Sales engine for founder led lower-middle market companies
This page is for founder led lower-middle market companies with 5 to 50 million in annual revenue. The goal is a repeatable sales engine that leaders can run every week. Use the short answers here, then follow the deep guides for steps, examples, and templates.
Questions and short answers
When is it time to move from founder led sales to a sales leader
Move when you can define the ideal customer, a simple process, and a working message that wins outside your network. Add a leader when there are more qualified meetings than you can handle and when coaching reps would lift results. Hire a builder who can sell and scale. Keep the founder in top deals and in product feedback loops.
From founder led to sales leader
How do I structure territories and quotas
Start with account potential and segment fit. Use named accounts for enterprise and simple geographic or vertical splits for the rest. Keep books balanced so each rep has a fair shot. Set quotas with a mix of top down goals and bottom up pipeline math. Review twice a year. Protect customer relationships when reassigning accounts. Design territories and quotas
What should a simple sales compensation plan look like
Pay for the outcomes you want. Keep two or three measures such as new annual contract value, plan renewals, and on time collections. Use a clear target earnings and a simple accelerator for over plan. Add a cap only to protect margin on outlier deals. Share one page rules and five examples so every rep understands how to win. Simple sales compensation plan
Which CRM data actually matters at our size
Track the few fields that predict revenue. Account, contact, stage, next step with a date, amount, source, and expected close date. Add a short reason for win or loss. Review stage conversion and deal age by segment each month. Clear old or idle deals so the pipeline is real. Use dashboards that leaders and reps both open every week. CRM data that matters
How do I shorten long sales cycles with enterprise buyers
Map the buying process early. Confirm the problem, the value, the economic buyer, and the legal and security steps. Co write a mutual action plan with dates. Use paid pilots that prove value fast and include the next order. Bring delivery leaders into late stage calls to reduce risk. Keep a short risk log and clear blockers every week. Shorten enterprise sales cycles
What is the best way to win RFPs without wasting time
Qualify hard. Bid when you shaped the problem or when you have a real edge. Use a no bid rule when you are column filler. If you bid, write the executive summary first and tie answers to clear outcomes. Reuse a tight answer library and keep proofs current. Run a fast red team review and debrief every RFP to improve the next one. Win RFPs without waste
Related links
Revenue model and pricing
Marketing and positioning
Strategy and growth
Last updated: August 27, 2025
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