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Your first five hires will make or break your business

Written by Graham Charlton | 11 July 2025

Why every early-stage startup needs these five people, and how to set them up to thrive. 

The make-or-break moment that decides whether  your startup flies or fails isn’t product-market fit, seed funding, or even your first customer.

These are all important factors, of course, but your first five hires shape more than output. 

They define the culture, set the standard, and carry the weight of execution while the company is at a critical stage. 

Your culture isn’t defined by a mission statement, it’s shaped by how your team behaves every day.

The values they work by, how they handle problems, and how they communicate are all set in the early months and your first five hires play a huge role in defining what it looks like. 

In other words, if you hire people who thrive on collaboration, open feedback, and moving quickly, that’s the culture you’ll build. But hire people who prefer rigid processes and working in silos, and that will shape your culture in a very different way, even if that’s not what you intended.

Get it right, and you’ll have a trusted team who can turn your vision into reality. 

In this post, we’ll look at the five essential archetypes every startup team needs, why their roles matter more than their titles, and how to design these roles for maximum impact. 

Let’s meet your founding team...

1. The Builder

The one who actually makes the thing. This may be the CTO, Lead Engineer, Product Manager, or Technical Co-founder. 

Every startup needs a maker. Someone who doesn’t just understand the product, they bring it into existence.

The Builder is more than a coder or designer. They’re the ones who can take a scribbled napkin sketch and turn it into something real, functional, and delightful.

Why it matters

Without a product, there’s no startup, and if the product isn’t good, there’ll be no traction. The Builder isn’t just shipping code, they’re bringing your value proposition to life.

Crafting their role:

  • Don’t overload them with strategy too early. Let them build first.
  • Give them direct access to user feedback as this sharpens decisions.
  • Protect their time like gold. Every meeting is an opportunity cost.

Watch out for...builders who want to reinvent everything from scratch. You need progress, not a thesis on software architecture.

2. The Storyteller

The one who makes people care. Perhaps the Head of Marketing, Content Lead or a Brand Strategist.

It’s not enough to build a great product. Someone has to tell the world why it matters. That’s the Storyteller’s job.

They craft your narrative, shape your tone, and get people excited about what you’re doing, whether it’s a one-liner on your homepage or a thread that goes viral.

Why it matters

The early days are all about momentum. You need to attract users, investors, and talent, and great storytelling does that better than any pitch deck.

Crafting their role:

  • Let them find the story, not just repeat your talking points.
  • Pair them closely with the Builder. The best stories are product-driven.
  • Give them room to experiment. Early marketing is art and science.

Watch out for... over-reliance on performance marketing too early. You need belief before you need conversion.

3. The Challenger

The co-pilot who asks the hard questions, the COO, Strategy Lead, or Co-founder. 

Every founder needs someone who pushes back. The Challenger doesn’t just say yes, they ask why.  

They pressure-test assumptions, spot blind spots, and help you steer the ship with clearer eyes.

Why it matters

Startups move fast. Too fast, sometimes. The Challenger is the one who makes sure you’re running in the right direction, not just quickly.

Crafting their role:

  • Make space for dissent. If you punish challenges, you kill strategy.
  • Clarify the decision-making boundary..
  • Respect the invisible labour of emotional support. Co-founders carry a lot.

Watch out for...people who challenge everything without bringing solutions. That’s cynicism, not strategy.

4. The Fixer

The person who makes chaos disappear, job titles include Ops Lead, and Chief of Staff. 

Every startup hits messy, unglamorous problems: invoices, onboarding, payroll, investor updates, tools that break, customers who ghost. The Fixer handles them all.

They bring order to chaos, and without them, you’ll be buried in admin while your product stalls.

Why it matters

Founders should be driving the business forward, not drowning in admin. A strong Fixer clears the clutter and creates space for real progress.

Crafting their role:

  • Prioritise versatility over pedigree. Scrappy beats shiny.
  • Keep their scope wide, but their priorities focused.
  • Celebrate the quiet wins. Fixers often go unthanked.

Watch out for...over-reliance. Burnout risk is real if they become the default for everything.

5. The Firestarter

The one who gets early customers on board. Typical titles include Sales Lead, Partnerships Manager, and Growth Lead.

It doesn’t matter how clever your solution is—if no one’s buying, you’re not a business.

The Firestarter is the spark. They turn cold leads into warm intros, get those first five (then 50) customers over the line, and keep the feedback loop alive.

Why it matters

Revenue, or the path to it, changes everything. Investors listen. Confidence builds. And the product gets sharper.

Crafting their role:

  • Involve them in product conversations. Objections fuel iteration.
  • Give them tools and stories to sell. 
  • Align on what traction means and how you’ll measure it.

Watch out for. Bringing in big-company hires too soon can backfire. At this stage, you need a resourceful closer, not someone who lives in spreadsheets.

How top startups built their teams

Still think this is just theory? Here’s how some of the world’s most successful startups decided on their first five hires. 

Shopify

Early hires included:

  • Daniel Weinand: Designer (Builder)
  • Cody Fauser: CTO(Builder)
  • Harley Finkelstein: CMO (Storyteller)
  • Craig Miller: Growth (Firestarter)
  • Bobby Morrison: Sales (Firestarter)

Shopify made product and storytelling central from day one and scaled fast by hiring early believers who could execute, not just theorise.

Slack

Early hires included:

  • Cal Henderson: CTO (Builder)
  • Anna Pickard: Editorial Lead (Storyteller)
  • April Underwood: Head of Platform (Challenger)
  • Eric Costello: Frontend Engineer (Builder)
  • Bill MacaitiS: CMO (Storyteller)

Slack’s tone of voice was a strategic weapon, shaped early by Anna Pickard. They also invested in product polish and integration from the start.

Stripe

Early hires included:

  • Greg Brockman: CTO (Builder)
  • Diana Avila: Compliance (Fixer)
  • Krithika Muthukumar: Marketing (Storyteller)
  • Michael Siliski: Risk (Challenger)
  • Will Gaybrick: CFO (Challenger)

Stripe’s early team was intensely focused on trust, developer experience, and operational rigour, all fuelled by strategic early hires across product, ops, and narrative.

Image credit

Summary. The right five unlock everything

Here’s a quick recap of the five early-stage archetypes:

  1. The Builder. Makes the product real
  2. The Storyteller. Gets people to care
  3. The Challenger. Sharpens thinking and strategy
  4. The Fixer. Clears chaos and creates leverage
  5. The Firestarter. Brings in early revenue and momentum

The secret isn’t just in who you hire, but how you set them up to succeed. Craft roles, not boxes. Focus on impact, not hierarchy. And build a team you actually want to be in the trenches with.

What to do next

If you're a founder getting ready to scale:

  • Review your current team through this lens: are there gaps in these archetypes?
  • Reframe open roles using these personas. What’s the real job to be done?
  • Share equity fairly and transparently. Early hires deserve to share in the upside.