Meet the Makers: Christian Castorena, Leave Quality Manager

At Tilt, our work is only as strong as the people who build it. And when it comes to leave compliance — the part of leave that can feel the most rigid, intimidating, or high-stakes — Christian Castorena  is one of the makers turning complexity into clarity and care. This month, we sat down with him to talk about the fast-moving world of leave laws, the heart behind compliance, and how his work shapes what we’re building with Tilley. 

Q1. Leave laws are changing fast. What has been the most exciting or challenging part of working in leave compliance during a time of so much legislative movement?

What’s wild about leave right now is that it feels like the ground is always moving under your feet… and I actually love that. Every new law tells a story about someone who went through something so difficult that we collectively said, “We have to do better.” Behind every statute is a real person whose experience shaped protections for everyone who comes after them.

The challenging part is that employees and HR don’t feel the excitement of legislative movement. They feel life crises: being sick, caring for a loved one, or facing an unexpected loss, all while wondering how to protect their job or paycheck. That’s the part that stays with me. 

My team’s job is to stand in that chaos and say, “You don’t have to carry all of this and learn the law at the same time. We’ve got you. We’ll help make sense of this." The exciting part is getting to turn all of that complexity into protection. I get to take dense, technical rules and turn them into something that sounds like, “You’re not alone. You’re covered. Here’s your path, and here’s what happens next.”

And I don’t do that alone. I’m fortunate to work with some of the most talented partners in leave compliance—true leave nerds ( I can say that because we proudly own it) who share the same passion for making this movement meaningful. Together, we stay energized by watching these laws evolve and seeing the real impact they create. Watching these laws evolve and knowing we get to play even a tiny part in making that evolution feel safer and more humane for people—that’s what keeps me energized.

Q2. As someone on the leave compliance team, you play a critical role in what we’re building at Tilt. How does compliance shape the way we develop Tilley and other innovative tools that support a better employee experience?

For us, compliance isn’t the brake pedal—it’s the steering wheel.

Tilley and every other tool we build only matter if people can trust them when it truly counts. That kind of trust doesn’t start with clever features; it starts with respecting the rules and being honest about what we do and do not know.

When we’re building, I’m constantly gut-checking: “If this were me, my partner, my parent, or my best friend on leave, would this answer feel safe? Would I feel okay relying on this in the middle of a crisis?”

That’s why we obsess over things like:

• Explaining why a rule applies, not just dropping a citation and walking away.
• Being careful with numbers, timelines, and eligibility so we never casually overpromise something as serious as income or job protection.
• Designing tools that know when to say, “This is bigger than a bot—this needs a human.”

Compliance gives Tilley a moral center. It makes sure our innovation isn’t just about speed, efficiency, or automation for its own sake. It’s about building something that can sit with people in some of the hardest chapters of their lives and still be worthy of their trust. If our tools can hold even a little bit of their fear and confusion and turn it into clarity and dignity, then we’re building the right things.

Q3. Compliance is often seen as rigid, but your work is ultimately about care. How do you keep humanity at the center of something so rules-heavy?

I think of compliance as the scaffolding around care.

The rules are there so that when someone’s world tilts—when a diagnosis lands, a baby comes early, a parent’s health declines, or grief hits out of nowhere—there’s a structure strong enough to keep their job and paycheck from collapsing with everything else.

To keep it human, I try to never lose sight of the moment on the other side of the screen. Someone might be opening a designation letter at 2 a.m., in the half-light of their phone, after putting a baby back to sleep. They might be sitting in a hospital hallway. They might be at their kitchen table with a calculator, wondering how they’re going to make next month’s rent if they take the time they really need.

That is not the moment for cold, legal-speak. That’s the moment for, “Here’s what this actually means in your world. Here’s what you can expect next. Here are the choices you still have.”

So I ask a lot of “How would this feel?” questions.Would this wording make someone feel blamed? Would this timeline feel impossible? Is this process giving them dignity and real options, or just a list of deadlines?

I fight for plain language. I push for workflows that don’t treat people as problems to manage but as humans whose lives are in a fragile chapter. And internally, even when we’re talking about regulations, risk, or audit findings, I try to bring us back to this truth: every policy, every step, every letter, every system change touches a real person’s life. If we remember that, the work stops being just “rigorous” or “compliant”—it becomes an act of care.

Q4. Having started as a Leave Success Manager and now serving as a Leave Quality Manager, you’ve seen compliance from multiple angles. Can you share a bit about that journey and how your perspective has evolved?

Starting as a Leave Success Manager taught me what leave feels like up close—messy, emotional, and deeply personal.

I’ve been on a call with people who were crying so hard they could barely get their words out, and with others who were laughing with relief because they finally felt like someone was in their corner. I’ve supported people who were trying to be strong for everyone else while quietly falling apart themselves.

One of the moments that has never left me: a birthing parent once texted me a picture of their newborn just an hour after delivery. I wasn’t family. I wasn’t a lifelong friend. I was their LSM. But in the weeks leading up to that day, we had built a relationship rooted in trust, safety, and care. For them, I wasn’t just “the person doing the paperwork”—I was part of the story of how they made it to that moment.

I’ve walked employees through pregnancy disability, bonding leave, medical treatment, and return-to-work transitions with so many “what if”s in the air. I’ve guided people taking their very first leave of absence, who were terrified of “doing it wrong,” and people who’d been through the process before but were going through something harder this time. Over and over, I learned that for them, this isn’t “a case.” This is the moment everything else in their life has to bend around.

Now, as a Leave Quality Manager, I get to zoom out and ask different questions:

How do we make sure that level of care and accuracy doesn’t just depend on which teammate you happen to get on a Tuesday afternoon? How do we bake that consistency and compassion into the system itself?

Instead of just fixing one case at a time, I get to:

• Hunt down patterns that could hurt people if we don’t catch them.
• Build safeguards so the system itself notices risk and raises a hand.
• Partner with teams across Tilt so that our tools, our training, and our audits all line up to protect people—not just sometimes, but every time.

The journey has taken me from being a helper inside individual stories to being a builder of the stage those stories play out on. But at my core, my perspective hasn’t changed: every datapoint we see is a real human being holding a lot on their shoulders. If we never forget that, then the quality work we do stops being just “correct”—it becomes intentionally, deeply human.