Startup Hiring Resources
Honest, founder-first advice on building and scaling startup teams.
HIRING GUIDES FOR FOUNDERS: FIRST SALES HIRES, SENIOR LEADERS & COMMISSION PLANS
Drawn from 20 years and hundreds of startup hires - what actually works, what fails, and how to avoid costly mis-hires.
Building your first sales team?
Two founder guides for pre-Series A startups: how to hire your first sales team and design a commission plan that attracts strong sellers without overpaying.
Built for UK/US founders hiring their first commercial team.
Recruiter vs DIY hiring: when founder-led hiring stops working
Founder-led hiring starts to break around 15-30 headcount - if roles are slow to fill, misaligned, or senior, it’s usually time to bring in a recruiter.
Simon Benson · 5 min read
How to hire your first senior leader (and avoid expensive mistakes)
Hiring a senior leader without stage clarity or a scorecard leads to slow, biased decisions and expensive mis-hires that stall momentum.
Simon Benson · 8 min read
When your sales team depends on you
If founder-led selling is still driving revenue as you try to scale, another AE often won’t fix it. Here’s how to tell when it’s time to hire your first sales leader.
Simon Benson · 4 min read
How hiring changes by startup stage
A great hire at Seed can be the wrong hire at Series B. Here’s how hiring needs to change as your startup grows.
Simon Benson · 3 min read
When to cut a bad hire during probation (startup checklist)
New hires underperforming without clear, tracked progress often get kept too long or cut too early - use a structured checklist to make a fair, timely call.
Simon Benson · 6 min read
Buying an ATS won’t fix a broken hiring process
An ATS won’t rescue slow feedback, unclear ownership, and a messy hiring process. It will just formalise the mess.
Simon Benson · 3 min read
How to design your first sales commission plan
Most first sales commission plans fail by overcomplicating pay or misaligning incentives - keep it simple, tied to one outcome, and documented clearly.
Simon Benson · 7 min read
6 tips to improve your hiring process
In a candidate-led market, unclear requirements, inconsistent interviews, or slow decisions lead to bad hires or losing strong candidates to faster processes.
Simon Benson · 3 min read
Startup recruitment essentials: navigating your First Hires Effectively
First hires set the foundation - poorly scoped roles, weak interviews, or unclear growth paths lead to costly mistakes that are hard to undo later.
How to maximise the benefits of your contract workforce
Contractors add speed and expertise, but over-reliance without clear onboarding, ownership, and long-term skill building creates gaps in capability and culture.
Simon Benson · 7 min read
Crafting engaging job ads: a guide to stand out in the talent marketplace
Generic job ads kill engagement - clear titles, real day-to-day detail, and a credible picture of the role and environment are what attract strong candidates.
Simon Benson · 4 min read
How to onboard remotely & increase staff retention
Weak onboarding - especially early or remote - leads to confused hires, slow ramp, and avoidable attrition during probation.
Simon Benson · 6 min read
Strategies for inclusive hiring: eliminating unconscious bias effectively
Unconscious bias leads to inconsistent, unfair hiring decisions - without structured criteria and processes, you end up hiring on instinct rather than evidence.
Simon Benson · 5 min read
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