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_partnershipEPISODE 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-overviewCONNECT 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 showGUEST 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 (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnershipEPISODE 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-overviewCONNECT 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 showGUEST 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 (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnershipEPISODE 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-overviewCONNECT 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 showGUEST 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. SPONSORS:ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnershipEPISODE LINKS: • Schedule 1:1 Coaching Consult: https://calendly.com/jessewoodbury/1-1-coaching-overviewCONNECT 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 showGUEST 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. SPONSORS:ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnershipEPISODE LINKS: • Re-engagement Email Template: https://www.salesplayers.co/posts/copy-my-re-engagement-email-templateCONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • 1:1 Coaching: https://calendly.com/jessewoodbury/paid-coaching-sessionHELP 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 showGUEST 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.SPONSORS:ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnershipEPISODE LINKS: • Aug '25 Coaching Promo ($99 Sessions) Book at: https://calendly.com/jessewoodbury/paid-coaching-sessionCONNECT 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 showGUEST 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. SPONSORS:ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnershipSPONSORS:ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnershipEPISODE 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-sessionCONNECT 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 showGUEST 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.SPONSORS:ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnershipEPISODE LINKS: • