A playbook
Hire and ramp your first rep
Stop being the only person who can sell it, without setting fire to a year of runway.
4 steps, 64 questions underneath
-
1
Hiring and ramping GTM people
Your first sales hire, the interview loop, the ramp plan, and knowing early when someone is not going to make it.
When do I stop selling myself and hire my first salesperson? 5 → What does a good first sales hire actually look like, and what should I not fall for? 5 → I have been offered the first sales hire job at a startup. What should I check before I say yes? 4 → How do I interview a salesperson when I have never sold for a living? 3 → What should a new rep's first 90 days actually look like? 5 → All 16 questions in Hiring and ramping GTM people → -
2
Comp, quotas and territory
Comp plans, quotas, OTE and accelerators, territory and segment design, in dollars and in rupees.
I have been handed a comp plan. How do I work out what I will actually earn? 5 → What do OTE, pay mix, accelerator, draw and clawback actually mean? 4 → I am a founder writing my first sales comp plan. What is the simplest thing that works? 4 → What is a fair quota for my first rep when we have no history to go on? 5 → How do I set quotas that most of the team can actually hit? 5 → All 16 questions in Comp, quotas and territory → -
3
Running a sales process and closing
Discovery, demos, qualification, champions, procurement and the last mile to a signature.
I have a call booked with a real prospect tomorrow. What do I do on it? 4 → Founder-led sales sounds terrifying. Why can I not just hire a salesperson? 4 → How do I know if a deal is real or if I am being strung along? 4 → My demos go well and then the deal stalls. How do I stop that? 5 → How do I turn random wins into a sales process someone else can run? 4 → All 16 questions in Running a sales process and closing → -
4
Forecasting and GTM metrics
Pipeline coverage, stage conversion, CAC payback, magic number, and calling a number you can defend to a board.
What is pipeline coverage and how much pipeline do I actually need to hit my number? 4 → How do I work out CAC payback when I do not have a finance team? 5 → What is the magic number and should I care about it at my stage? 4 → Which handful of GTM numbers should a first time founder actually track? 6 → How do I calculate conversion rates by stage, and what do I actually do once I have them? 4 → All 16 questions in Forecasting and GTM metrics →