Sam Schulte is Vice President, Product Engineering at Inspirato, a luxury hospitality and travel subscription company. He started his career as a software developer at TransUnion and later moved to ProLink Solutions, a software company that offers solutions for the affordable housing sector. Sam held business analyst and product owner roles at ProLink before transitioning to product management at Inspirato.
In our conversation, Sam talks about the delicate balance between innovation and scale and the importance of not overwhelming customers with new product offerings. He shares how he emphasizes over-communication and “meeting people where they’re most comfortable” to keep everyone updated within his teams. Sam also discusses how Inspirato ideated and launched a “loyalty program within a loyalty program” to drive more stickiness within the member group.
Inspirato has always been a luxury membership club for travel. We have a curated list of luxury travel accommodations that we provide to our customers — the majority of which we have exclusive access to and control and manage. That gives us the ability to have full control over not just the accommodation, but the service paired with it.
We have been operating this membership model since our inception in 2011. Eventually, we started diversifying the portfolio with additional types of accommodations to add breadth and depth to member favorite destinations. For example, you may not always need a three- or five-bedroom home when you travel. You might just want to stay in a nice luxury hotel in one of the premium rooms that they have. We started getting serious and scaling the types of hotel accommodations that we added to our portfolio, ultimately pairing them with what we call our residence portfolio.
The idea of a subscription started to become more and more appealing from an opportunity standpoint, so we developed Inspirato Pass. You can subscribe either monthly or annually — that provides access to highly valuable trips within our curated luxury collection of homes and hotels.
To give you a little bit of background, for most of my tenure at Inspirato, I was one of the people who helped build the product management function. Like many companies, we had been operating within our technology department, but we were still organized by function. We had a centralized product management team, a centralized engineering team, a quality team, etc. That’s how we evolved and grew as a technology organization. Then, over this past summer, it became clear that it was time to look at a transformation. We wanted to make sure we could inject more predictability into the rest of the organization in terms of value creation but also deal with some capacity constraints like many companies are facing now.
We wanted to look at shifting to more of a dynamic model where our teams within technology are more empowered and embrace full ownership of what value is created. That starts from the vision and priorities to execution and having that sense of unified accountability. In practice, we’ve decentralized those functions. We still have many people in those roles who are part of a team that rolls up and reports to one person.
In my role, I have product managers, engineering leaders, and scrum/agile ops reporting to me. I’m accountable for a larger portion of our technology ecosystem in terms of revenue-generating value streams. We’ve reorganized and introduced this transformation that we’re now four or five months into.
At least from my perspective, it’s about over-communication — to the point where you’re almost feeling like it’s too much, except it really isn’t. What I mean by that is ensuring that you are leveraging multiple channels to communicate, be it updates or asking questions, and meeting folks where they’re most comfortable.
I often find that I am using multiple mediums to communicate the same thing. At times, that can feel inefficient, but I remind myself that not doing so creates more problems that can slow you down. Specifically, there are some checkpoints that I have with my team to make sure that communication is happening. Aside from 1:1s, I have department meetings multiple times a week. One is more focused on looking ahead and aligning on priorities and vision at the beginning of the week, while the other is specific to status and execution around what’s in-flight. The most important thing is that those aren’t updates for just me. Rather they’re updates for people in various functions to stay informed about things that could have some type of dependency or impact on what might be done by another group.
It’s had an impact on the entire company in terms of how we operate. That absolutely applies to product strategy as it relates to the technology solutions that I’ve helped own and shape over the last several years. It has introduced a variety of needs in areas that present a lot more conflicts with priorities.
For example, there were some things that we really wanted to do from an innovation or a user experience standpoint that we weren’t able to do the way we wanted. Much of our focus, and rightly so, has been making sure we shore up some of our backend systems, processing, and data governance around making sure that we are reporting the right information publicly when required.
Our rewards program that I mentioned is a recent example of an innovation where we’re at that tipping point to scale. When you think of Inspirato’s dynamics, it’s a membership club. In and of itself, it’s already sort of a loyalty program. When you become a member of Inspirato, you are naturally indicating a preference for our brand because you’re paying for exclusive access, certainty, and service within our portfolio. When you think about it that way, you already have this loyalty concept baked into the model. As we’ve evolved as an organization, we’ve seen the opportunity to really drive even more of that loyalty within our own member group.
