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The UpKeep Sales Journey with Garris Yeung

We talked with Garris Yeung, Senior Director of Sales, to get a glimpse into his journey from being UpKeep’s first ever sales hire to building out our entire sales team! We are excited to share his story, and how he has built a team on the foundation of compassion, curiosity, and championing change.


Humble Beginnings

In 2018, my wife and I made the big decision to move to Los Angeles after I accepted a new position as Director of Sales at a start-up called UpKeep. Driving into the office, I had normal first-day jitters for someone joining a tight-knit 8 member team, but my nerves went beyond that because I was also the first sales hire ever. My mission was to get to know the team, educate myself on the product, and prove why sales, as an entire organization, was needed at UpKeep.

You see, up until that point, UpKeep had seen a lot of success with no sales support. Plenty of customers had found the product on their own. And, to say our CEO, Ryan, was wary of the impact Sales could have would be an understatement.

No big deal, right?

Joking aside, I was up for the challenge. From the start, I saw the product’s value for the blue-collar workforce and believed in our potential for massive impact if we were to bring on a smart, compassionate sales team that sought to help this workforce through technology.

From my very first dial, I was out to prove that a sales team’s job is to help potential prospects navigate the difficult process of change when it comes to adopting a new software.

“For three to six months, I was on the ground selling alongside my reps to build a customer-first sales motion.”

Learning to Speak the Same Language

The people we were targeting were not totally sold on technology as a valuable solution for their pain-points just yet, so I saw our roles as being educators. We wanted our reps to be industry experts, not just product experts. The sales organization I wanted to build would be evangelical within the industry. It was never about selling features, so we read books, took courses, and, most importantly, listened. We spoke with hundreds of businesses, each time learning a little more. With time, we proved that our customers were coming off outdated pen and paper systems and were looking to us for expertise on how a mobile-first solution could make their days, jobs, and lives easier.

“From day one, we considered it our duty to encourage the wider maintenance industry to rethink the status quo using insights and best practices from our technology. And, it worked.”

I wanted sales representatives to be customers’ first allies – to help them become advocates for change in their own company. This, in turn, made prospects champions of our product. And, within the next two years we grew the sales team to 25 people, 10 times our revenue run rate, 2 times our average selling price. But, above all, we established ourselves as industry leaders within our segment.

Being Compassionate Advocates

We’ve grown a ton since those early days. As we built out the sales organization, compassion and curiosity have been central in our hiring. We believe every person on the sales team should seek to understand and empathize with the struggles of our customers so we can always craft solutions for any problem, big or small. Many of our reps have a special connection to our industry and are focused on really helping, since they either worked in blue-collar industries themselves or have deep family ties to it. I don’t get that many opportunities to jump on the phones anymore; but, when I listen in on my team’s demos, I see my initial vision for our team in full effect.

“When you talk to our team, you’re not talking to a product expert who can sell generic software features, you’re talking to someone who cares deeply about your blockers, your business opportunities, and offers solutions both in the product and outside it.”

Often, these tailored conversations are the first time our customers have ever had an ally on their side, leading to incredibly rich conversations full of trust and feedback.

Championing Change Internally and Externally

Because we have the privilege of talking to so many customers, Sales is also then able to pass this valuable feedback to the rest of our organization. We share how our customers are using our product today and how we could evolve our offerings in order to better serve our prospects. On any given day, anyone at UpKeep from the CS to Product/Engineering departments looking for more information about the needs of our customers can ask anyone in Sales, and they will receive valuable, foundational knowledge about the nuances of our customers.

This creates an amazing cycle of growth to the benefit of our customers because all of our new features and services are rooted in what we as an organization have learned from talking directly with them.”

The COVID-19 pandemic has forced the world to finally recognize the important work done by our customers. I’m so excited to help our industry as it benefits from the inevitable innovation ahead. We’re seeing upward growth across the entire maintenance industry, and lots of customers see the tides changing. My hope is that we can partner with our current and future customers to embrace these new innovations and drive change within their businesses together.  Sales’ commitment to the maintenance industry will always be the same as it was on my first day – we’re here to serve, to educate, and to advocate. We will work tirelessly to make sure no one is left behind when the next big wave of innovation rolls in.

And if your boss is wary of change? Don’t worry – I can coach you through that too.