Sales Players

Jesse sits down with his former sales leader Vince Beese, the only exec he’s ever seen cold call procurement to get a deal done. They break down Vince’s new book Red Zone Selling, including tactical plays for managing late-stage deals, building mutual action plans that actually work, and why enterprise sales is more like football than most reps realize. If you're selling big deals in a competitive market, this one's a masterclass.

SPONSORS:

ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership

EPISODE LINKS:

• Connect with Vince: https://www.linkedin.com/in/vbeese/

• Red Zone Selling Launch: https://40974935.hs-sites.com/red-zone

• Red Zone Selling Newsletter: https://www.linkedin.com/newsletters/7252747286076698624/

CONNECT WITH JESSE:

• LinkedIn: https://www.linkedin.com/in/jessewoodbury/

• Website: https://jessewoodbury.com/

HELP GROW SP:

• Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Get a weekly email from SP: https://www.salesplayers.co/

• Subscribe!

• Leave a rating, write a review, and share

• Check out the above sponsors, it's the best way to support the show

GUEST HIGHLIGHTS:

Morgan J. Ingram, Chris Orlob, Ian Koniak, Jeb Blount, Brandon Fluharty, Scott Leese, Sarah Brazier, Jamal Reimer, Jen Allen-Knuth, Andy Paul, Collin Mitchell, Tim Zielinski, Christian Banach, Rajiv 'RajNATION' Nathan, Belal Batrawy, Christine Rogers, Chris Beall, Patrick Baynes, Jeroen Corthout, Nate Nasralla, Gabe Lullo, Vince Beese, Brandon Bornancin, Girish Redekar, Guillaume Moubeche, Lloyed Lobo, Corey Quinn, Danny Delvecchio, Tom Slocum, Todd Busler, Richard Harris, Krysten Conner, Dan Goodman, Kris Rudeegraap, Rachit Kataria

© Sales Players, LLC

Jesse shares 20 proven sales plays he turns to when deals stall, pipeline dries up, or nothing seems to be working. These are high-leverage, momentum-building activities that have helped him bounce back from slumps and close big deals.

SPONSORS:

ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership

EPISODE LINKS:

• https://www.salesplayers.co/posts/20-high-leverage-sales-activities

CONNECT WITH JESSE:

• LinkedIn: https://www.linkedin.com/in/jessewoodbury/

• Website: https://jessewoodbury.com/

HELP GROW SP:

• Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Get a weekly email from SP: https://www.salesplayers.co/

• Subscribe!

• Leave a rating, write a review, and share

• Check out the above sponsors, it's the best way to support the show

GUEST HIGHLIGHTS:

Morgan J. Ingram, Chris Orlob, Ian Koniak, Jeb Blount, Brandon Fluharty, Scott Leese, Sarah Brazier, Jamal Reimer, Jen Allen-Knuth, Andy Paul, Collin Mitchell, Tim Zielinski, Christian Banach, Rajiv 'RajNATION' Nathan, Belal Batrawy, Christine Rogers, Chris Beall, Patrick Baynes, Jeroen Corthout, Nate Nasralla, Gabe Lullo, Vince Beese, Brandon Bornancin, Girish Redekar, Guillaume Moubeche, Lloyed Lobo, Corey Quinn, Danny Delvecchio, Tom Slocum, Todd Busler, Richard Harris, Krysten Conner, Dan Goodman, Kris Rudeegraap, Rachit Kataria

© Sales Players, LLC

Jesse (who is not giving financial or investment advice) shares why tech sellers have a huge advantage when it comes to building wealth and financial security. He shares a few things you can do to develop financial security which will enhance your selling career.

SPONSORS:

ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership

CONNECT WITH JESSE:

• LinkedIn: https://www.linkedin.com/in/jessewoodbury/

• Website: https://jessewoodbury.com/

HELP GROW SP:

• Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Get a weekly email from SP: https://www.salesplayers.co/

• Subscribe!

• Leave a rating, write a review, and share

• Check out the above sponsors, it's the best way to support the show

GUEST HIGHLIGHTS:

Morgan J. Ingram, Chris Orlob, Ian Koniak, Jeb Blount, Brandon Fluharty, Scott Leese, Sarah Brazier, Jamal Reimer, Jen Allen-Knuth, Andy Paul, Collin Mitchell, Tim Zielinski, Christian Banach, Rajiv 'RajNATION' Nathan, Belal Batrawy, Christine Rogers, Chris Beall, Patrick Baynes, Jeroen Corthout, Nate Nasralla, Gabe Lullo, Vince Beese, Brandon Bornancin, Girish Redekar, Guillaume Moubeche, Lloyed Lobo, Corey Quinn, Danny Delvecchio, Tom Slocum, Todd Busler, Richard Harris, Krysten Conner, Dan Goodman, Kris Rudeegraap, Rachit Kataria

© Sales Players, LLC

Jesse sits down with "Fidel Cache Flow," an anonymous tech seller who’s built a cult following on Sales Twitter with unfiltered takes on career growth, wifi money, and escaping the W2 grind. Fidel runs Desperados, a fast-growing private community for sellers looking to build income beyond quota. In this episode, they dive into contract stacking, virtual assistants, building while employed, and why aiming for #1 on the leaderboard might be the wrong game.