As a result, we launched Inspirato Rewards this past fall, and that was something that had been an idea for a long time. We finally hit a point over the summer where there was enough conviction and alignment that we saw the need for it. But we need to be mindful of how we now nurture that program because, again, it’s early in its inception. Right now, we’re being very careful about introducing new ideas and concepts to our customers because over the years, we’ve tried a lot of innovative things that have caused a fair amount of confusion. How do we make sure that with this new rewards program, we are spending the right time to educate and inform our customers?
That historically hasn’t always been the case. When we think about scaling and innovation, that’s an example where we’re really trying to balance both with this program. It’s a strategic idea that we think has introduced a good amount of innovation and value for our customers, but we also want it to be an avenue for growth for years to come.
We have a few ways that we can get insight from our customers. Once you become a member of Inspirato, our very talented and dedicated member success team gets to know who you are and your travel habits. Where do you like to go? Who do you like to go with? What time of year do you go? When you travel, what are the things that you like to do? We have people who already have a really great understanding of who some of our core customer personas are, as well as individual customers themselves.
Through that channel, we make sure we’re getting the right insight and input from those folks within the company, but also have direct conversations with our customers. We’ll do informal conversations or formal things like focus groups or satisfaction surveys. We also rely heavily on our marketing, consumer insights, and product design teams to provide a lot of really valuable research data, both quantitative and qualitative, that we can leverage. We pair that with our product design team, which does a significant amount of testing as far as content.
We have a lot of different ways to research ideas and use that to ultimately make what we believe are defined hypotheses and, ultimately, make those bets.
There were a couple of compelling product innovations in the ideation phase last spring. While those ideas didn’t come to fruition based on our research, they shared foundational elements that led us down the path toward what is now Inspirato Rewards. It was exciting to see the idea evolve into a compelling value proposition for our customers through a highly collaborative process and in a relatively short time. You never know where inspiration and good ideas will come from, so it was another example of why it’s so important to keep an open mind to new ideas.
There was sort of this sentiment like, “Isn’t Inspirato already a loyalty program because it’s a membership club?” It took a little bit of time also for us to get comfortable with that mindset of a loyalty program within a loyalty program if you will. As it became more and more apparent what this could be and how valid it could be, it gained more and more traction. Ultimately, we were able to execute it. We were seeing some really positive early signs of adoption from our customer base. Now, it’s on us to be very disciplined to not try and introduce too many changes and be thoughtful that our customers fully understand the program.
That particular initiative is from several years ago when I was part of a different team at Inspirato. I touched on this before with regard to us getting more and more serious about hotels and how we can scale that offering to our customers. This was sort of a way to empower that. We essentially built an inventory hub with capabilities to connect to multiple distribution partners. It allows the mapping and normalization of that content across various providers into one cohesive, consistent data set. We can then merchandise and market it to our customers.
It empowered the business to grow our portfolio in a way that we hadn’t been able to do yet. It continues to be one of the key components of what we offer to our customers in terms of how someone can browse and book a luxury hotel through our platform.
I think there are some core problems in the alternative accommodation space like vacation rentals. It’s exhausting to try and find something that you may want to book. You’ve got so many competitor sites. You have sites that kind of try and provide everything together, but inevitably, there’s a deterioration in user experience depending upon what you’re looking at. Within the industry itself, all of these property managers are using dissimilar tools to put out the same content across all of those channels. Even though you’re looking at all of these different platforms, it’s the same thing with a different skin. As a consumer, I find it really tiring.
I think whoever can start to create more brand loyalty and stickiness within the space is going to see a significant amount of growth and opportunity to differentiate. I look at where the space is now as similar to the way hotels were 10–15 years ago. You had all of these different hotel chains and you could go and browse all of the different hotel websites, but then Kayak came about and gave you a great way to see everything. That was awesome, but then the hotels got sophisticated and started giving you reasons why you should book directly with them, like loyalty statuses.
There’s no such thing as that for vacation rentals. There isn’t that stickiness that you see in hotels in an alternative accommodation space. I personally think that this is ripe for disruption.
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