Friends,

I’ve settled into my first week ‘back at work’ since returning from my Euro-adventure, and I’ve decided I’m never holidaying in October again.

Not because I didn’t love my trip (I did). Not because the jet lag was bad (it was). But a few things have made it really clear that I need to choose a better time of year to take a break. Here they are, so you might learn from my mistakes.

First. I left it too long to take a break. And I felt it.

2025 has been a slog. I spent 10 and a half months of this year working (like crazy) towards a nice big break at the end of the year, and I suffered for it. One thing was clear, I need more frequent recharges. Something I’ll be taking into my 2026 planning.

Second. I had more inbound in October/November than any other time of the year. This wasn’t something I could easily have predicted (being only my second year), but it’s something I’m absolutely conscious of now. The second I started winding down for my break, I had the biggest influx of interest in working together, more than any other time of the year, and it cost me work with some of the most exciting companies. It’s given me some great signals on when I need to plan to be working vs away in the future.

Third. The momentum now I’m back, feels off. Don’t get me wrong, I am incredibly self-motivated, but there’s something about the vibe of the end of the year that I find incredibly distracting. Especially when I’m back from my ‘end of year break’ and starting to think about 2026. Everyone else is winding their year down, and I kind of want to be part of that. It’s not a huge issue, but the vibe feels less productive.

On the flip side, southern Europe in October/November is awesome. Cooling down but not hot/cold. Change in season/colours is gorgeous (Turin and Tuscany in particular was 😍). Very few tourists, but everything is still accessible. I had an amazing time.

So tell me, what time of year do you prefer to holiday, and where?

Enjoy this week’s edition ✌️

Matt

You’ve seen how they think: modern, data-led, and ahead of where AI is taking compensation and Total Rewards. Now see what that looks like in practice.

CandorIQ’s AI agents turn the slowest, most manual parts of comp planning into instant, reusable workflows.

No more spreadsheet archaeology. No more chasing headcount numbers. No more stitching together analyses that should have lived in one place from the start.

With CandorIQ, teams get real operating leverage:

You already trust their thinking. Now see the system that makes it real.

Interested in sponsoring the FNDN Series? Drop me a line!

Know a startup Head of People looking for answers 🙋 why not forward this to them for some instant karma? ✨

This weeks edition comes from someone I’ve followed for a long time, and deeply respect in the startup People space, Melissa Theiss (also a previous podcast guest!). Melissa has been the Head of People at four different startups, and now leads the People function for the creator platform, Kit.

In this breakdown, you’ll get a deep guide into how to tackle one of the most challenging aspects of being in a startup, the headcount planning process. Something I’m sure many of you will find helpful as we step from 2025 into 2026.

Matt

Picture this: It's mid-December, and Sarah, the newly hired Head of People at a Series B SaaS startup, walks into her first annual planning meeting.

The CFO opens his laptop and projects a spreadsheet onto the conference room screen. "Based on our current burn rate and the headcount we added last quarter, we can afford approximately 12 more hires next year."

The VP of Engineering immediately jumps in: "I need at least 8 of those for my team. We're already underwater on the product roadmap."

The VP of Sales counters: "I need 6 SDRs and 3 AEs just to hit our pipeline targets."

The CEO looks exhausted. "Let's just split the difference and revisit this next quarter."

Sarah sits there thinking: Wait. Nobody has mentioned what we're actually trying to achieve.

3 months later, the company misses its revenue target by 40%. 6 months after that, they're doing layoffs because they hired for the wrong positions.

This is what happens when you start annual planning with the wrong question.

Most startup annual planning processes get the order wrong.

They start with: "How many people can we afford to hire?"

Instead of: "What do we need to achieve, and what does that require?"

When you start with "how many people can we afford," you're operating from scarcity and incrementalism. You take your current org chart, add a few roles where teams are stretched thin, and call it a plan.

But your current org chart reflects the company you were building six months ago—not the company you need to become in the next twelve months.

Here's the approach I use with clients that consistently produces better outcomes.

Before you touch your headcount planning spreadsheet, answer these questions:

What is your revenue or growth target for next year? Not a range—a specific number your leadership team agrees represents success.

What commercial goals need to happen to hit that target? Are you entering a new market? Launching a product line? Monetizing features that are currently free?

For VC-backed companies: What needs to be true to raise your next round given the current or expected fundraising environment? How long do you have before you need to raise based on your cash runway?

At a startup, you're building three products simultaneously.

Your annual plan needs to account for all three.

You need both perspectives to create a headcount plan that's simultaneously strategic and operationally realistic.

Let's say your revenue target is $20M next year, and you want to maintain approximately $200K ARR per full-time employee. That gives you a maximum of 100 people.

Start with a completely blank org chart. Don't pull up your current structure—build from scratch based purely on what you need to achieve your goals.

Your leadership team sets the parameters first. For example:

Where do these ratios come from? Start with industry benchmarks for companies at your stage and business model—then adjust for your specific context.

A B2B enterprise SaaS company struggling with customer retention needs different ratios than a PLG company hungry for more inbound leads.

I call this approach "industry-informed, context-driven."

Within these constraints, map out your ideal org chart. What roles do you need? What does the reporting structure look like? Who needs to be hired in Q1 versus Q4?

Have your VP of Sales calculate exactly how many SDRs and AEs they need to hit pipeline targets—based on realistic quota attainment rates.

Have your VP of Engineering estimate the team size required to ship the product roadmap on time—accounting for tech debt and infrastructure work.

They're working within the top-down parameters you set, but adding operational detail that only people close to the work can provide.

Aggregate these departmental plans and map them onto an org chart.

Put your top-down zero-based org chart next to your bottom-up aggregated org chart. Where do they differ?

Now compare both of these future-state org charts against your current org chart.

This three-way comparison forces the strategic conversations that most leadership teams need to have.

This is where you determine exactly where you need to:

These conversations are uncomfortable, but necessary. If your annual planning process doesn't require difficult tradeoffs, you're probably not being honest about priorities.

This locks you into past decisions and prevents strategic shifts. The zero-based approach forces you to justify every single role from scratch.

Your CEO and CFO don't have the detailed operational knowledge to build realistic plans alone. Your Director of Marketing knows pipeline conversion rates. Your engineering leads know which parts of your infrastructure need reinforcement. Involve them early.

If you only collect departmental wish lists, you'll end up with requests for 47 people when you can afford 12. You need top-down strategic constraints to force real prioritization.

👉 Tip: Ask department heads to submit ranked-choice headcount plans instead of single wish lists.

Have them prioritize their requested roles from most to least critical, with clear justification for why each role matters. This forces leaders to think strategically about trade-offs before budget conversations begin.

Even better—encourage your ground-level leaders to identify non-headcount methods to accomplish business goals. The best solutions often come from process improvements, automation, or reorganizing how work gets done rather than simply adding more people.

The best annual plans aren't spreadsheet exercises. They're strategic documents that connect your growth ambitions to the people and resources needed to achieve them.

If you enjoyed this post or know someone who may find it useful, please share it with them and encourage them to subscribe.

When you’re ready, here’s three ways I can help you:

1. Tools & resources
Resources and tools that give you what you need to build your own startup compensation practices.

2. Comp consulting
I run FNDN, a global comp consultancy that builds compensation practices that are clear, fair and competitive for startups.

3. Startup People Summit
I run the Startup People Summit, a one day annual event focused on creating the playbook for startup people practices. Grab recordings from past events, or subscribe to the newsletter to join the next event.