SSA#37: Enterprise Sales Secrets

Enterprise Sales Secrets

10 Lessons From A 7-Figure AE

Happy Wednesday to 12,046 SaaS sales professionals!

Yesterday we had an amazing guest speaker in the SaaS Sales Academy: Gilberto Picareta.

Gilberto was my AE when I was a BDR at Salesforce. Together we sourced & closed millions in ARR. During that time I learned some invaluable lessons from him. He remains one of my closest mentors until today.

Here are Gilberto's Top 10 Enterprise Sales Secrets, summarized from yesterday's live masterclass👇


Success Story From Our Coaching Program:


Q1 is known to be the toughest quarter of the year, and Karishma is already crushing her quota! Way to go, Karishma!


How To Prospect Into Enterprise Accounts

  1. Most sellers are too lazy when it comes to following up. The reality is: it takes 6-12 touch points (per prospect!) to get a first response.
  2. Monitor your entire patch in Sales Navigator. Triggers like job changes, for example. New C-level hires are very open to talk since they're still in the onboarding process.
  3. First, go top-down: target C-level executives with a generic pitch. If you cannot book a C-Level meeting, continue bottoms-up. Target staff level or middle management. They are the subject matter experts and can involve people higher up in the hierarchy.
  4. BDRs and AEs must align on a tiered strategy. Go DEEP instead of wide. Focus on the 20% of accounts that will bring 80% of the pipeline & revenue. Use Sales Navigator search filters like headcount, headcount growth, company revenue, sweet-spot industries, funding or buyer intent.
  5. The job of a BDR is not just to book the first meeting. She should be a running mate for her AE and help drive deals to a stage 4 (at Salesforce, qualified demo with decision maker). This helps the AE to close more deals, and helps the BDR build the skillset required to excel in a full cycle sales role. Win-win.


How To Win Enterprise Deals

  1. You need to sell a vision to the C-suite. Companies are resistant to change, especially when they are doing well. You need buy-in from the entire C-suite on your vision of a better future.
  2. Bring in implementation partners as early as possible. Ideally in the first discovery. If you want to scale your sales process and win 15 new mid-market logos in 5 years (like Gilberto) you need to have your partners do some of the selling for you.
  3. Selling in the enterprise space requires orchestrating a team of 20+ people. You need to be relationship builder and project manager at the same time.
  4. Enterprise sales cycles are like free consulting projects. Multiple discovery interviews, process workshops, demos and presentations. The prospect would pay $80,000 to $100,000 to get this kind of value from a top consulting firm. But you offer that value to them for free - in exchange for a verbal commitment from a C-level buyer.
    This commitment means: if the evaluation is successful, if you can fulfill our needs and requirements and justify the financial value of your solution, we will sign a contractual agreement by date X. This is called a mutual action plan (MAP).
  5. You can run the best sales cycle and have the best product, but if your competitor is 50% or more cheaper, you simply need a 100% better business case. If they can do the same scope for less, you will loose 10/10 times.


Thank you for this masterclass in enterprise selling, Gilberto!

Every month we have a new guest speaker in the SaaS Sales Academy.

They hold a 1-hour masterclass in their domain of expertise.

See you next week!


Want to increase your sales quota attainment by 25-50% in 90 days?

We have helped 69 private coaching clients do exactly that in the SaaS Sales Academy. If you are interested




SSA#37: Enterprise Sales Secrets

May 21, 2024

SSA#36: Cost Of Inaction

May 15, 2024

SSA#35: SPIN Your Discovery

May 07, 2024

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Christian Krause

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