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Winning by Design

4 resources from Winning by Design we point people to, and the questions each answers.

📖 Book
✓ Link checked Paid Advanced

The most systematic treatment of recurring revenue as an engineered system rather than a set of departments, with 250+ blueprints you can lift. For leaders building the engine, not for someone still finding the first ten customers.

Revenue Architecture

From Winning by Design by Jacco van der Kooij 556 pages

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Answers How do I turn the thing that worked when I did it into an engine someone else can run? What do the very best GTM teams do that everyone else does not? What separates a great VP of Sales from a merely good one? What does world-class RevOps look like, and when does a company actually need it? Do we need to create a new category, or should we position inside one that already exists?
📊 Report
✓ Link checked Freemium Intermediate

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 vocabulary most modern RevOps teams have quietly standardised on.

The Bowtie Standard

From Winning by Design by Winning by Design 46 page PDF

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Answers What does a RevOps person actually do all day? How do I break into RevOps when I have never had the title? Our numbers live in five different tools and none of them agree. How do I build one source of truth? Marketing says they sourced the pipeline, sales says they did. How do I settle attribution without starting a war? We are paying for twenty plus GTM tools and I cannot justify half of them. How do I cut the stack? How do the best run companies keep sales, marketing, product and finance moving in step week to week? What does a genuinely best in class GTM data model look like, not just a tidy CRM? How do I calculate conversion rates by stage, and what do I actually do once I have them? Our win rate dropped this quarter. How do I work out why rather than just guessing?
Answers What does a genuinely best in class GTM data model look like, not just a tidy CRM?
📄 Article
✓ Link checked Free Advanced

Five design rules worth memorising, including show causality and keep the payout cycle under 60 days, plus a business case method for setting targets from total team cost rather than from wishful top down math.

Compensation for SaaS Sales Organizations

From Winning by Design 15 min read

  • With no proven LTV, keep combined SDR, AE and CSM OTE under 40 percent of year one revenue, or 60 percent at 2+ year LTV.
  • A 1 in 5 win rate is the SaaS norm, versus 1 in 3 in perpetual license sales.
  • Working the SDR model backwards: 40K variable over 150 leads is about 250 dollars per SQL, or 1,250 per closed deal.
  • With a sales cycle up to 90 days, 90 days is the common onboarding period; complex products take six to nine months.
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Answers How should SDR, AE and customer success comp actually differ, and why? Do SPIFFs work, or do they just teach the team to wait for the next one? How do I build a comp plan that pays for the strategy we actually have this year? My comp plan is being gamed. How do I find it and fix it mid-year? How do the best-run comp teams operate the plan through the year, not just design it? How do the best companies pay reps in a hybrid or product-led motion where the product sourced the deal?
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