Let me tell you, the impostor syndrome around all this has been real for the last few weeks. I’ve swung between wild optimism and high-octane cynicism, depending on what time of the day it is.
But we’re here now, and as I read somewhere recently:
“Waiting for the perfect moment is like waiting for your cat to fetch. Entertaining, but never happening.”
Which means that we’re doing this. And, I’m thrilled that you’re a part of it.
I started this because, year after year, in recruiting roles, I kept seeing the same things break down: rushed hires, vague roles, interview processes with no structure, godawful onboarding, and good people leaving too soon. Founders were building great products but winging their hiring.
And none of this is intentional, by the way. No one wakes up in the morning planning to mess up a hire. But they do wake up, not sure what to do.
In addition, I’ve seen exceptional people struggle to get the roles they want because they’re on the other side of the interview process and are equally unsure.
So I’m building a place where teams and talent can access real-world, battle-worn methods, tips, insight and advice. I want it to be better than anything else out there.
For talent, it could be something like this from Paul Perrett – CFO at Aconex, sold for $1.6 Bn, and CEO of Messagemedia, sold for $1.7 Bn, now founder of Firmable.
Captions are auto generatedPlayPaul Perrett
Or for teams, it could be something like this from Ben Mostafa, who joined Messagemedia as an Engineer and left 10 years later as the CTO.
Captions are auto generatedPlayBen Mostafa
Most of this is planned out, but I’m more interested in what problems you’re facing, and I’ll help you in the form of playbooks, templates. prompts and Podcast guests who’ve experienced the same thing.
So essentially, I’m co-creating this with you.
I’ll even get on a call with you if you’re a paid Substack subscriber. I’ve already hopped on a couple of calls and talked through some real-world job-seeking and hiring challenges.
Most of this content will apply to anyone who’s hiring or looking to get hired. For the most part, though, I’m looking at things through a startup lens. That said, good hiring is good hiring regardless of the stage of your business. Same goes for shoddy hiring, of course.
Anyway, onto the good stuff.
A quick word on LinkedIn profiles
I dont think enough people utilise the featured section of their profile. It sits between your services and activity sections and has 3 panes that you can fill with content. If you’re a job seeker, this could be a written piece about how you delivered something, a video of you describing how you solved a tricky problem and so on. Use it as a place to showcase your particular expertise.
Mine has links to StartUp Hiring and my consulting business, Crew.
Will it solve all your job search problems? No. Is it a 1% that might make a difference? Possibly. Give it a go.
LinkedIn Page with info on how to set it up here
For Founders:
If you’ve ever found yourself saying “We just need someone good,” you’re not alone. But if you’re leaning on your network for referrals before getting clear on what you need, chances are you’re about to hire someone who feels right, but isn’t.
That’s how founders accidentally hire for familiarity, not capability.
It’s also how you end up six months in, trying to manage around a bad fit who was never set up to succeed.
Your network probably isn’t the problem. They all want to help you. A lack of clarity probably is.
Here’s what happens when you start hiring before you’ve properly defined the role:
- You sell the opportunity instead of defining the outcomes
- You over-index on trust or enthusiasm, and under-index on the correct skills, experience and motivation
- You ask vague questions and get vague referrals
So before you post anything, or ask “Do you know anyone good?” Try this first.
Because your first ten hires will shape your company more than your first hundred customers.
This is a sample of the type of content Paid subscribers will get in addition to Podcast breakdowns, playbooks, templates and more.
“The Clarity Framework”
This is a great way to clarify how you describe your business status, the role you’re hiring and how you work, which are all things that people want to know about as much as compensation and benefits.
They’re also things that you should be clear on, to set expectations of how work happens, not just what work happens.
So think through these questions yourself and start formulating a simple but clear description of just where you’re at.
Section 1: Current Business Status 📌 What stage are you at, and what’s going on right now?
Example: “Hey, I’m [Your Name], founder of [Startup]. We’re a [stage: Pre-Seed / Pre-Revenue / MVP-ready] startup building [problem/solution statement]. Right now, we’re [what you’re doing / building / testing].”