SPONSORS:

ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership

EPISODE LINKS:

• Follow: https://x.com/FidelCacheFlow

CONNECT WITH JESSE:

• LinkedIn: https://www.linkedin.com/in/jessewoodbury/

• Website: https://jessewoodbury.com/

HELP GROW SP:

• Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Get a weekly email from SP: https://www.salesplayers.co/

• Subscribe!

• Leave a rating, write a review, and share

• Check out the above sponsors, it's the best way to support the show

GUEST HIGHLIGHTS:

Morgan J. Ingram, Chris Orlob, Ian Koniak, Jeb Blount, Brandon Fluharty, Scott Leese, Sarah Brazier, Jamal Reimer, Jen Allen-Knuth, Andy Paul, Collin Mitchell, Tim Zielinski, Christian Banach, Rajiv 'RajNATION' Nathan, Belal Batrawy, Christine Rogers, Chris Beall, Patrick Baynes, Jeroen Corthout, Nate Nasralla, Gabe Lullo, Vince Beese, Brandon Bornancin, Girish Redekar, Guillaume Moubeche, Lloyed Lobo, Corey Quinn, Danny Delvecchio, Tom Slocum, Todd Busler, Richard Harris, Krysten Conner, Dan Goodman, Kris Rudeegraap, Rachit Kataria

© Sales Players, LLC

Jesse breaks down 23 hard-earned truths about enterprise sales that every seller should know

SPONSORS:

ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership

EPISODE LINKS:

• Read the 23 Truths: https://www.salesplayers.co/posts/23-absolute-truths-about-enterprise-selling

• Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview

CONNECT WITH JESSE:

• LinkedIn: https://www.linkedin.com/in/jessewoodbury/

• Website: https://jessewoodbury.com/

HELP GROW SP:

• Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Get a weekly email from SP: https://www.salesplayers.co/

• Subscribe!

• Leave a rating, write a review, and share

• Check out the above sponsors, it's the best way to support the show

GUEST HIGHLIGHTS:

Morgan J. Ingram, Chris Orlob, Ian Koniak, Jeb Blount, Brandon Fluharty, Scott Leese, Sarah Brazier, Jamal Reimer, Jen Allen-Knuth, Andy Paul, Collin Mitchell, Tim Zielinski, Christian Banach, Rajiv 'RajNATION' Nathan, Belal Batrawy, Christine Rogers, Chris Beall, Patrick Baynes, Jeroen Corthout, Nate Nasralla, Gabe Lullo, Vince Beese, Brandon Bornancin, Girish Redekar, Guillaume Moubeche, Lloyed Lobo, Corey Quinn, Danny Delvecchio, Tom Slocum, Todd Busler, Richard Harris, Krysten Conner, Dan Goodman, Kris Rudeegraap, Rachit Kataria

© Sales Players, LLC

The best candidates don’t just show up, they sell themselves at every step. In this episode, Jesse shares the high-leverage interview plays that get offers in today’s brutal job market.

SPONSORS:

ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership

EPISODE LINKS:

• Join the FREE Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview

CONNECT WITH JESSE:

• LinkedIn: https://www.linkedin.com/in/jessewoodbury/

• Website: https://jessewoodbury.com/

HELP GROW SP:

• Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Get a weekly email from SP: https://www.salesplayers.co/

• Subscribe!

• Leave a rating, write a review, and share

• Check out the above sponsors, it's the best way to support the show

GUEST HIGHLIGHTS:

Morgan J. Ingram, Chris Orlob, Ian Koniak, Jeb Blount, Brandon Fluharty, Scott Leese, Sarah Brazier, Jamal Reimer, Jen Allen-Knuth, Andy Paul, Collin Mitchell, Tim Zielinski, Christian Banach, Rajiv 'RajNATION' Nathan, Belal Batrawy, Christine Rogers, Chris Beall, Patrick Baynes, Jeroen Corthout, Nate Nasralla, Gabe Lullo, Vince Beese, Brandon Bornancin, Girish Redekar, Guillaume Moubeche, Lloyed Lobo, Corey Quinn, Danny Delvecchio, Tom Slocum, Todd Busler, Richard Harris, Krysten Conner, Dan Goodman, Kris Rudeegraap, Rachit Kataria

© Sales Players, LLC

Jesse breaks down the 10 traits that separate good reps from top-performing enterprise and mid-market sellers. After a decade in tech sales and five years interviewing the best in the game, he shares what it really takes to sell at the highest level.

SPONSORS:

ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership

EPISODE LINKS:

• Read: https://www.salesplayers.co/posts/top-tech-sellers-share-these-10-traits

• Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview

CONNECT WITH JESSE:

• LinkedIn: https://www.linkedin.com/in/jessewoodbury/

• Website: https://jessewoodbury.com/

HELP GROW SP:

• Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Get a weekly email from SP: https://www.salesplayers.co/

• Subscribe!

