How to hire and how to start as a first functional hire
This issue is about that super early-stage hire, your first proper functional lead. For founders, it means letting go of something you’ve controlled since day one. For the person stepping into the role, it means building from scratch with limited playbooks and high expectations.
Both sides want it to work, but good intentions aren’t enough. The reality is messier than either party expects: unclear boundaries, shifting priorities, and the constant tension between moving fast and getting it right.
So, how do you actually make it work? That’s what we’re discussing….
(In truth, these points work for anyone in a new role that wants to succeed)
How to Nail Being The First Functional Hire
AKA: How to make a big impact without stepping on toes
You’ve just joined a startup as the first person in your function. Product, marketing, sales, CX, design; it doesn’t matter. You’re not just stepping into a role. You’re stepping into a story that’s already in motion.
There are probably no processes. No playbooks. No clean handover document with your name on it. But there is a team that’s been grinding to get to this point—and they’ve made a thousand decisions along the way, usually under pressure, with whatever data they could scrape together.
Your job isn’t to challenge all of that.
It’s to understand it first.
Only then can you determine what to keep, what to discard, and what to build next.
1. Context Is Your Greatest Advantage—But You’ll Have to Earn It
In your first few weeks, you’re basically a detective. You’re trying to understand the context behind everything. Both internal and external.
Things like: How the business operates (not how it says it does), how it makes money (or burns through it), what customers really think of the product, how onboarding happens, how support happens, and so on.
That means asking why a certain system was chosen, digging into how priorities were set, exploring what trade-offs have already been made, and noticing how the team communicates, makes decisions, and recovers from missteps.
It’s tempting to jump in and start fixing things. That’s natural, you were hired to bring expertise, momentum, and fresh eyes.
But the best early hires don’t rush to optimise.
They start by understanding why things are the way they are.
You can probably never have too much documentation at this point. Often, you’ll jot something down in a discussion that doesn’t feel hugely relevant, but a week later, it’s the missing piece of the puzzle you’ve been hunting for.
2. Communication Is Half the Job (and Tone Matters More Than You Think)
At this stage, there’s likely no system, you are the system.
So, how you communicate sets the tone for how your entire function operates. It’s not just about sharing updates, it’s about building trust and reducing friction. Especially with founders and early team members who’ve been making rapid-fire decisions for months, often flying solo.
This sort of statement will prove helpful and set the right tone early on:
“You’ll probably get loads of questions from me over the next few weeks—about how things work or why a decision was made. I’m only ever trying to understand context, not judge past decisions. If I word something clumsily, just nudge me.”
This kind of framing goes a long way. Because your questions are important, but how you ask them matters just as much.
Respect the work that’s come before you. Acknowledge that every startup decision involves trade-offs (usually under intense pressure). Make it clear you’re here to build with them, not unpick everything they’ve done.
🟡 Instead of: “This seems like a weird choice—why did we do that?”
✅ Try: “I’d love to understand the thinking behind this—was it based on a technical constraint or something else at the time?”
Communicate like someone who’s here to help. Ask questions like someone who wants to learn. That combination builds confidence on both sides.
When you get that right, when the team feels respected, informed, and aligned, you can move much faster, with way less friction.
3. Use Data to Influence—Even if It’s Just a Pattern
Early startups are often light on formal data. That doesn’t mean you can’t be evidence-led.
Talk to users. Watch support threads. Sit in on demos. Gather scraps and patterns and use them to shape your thinking.
You don’t need to make sweeping statements. Just show that your thinking is grounded in what’s actually happening.
“I’ve spoken to 10 users this week. 6 of them dropped off after trying to use the dashboard. Sounds like onboarding or first-use friction might be a blocker. Let me spend some time thinking through some quick wins to improve this.”
Even directional data builds credibility. It’s how you influence product, shape messaging, or shift priorities—without stepping on toes.
You’re not saying, “I know better.” You’re saying, “Here’s what the users are telling us. What do you think we should do about it?”
Side note: Especially in an early-stage business, the more people talking to customers, the better. Everyone’s objectives should be grounded in improving something for an actual customer.
4. Expect Ambiguity And Be the Calm in the Chaos
This bit’s not a surprise, but it’s worth saying: it’s likely that very little will be fully figured out.
You’ll be context-switching, firefighting, and sometimes making decisions in a vacuum. That’s not failure. That’s the job.
What I’ve seen work really well is treating ambiguity like a puzzle, not a problem. You’re not just operating, you’re helping define how things should work.
