Sales Players

Jesse shares a real-life look at how he juggles tech sales, content creation, fitness, and family life each week.

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 shares real strategies for SDRs looking to break into AE roles, drawing from his own journey from SDR > SDR Leader > Enterprise AE.

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 gives his take on why you should consider spending the first few years of your career in an office.

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

• 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 his basic process for negotiating compensation as a tech seller.

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

• 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 talks about mindset shifts sellers can embrace for long-term success.

SPONSORS:

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

EPISODE LINKS:

• Pre-Order Commission Impossible! - https://www.salesplayers.co/products/ci

• 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

• 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 ideas for how you can become a more fierce competitor in your deals.

SPONSORS:

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

EPISODE LINKS:

• Mutual Action Plan: https://docs.google.com/presentation/d/1br4CrpdOq-3ToypxCTWQ75Ea9DbKtpWSU_bTcKK_TiE/edit#slide=id.p

• 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

• 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

Rachit Kataria is the Co-Founder & CEO of Centralize (https://www.usecentralize.com/) an all-in-one deal collaboration platform for enterprise revenue teams backed by Y Combinator. In this episode, Rachit shares his career story, the origins of Centralize, and the AI opportunity for Enterprise Sales.

SPONSORS:

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

EPISODE LINKS:

• Website: https://www.usecentralize.com/

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

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

• 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

© Sales Players, LLC

Jesse shares how he is planning to navigate the uncertain times ahead and asks for feedback on what direction to take the show. Please reach out on Slack, InMail, or email [email protected] to share: #1 What keeps you coming back to the show? #2 What topics would you like to hear more about? For a few of you, I'll pay you for your time giving me feedback on how I can make Sales Players better. Thank you!

SPONSORS:

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

EPISODE LINKS:

• Mutual Action Plan: https://docs.google.com/presentation/d/1br4CrpdOq-3ToypxCTWQ75Ea9DbKtpWSU_bTcKK_TiE/edit#slide=id.p

• 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

• 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

Jesse shares the 10k play for developing a PoV when reaching out to executives at public companies.

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

• 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

© Sales Players, LLC

Jesse shares thoughts on the current state of the market and some insights on the importance of finding a niche or specialization in your tech sales career.

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

• 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

© Sales Players, LLC