Episode 310: Why Most Sales Strategies Fail, and How Great Leaders Actually Win the Midgame. episode artwork

EPISODE · Feb 16, 2026 · 19 MIN

Episode 310: Why Most Sales Strategies Fail, and How Great Leaders Actually Win the Midgame.

from Developing The Leader Within Podcast · host Enrique Acosta Gonzalez

In this dynamic episode of the Developing the Leader Within Podcast, we are joined by Rich Bishop, the VP of Revenue Operations at Order Groove and host of the Mid Game Mindset podcast. Rich brings over 15 years of experience in revenue operations, finance systems, and go-to-market strategies, sharing insights on why most sales strategies fail and how effective leaders navigate the mid-game of sales.Rich emphasizes the critical importance of alignment within executive teams and how misalignment can derail customer experiences. He discusses the common pitfalls leaders face when transitioning from tactical execution to strategic oversight, especially during key growth inflection points. Through his extensive career, Rich has witnessed firsthand how the environment in which sales teams operate can dictate their success, highlighting the need for structured processes and support systems.You will learn the following:1. The significance of alignment within executive teams and its impact on customer journeys. 02:422. How to identify and address strategic disconnects that hinder execution. 05:303. The importance of structured processes for onboarding and supporting sales reps. 07:444. Mindset shifts required for successful sales leaders transitioning from individual contributors. 09:545. The balance between leveraging technology and fostering human relationships in sales. 12:56To get in contact with Rich: LinkedIn: ⁠https://www.linkedin.com/in/richbishop2Website: ⁠⁠⁠⁠⁠http://www.midgameconsulting.comPodcast: ⁠https://www.youtube.com/@TheMidgameMindsetThis episode is sponsored by   Triad Leadership Solutions  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ https://triadleadershipsolutions.my.canva.site⁠⁠⁠⁠⁠⁠⁠Our podcast is sponsored by   The Global Trends MagazineWebsite: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.gc-bl.org/global-trends⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Outlier Project   Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://theoutlierproject.co⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ascend MeditationsWebsite: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.ascendmeditations.app⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Chop AiWebsite: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.chopai.app⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Castle and Compass AdventuresWebsite: ⁠⁠⁠⁠⁠⁠⁠https://castle-and-compass-adventures.com⁠⁠⁠⁠⁠⁠⁠Bonefrog Coffee CompanyWebsite: ⁠⁠⁠⁠⁠⁠⁠https://bonefrogcoffee.com⁠⁠⁠⁠⁠⁠⁠Coupon code: DTLW BoomcasterWebsite: ⁠⁠⁠⁠⁠⁠https://www.boomcaster.com/⁠⁠⁠⁠⁠⁠SupaPassWebsite: ⁠https://supapass.com⁠Make sure to Catch us streaming on Roku and Amazon Fire TV on the Purpose Place Network.Also catch our Exclusive Members only content “Going Deeper Within” on the Lions Guide Academy.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.lionsguide.com/gdw⁠⁠⁠⁠⁠

In this dynamic episode of the Developing the Leader Within Podcast, we are joined by Rich Bishop, the VP of Revenue Operations at Order Groove and host of the Mid Game Mindset podcast. Rich brings over 15 years of experience in revenue operations, finance systems, and go-to-market strategies, sharing insights on why most sales strategies fail and how effective leaders navigate the mid-game of sales.Rich emphasizes the critical importance of alignment within executive teams and how misalignment can derail customer experiences. He discusses the common pitfalls leaders face when transitioning from tactical execution to strategic oversight, especially during key growth inflection points. Through his extensive career, Rich has witnessed firsthand how the environment in which sales teams operate can dictate their success, highlighting the need for structured processes and support systems.You will learn the following:1. The significance of alignment within executive teams and its impact on customer journeys. 02:422. How to identify and address strategic disconnects that hinder execution. 05:303. The importance of structured processes for onboarding and supporting sales reps. 07:444. Mindset shifts required for successful sales leaders transitioning from individual contributors. 09:545. The balance between leveraging technology and fostering human relationships in sales. 12:56To get in contact with Rich: LinkedIn: ⁠https://www.linkedin.com/in/richbishop2Website: ⁠⁠⁠⁠⁠http://www.midgameconsulting.comPodcast: ⁠https://www.youtube.com/@TheMidgameMindsetThis episode is sponsored by   Triad Leadership Solutions  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ https://triadleadershipsolutions.my.canva.site⁠⁠⁠⁠⁠⁠⁠Our podcast is sponsored by   The Global Trends MagazineWebsite: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.gc-bl.org/global-trends⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Outlier Project   Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://theoutlierproject.co⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ascend MeditationsWebsite: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.ascendmeditations.app⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Chop AiWebsite: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.chopai.app⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Castle and Compass AdventuresWebsite: ⁠⁠⁠⁠⁠⁠⁠https://castle-and-compass-adventures.com⁠⁠⁠⁠⁠⁠⁠Bonefrog Coffee CompanyWebsite: ⁠⁠⁠⁠⁠⁠⁠https://bonefrogcoffee.com⁠⁠⁠⁠⁠⁠⁠Coupon code: DTLW BoomcasterWebsite: ⁠⁠⁠⁠⁠⁠https://www.boomcaster.com/⁠⁠⁠⁠⁠⁠SupaPassWebsite: ⁠https://supapass.com⁠Make sure to Catch us streaming on Roku and Amazon Fire TV on the Purpose Place Network.Also catch our Exclusive Members only content “Going Deeper Within” on the Lions Guide Academy.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.lionsguide.com/gdw⁠⁠⁠⁠⁠

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Episode 310: Why Most Sales Strategies Fail, and How Great Leaders Actually Win the Midgame.

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This episode was published on February 16, 2026.

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In this dynamic episode of the Developing the Leader Within Podcast, we are joined by Rich Bishop, the VP of Revenue Operations at Order Groove and host of the Mid Game Mindset podcast. Rich brings over 15 years of experience in revenue operations,...

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