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Ep 285 – Melissa Theiss (Head of People Operations, Kit)
Published about 1 month ago • 6 min read
Go listen to the latest episode of The Modern People Leader — where we sat down with Melissa Theiss, Head of People Operations at Kit, to talk about how People leaders can think like business leaders — without getting an MBA.
If you’ve ever been told to “be more strategic” but weren’t given a clear roadmap for how to do it, this one’s for you.
Here’s what stood out most from the conversation. ⬇️
“When you have to make forced trade-offs, start with what the business needs first.” — Melissa Theiss
1. If you don’t know how the business makes money, start there
Melissa’s first question for any People leader is simple:
“How does your business make money?”
It sounds obvious. But it’s amazing how many HR leaders can’t describe the revenue engine, cost structure, or growth model of their company.
She uses a simple framework borrowed from VC: Track, Racehorse, Jockey.
Track = The market. Is it growing? Fragmented? Competitive?
Racehorse = The business model. How does the company actually generate revenue?
Jockey = The leadership team. Are they capable of executing?
The goal isn’t perfection. It’s fluency. Because if you can’t connect People decisions to the revenue engine, you’ll always feel one step behind.
📉 Behind a 24% Attrition Risk Impacting Revenue
Here’s a quick story about a ~1,000-employee company that had clear business goals: Increase revenue. Improve customer retention. Strengthen pipeline-to-PoC conversion.
On paper, things looked fine. But they were dealing with a 24% attrition rate - including 20% of key employees tied to revenue goals.
The real opportunity wasn’t just cutting attrition - it was preventing the loss of the 20% of employees most critical to business results. With Compete, they were able to quantify the business impact and take action proactively.
The impact wasn’t just HR-related. It was directly tied to revenue momentum.
Using Compete, the leadership team:
Identified which managers and compensation patterns were driving regretted attrition
Quantified the business impact of losing top performers
Shifted from reactive exits to proactive retention strategy
Turned workforce data into board-ready recommendations
Instead of waiting for analysts to run weeks of reports, they connected workforce risk directly to business targets.
The result? Clear action. Focused retention. Measurable business protection.
👉Book a conversationto see how Compete turns workforce data into business impact.
2. Business acumen isn’t about being comfortable — it’s about building reps
A lot of HR leaders carry what Stephen called “head trash” around business topics.
“I didn’t go to business school.” “I’m not a finance person.” “That’s not my lane.”
Melissa’s advice? Start small and build the muscle.
Read finance newsletters. Take a bite-sized course. Learn how to read a P&L. Put yourself in industries you actually care about so curiosity does some of the heavy lifting.
“Pick your battles and pick where you can make it a little bit easier.”
You don’t need to become a CFO. But you do need to understand gross margin, revenue drivers, and risk — because every People decision ultimately ties back to them.
3. Run a People Ops maturity diagnostic — and score it like a product
After understanding the business, Melissa runs what she calls a People Ops organizational maturity diagnostic.
It evaluates 13 domains — everything from compensation philosophy to compliance to talent acquisition — and produces a maturity score.
Her benchmark?
“If you’re 80% or above for your size and stage, you’re probably not slowing the business down.”
The beauty of this approach:
It forces clarity on what “good” looks like at your stage.
It prevents overbuilding (no 5,000-person bureaucracy for a 50-person startup).
It gives you a data-backed way to say “no” or “yes, but.”
And she doesn’t treat it as a one-time audit. She re-runs it quarterly and ties improvement to OKRs.
Low scores go up quickly. High scores take real work. That’s the point.
💼 Rethinking backup care for modern teams
Quick question: when was the last time your backup care benefit truly worked? Employees could use it easily, complaints were minimal, and costs stayed reasonable?
That question has been top of mind for us lately. With Stephen navigating life with a newborn plus two teenage daughters, and Daniel raising a toddler, we started evaluating benefits based on whether they’ll actually show up when real life gets messy.
A lot of employers are realizing their backup care program isn’t keeping up. Traditional options are often rigid, expensive, and built around one-size-fits-all networks - which means they don’t get used the way they’re supposed to.
That’s why more employers are switching to Wellthy Backup Care.
Here’s what that looks like in practice:
Flexible backup care for kids, adult dependents, and even pets
A vetted provider network or white-glove help from a Wellthy expert
Fully customizable programs with pay-as-you-go pricing
Melissa argues that “people first” can actually be bad business.
“If you don’t put the business first, at the end of the day, you won’t have the people.”
She prefers the term people-centric — meaning:
The business comes first.
But every business decision is made with deep consideration of its impact on people.
It’s a subtle but powerful shift.
We’ve all seen overly generous benefits or unsustainable programs get rolled back during downturns. That whiplash hurts trust more than thoughtful restraint ever would.
Sometimes the most people-centered thing you can do is protect the long-term health of the business.
💙 Make leave feel human - not chaotic
In one of our recent webinars, we talked about how leave is usually put into three buckets: compliance and pay, business continuity, and the very real human experience happening at home.
This couldn’t have hit harder for me and Stephen. We both recently became parents - and it showed how complex leave can be, even on a tiny team.
That’s exactly what Tilt is built for.
Tilt is a leave experience platform that manages all types of leave, nationwide - from FMLA and PFL to everything in between - while giving HR, managers, and employees clear visibility into what’s happening. It combines compliant leave management with a genuinely human experience.
Here’s what that looks like in practice:
Personalized leave plans for every employee
Role-based visibility for HR, managers, and employees
AI that automates admin and answers routine questions
Compliance-backed, expert support
It turns leave from paperwork into a people-first leave experience.
6. Tie it all together: weight the inputs, then choose intentionally
After:
Understanding the business (Track, Racehorse, Jockey)
Scoring People Ops maturity
Running a listening tour
You’ll have more ideas than capacity.
That’s when strategy actually begins.
Melissa weighs three inputs:
What does the business need most right now?
Where is People Ops maturity lagging?
What are employees asking for?
In an ideal world, they’re balanced.
In reality?
“When you have to make forced trade-offs, start with what the business needs first.”
Then fit maturity improvements and employee requests into the remaining space.
It’s not always clean. It’s not always equal. But it’s intentional.
And that’s what separates reactive HR from strategic People leadership.
The Business of People
By Melissa Theiss
Scaling a startup isn’t just about product and funding—it’s about people. The Business of People is a biweekly newsletter that helps people leaders learn to think like business leaders. You'll get tips, tricks, tactics, and templates to build high-performing teams, scale operations, and drive commercial success.
We’ve learned from the best HR leaders so you can lead like the best. Our newsletter brings you lessons from CHROs, Chief People Officers, and work pioneers who are reshaping the way we work. Through their stories, you’ll discover what’s working, what’s not, and how they’ve built their careers—giving you practical insights to shape what’s next for HR and for your own leadership.
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