- Prioritise ruthlessly (and explain your reasoning)
- Write things down (even if they’re messy first drafts)
- Leave behind templates or notes for whoever comes next
If you do this well, you’ll scale your own value without having to be the person holding everything together forever.
As Daragh Kan, said in an earlier episode of the podcast: “Documentation is selfish — it means I don’t have to say the same thing ten times.”
TL;DR – How to Win as the First Hire
✅ Understand context before you act
✅ Communicate with clarity and care
✅ Influence with insight—especially from users
✅ Expect ambiguity—and build through it
✅ Think beyond your job—lay foundations for the next person
What I learned from speaking to a ScaleUp stage product expert
Erica Wass has built and led product teams across major companies like Bloomberg and Zendesk, and now consults with early-stage businesses through Brainmates. She’s scaled product functions through hypergrowth, managed distributed teams across continents, and developed hiring frameworks that actually work under pressure.
What stands out about Erica’s approach is her focus on outcomes over activity. She’s lived through the evolution from feature factories to strategic product leadership, and her perspective comes from doing the hard work of building scalable product organisations, not just talking about it.
Here is the link, and here are three insights that challenged my thinking.
1. Hire for capability, customer curiosity, and communication—in that order
“The number of PM interviews I’ve had where people wouldn’t mention the customer… that doesn’t matter, but the fact that they’re focused on the customer outcomes and the business outcomes.”
Erica’s hiring framework is deceptively simple: capability (can they do the strategic and tactical work), customer curiosity (do they instinctively think about user impact), and communication (can they bring people along on the journey).
This resonates because I’ve seen brilliant individual contributors fail in product roles simply because they couldn’t tell a compelling story or align cross-functional teams. Product managers “manage no one, but lead everyone”—without communication skills, even the best strategy dies in meeting rooms.
2. Perfect candidates are a myth—plan for trade-offs
“There’s pretty much always compromises. Are we prepared to compromise on time? Are we prepared to compromise on the original experience profile? Are we prepared to compromise on salary?”
Erica reframes hiring as a three-way trade-off between speed, experience profile, and compensation. This shifts the conversation from “finding the perfect person” to “what are we willing to sacrifice to get someone good enough to drive us forward?”
The insight here is treating hiring like product market fit—understanding your total addressable market of candidates, then making conscious decisions about where to be flexible. If there are only 20 potential candidates in your geography who match your ideal profile, maybe your ideal profile needs adjusting.
3. Distributed leadership requires intentional vulnerability
“I was shoving pizza in my mouth… and he was like, “I was immediately at ease” What I realised over time was that while he’s working and asking me a question… I had greater transparency in that relationship.”
When Erica took on leading a team in Dublin from Melbourne, she discovered something counterintuitive: the constraints of remote leadership made her more authentic. Late-night calls meant she was more casual, more human, more transparent than in formal office settings.
This challenges the assumption that remote leadership is harder. Sometimes the best management happens when you’re not trying to manage—when you’re just being genuinely helpful to someone trying to do good work.
Final thought
Erica brings the strategic thinking of a senior leader with the practical wisdom of someone who’s hired hundreds of people. She’s direct about what works and honest about what doesn’t.
“Companies are seeking PM individuals who can interpret analytics, connect insights to strategy, deliver measurable results. This isn’t new. This is what product is.”
That’s the kind of clarity every scaling team needs more of.
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Getting Your First Head of [Function] Right
Hiring your first functional lead (whether it’s sales, product, marketing, design, or customer success) is a milestone. It means you’ve built something worth scaling. It also means you’re about to hand over a chunk of your business to someone who isn’t you.
That should feel exciting. If it feels terrifying, this might help.
Most likely, you or the team have been juggling this function alongside everything else. But that’s become unmanageable, so now you need someone else to own it.
Here’s what I’ve learned about getting this hire right.
1. You’re hiring an architect, not a doer.
You’re not hiring someone to slot into an existing machine. You’re hiring someone to build the machine, write the manual, and probably redesign it three times in the first six months.
That means they’ll set up how the work gets done, decide what gets measured, and create the processes that’ll either scale beautifully or break spectacularly.
Before you write that job description, ask yourself: “Are we hiring someone to execute something we already understand, or to figure it out as they go?”
If it’s the latter (and it usually is) they’ll need more than just functional expertise. They’ll need judgment, communication skills, and the ability to make calls when the path isn’t clear.
Do they need to have done it before?