• Leave a rating, write a review, and share

• Check out the above sponsors, it's the best way to support the show

GUEST HIGHLIGHTS:

Morgan J. Ingram, Chris Orlob, Ian Koniak, Jeb Blount, Brandon Fluharty, Scott Leese, Sarah Brazier, Jamal Reimer, Jen Allen-Knuth, Andy Paul, Collin Mitchell, Tim Zielinski, Christian Banach, Rajiv 'RajNATION' Nathan, Belal Batrawy, Christine Rogers, Chris Beall, Patrick Baynes, Jeroen Corthout, Nate Nasralla, Gabe Lullo, Vince Beese, Brandon Bornancin, Girish Redekar, Guillaume Moubeche, Lloyed Lobo, Corey Quinn, Danny Delvecchio, Tom Slocum, Todd Busler, Richard Harris, Krysten Conner, Dan Goodman, Kris Rudeegraap, Rachit Kataria

© Sales Players, LLC

Jesse shares the unfiltered story of his time as the founding AE at a seed-stage startup. From landing the role on a mountain bike trail to building sales ops from scratch, it's a raw look at what early-stage startup life is really like.

SPONSORS:

ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership

EPISODE LINKS:

• Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview

CONNECT WITH JESSE:

• LinkedIn: https://www.linkedin.com/in/jessewoodbury/

• Website: https://jessewoodbury.com/

HELP GROW SP:

• Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Get a weekly email from SP: https://www.salesplayers.co/

• Subscribe!

• Leave a rating, write a review, and share

• Check out the above sponsors, it's the best way to support the show

GUEST HIGHLIGHTS:

Morgan J. Ingram, Chris Orlob, Ian Koniak, Jeb Blount, Brandon Fluharty, Scott Leese, Sarah Brazier, Jamal Reimer, Jen Allen-Knuth, Andy Paul, Collin Mitchell, Tim Zielinski, Christian Banach, Rajiv 'RajNATION' Nathan, Belal Batrawy, Christine Rogers, Chris Beall, Patrick Baynes, Jeroen Corthout, Nate Nasralla, Gabe Lullo, Vince Beese, Brandon Bornancin, Girish Redekar, Guillaume Moubeche, Lloyed Lobo, Corey Quinn, Danny Delvecchio, Tom Slocum, Todd Busler, Richard Harris, Krysten Conner, Dan Goodman, Kris Rudeegraap, Rachit Kataria

© Sales Players, LLC

Jesse breaks down the exact cold call routine he uses daily to drive pipeline.

SPONSORS:

ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership

EPISODE LINKS:

• Want to get better at cold calls? Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview

CONNECT WITH JESSE:

• LinkedIn: https://www.linkedin.com/in/jessewoodbury/

• Website: https://jessewoodbury.com/

HELP GROW SP:

• Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Get a weekly email from SP: https://www.salesplayers.co/

• Subscribe!

• Leave a rating, write a review, and share

• Check out the above sponsors, it's the best way to support the show

GUEST HIGHLIGHTS:

Morgan J. Ingram, Chris Orlob, Ian Koniak, Jeb Blount, Brandon Fluharty, Scott Leese, Sarah Brazier, Jamal Reimer, Jen Allen-Knuth, Andy Paul, Collin Mitchell, Tim Zielinski, Christian Banach, Rajiv 'RajNATION' Nathan, Belal Batrawy, Christine Rogers, Chris Beall, Patrick Baynes, Jeroen Corthout, Nate Nasralla, Gabe Lullo, Vince Beese, Brandon Bornancin, Girish Redekar, Guillaume Moubeche, Lloyed Lobo, Corey Quinn, Danny Delvecchio, Tom Slocum, Todd Busler, Richard Harris, Krysten Conner, Dan Goodman, Kris Rudeegraap, Rachit Kataria

© Sales Players, LLC

Jesse reminds sellers why understanding the product matters, especially when selling to IT buyers.

SPONSORS:

ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership

EPISODE LINKS:

• Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview

CONNECT WITH JESSE:

• LinkedIn: https://www.linkedin.com/in/jessewoodbury/

• Website: https://jessewoodbury.com/

HELP GROW SP:

• Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Get a weekly email from SP: https://www.salesplayers.co/

• Subscribe!

• Leave a rating, write a review, and share

• Check out the above sponsors, it's the best way to support the show

GUEST HIGHLIGHTS:

Morgan J. Ingram, Chris Orlob, Ian Koniak, Jeb Blount, Brandon Fluharty, Scott Leese, Sarah Brazier, Jamal Reimer, Jen Allen-Knuth, Andy Paul, Collin Mitchell, Tim Zielinski, Christian Banach, Rajiv 'RajNATION' Nathan, Belal Batrawy, Christine Rogers, Chris Beall, Patrick Baynes, Jeroen Corthout, Nate Nasralla, Gabe Lullo, Vince Beese, Brandon Bornancin, Girish Redekar, Guillaume Moubeche, Lloyed Lobo, Corey Quinn, Danny Delvecchio, Tom Slocum, Todd Busler, Richard Harris, Krysten Conner, Dan Goodman, Kris Rudeegraap, Rachit Kataria

© Sales Players, LLC