Sales Advice for Founders

I was a construction engineer by training. I never aspired to be a sales expert, but my journey as a founder, scaling a B2B startup to $100 million in ARR, made me into one. Here is my advice for anyone who wants to get great at B2B sales. This should be a useful, albeit shallow list. I plan on writing more. If you want me to go deeper on any of these points, help me prioritize which ones.
  1. Build something people want and believe in the power of your product. People can tell if you’re trying to sell them garbage. And people love buying products from trusted partners.

  2. Establish a clear customer definition and make sure everyone on your team knows it.

  3. Put yourself in your customer’s shoes — understand their fears and desires; keep all of these in mind.

  4. Find the biggest pain point your customer has; focus all product and sales conversations around solving this pain point for them.

  5. Identify users, buyers, deployers, and trainers.The larger the company, the more likely these will be different people and departments and you will need to sell to (or around) all of them.

  6. Learn how money flows in your customer's organization. What budget line items can be used to pay for your product?

  7. It is hard for teams to create a new budget that doesn’t exist in their financial plan, but not impossible for something that has excellent return on investment.

  8. Create a database of companies and users who should use your product, then talk to them, and document every interaction.

  9. In the early days, use a spreadsheet for as long as you can to track customers until your life sucks so bad you don’t mind it sucking a little more to deploy Salesforce.

  10. Midmarket is no man’s land. Is your product’s sweet spot in SMB or Enterprise?

  11. Slice your market into different perspectives so you can understand the potential levers for growth. Consider segmentation by geographic regions, customer profiles, and industries.

  12. Plot your customers onto a cross section where x-axis is how much they pay you and y-axis is growth potential. Prioritize your time and investment with everyone who shows up in high growth potential.

  13. Do not let anyone waste your time or energy. Disqualify the tire kickers quickly. 

  14. Get prospects into the right swim lanes. Is this a $50 deal or a $50,000 deal? Allocate time proportionally to customer potential.  

  15. Never leave a meeting without knowing the next step. Say: “What are the next steps before you can make a decision?”

  16. Lead the customer. Help them organize at every step. Help them in ways that don’t scale.

  17. Shrink your sales cycle every chance you get. If a prospect asks you to call them next week, call them on a Monday, not Friday.  If a prospect asks you to touch base next month, reach out in week 3 not week 4. 

  18. In general, time kills all deals.

  19. Listen more than you speak.

  20. Track and be curious about every objection. These are learning moments for you. Do not be defensive.

  21. When your customer is talking to you, they’re not talking to your competitor. 

  22. Don’t be afraid to test out pricing. You can always change it later and grandfather your existing customers in on the old plan for some generous duration.

  23. When presenting pricing: present the facts, stop talking, listen and watch body language from your prospects. There is no need to justify how much you charge.

  24. Ask for their business: “What do you need to sign today?”

  25. Go towards where it hurts, ask the questions you’re scared to hear the answers to. 

  26. Keep a healthy paranoia. Deals are not done until money is in your bank account. 

  27. Review and document every win. There should be patterns including the number of and type of correspondences, what resonated, and the people involved. These patterns should become the foundation of your sales process and playbook.