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Allego Welcomes Sales Enablement Leader Chester Liu

Sales enablement expert Chester Liu has joined Allego as Vice President of Growth. He has a passion for understanding the customer journey and extensive experience designing sales processes that reduce the traditional friction between buyers and sellers, leading to higher sales and more satisfied customers.

> Connect with Chester on LinkedIn

With over twenty years in the software industry, nearly ten in sales enablement, and an MBA from the MIT Sloan School of Management, Chester has a proven track record of building successful sales enablement teams and programs.

His experience includes helping to take Black Duck Software from startup to successful $547M exit via acquisition by Synopsys, then scaling the sales team from startup to enterprise. His previous companies include RSA, the security division of EMC, Qlik, and WSI.

Because of the current global health crisis, sales enablement managers must get new hires up to speed and keep teams on track in a world where face-to-face meetings are impossible. We asked Chester a few questions about sales and the challenges facing sales enablement managers today.

How do you think your colleagues would describe you?

Some people say I’m a maverick—always looking for insights and innovations that drive change and improvement. I get bored if we’re still doing things the same way month after month. There’s always room for improvement, no matter how small.

Why did you decide to join Allego?

Having been a sales enablement professional for seven years and working closely with sales management and reps, and even closing some of my own opportunities, I felt like making the next step in my career. I have managed small teams before, but Allego gives me the opportunity to impact the personal and professional success of many more people. Also, since Allego is the most comprehensive yet amazingly easy to use sales enablement platform—and has the most ego-free culture I’ve ever seen in a company—it is a match made in heaven.

What skills from your past experience do you bring to Allego?

As a long-time sales enablement practitioner, I can help Allego with both messaging to my peers and training our reps on the sales enablement worldview. I’ve also spent years building up well-defined and successful sales processes and skills, and can readily adapt them for use at Allego.

What’s the biggest challenge you see sales leaders and sale enablement managers facing today?

It’s an issue of idealism vs. practicality. Ideally, they know they should be doing more coaching, more skill-building. But in practice they’re too busy putting out fires and working on must-win deals and other priorities fall by the wayside. They need a way to do the coaching asynchronously so their calendars aren’t booked solid with wall-to-wall meetings.

What advice do you have for sales enablement managers?

Become a hero to your sales team by designing and building systems and practices that they will truly use to become successful. From the toolstack perspective, I’ve seen too much shelfware, because having too many tools causes confusion and friction. There should only be one go-to platform for learning and content. Having separate tools for reinforcement or coaching just creates confusion and lowers adoption rate.

From the content perspective, don’t just build content and throw it over the wall. Have a plan for getting buy-in before you even write a single word, and involve the reps in building and deploying it. Let them comment and provide feedback throughout the development cycle, not just at the beginning or the end. They will be your champions. Lone ranger sales enablement folks rarely succeed.

What is an innovation you’d like to see more sales enablement professionals using?

Sales enablement professionals are on the front lines and face new challenges every day, especially in the current crisis. Yet many organizations are using outdated training and enablement approaches. Their onboarding and training tools and processes haven’t kept pace with the times. I would like to see every team adopting a modern mobile and video-based readiness platform to equip reps for an increasingly complex buyer journey.

I once was a complete skeptic on the power of video to engage people because I was only used to long-form videos from webinars and corporate learning platforms. The use of bite-sized videos really forces content creators to be concise, and makes the experience for the learner so much more engaging.

What’s a goal that you want to accomplish in the next year?

Build a repeatable sales model for success at Allego, allowing us to scale our sales team fast without the typical headaches that come with it. I also want to excel at drinking our own champagne, using Allego to create hot seat exercises, express new ideas for feedback, and using Allego as not just a content repository, but also a place to gather and make sense of tribal knowledge that is spread throughout the talented people at Allego.

What are you happiest doing when you’re not working?

Definitely taking out my extra energy on smashing tennis balls for the win. I play with a group of guys and whether I win or lose, the friendly competition gets me fired up for the rest of the week.  I am also an avid snowboarder, but with climate change and less snow in New England, it’s been a challenge to get out on the slopes as much as I want to. Maybe I will take up surfing, who knows?

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