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10 Questions Your Venture’s CEO Should be Asking Their VP of Sales

December 4, 2018

By: Dennis Ensing

In addition to my role as CEO of SWO Angels, I work as a Scale Growth Coach with the MaRS Discovery District in Toronto. The ventures I work with are in our Enterprise sector team and we work towards scaling their growth. Scaling ventures have over $5 million revenue, significant market traction and are experiencing high rates of annual revenue growth.

Some of the coaching that I do, combined with other Venture Services resources and programs, is giving the venture a new lens to use for their sales, marketing and operations teams – defining, then tracking, the right metrics, using them correctly as the means to their desired end, and then structuring the teams optimally.

As a venture transitions from Growth to Scale, its ability to efficiently repeat earlier successes and continue high rates of growth becomes more difficult. For a long, but interesting read on this and a study of the underlying growth metrics, see this research recently published by Charles Plant of the Impact Centre at the University of Toronto.

This is the first post in a series I plan to write on these scaling challenges in the coming months. I hope that it will be helpful to our members and other investors in high growth ventures looking to pass along advice & suggestions to their investee companies’ founding teams and CEOs.

Assess their Priorities

  1. What are YOU doing to close the Top three opportunities? (VP of Sales should own these deals)
  2. What actions have you taken to grow the pipeline this week? (careful . . . Marketing is usually a red herring here)
  3. What is your pipeline bleed factor? (the pipeline bleed factor is the ratio of the beginning pipeline for the quarter divided by the final closed amount for the quarter)
  4. What is the lifetime value of our five biggest customers – and what is our strategy to achieve this value (mutually)?

Assess team talent

  1. Who are the three sales candidates in the talent pipeline to allow us to grow or upgrade our team?
  2. How do you separate (define) “A” players from “B” players from “C” players?
  3. How would they rate your sales onboarding course, and does it provide a clear set of tests that help weed out the non-performers in the first few weeks?

Assess market advantages

  1. What are the 3 things we offer out customers that massively differentiate our offering?
  2. What is your territory growth strategy for the next 18 months with forecasted revenue?

Assess leadership capabilities

  1. What metrics are you watching? What are you coaching?

These 10 questions will help ensure that your growing enterprise remains focused and will continue to progress in both the short and long term.