Sittercity Leadership & Management

What’s a quotable hallmark of good management on your team — and how is it reinforced weekly? 

Business management expert and author Patrick Lencioni said, “Direct and personal feedback really is the simplest and most effective way of motivation.” 

This quote has stuck with me because I’ve seen it play out over and over. Providing feedback that is direct, timely and specific is the single most effective thing I can do for my team’s growth. It’s not the kind that only shows up in an annual review, but the kind that happens close to the moment and is tailored to the person receiving it.

I take time to truly get to know my team: what motivates them, what challenges them, what they’re working toward and where they want to go. That’s what makes feedback stick. It’s not just about gaps; it’s equally important to name what’s working and why because people grow when they understand the full picture.

I meet with direct reports weekly and indirect reports quarterly, and I regularly ask for upward feedback in return. People can tell when feedback comes from a place of care. That’s what builds trust and helps them actually receive it.

Which forum or artifact keeps priorities obvious?

At Sittercity, we keep priorities visible in two ways: a weekly habit and a quarterly reset.

Every quarter, we roll out our objectives and plans companywide so each team knows what we’re working toward and why. We start with a look back at the previous quarter, remaining honest about what we hit, what we didn’t, and what got in the way. The planning process itself is cross-functional by design, so every team can see not just their own priorities but the constraints and dependencies shaping everyone else’s roadmap. That context is what turns a wishlist of work into something people can actually work from.

Week to week, our KPI meeting keeps us on track. We review the metrics that move the needle, check in on the roadmap, and dig into anything that isn’t trending the way we expect. Every metric has an owner, so accountability is never ambiguous. When something surfaces that needs follow-up, it becomes an action item with a name attached, and we review it the following week. The follow-through is built in.

What part of the strategy excites people — and what metric shows progress?

Our goal at Sittercity is simple: to deliver for families who need trusted care and caregivers who need meaningful work. When we do that well, everything else follows.

That’s what we’re really watching; not just registration or revenue numbers — though those are absolutely important — but whether the network is alive and delivering on its promise. Are caregivers active, trustworthy and available? Are families finding the right fit when they need one? Sittercity has been around for 25 years because we’ve never optimized for short-term gains at the expense of the people using the platform. That’s what excites our team most — when we can see the network working the way it should.

Part of that is making sure wins don’t go unnoticed. In Slack, shoutouts happen in real time on big days when something launches or a number lands the way we hoped. Our weekly KPI meeting is also a place where we call out what’s going well, not just flag what’s off. When a goal gets hit or something important gets shipped, we take the time to recognize the people whose work made it happen — the tiny wins and the big ones.