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, 16 questions underneath, read for doing the work

1. 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.

   What should a new rep's first 90 days actually look like?

   The gist The first 30 days are absorption: product, market, recorded calls, and shadowing you on live deals until they can pitch it back without notes. Days 31 to 60 are supervised reps, they run the call and you sit in silently, then debrief. Days 61 to 90 they own deals and you inspect the pipeline, not the person. Median AE ramp is around four months and enterprise can be nine to twelve, so treat month three as first deal territory, not full quota. Write the milestones down before they join, because a ramp plan you improvise is a ramp plan you cannot hold anyone to.

   📖 Founding Sales, Chapter 12: High-Impact Sales Onboarding and Training A concrete onboarding curriculum you can copy: cohorts, drilling, peer sparring and shadowing, with the argument that practice matters more than th... 4 questions on hiring and ramping gtm people →
2. 2
   Comp, quotas and territory

   Comp plans, quotas, OTE and accelerators, territory and segment design, in dollars and in rupees.

   How do I set quotas that most of the team can actually hit?

   The gist Set them top down and bottom up, and treat the gap between the two as information rather than a negotiation. Top down is the revenue target divided across capacity. Bottom up is what each rep can realistically produce given their territory, pipeline and cycle. A healthy plan lands with roughly two thirds of reps between 80 and 100 percent attainment, a fifth clearly above, and a small tail below. If almost everyone misses, the quota is wrong, not the team, and across SaaS more than half of reps missed in recent quarters. If almost everyone clears it easily, you left money on the table and your accelerators are about to hurt.

   📄 Sales Quota Planning: How to Align Targets and Drive Results The practical method for combining top down targets with bottom up rep feedback, and the attainment bell curve to aim for: 60 to 70 percent around ... 4 questions on comp, quotas and territory →
3. 3
   Running a sales process and closing

   Discovery, demos, qualification, champions, procurement and the last mile to a signature.

   How do I know if a deal is real or if I am being strung along?

   The gist Write down what you know against a qualification frame and the gaps become obvious. MEDDPICC is the common one: metrics they care about, the economic buyer, decision criteria, decision process, paper process, the pain you are implicating, your champion and the competition. If you cannot name the economic buyer or describe the paper process, you do not have a deal, you have an interested person. The single best test of a champion is whether they will do something for you, like get you a meeting with their boss or send you the security questionnaire. Be willing to disqualify early and loudly, because a clean no in week two is worth more than a maybe that dies in your forecast in month four.

   📄 MEDDIC / MEDDPICC Sales Methodology and Process The reference explanation of all eight letters from the people who own the methodology, free to read. Use it as a deal checklist: the letters you c... 4 questions on running a sales process and closing →
4. 4
   Forecasting and GTM metrics

   Pipeline coverage, stage conversion, CAC payback, magic number, and calling a number you can defend to a board.

   How do I calculate conversion rates by stage, and what do I actually do once I have them?

   The gist Calculate them on a cohort, not on a snapshot. Take every opportunity created in a month, follow that same set forward, and measure what share reached each later stage. Snapshot ratios (stage two divided by stage one today) mix cohorts moving at different speeds and will mislead you. Once you have the curve, do three things: find the single worst step, since one stage usually leaks far more than the rest and that is where your attention belongs; measure time in stage alongside conversion, because a stage where deals sit for eleven weeks is a qualification problem wearing a conversion costume; and use the rates to work backwards into how much pipeline each rep needs, which turns a vague target into an activity plan.

   📊 The Bowtie Standard The clearest single document on what a revenue data model should look like end to end, from lead through renewal and expansion. It is the vocabular... 4 questions on forecasting and gtm metrics →