A year ago, I joined UpKeep to help make the lives of the the underserved labor around the world better. Up to that point, I never really saw myself working at a B2B SaaS startup building maintenance and reliability software. Coming from Ticketmaster where I ran Consumer Products and Open Platform, this was a big change for me.

I took the job because I believed in the team, the mission, and the business. Also, taking on both Product and Engineering at a fast-growing B2B SaaS startup was an interesting challenge for me, both personally and professionally.

As I reflect on my journey at UpKeep over the past 12 months, the one word that keeps popping in my head is team. At UpKeep, our ability to build and nurture teams, both internally and externally, is unparalleled. We call our external team community. If you’re affiliated with UpKeep in any way shape or form, you’re part of the team.

As a team, we’ve gone through so much together. From the expected trials of a rapidly growing business to the uncertainty of a global pandemic, we’ve gone through it all with incredible grace and aplomb. I’m so proud of the team and what we’ve accomplished together in such a short amount of time.

Where We Were

On my first week at UpKeep, we had a business disruption in the form of an outage. The app was down and customers were calling. The night before, we had a product release–one of many that week. It was intense, but that week taught me the lay of the land and helped me identify areas of opportunity pretty quickly.

The Product and Engineering team at that time was comprised of small group of talented engineers who were working on many new features at the same time, pushing them out to production at lightning speed. Releases went out daily. Velocity was through the roof! The product and the business were growing at a pretty good clip.

This was great, but the quality of the user experience (i.e. ease of use, consistency, and reliability) suffered as a result. Quality might not matter as much to a burgeoning startup that is trying to figure out its product/market fit, but by the time I was hired, we were beyond that point and well into our hyper-growth phase.

It was very clear to me that the most important thing we needed right there and then was to stabilize the product. We didn’t need new features. We needed to ensure the features we already had worked well and to our customers’ expectations. I still tell my team: a feature customers don’t have is a feature they don’t miss. A feature they have that isn’t working right, is a feature driving them away.

Building Blocks

Our sole objective for the rest of 2019 was to focus on quality, stability and security. Only then we could start unlocking new features for our customer again reliably. I embarked on hiring the best team I could assemble to help drive that vision forward. By the end of 2019, we had most of our A team assembled, some critical agile processes implemented, and our infrastructure bolstered.

As our business grew, our customers were getting larger in size and their expectations were getting higher. That’s why it was imperative that we hired the right product, project, design, and engineering talents that can help deliver to those expectations.

Moving away from a single talent spread thin across many work streams to dedicated pods with the right composition of talent was a critical decision to bring focus and consistent quality to the work we do. Eliminating fractured focus was my main objective. Fractured focus generated mediocre work which led to outages.

Now, with dedicated talents focusing on specific work streams, we are able to deliver a high quality, consistent, and reliable experience to our customers.

Of course, none of it is without challenge. The team has faced challenges along the way due to the existing tech debt and our understanding of it. The team had to learn the system from scratch. There’s no documentation. Over time, we were able to work with the tech debt and pay it down strategically to help expedite the Time to Value for our customers. We also created proper documentation of the system to make it easier for anyone new to get onboarded quickly.

Decisions Decisions

The job of a leader is to make decisions. If you’re an xVP or C-level leader and you’re not making hard decisions daily, something’s wrong. Seeking comfort in indecision is not an option. Nothing is more debilitating than an indecisive leader.

Over the past 12 months, I’ve made a lot of decisions. For most, the jury’s still out, but for some, they were critical in getting us to where we are today. Below are five major decisions we made along the way:

Decision #1

The most important decision any leader will need to make at one point or another is building an effective team. Right out the gate, I made hiring the right talent my first priority. Hiring the right product, project, design, engineering, and devops talents was a critical driver to us being here today.

Decision #2

Another strategic decision that’s proven boon to us is the focus on data. We’re about to launch our Upkeep Analytics platform to provide actionable insights to our customers. It’s a start. This development, which took months for us to realize, has been met with overwhelming excitement by the very customers we need to grow our business. The decision to focus on data has already proven to be the right decision for us.

Decision #3

One decision I made in my early days at UpKeep, which wasn’t popular at the time, was halting the release of a major product release due to lack of quality–the experience was lacking and the performance was poor. The delay lasted 6 months. By that point, we had been talking about this product to our customers and we’re looking forward to its release. It was a hard decision to make.