Section 2: Next Business Milestone 📌 What’s the next big milestone you need to hit, and why does it matter?
Example: “Our next major milestone is to [e.g., onboard 100 design partners, hit $10K MRR, launch v2]. This unlocks [fundraising/retention/credibility/customer validation].”
Section 3: Why You Need This Person 📌 What gap are you trying to fill with this hire?
Example: “To hit this milestone, we need someone who can [define what this person does or solves]. This is why this role matters now, not in 6 months.”
Section 4: The Deliverables 📌 What should this person actually deliver in their first 90 days?
Example: “In the first 90 days, you’ll be expected to:
- Conduct 10 user interviews
- Ship v1 of our customer dashboard
- Define our analytics event schema
- Run experiments to test conversion levers”
Section 5: Working Style & Culture Fit 📌 Describe how your team operates right now, so people can self-select in or out.
Use this format:
“We’re a team of [number] working across [tools/platforms].
Optional Sign-off / CTA
“Sound like a good adventure? DM me / email me / apply here: [contact info]”
✍️ Founder’s AI Prompt — “Write My Hiring Message”
Use this prompt in ChatGPT, Claude, or your AI tool of choice:
🔧 AI Prompt (Copy + Paste this)
You are a startup founder looking to write a compelling, founder-led hiring message for a key early hire.
I’ll provide you with key details below. Please generate three different versions of the message:
1. A short but engaging LinkedIn post
2. A direct message I can use in emails or DMs to reach out to someone specific
3. A forwardable email I can share with my network to help spread the word
The tone should be:
– Human, clear, and founder-led (not written like a corporate job ad)
– Optimistic but grounded
– Honest about what stage we’re at and who will thrive vs struggle
—
Here are my inputs:
1. Startup Name: [Insert name]
2. Stage: [Pre-Seed / Pre-Revenue / MVP / Post-launch]
3. What we’re building: [Problem/solution in 1–2 lines]
4. What we’re doing right now: [What’s in motion? What are you building or testing?]
5. Our next milestone: [e.g. onboard 100 users, hit $10K MRR, launch public beta]
6. Why we need this hire: [What gap are they solving? Why now?]
7. What they’ll deliver in 90 days: [List 3–4 deliverables]
8. How we work: [e.g. async in Notion, remote-first, testing quickly]
9. Who thrives here: [e.g. people who like solving messy problems, wearing multiple hats]
10. Who might find this hard: [e.g. those who need a lot of structure or polish]
11. Call to Action: [How should people reach out? DM? Link? Email?]
—
Please return:
1. A polished LinkedIn post
2. A personal message for cold outreach
3. A “Help me hire” email I can send to my network
✅ Example Output Using Fictional Inputs
Founder Inputs:
- Startup Name: SnipStack
- Stage: MVP-ready
- What we’re building: A tool that lets creators instantly turn long videos into ready-to-post short clips using AI.
- What we’re doing: Building V1, testing with early design partners.
- Next milestone: Get 100 beta users and ship v1.1 with user feedback.
- Why we need this hire: We need a founding designer to help shape the product, UX, and early brand.
- Deliverables:
- How we work: Remote, async, daily build-measure-learn cycles
- Who thrives: People who like scrappy problems, building from scratch, and autonomy
- Who might struggle: Folks who need rigid specs or polished systems
- CTA: DM me or email simon@snipstack.ai
📢 LinkedIn Post
Headline: Looking for a product-minded designer to join me as hire #5 at SnipStack.
Body: We’re building a tool that helps creators turn long videos into scroll-stopping shorts—instantly. We’ve just shipped our MVP and have early testers giving great feedback. Now we need help shaping the product into something people love.
If you’re a designer who loves working in early stages—talking to users, experimenting fast, sketching rough ideas and iterating daily—this is your jam.
Deliverables? Yep: 🔹 Own the onboarding experience 🔹 Define our design system 🔹 Collaborate on our mobile UX 🔹 Inject some delight into our UI
We’re async, scrappy, and shipping daily.
If this sounds like a good adventure—or you know someone who’d love it—DM me or email simon@snipstack.ai.
