The desire for safety stands against every great and noble enterprise — Tacitus The second mouse gets the cheese! — Terry PratchettIt’s a listicle kind of night. And the topic is B2B Saas!

1. The broader the product, and the more pains it promises to address, the “easier” it will be to sell. It’s like casting a larger net, or putting on a buffet. 2. The breadth of a product has an exponential impact on product complexity, cost to service, cost to market, cost to sell, and cost to remain agile 3. The broader the product, and the more diverse the customer population, the harder it will be to innovate in such a way as to keep all customers happy 4. A product that can be used to achieve a goal for savvy customers is not the same as a product that delivers that outcome to all customers 5. Early deals/customers bought into the dream and got lots of love. Their churn and retention rates are not representative 6. It is virtually impossible to think clearly when considering the true costs and rewards of building a feature to close a deal. But sometimes it works out 7. Can you hire a reasonably smart 24-year-old, without a Rolodex, and have them close quality deals in 4–6 months? Test that out 8. At some point, you’ll have a quarter that invites the skeletons out of the closet. You can soften this blow if you keep your ears to the ground and listen to the front-lines 9. Sales indicate you’ve discovered a pain worth solving. Usage and renewal indicate that your product solves that pain 10. No news is not good news. Welcome the feature requests, blistering feedback, and support tickets (to a point). It shows someone is taking notice 11. Rapid growth and learning aren’t always great bedfellows. Resist the urge to lock down structures, processes, comp plans, or pricing to the point that you stop experimenting 12. Doubling the size of your team does not make it 2x more efficient OR effective 13. Be diligent about calculating your cost of acquisition (CAC). What was involved in closing the deal? Who was involved? 14. Will someone take you to their next job? That’s an excellent sign 15. In the case of a highly aspirational product, don’t be too critical of churn. Sometimes it just isn’t a great fit, and that’s OK. 16. You can explain NPS away. But the reality remains 17. Beware of the platform trap. Yes, you will draw in prospects who wanted everything “all in one place”. Can you deliver that better than a selection of best in breed products? 18. Have a reason to exist beyond growing, and meeting quotas. Those are things required to realize your higher mission, not an end unto themselves 19. Keep a tab on sales and support heroics. The goal is to make that not necessary rather than making it commonplace. Those early hires get tired! 20. Demonstrating ROI is a product mandate, not just something you put in your sales presentations. If you aren’t producing results and outcomes, it will eventually come back to haunt you 21. If the customer was not actively using the competitor’s product, then it’s likely that they weren’t your competitor. You didn’t displace them. The same forces (the status quo in their organization) will also challenge usage of your product 22. Customers expect startups to innovate/expand their product. That’s part of the reason for buying. Couple that with founders selling, and you’ll have big shoes to fill down the road 23. In many domains (e.g. analytics, AR, machine learning, mobile, etc.) you’ll get a lot of experimental budgets thrown your way. Differentiating between experimental budget and real budget can be difficult 24. Understand why each customer purchased your product. The “real” why even if it doesn’t fit into a neat box on a spreadsheet 25. Hopefully, using your product will inspire your customers. But if you haven’t addressed their use case lately, it may encourage them to replace you now they’ve figured out what outcomes they can drive 26. Keep a watch out for the non-competitor who is learning from all of your mistakes, and all of your progress. Especially if they have a lot more money 27. Low total cost of ownership (TCO) is a double-edged sword. Without skin in the game, it can be difficult to differentiate experimentation from commitment 28. Keep things simple! It is tempting to think you’ve expanded your ability to do multiple things at once. The reality is that things are still changing quickly and that you’re likely still in learning mode (vs. execution mode) 29. When trying to understand value, look for a benchmark purchase in the organization. How much do they spend on coffee, lunches, and onboarding their new employees? 30. It’s almost always easier to go upmarket with a validated product than it is to target SMBs after pursuing “enterprise” sized deals 31. Watch out for having too many cooks in the kitchen. Especially experienced cooks. You’ll have to say no to 95% of your good ideas, even if they don’t involve engineering, and that can be hard for folks who know the “right” things to do 32. Beware of strong relationship selling. If you’re a sales ninja, it can be relatively easy to persuade someone to buy. Ask how you’ll make that customer successful, and whether you have other customers that look just like this customer 33. The word “enterprise” is often misleading. There are plenty of companies who will pay enterprise amounts, but who don’t require an enterprise sales approach 34. Watch for the invisible costs of your current approach, and try to anticipate when you’ll need to pay off the interest (and at what rate). Carrying technical, UX, team culture, or learning debt will eventually need to be paid off. When? 35. Look at your marketing and messaging. If you keep waffling between multiple messages and pitches, ask yourself why that is happening. Schizophrenic product? Too broad? Broad on purpose?