the skills to coach, provide feedback, and create space for learning.
“Not every team meeting has to be a pipeline review. That’s a missed opportunity. Make space to practice. Your team has immense experience you can tap into. Somebody on your team has unlocked a deal in a unique way — crowdsource those best practices.”
He stresses the importance of practicing the craft of selling, much like practicing a sport or an instrument. “People rush home to practice piano, guitar, or hockey, but rarely do we practice our craft. And those other things aren’t (usually) paying the bills.”
Andrew also highlights the power of peer-driven influence. High performers, he explains, are often the most effective at driving adoption across the team. “No one will care if I get in front of a sales team and tell them this is how you should do it. But if their peers, the best of the best, are evangelizing that approach, everyone wants to follow suit.”
His advice? Find someone who’s successful selling your product or service, and make their framework or approach work for you and your team.
Andrew is a seasoned sales enablement leader with two decades of experience helping global sales teams thrive. Having lived and worked in Canada, France, and the US, he brings a unique international perspective to building strategies that drive performance and create strong, cross-cultural relationships. Known for his entrepreneurial drive, Andrew is passionate about creating tools, training, and partnerships that deliver lasting impact.