✉️ Direct Outreach Message (DM or Cold Email)
Hey [First Name]—I’m working on something I think you might find interesting.
SnipStack helps creators turn long videos into ready-to-post short clips using AI. We’ve just launched our MVP, and we’re testing with early users.
I’m looking for a founding designer to help shape the product, UX and brand as we scale. It’s early, so the right person will love working scrappy—sketching, testing, and iterating fast.
Let me know if this sounds like your kind of thing (or if you know someone you rate highly that I should talk to).
Happy to send more details or jump on a quick call. Simon simon@snipstack.ai
📤 Forwardable Email to Network
Subject: Know a brilliant designer who loves early-stage?
Hey friends,
I’m looking for a founding designer to join me at SnipStack—a tool that helps creators instantly turn long videos into short, ready-to-post clips.
We’ve just shipped our MVP and are working with design partners. Our next milestone is hitting 100 beta users and shipping V1.1 based on feedback.
I need someone who can:
- Rebuild our onboarding flow
- Define our design system
- Co-own the mobile UX
- Inject product personality into the UI
We work async and fast. Great for people who like ambiguity and autonomy. Less ideal for those who need a lot of polish or structure right now.
If anyone comes to mind, I’d love an intro—or feel free to forward this directly. Thanks so much! Simon simon@snipstack.ai
Try this or customise it to suit your needs, or use it as inspiration for something else. I really don’t mind. Let me know how it works for you.
The StartUp Hiring Podcast: Paul Perrett
Paul Perrett has helped scale some of Australia’s most successful B2B tech companies:
CFO at Aconex $1.6Bn exit, CEO at Messagemedia $1.7Bn exit, and now Co-Founder at Firmable. He’s led through multiple growth stages, raised funding, and built teams from early traction to scale.
Here are three things that stuck with me from our conversation. tl:dr – Link Here
1. Don’t over-index on pedigree — hire for fit and adaptability
“A lot of the mistakes I’ve made in hiring have been when someone else said, ‘Just get someone who’s done it before.’”
Paul’s seen this go wrong more than once. He talks about how startup teams often fall into the trap of assuming that experience in a similar-sounding role means someone will succeed in a new context. But startups change fast. Market needs shift. Playbooks evolve.
This makes sense to me because I’ve seen first-hand that repeatable success doesn’t always translate across environments. Paul’s approach — to go back to first principles and focus on adaptability, curiosity and context-matching — feels far more grounded.
2. Set clear expectations early, even if it risks turning someone off
“The more someone really understands what the environment is and what it’s going to take to be successful, the better their chances — and yours.”
Paul’s learned to be clear with candidates, even if it means some choose to walk away. He’ll spell out what the job actually looks like, where the ambiguity is, and where the trade-offs are.
What I like about this is how honest it is. If someone decides not to proceed, that’s usually a good thing — not a missed opportunity. Paul calls this the ‘anti-sell’ and he’s right. Better to lose someone early than hire the wrong fit in a rush.
3. Leadership must scale alongside the company
“You need to evolve how you lead as your company grows — or your team will outgrow you.”
Paul describes the shift from hands-on founder to structured executive. At some point, the generalist has to give way to functional expertise. And team leads need to think bigger, lead others, and contribute more strategically.
I’ve seen this play out so many times — someone who crushed it at five people but gets stuck at 50. What I like about Paul’s thinking is how much emphasis he places on self-awareness. He’s not looking for perfect leaders. He’s looking for people who know what they’re good at, where they’re growing, and who can be coached.
Final thought
Paul is the kind of leader who’s not afraid to jump in, get his hands dirty, and unblock his team when it counts. But he also knows when to step back and let others lead.
“There’s nothing more powerful than quietly unblocking something for someone, even if no one else sees it.”
That sort of leadership builds trust. It’s not loud. But it compounds.
That’s it for this issue. I really hope you found something useful or interesting. If not, please keep it to yourself 🥴.
If you’d like early access to the future newsletters & podcasts, and premium content, then please consider subscribing. Please also don’t be shy about suggesting challenges or problems you’d like addressed.
Until next time 🫡
