Your first revenue hires shape everything that comes after them. These posts cover when to make each hire, how to set them up to succeed, and how to tell whether it’s working. They’re written for founders moving from founder-led sales to a team, roughly seed to Series A.
Am I ready to hire?
Start here: Preparing for your first sales hire: A checklist for Founders
Before you hire: the two questions that determine who (and how much) you need – the expertise + capacity test for every role
The Founder’s Transition Playbook: From Heroic Selling to a Scalable Revenue Engine – when and how to hand off founder-led sales
The 5 GTM Hiring Mistakes That Quietly Drain Seed & Series A Runway – the costly ones to avoid
When should I make each hire?
Start here: When to hire your first AE
When to hire an SDR – when an SDR makes sense at an early-stage startup
When to hire your first VP of Sales – the timing, what to look for, and what to do meanwhile
When to hire RevOps – RevOps as the engineer of your GTM
When to hire your first customer success manager – the four variables that set the timing
How do I scale the team without burning cash?
Start here: More salespeople ≠ more revenue
How to build a sales hiring plan that turns headcount into revenue – six steps to plan the hires, the support, and the time before they pay off
How to reduce your odds of failure with your first sales hire – why so many startup sales hires fail, and how to beat the odds
How do I hire (and pay) the right person?
Start here: Why you need to create an Ideal Candidate Profile for sales hiring
A founder’s guide to building a sales comp plan – a plan that works for you and your AEs
The Multiplier Matrix: A framework for top talent – assess impact when hiring, developing, and retaining
Why Entrepreneurs Need Intrapreneurs Around Them – the people who multiply a founder’s impact
How do I set new hires up to succeed?
Start here: Your new sales hire’s first 6 weeks: An onboarding roadmap
How to ramp up as your startup’s first marketer – an 8-week plan for your first marketing hire
Sales hiring: Expectation management & leading indicators of success – what to expect, and when
Is it the sales rep, or is it you? A founder’s diagnostic for failing sales hires – what to check before you make a call on a struggling hire
Should I hire fractional or full-time?
Start here: The Fractional vs Full-time Decision (part 1)
The Fractional vs Full-time Decision (part 2) – the qualitative side of the decision
What do fractional GTM execs actually do? – the types and what they do day to day
How to find and evaluate fractional execs – where to find them and what to ask