Scott Leese 6x Leader + Founder + 3x Author - Seller Realities + Go To Work

10/18/23 • 39 min

Our Guest: Scott Leese is a six-time Sales Leader and a two-time best-selling Amazon author in the category of sales. He maintains active communities like GTM United and is also focusing on helping companies build revenue-driving motions across the organization.

Episode Topics:

Scott's view on shifting away from traditional VP career paths and expectations.
What are the qualities to look for in someone who is a first-time VP of Sales?
Scott’s advice for someone who is considering transitioning into an account executive (AE) role + Director/VP Sales level.
The type of leaders or CEOs that Scott gets along with.
Overall framework of the evolution of Sales from Go-To-Market to Go-To-Network.
What type of seller performs best?
Scott on the sales productivity of Go-To-Network approach versus cold outbound strategy.
Scott's take on Sapphire Non-AE GTM Bloat - 90% of GTM spend is non-AE, down from 70% in 2018.
Strategies or approaches that are currently successful in the broader environment.
Scott elaborates his Linkedin post on self-inflicted errors: “Most deals die from predictable self-inflicted errors. Avoidable problems turn into cyclical failures caused by a lack of focus on reverse engineering root causes.”

Resources:

https://www.surfandsales.com/

https://twitter.com/SaaSletter/status/1700517476017246334?s=20

https://www.linkedin.com/posts/scottleese_you-dont-get-good-at-anything-by-giving-activity-6990657671431405568-lVpl?utm_source=share&utm_medium=member_desktop

About Cloud Radio by Cloud Ratings:

Made for "full stack" cloud + SaaS operators, Cloud Radio is a SaaS podcast covers all aspects of the business of software.

Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.

https://cloudradio.cloudratings.com/

https://twitter.com/SaaSletter

https://www.saasletter.com/

About Cloud Ratings:

Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.

Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software.

Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.

https://cloudratings.com/

Episode Topics:

Scott's view on shifting away from traditional VP career paths and expectations.
What are the qualities to look for in someone who is a first-time VP of Sales?
Scott’s advice for someone who is considering transitioning into an account executive (AE) role + Director/VP Sales level.
The type of leaders or CEOs that Scott gets along with.
Overall framework of the evolution of Sales from Go-To-Market to Go-To-Network.
What type of seller performs best?
Scott on the sales productivity of Go-To-Network approach versus cold outbound strategy.
Scott's take on Sapphire Non-AE GTM Bloat - 90% of GTM spend is non-AE, down from 70% in 2018.
Strategies or approaches that are currently successful in the broader environment.
Scott elaborates his Linkedin post on self-inflicted errors: “Most deals die from predictable self-inflicted errors. Avoidable problems turn into cyclical failures caused by a lack of focus on reverse engineering root causes.”

Resources:

https://www.surfandsales.com/

https://twitter.com/SaaSletter/status/1700517476017246334?s=20

https://www.linkedin.com/posts/scottleese_you-dont-get-good-at-anything-by-giving-activity-6990657671431405568-lVpl?utm_source=share&utm_medium=member_desktop

About Cloud Radio by Cloud Ratings:

Made for "full stack" cloud + SaaS operators, Cloud Radio is a SaaS podcast covers all aspects of the business of software.

Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.

https://cloudradio.cloudratings.com/

https://twitter.com/SaaSletter

https://www.saasletter.com/

About Cloud Ratings:

Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.

Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.

https://cloudratings.com/

Previous Episode

Ashley Acosta - Founder + CEO of Maca - SaaS Pricing: Fix The Leaks

Our Guest: Ashley Acosta, Founder and CEO of Maca. Previously, Ashley was the VP of Revenue at Pipe, on the founding team at Brex, and a Mentor at First Round Capital. Now, she's pioneering the first operating system for value-based pricing through Maca, empowering growing companies to achieve greater revenue efficiency through AI-driven data insights.

Episode Topics:

How much potential revenue are companies losing by not optimizing their pricing strategies?
Maca’s methods of sourcing data + understanding their insights engine.
Ashley's insight on the growing complexity of revenue management in growing companies and hidden revenue channels.
Twitter Question #1: What are the top key results in metrics to determine pricing effectiveness?
Twitter Question #2: How do you think about testing pricing and gathering learnings for long sales cycle products?
Ashley expounds on her Tweet: “Test pricing using your sales levers, not by changing your list price. This will promote learnings about internal levers faster and you'll be less likely to upset your customers by changing pricing on your website, requiring less internal uplift to change pricing.”
How to determine pricing decisions + levers for software products by understanding overall ROI at the feature level
Benefits of Maca's data-driven model over the traditional pricing consultant model (i.e. engaging Simon Kucher).
The scale and type of software companies that Maca works with.

Resources:

https://maca.io/

https://www.linkedin.com/in/ashley-acosta-8aa28132/

https://twitter.com/ashleyacosta75/status/1678455416261419022

https://cloudratings.com/roi-of-it-software/

https://cloudratings.com/software-roi-drivers/

About Cloud Radio by Cloud Ratings:

Made for "full stack" cloud + SaaS operators, Cloud Radio is a SaaS podcast covers all aspects of the business of software.

Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.

https://cloudradio.cloudratings.com/

https://twitter.com/SaaSletter

https://www.saasletter.com/

About Cloud Ratings:

Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.

Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.

https://cloudratings.com/

Next Episode

Scott Brinker - Martech in 2024

Our Guest: Scott Brinker, VP of Platform Ecosystem at HubSpot, shapes Hubspot's platform strategy and leads business programs for its global technology partner ecosystem. He is also an editor at chiefmartec.com, with over 50,000 readers, analyzing topics at the intersection of marketing, technology, and management.

Episode Topics:

How much does Scott Brinker see AI impacting marketing headcount?
Scott on the need to adapt and rethink categorizations in light of the evolving MarTech landscape.
What are some concerns about the sustainability of the current level of saturation in the martech industry?
How should companies in the torso (top 100 companies) and head (top 10 companies) navigate the presence of a large number of competitors in the long tail (12,000 companies)?
What does composability truly mean for MarTech?
The business and technical risk of composability.
Scott's recommendations and principles to CMOs and marketing leaders for implementing composability.
How does competition among major platforms provide opportunities and leverage for smaller, long-tail partners in ecosystems?

Sources:
https://chiefmartec.com/2023/12/major-trends-in-martech-for-2024-the-real-changes-underway-in-a-99-platitude-free-report/

https://chiefmartec.com/2023/10/products-in-the-long-tail-of-martech-have-a-wide-range-of-different-strategies-and-aspirations/

https://www.saasletter.com/p/mckinsey-cloud-roi-ai-roi

About Cloud Radio by Cloud Ratings:

Made for "full stack" cloud + SaaS operators, Cloud Radio is a SaaS podcast covers all aspects of the business of software.

Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.

https://cloudradio.cloudratings.com/

https://twitter.com/SaaSletter

https://www.saasletter.com/

About Cloud Ratings:

Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.

Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.

https://cloudratings.com/