Staff & Training

Customer Success Mission, Vision, and Strategy at UpKeep with Joseph Schmitt

Ryan Chan

We talked with Joseph Schmitt, VP of our Customer Success Department, to get a glimpse into his journey of how he got to where he is today at UpKeep. We are excited to share his story, and how he and his team have embedded the customer experience at the heart of UpKeep!

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Customer Success Mission: To ensure the lifelong success of our customers and empower them to become world class maintenance teams.

Customer Success Vision: Our vision is to be a partner to our customers and act as one team. Our customers’ successes are our own.

Customer Success Strategy: We achieve these outcomes by going above and beyond for our customers – providing incredible service and driving product adoption. We believe authentic relationships start and end with listening and understanding.


The Beginnings

As UpKeep technologies announced our $36M Series B fundraise, bringing our total funding to $50M, I’ve found myself reflecting on the crazy, unexpected – and sometimes scary – journey that brought me here as VP of Customer Success.  

Five years ago, I was the store manager at the Starbucks on Larchmont Blvd. The coffee giant’s culture and processes embedded themselves deeply in my customer philosophies as I jumped into being the first Manager of Customer Success at another Los Angeles startup, PatientPop. With time, my CS expertise grew with the company. Before I left, I led three teams with 20 direct reports. And then –  I received a LinkedIn message from a CEO named Ryan Chan. I left PatientPop to kick off the most exciting challenge of my life.  

Today, I lead our department of 13 rockstar individuals – all of us dedicated to revolutionizing the maintenance industry, one customer at a time. What were the crucial milestones that got us to this place? What have I learned as I helped build our startup from the ground up? And what do I see on the horizon for CS, UpKeep and the maintenance industry as a whole? Read on to hear these thoughts and more. 

Where we were…

When I first started at UpKeep in 2017, we were five employees (two engineers, Ryan, one sales person and myself) sharing a co-working space with a real-estate agency, a video-game startup, and a snack company. That small (but mighty!) team had proven that the maintenance industry was hungry for innovation, already amassing hundreds of customers around the country in just a year. I rolled up my sleeves and set out to build the company’s first full department, Customer Success.

Being UpKeep’s one-man department enabled me to develop so many parts of the CS process. How should we handle support tickets? How can we be proactive in bringing value to our customers? What’s the most effective way to complete implementations? During this early phase, there were no shortages of new questions and challenges, and no two days were the same. Having a direct connection with our customers and coming along on their CMMS journey was incredibly rewarding.  And all of the lessons I was learning were crucial when the time came to grow the CS team. 

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“To lead effectively when building something from the ground up, I had to put in the time myself. Speaking to customers, trying the process myself, then failing all on my own was crucial.”


When onboarding our second CS hire, Jason, I could confidently share the ‘why’ behind everything we did. All of our processes were built from working directly with our customers and adapted to meet their unique needs. I was able to be very hands-on during their onboarding, and could share where I thought these processes and tasks could be improved even more.

This second hire in CS was a bit untraditional – we hired a Customer Support Representative to join the team. It was critical for me to build the team in this way because I believe whole-heartedly, “Amazing Customer Success starts with great support.” We intentionally said, “No matter your company size, no matter if you’re on a paid or free plan, all of our customers are going to get the same level of dedication and support.” 

A focus on support became super important to UpKeep’s success because it lent itself to another learning I gathered during the first year of UpKeep’s journey:

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“One of the biggest challenges that can affect customer facing teams at an early stage startup is the product experience.  Focusing on support and making it critical to our business expedited the feedback cycle from customer →  CS → Product and back. This brought value to them faster than any of our competitors, and ensured that the CS and Product teams walked in lockstep, instead of acting as opposing forces.”


Once the Customer Support function was up and running, we then moved on to building out even more CS roles before actively recruiting for other departments. 

In hindsight, building CS first was crucial to UpKeep’s success because it reinforced that the customer experience was the heart of our company. Every single new employee that was brought on was trained by a CS team member. Sales, Product, Operations, and Marketing – all of these departments were onboarded using a customer-focused lens. When we say one of our values is Customer Commitment – this is perhaps our most salient example of walking that walk.

Something else that was fundamental to UpKeep’s success was our eagerness to seek feedback, and more importantly, act on it for more than just our customer’s happiness with our product. We released surveys to our customers on just about everything (and I mean – everything). The learning?

