Patterns

Feature Request Triage

When to use: whenever a customer asks for a feature. How: sort it as a Crackpot (decline), No-Brainer (build), or In-Between. For In-Betweens, ask what the use case is, what share of customers would use it, and whether it fits your vision. At 5–10%, check whether those users are power users and, if so, build it hidden and turn it on by request. At 20% or more, consider building it. For big requests, consider an integration. Trade-offs: you will say no to many good ideas. That is the job.

Customer Conversation Round

When to use: to strengthen product-market fit or before building a feature. How: talk to prospects, customers, people who didn’t buy, and people who cancelled. Ask open-ended questions about their flow, problem, current and past tools, and frustrations. Keep your product out of it. Trade-offs: it takes time, and you may hear things you don’t want to hear.

Enter a Mature Market

When to use: competing against large incumbents once you have a foothold. How: pick an angle. Price: more than 80% of the product for half the cost. Sales model: public pricing and self-serve against demo-first sales and setup fees. Product: modern UX and fast shipping. Then target the incumbent’s frustrated users and position as the underdog. Trade-offs: low price and a fresh product are temporary advantages. Raise prices and build a lasting moat.

Value-Metric Tiering

When to use: designing or revising pricing tiers. How: segment customers by size and usage. Pick a value metric tied to their success (subscribers, usage, or seats if users see different things). Scale it across tiers, add feature gating only if needed, and price enterprise at 10–20× the standard plan. Trade-offs: combining value metrics with feature gating gets complicated quickly.

Credit-Card Trial Experiment

When to use: considering trials without a credit card. How: first check you have more than $20K MRR, know your metrics by heart, and can handle about 10× the trials. Drop the card for one to two months, change nothing else, and watch trial-to-paid, churn, and spam daily. Trade-offs: more trials and support work. Reading downstream churn may take about two months.

Price Increase Rollout

When to use: every 6–12 months, or whenever “too expensive” complaints are rare. How: choose a method: reduce the value metric, hide the lowest tier, raise prices across the board, or go upmarket at 10×. If unsure, make a reversible change and watch new cohorts. Apply the Rule of 10 to existing customers. Give 2–4 months’ notice using the six-part announcement. Trade-offs: some customers will be angry. Never promise lifetime grandfathering.

Leaky Funnel Diagnosis

When to use: before spending more on traffic, or when growth stalls. How: work from the bottom up. Check happiness and churn (onboarding or product-market fit), then trial-to-paid (onboarding or sales), then visitor-to-trial (value proposition, copy, positioning), then traffic by source. Trade-offs: you need enough volume for patterns to show.

Choose Marketing Approaches

When to use: deciding where to market next. How: filter approaches by ACV, speed, cost, and scalability. Score the rest with ICE. Start one fast and one slow approach. Keep a marketing changelog and track cost and results per channel. Trade-offs: scores are guesses. Compare results with them to train your judgment.

Minimum Viable Integration

When to use: integration marketing with a partner. How: agree on joint promotion first. Ship a basic version (for example, pasted API keys instead of OAuth), promote it, then improve the integrations customers use most. Trade-offs: a rough first version may need rework.

Sign-up Attribution

When to use: always, and especially when founders say “word of mouth.” How: ask how customers first heard of you and where they heard just before signing up. Set cookies for referral source and landing page on the first visit, save them at sign-up, and pass them to your analytics or billing tools. Trade-offs: you will never attribute 100%, but some data beats none.

Demo Routing by Value Metric

When to use: a high-touch or dual funnel with many small prospects. How: the “Book a Demo” form asks for the value metric (for example, subscriber count). Below a cutoff, show a 10-minute recorded demo. Above it, show a scheduling link. Raise the cutoff as sales capacity allows. Trade-offs: early on, demo everyone to learn the market.

Consultative Demo

When to use: every sales call. How: qualify first (budget, timeline, problem). Follow a script. Ask about the problem, current solution, organization size, category knowledge, and decision process. Show only what solves their problem. Say no to poor fits, follow up, and take payment on the call when possible. Trade-offs: turning away poor fits loses short-term revenue but saves churn and support.

Next-Hire Selection

When to use: deciding which role to hire next. How: track your time for one or two weeks, group tasks by department and role, then ask the five questions: bad at, good at but don’t enjoy, could stop, could hand off, would most grow the company. Trade-offs: there is never enough money for every role. Support usually comes first.

Plateau Check

When to use: monthly, or when planning growth. How: divide new MRR per month by monthly churn to get maximum MRR. If it’s too close, lower churn or raise new MRR now. Trade-offs: fixing a plateau often needs strategic changes, not small tweaks.

Churn Segmentation and Exit Email

When to use: when churn is high or unclear. How: split churn by pricing tier, marketing channel, and sign-up cohort. Within ten minutes of each cancellation, send a short email from a founder asking why, and invite even a four- or five-word reply. Trade-offs: segmenting by channel needs attribution set up in advance.

Optionality Mapping

When to use: when a problem feels business-ending. How: check whether it’s truly a roadblock (API shutdown, existential lawsuit). If not, write down three or four fallback options. None will be ideal, but none should end the company. Trade-offs: it doesn’t remove the problem, only the false sense that it’s fatal.

Founder Retreat

When to use: before big decisions, or once or twice a year. How: spend 48–72 hours alone with a notebook, without podcasts, books, or films. Reflect, then turn your insights into actions for the next year. Trade-offs: it is hard to step away when things are busy, which is often when it helps most.