Friends,

This is the first edition in my new format, where I’m sharing shorter, deeper, and more frequent editions on everything to do with compensation. 

I’m aiming to make these go a step further in being practical, arming you with the tools, resources and steps to take in embedding some of the compensation practices we explore in the series.

I’d love to hear what you think.

I haven’t been particularly loud about it here, but for those who don’t follow me on LinkedIn, I’ve been working on something I’m really excited to share with people professionals in the APAC region.

The Startup People Summit is shaping up to be the event for those building and scaling a startup people function. It’s packed with 30+ speakers from across the region, all with distinct experience doing exactly that. 

If you’re looking for a 1-day virtual event that will give you a lot of the insights and practices necessary to run a people function, this is it. And it couldn’t be more value for money — early bird tickets are on sale now for $50 AUD. Crazy good value.

Outside of work, I’ve been living on a ✈️ between client visits and conferences. But the one upside is it gives me time and space to enjoy all the delicious shows that are on. I’ve finished with White Lotus season 3 (didn’t rate it tbh, what did you think?). I’m now into everyone’s favourite dungeon master, with the last season of You. By the time this comes out I’m hoping Oscar Piastri will be gearing up for another 🥇to follow his incredible start to the season. I am pumped at the prospect of an Aussie F1 champ.

Buckle up for one of my favourite new connections, Melissa Theiss, who joins me for the next few episodes in some of the most practical and no-fuss solutions to a lot of comp challenges.

That’s it for me this week, enjoy your weekend.

Matt

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Avoiding Cookie-Cutter-Compe

with Melissa Theiss, Head of People Ops at Kit

Startups often get stuck in the same routine when they think about compensation. 

In the early stages, they conserve cash with below market offers and substitute generously with equity. 

The more a startup matures, the more that practice inverts — as the company's equity inevitably becomes more valuable, and cash more plentiful — offers tend to emulate the market on salaries, and dial down on equity.

But what if that didn’t have to be the only option?

In this episode of the FNDN Series, I sat down with Melissa Theiss, Head of People at Kit and founder of Fledge, to talk about how startups can avoid cookie-cutter compensation — and build pay practices that are aligned, defensible, and truly fit-for-purpose.

Melissa brings a deeply commercial lens to People strategy, and in this conversation, she didn’t hold back. We got into the nuts and bolts of designing comp philosophies that reflect your business model, attract the right people, and stand up to scrutiny.

Here's what we covered:

• Melissa highlighted why your comp philosophy should be derived from your business strategy — not a template — and how to extract real design principles through structured leadership conversations.

• We explored how startup exec teams often disagree on comp issues because they’ve never aligned on their first principles — only on one-off decisions.

• Melissa shared how she uses the “Even Over” framework to break decision deadlocks and force clarity when trade-offs are unavoidable.

• We talked about the human side of compensation — how employees engage with pay, and why everyone should be able to answer: Why am I paid what I’m paid, and how do I earn more?

• Melissa gave a brilliant example of a startup that paid at the 25th percentile — intentionally — and still attracted top-tier talent by being brutally clear about who they were optimising for.

• She also shared how over-complicated incentive plans fail — if your plan can’t be explained in 15 seconds, it’s probably not working.

• Finally, we discussed the myth that paying more always attracts better talent — and why clarity, culture, and honesty often go further than cash.

My 5 Key Takeaways:

1. Build a comp philosophy that repels as well as attracts. Your compensation strategy shouldn’t appeal to everyone — and it shouldn’t try to. It should speak directly to the kind of talent that thrives in your company’s environment, while being honest about the trade-offs. Melissa shared how aligning pay with a clear talent thesis helped one startup attract top performers even at the 25th percentile — because the value proposition was sharp and specific.

2. Start with principles, not practices. Most comp debates happen at the level of surface decisions — bonuses, bands, sign-on offers — without clear agreement on what the business actually believes about pay. Getting leadership aligned on 5–8 compensation design principles gives you a shared foundation to work from. It turns every pay conversation into an exercise in applying values, not fighting over exceptions.

3. Use “Even Over” decisions to force clarity. Melissa’s “Even Over” framework is a tool to uncover hidden priorities: do you value rewarding new hires even over retaining internal equity? Do you favour rewarding top performers even over internal consistency? These kinds of forced choices reveal what matters most when the trade-offs get real — and help teams move from vague alignment to actionable decisions.

4. Communicate compensation clearly and humanly. Every employee should be able to answer three questions: Why am I paid what I’m paid? What do I actually earn? How do I earn more? When those answers aren’t clear, trust breaks down. It’s not about radical transparency — it’s about offering clarity and predictability so people know how to navigate your system.

5. Simple beats sophisticated when it comes to incentives. Over-engineered comp plans often fail because no one understands them. If your sales plan takes more than 15 seconds to explain on a call, it’s probably not having the impact you want. Simplicity builds trust and makes it easier to default to generosity when unexpected situations arise — instead of being ruled by edge-case policy.

This one’s packed with practical wisdom — and a reminder that comp isn’t just about numbers. It’s a tool for culture, clarity, and commercial alignment.

You can follow or connect with Melissa Theiss on LinkedIn.

Melissa has a great newsletter, which you can subscribe to here.

Interested in working with Melissa, check out her site here.

Listen, watch or read the full interview here.

Got a specific topic you want me to cover or a guest you’d love to nominate? Hit reply to this email and let me know.

That’s all for this week.

Sure, this is technically the end of the newsletter, but we don’t have to end here! I’d love this to be a two-way chat, so let me know what you found helpful, any successes you’re seeing, or any questions you have for me.

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