Stop churn and grow accounts

The revenue you don't have to win twice is the cheapest revenue you will ever get.

3 steps, 12 questions underneath, read for leading a gtm team

1. 1
   Customer success and retention

   Keeping the customers you already won, and the team that does it.

   How do I structure a customer success team once one person is not enough?

   The gist Pick your organising axis on purpose. By segment (enterprise, mid market, SMB) is the default and works when your customers differ mostly in size. By lifecycle stage (onboarding specialists, then ongoing CSMs) works when onboarding is genuinely hard and separate skills. By engagement model (high touch versus digital) is what you graduate to when the long tail is too big to cover one to one. Do not run all three at once. Whichever you pick, set the ratio deliberately: roughly $1M to $2M ARR per CSM keeps the function honest, and anything much lower needs a reason you can say out loud.

   📄 Customer Success Team Structure: The Ultimate Guide Lays out the three real ways to organise a CS team (by segment, by lifecycle stage, by engagement model) and what each one costs you, which is the ... 4 questions on customer success and retention →
2. 2
   Expansion, upsell and churn

   Growing revenue inside accounts you already have, and stopping the leaks.

   How do I move net revenue retention from around 100 percent to 120 percent?

   The gist Do it in the right order. First stop the leak, because expansion built on a leaky base is exhausting: fix involuntary churn, then find the segment doing most of your gross churn and either serve it properly or stop selling to it. Only then build the expansion motion, and be specific about which of the three types you are pursuing (more seats, a second product to the same buyer, or the same product to a new department), because they need different plays and different people. Give someone the NRR number as their number. Diffuse ownership is why most companies stay parked at 100.

   📄 8 Things I Learned from Dave Kellogg About Net Dollar Retention The Gainsight CEO on why CS should own an NDR number rather than just a churn number, including the idea of giving every CSM their own book of MRR ... 4 questions on expansion, upsell and churn →
3. 3
   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 call a quarterly number I can actually defend to my CEO and my board?

   The gist Build it three ways and show the range, not a single figure: bottom up from deal level commits with entry criteria applied strictly, top down from historical stage conversion applied to today's pipeline (the version that ignores rep optimism), and a capacity view of productive reps times realistic productivity. If the three land within about ten percent of each other, call the middle and sleep. If they diverge badly, that divergence is the real finding and you should present it as such rather than quietly averaging it away. Then say out loud what would have to go wrong for you to miss and what would have to go right to beat it. A number offered with its assumptions is defensible, a number offered alone is just a promise.

   📄 The Definitive Way to Measure and Grade Sales Forecast Accuracy Defines accuracy against the day one forecast rather than the revised one, which is the single change that makes the metric honest. Includes the gr... 4 questions on forecasting and gtm metrics →