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“Never shy away from soliciting feedback. Act on it quickly, and articulate with the customer directly. The more customers understood that we were a company that listened to their opinions and experiences, the more they were willing to proactively share feedback with us directly versus publicly. This gave us the competitive advantage we have today.”


In one of our proactive conversations seeking feedback, we heard from a customer themself: “With our last CMMS, we never spoke to a human more than twice in two years. I’ve spoken to your team at least 20 times through implementation alone. It makes all of the difference.” 

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“Being human and letting our customers know we’re growing with them makes customers trust in us as a partner. Progress over perfection isn’t just an internal value – it’s one we practice with our customers too.”


Where we are today!

As I mentioned previously, in the early days of the company, I had a hand in every single CS activity at UpKeep. Then the CS team grew to three teammates – then four  – and finally we couldn’t fit in one tiny office anymore. While we each had our own responsibilities, it wasn’t uncommon for us all to lend a hand with support, lead an implementation, and do proactive outreach to our book of business all in one day. It was all-hands on deck and our team excelled at manning all CS stations as needed. At around 50 company employees, however, we saw the need to move from all acting as flexible generalists to seasoned specialists.  

This shift has allowed us to better leverage our number one resource: time. Every CS teammate’s time is now directed towards as much customer-facing interaction as possible. Today, the CS team is growing and specializing: each member of the team works on testing and refining specific playbooks instead of firefighting as needed. They don’t need to worry about context switching between tasks taking valuable time away from CS team members. Delegating management responsibilities was part of this specialization process as well! By promoting CS talent into management, I’ve found that I can now focus on more high-level, strategic initiatives.

My fourth learning is all about this journey to a more specialized team:

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“As we continue to specialize the roles of CS team members and have employee’s own specific areas of a customer’s journey with us, we’re able to offer better support and experiences to our customers. This focused support ultimately leads to the customers being more successful in their business goals.”


As the product becomes more specialized, we’re going to need CS teams to support that so we always have the right person ready to answer our customer’s more and more complex questions. 

However, the path to specialization has also been one of our biggest challenges. As the company went through its growth journey, our veteran team members had to go through it too. Of course, change can be uncomfortable – and there were road bumps –  but I’m proud of how my team has stepped up to meet this new reality. The UpKeep CS team is very self-driven and I’ve made it a point to manage them in a way that gives them as much autonomy as possible. With a team that takes extreme ownership, asking them to transition to focusing on a single step in the CS journey and OWNING it was easy. Each and every teammate took their specialty – from Implementation, Customer Success, Customer Support, Post-Implementation and RAN with it. The team tried new things. They took in feedback. And they learned first hand how to better help our customers. In truth, as a manager, that’s all you can ask for!

What’s Ahead?

There’s so much growth and evolution on the horizon. 

As a department, we’re still working on how to best articulate value to our customers – especially the larger customers with more mature maintenance processes already in place. We’re always seeking more industry knowledge so we can speak expertly in the language of our customers, but how can we get there 10x faster?

There are also some other topics on my mind:

  • How do we create more product led growth? 
  • As the next generation of maintenance enters the industry, how will their expectations of technology change? Who is the technician of the future and can they provide value in a remote position? How can we anticipate their needs and prepare ourselves now to be partners for them?
  • How can we continue to show up for our community?

However, if I were to pick ONE thing to measure our success as a department, it’s simple.

It’s all about achieving customer outcomes. Are we an extension of our customers’ teams that helps them reach their business goals? Are we the first email they send out when they’ve reached their once lofty production goal? Do we help our customers receive more budget for their maintenance team? 

Our customers’ successes are our own successes. 

The TLDR Version

Where we were — “We Start With Our Customers First”

  1. We were a small team dedicated to providing the absolute best customer experience in every single fashion
  2. Customer Success was one of first departments to be built since we’ve always put our customers at the core of the entire company

Where we are and what’s made our team special — “Customer Feedback Drives Our Every Decision”

  1. Our ability to listen to our customers, take in feedback, adapt and change to our growing customer needs regardless of which department you were in.
  2. We’ve always given every single customer — whether you pay us or not, the same level of outstanding support. We believe that every single customer, paying or not, provides unique feedback that pushes us to be better.

What’s ahead – -“Supporting our Customers With Breadth and Depth”

  1. Becoming an extension to our customer’s team with deep industry expertise
  2. We continue to specialize our team to have the breadth and depth to support our customers to go above and beyond for them.

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