Jesse shares lessons on making the most of the tech sales career opportunity.

SPONSORS:

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

EPISODE LINKS:

• 20 Questions Download: https://docs.google.com/document/d/1Ko2yqyLeZ-GdVCDaiROomtZrvvNw50Y3/edit

• Schedule 1:1 Coaching Consult: https://calendly.com/jessewoodbury/1-1-coaching-overview

CONNECT WITH JESSE:

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

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

Lessons on (personal) brand building from 5 years of hosting this podcast.

SPONSORS:

ChatAE: https://www.chatae.ai/

EPISODE LINKS:

• 20 Questions Download: https://docs.google.com/document/d/1Ko2yqyLeZ-GdVCDaiROomtZrvvNw50Y3/edit

• Schedule 1:1 Coaching Consult: https://calendly.com/jessewoodbury/1-1-coaching-overview

CONNECT WITH JESSE:

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

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 go-to questions for introducing friction in your deals.

SPONSORS:

ChatAE: https://www.chatae.ai/

EPISODE LINKS:

• 20 Questions Download: https://docs.google.com/document/d/1Ko2yqyLeZ-GdVCDaiROomtZrvvNw50Y3/edit

• Schedule 1:1 Coaching Consult: https://calendly.com/jessewoodbury/1-1-coaching-overview

CONNECT WITH JESSE:

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

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 insights on trends he's hearing about from conversations with sales leaders, founders, and recruiters etc.

EPISODE LINKS:

• Schedule 1:1 Coaching Consult: https://calendly.com/jessewoodbury/1-1-coaching-overview

CONNECT WITH JESSE:

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

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 his approach to building pipeline from the closed-lost deals in your territory.

EPISODE LINKS:

• Re-engagement Email Template: https://www.salesplayers.co/posts/copy-my-re-engagement-email-template

CONNECT WITH JESSE:

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

• 1:1 Coaching: https://calendly.com/jessewoodbury/paid-coaching-session

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 five simple but powerful habits that increase your chances of closing more deals.

EPISODE LINKS:

• Aug '25 Coaching Promo ($99 Sessions) Book at: https://calendly.com/jessewoodbury/paid-coaching-session

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 ideas for getting yourself out there and building your network.

EPISODE LINKS:

• Order Red Zone Selling by Vince Beese: https://www.amazon.com/dp/B0FLLHQG13

• Aug '25 Only Coaching Promo ($99 Sessions) Book at: https://calendly.com/jessewoodbury/paid-coaching-session

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 five side hustles that B2B sellers can launch without leaving their day job. He walks through ideas he’s personally tested to turn sales skills into extra income while working full-time in tech sales.

EPISODE LINKS:

• Aug '25 Only Coaching Promo ($99 Sessions) Book at: https://calendly.com/jessewoodbury/paid-coaching-session

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