As I head off on parental leave, I find myself reflecting on my time at Tito so far. I wanted to capture five of the many lessons I’ve learnt on the job so that I can refresh my memory when I come back next year (and for anyone else who might find them interesting in the meantime).

From customer to team member

I joined Tito four and half years ago, having previously been a user of the app in my capacity as a marketing manager at a company running tech conferences. This former employer was actually the 31st account registered on Tito (and remains a loyal customer to this day), and I made myself known to Paul and Doc in those early days by being very vociferous with my feedback and feature requests!

When the time came for me to leave my old workplace, Tito revealed that they were interested in potentially hiring me to do marketing, but by that point I’d already accepted another job offer. Several months later, when I was desperately unhappy at my new company, I reached back out to Tito to see if they still needed a marketing manager but, alas, they had filled the role by then. I was crestfallen, until they said, “though we are looking for someone to head up Customer Experience”. I thought to myself: Well, I’ve been a customer… I’m totally qualified to do that!

Starting out as Customer Experience Lead

Turns out I had a lot to learn. I’d considered myself a power user of Tito, so naively expected that I’d be able to handle most enquiries with relative ease. I soon learnt several valuable lessons:

1. There are as many different ways to use a product as there are customers

It’s one thing to know what features your product has, but it’s another entirely to understand the way they’re actually being used in the wild. Customers often surprise you by using (or trying to use) a feature to achieve a totally unexpected goal. And when they do, it’s worth asking yourself two questions.

Firstly, is the feature designed in a way that might inadvertently confuse or mislead customers about what it’s for? (For a personal example, see Tito’s Activities). In this case, you might need to reconsider the UX/UI of the feature and/or create better documentation or tutorials to avoid customers feeling frustrated at something not working the way they expect it to.

Alternatively, you may question whether there are legitimate use cases you hadn’t predicted when conceiving and building the feature in question. It’s great when this is the case! Your customers have done discovery for you, and you now have the opportunity to share knowledge and inspiration with other customers and prospects, to help them get even more value out of your product.

2. There’s a huge range in customers’ technical knowledge

Sometimes we receive in-depth questions about our API or webhooks or super niche scenarios that require specialist knowledge to answer, typically from one of our engineers. And other times we get queries that seem so basic they actually confuse us more than the “difficult” questions at first.

One disadvantage of being a small team of people who are all very technically literate is that it can be easy to forget that not everyone has the same level of knowledge or familiarity with tech. And I’m not just talking product-specific experience. I mean use of computers and the internet in general. We try our best to meet customers wherever they’re at, but it can prove challenging when you lack a common language to seek further information or communicate a solution — for instance a customer not knowing what you mean by the word “browser”.

There are ways around this, of course: keeping language straightforward and avoiding jargon; using screenshots or screen-recordings to illustrate steps to follow; and even asking what may feel like basic questions to check our assumptions about what the customer is looking for. It’s a skill we get to practice often, as everyone in the team takes turns to cover support. Speaking of which…

3. Responding to support queries is the best product education you can ask for

After a couple of years leading CX at Tito, I moved on to head up our product development specifically. Up to that point I had no official product management experience, but my time intensively covering support stood me in good stead for what was to come next.

Apart from the aforementioned reasons support duty is eye-opening, it also presents you with a bunch of real-life scenarios you can test out, lets you know about users’ bugbears and most wished-for features, and reveals the ways your customers think and talk about your product. I cannot overstate how valuable this knowledge is when shaping, testing, building and writing documentation for new features.

Moving on to Head of Product

For the last couple of years (since just before the start of the pandemic, in fact), my primary role at Tito has been Head of Product Operations. In a nutshell, I’m responsible for overseeing the design, delivery and support of our two products: Tito, event registration software, and Vito, a platform for creating online hubs for events and communities. This means working closely with our incredible product team, who I’m going to miss dearly while I’m away! But before I start getting too sentimental, let me reflect on a couple more lessons I’ve learnt in this role:

4. Setting the right cadence is the key to momentum

We tried a couple of different lengths of development cycle (or sprint) before arriving at something that’s been working well for us for the last 17 months. That’s currently two weeks “on”, i.e. working on a clearly defined project with a specific outcome such as shipping a new feature, and one week “off”, i.e. working in a more freeform way on less defined but equally important tasks such as bug fixes, maintenance and personal interest projects.

We find this cadence sets a constraint that encourages us to be very intentional about what we’re building, and gets us into a habit of shipping regularly. Plus if something comes up that might otherwise distract us from our goals, we usually only have to wait up to a couple of weeks before we can tackle it (assuming it’s not super urgent).

Of course, no system is perfect. We’re a small team and we all take turns to cover support, which can easily take us off on a tangent if a gnarly bug rears its head, plus we have a generous holiday allowance so there’s often someone out of the office. But in the wake of the pandemic and how it impacted our business in unforeseeable ways, we’ve found this cadence allows us to be nimble enough to both plan ahead and re-evaluate and respond to changing priorities whenever we need to.

5. Document your processes, even if everyone already knows them

As I head off for a year without an additional person coming in to cover my responsibilities, I feel confident knowing that the existing team members picking up tasks on my behalf have everything they need to be successful. Not only have we taken care to develop a set of processes that work well for us, but we have the vast majority of them written down to refer to internally. This eliminates uncertainty and guesswork, and allows us to expend our efforts on what we’re working on, rather than how we’re going about it.

There’s so much more I could write about working at Tito and about what it’s taught me. But for now I’ll just say that, as excited as I am for the next chapter in my life (which has been a long time coming, but that’s another story!), I’ll really miss the team, the products, and our customers, and I look forward to seeing you all again around November 2023. 👋🏼

Team Tito

Team Tito: our company