Metrics that Measure Up

Lessons Learned from being a 6x SaaS VP Sales - with Scott Leese

March 23, 2021 Ray Rike
Metrics that Measure Up
Lessons Learned from being a 6x SaaS VP Sales - with Scott Leese
Chapters
Metrics that Measure Up
Lessons Learned from being a 6x SaaS VP Sales - with Scott Leese
Mar 23, 2021
Ray Rike

Experience is the best teacher. In this episode of the Metrics that Measure Up with Scott Leese we take a deep dive into how experience has informed his career journey.

Scott has over twenty years of experience as a six time SaaS VP of Sales, and most amazingly, his average tenure for each role was greater than 3 years in a role that typically experiences a 14-18 month tenure.  Scott shares some of his lessons learned and secrets to his sustained success.

First, Scott highlighted how critical a Sales Operations leader is to become the foundation of success.  Secondly, Scott talked about his own journey to learning how to hire better candidates which has a material impact on a VP Sales ability to be successful in early stage SaaS companies.

Next we talked about the important of "sales process" and why Scott says he would even design and implement a structured sales process even before he would hire the first sales resource.  Scott says one of the most common mistakes founders make is not to document the sales process that got them the first few deals, and provides insights into the initial scaling of the sales organization.

Stage appropriate VP Sales is a common topic and discussion amongst investors, founders, CEO's and even VP's of Sales. Scott's recommendation is to ensure that you design your VP of Sales career journey to embrace and experience every stage of growth.  Scott loved the role of being an early stage of VP Sales at SaaS companies, but did find that bias was created that certain "VP Sales" profiles get labeled as only an early stage VP Sales.  

This discussion led to why stock option programs that are historically based upon time - 4 years is the standard but should be aligned to size/growth accomplishments to reward achieving the goal versus a time horizon that is seldom achieved by the VP Sales in early stage SaaS companies.  The other option discussed was to agree on a one-time bonus based upon hitting a pre-defined revenue level, such as $25M or $50M.

Scott has leveraged his 20+ years of VP Sales experience to launch his own his own VP Sales consultancy, writing two books including "Rep to Sales Manager",  a quickly growing, weekly Thursday Night Sales event, the Surf and Sales event and most recently his own private patreon.  Scott highlighted that he built his network and the foundational elements of his entrepreneur journey while he was a full time, VP Sales.

Scott also shared how his side hustles, including real estate, his books proceeds and even hold the initial Surf and Sales event during his annual two weeks of PTO.  One caveat was ENSURE you are hitting your quota and goals before even considering taking this approach. During the episode we created the concept of "micro-entrepreneurship" which is an interesting step by step approach to moving from employee to entrepreneur.

Lastly, Scott discussed that his initial catalyst to building his LinkedIn following was trying to save money on sales rep recruiting.  As a result, not only did Scott eliminate the majority of his recruiting costs, he quickly saw the secondary benefit of building his LinkedIn following.  He supplement his outreach with content that he thought sales professionals were in desperate need to see, read and learn from and not be charged for this type of educational content.

If you love the world of B2B Sales,  and are considering creating your own company  some day, this is a great listen.



Show Notes

Experience is the best teacher. In this episode of the Metrics that Measure Up with Scott Leese we take a deep dive into how experience has informed his career journey.

Scott has over twenty years of experience as a six time SaaS VP of Sales, and most amazingly, his average tenure for each role was greater than 3 years in a role that typically experiences a 14-18 month tenure.  Scott shares some of his lessons learned and secrets to his sustained success.

First, Scott highlighted how critical a Sales Operations leader is to become the foundation of success.  Secondly, Scott talked about his own journey to learning how to hire better candidates which has a material impact on a VP Sales ability to be successful in early stage SaaS companies.

Next we talked about the important of "sales process" and why Scott says he would even design and implement a structured sales process even before he would hire the first sales resource.  Scott says one of the most common mistakes founders make is not to document the sales process that got them the first few deals, and provides insights into the initial scaling of the sales organization.

Stage appropriate VP Sales is a common topic and discussion amongst investors, founders, CEO's and even VP's of Sales. Scott's recommendation is to ensure that you design your VP of Sales career journey to embrace and experience every stage of growth.  Scott loved the role of being an early stage of VP Sales at SaaS companies, but did find that bias was created that certain "VP Sales" profiles get labeled as only an early stage VP Sales.  

This discussion led to why stock option programs that are historically based upon time - 4 years is the standard but should be aligned to size/growth accomplishments to reward achieving the goal versus a time horizon that is seldom achieved by the VP Sales in early stage SaaS companies.  The other option discussed was to agree on a one-time bonus based upon hitting a pre-defined revenue level, such as $25M or $50M.

Scott has leveraged his 20+ years of VP Sales experience to launch his own his own VP Sales consultancy, writing two books including "Rep to Sales Manager",  a quickly growing, weekly Thursday Night Sales event, the Surf and Sales event and most recently his own private patreon.  Scott highlighted that he built his network and the foundational elements of his entrepreneur journey while he was a full time, VP Sales.

Scott also shared how his side hustles, including real estate, his books proceeds and even hold the initial Surf and Sales event during his annual two weeks of PTO.  One caveat was ENSURE you are hitting your quota and goals before even considering taking this approach. During the episode we created the concept of "micro-entrepreneurship" which is an interesting step by step approach to moving from employee to entrepreneur.

Lastly, Scott discussed that his initial catalyst to building his LinkedIn following was trying to save money on sales rep recruiting.  As a result, not only did Scott eliminate the majority of his recruiting costs, he quickly saw the secondary benefit of building his LinkedIn following.  He supplement his outreach with content that he thought sales professionals were in desperate need to see, read and learn from and not be charged for this type of educational content.

If you love the world of B2B Sales,  and are considering creating your own company  some day, this is a great listen.