To my surprise, the team rallied behind the decision and there was very little pushback, even though no one really wanted to delay the release. That really stuck with me. It proved that everyone at the company was thinking about what’s good for our customers.

Decision #4

Focusing on sensors, or connected IoT devices, as a way to truly make the lives of technicians better through reliable, consistent asset monitoring 24/7 was something of a no-brainer for us. We made a strategic decision to bet on sensors back in September and now it’s become a staple of the UpKeep product offering.

Decision #5

The decision the company made from the onset to focus on mobile and make it a core competency of ours was something I doubled down on. Focusing on mobile-first development in the native format has been a huge differentiator for us in the marketplace. It helped us win deals and grow our business.

Customer Focus

Every company has an unfair advantage, whether it realizes it or not. Ours is the relentless focus on the customer embedded in our DNA. From the product managers and designers who are shadowing technicians and running customer interviews, to the developers and system architects who participate in ethnographic consumer research to understand how our users engage with the product. Everyone looks at the problems we’re solving from the lens of the customer.

I’ve been part of many teams in the past, and I can tell you that not every company truly focuses on the customer. That focus requires empathy and empathy isn’t something you teach. It’s either you have it or you don’t. This is why hiring the right team is critical.

Our purpose, which is our rallying cry, driving everything we do day in and day out, encapsulates our focus on the customer really well:

We believe in making the lives of the underserved labor around the world better through technology.

Unlike many of our competitors, we have a freemium product. Customers can check us out before they commit. That “dating period”, as I like to call it, is crucial in sealing the deal. Our job is to WOW the customer with the ease of use and simplicity of our product. Our goal is to make joining the UpKeep community a no-brainer. This is why the team is unwavering in their commitment to eliminate friction, expand self-service, and ensure the reliability of the platform.

Strategic Initiatives

Because we’re focused on the customer, the initiatives we choose to work on are directly related to making the customer’s life better. This runs the gamut from overhauling preventive maintenance to fully reimagining analytics and insights to creating meaningful integrations with 3rd-party providers.

As of this writing, we have overhauled the interaction model of our mobile applications to make them easier for technicians to use, and in the process of rolling out our very first Advanced Analytics platform for admins and decision makers. Our platform is now running on Kubernetes and we’re well underway to unlocking capabilities critical to our mid-market and enterprise customers.

To stay abreast of everything we do for our customers, check out our blog.

Where We’re Going

I’m really excited about what the future holds for UpKeep, and the maintenance and reliability space in general. In the post-COVID world, sanitization and safety protocols will become mandated and regulated. There’s no way around it. That’s something, I believe, UpKeep can help champion.

Maintenance is now essential for any company where humans interact, which is to say all companies . We can help set the standards for sanitization and safety, create the appropriate checklists for them, and make them easily achievable and trackable on our platform.

We’ve handled reactive maintenance well, and we’ll soon release our overhauled preventive maintenance experience, but the future is going to be about predictive maintenance––using machine learning and AI to find the problem before it occurs and guide the fix to minimize downtime.

Predictive maintenance, in my mind, is an ecosystem where advanced analytics, sensors, and open APIs converge to provide our customers with a robust system to collect data, synthesize it into information, and deliver it as insight on a timely manner. Achieving that milestone will be a huge inflection point in our trajectory as a business.

Measuring Success

For me success lies in unlocking value for our customers quickly and with high-quality. Quality is really important to me as it translates into trust. Whatever we work on, the end product has to be synonymous with high-quality (i.e. no friction, reliable, and predictable).

Quality is also measurable. How many incidents have been reported this week? This month? How many customer support tickets were filed this week? This month? What’s the NPS this week? This month? What’s the conversion rate on flow X?

This doesn’t mean that we stop experimenting. Innovation is critical to us as long as the expectation with the customer is set properly. Over-indexing on over-communication helps in that regard, which helps us draw a clear delineation between core, reliable capabilities and experimentation, especially with our customers. In the end, it’s all about expectations.

As we continue unlocking new capabilities and products, paying close attention to our customers’ ever-evolving needs and pain points is what ultimately going to make us successful as a company. It’s the only thing that will keep us honest and true to our purpose in making the lives of the underserved better.

Here’s to another great year!

I think in stories, and sometimes I write them down.

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