In an ideal world? Yes. Someone who’s been the first person in a function before will move faster. They’ve seen what works, what doesn’t, and they’ve probably made the costly mistakes on someone else’s time.
But let’s be realistic. Those people are rare. Especially in Australia, there just aren’t that many folks who’ve been “the first in.” And the good ones? They probably stayed and grew with those companies.
Plus, just because someone’s done it once doesn’t mean they want to do it again. Working directly with founders is rewarding but demanding. No structure, high pressure, blurred boundaries. I’ve spoken to plenty of people who’ve done it before and just don’t want to return to that early-stage chaos.
So what should you do? Try to find that experienced person if you have time. But also ask yourself: What’s more urgent, having someone in the seat fast, or holding out for the perfect background?
Here’s my take: Yes, experience matters. But someone who’s sharp, communicates well, self-starts, and is ready to step up? That can be just as powerful.
2. Define the outcome, not the job.
The best early hires rarely fit rigid job descriptions. The role will change by the time you hit your next milestone. What they do will change week to week. What matters is what they help the company achieve.
Instead of obsessing over a perfect job description, try this:
- What problem will this hire solve in the next 3-6 months?
- What does success actually look like?
- What are the key actions needed to get there?
Then write your job description backwards from that.
Instead of: “We’re hiring a Head of Growth to lead marketing campaigns” Try: “We need someone who can get us from 200 signups/month to 1,000.”
3. Hire for now. Plan for later.
Should this person be the future leader of the team? Not necessarily.
Sometimes your first hire is a doer who gets things off the ground. Sometimes they’re a future leader. But good individual contributors don’t automatically make good leaders. Sometimes they don’t even want to be leaders.
Have the conversation early, but don’t make commitments you might need to walk back later. If someone pushes for guarantees about future leadership roles, you can commit to supporting their development when the time comes.
4. Be honest about what the job actually is.
Early-stage roles are never clean.
Your first CS hire? They’re doing onboarding, support tickets, retention, and probably writing help docs too.
Your first PM? They’re doing QA, scoping features, and translating founder brain-dumps into coherent tickets.
Your first designer? They’re handling brand, UX, UI, email design, and maybe wrestling with Webflow on Friday afternoons.
Make sure candidates know this. Early hires thrive when the gap between expectation and reality is small.
5. Context is everything. Prepare for questions.
Early hires don’t just build the function they build how you work with that function. Context is everything to these hires. So expect questions like:
- Why were certain decisions made?
- What data informed past decisions?
- How do we prioritise what gets built next?
More often than not, they just want to understand. But it’s easy for founders to feel like their past decisions are being questioned. And they are, but usually from a place of wanting to understand, not criticism.
Be prepared for this. It might feel confronting at first, but it’s actually a good sign.
6. You’re about to be managed.
Your new functional lead will question assumptions and test your thinking. They might show you why that feature roadmap you built based on what you knew three months ago needs to change now that they understand user needs better.
This is the letting-go part. Your functional leads will manage your expectations and find compromises to keep moving forward. They need to be diplomatic and excellent communicators.
Just remember to look for these qualities during the hiring process.
The First Hire Reality Check:
- Don’t just hire a doer, hire an architect
- Define outcomes, not responsibilities
- Hire for now, plan for later
- Paint the real picture of the job
- Context is everything, expect questions
- Prepare to be managed
Getting this first functional hire right sets the tone for how you’ll scale every other function. Take the time to get it right, but don’t let perfect be the enemy of good enough.
The List
🧭 10 VC Firm Blogs That Are Full Of Value
Why This List Matters:
The best VC firms don’t just write checks—they share the insights that helped them spot winners before anyone else. These 10 blogs offer a masterclass in startup strategy, from the technical deep-dives at a16z to First Round’s battle-tested operating advice.
Whether you’re fundraising, scaling, or just trying to think like an investor, these resources cut through the noise with real analysis from people who’ve seen thousands of pitches and know what actually works.
The quality varies wildly across VC content, but these firms consistently publish insights worth your time. Some focus on specific stages or sectors, others take a broader view—but all offer perspectives you won’t find elsewhere.
Bookmark this list. Your competition probably isn’t reading them.
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Publishing schedule:
- Monday 10:30am – Monday by the Numbers: Data-driven insights on startup hiring trends
- Wednesday 1:30pm – The Main Issue: Comprehensive guide with advice for teams & talent, plus The List and latest podcast
- Friday 10:30am – Hot Takes Friday: My unfiltered opinion on what’s happening in startup land
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Simon
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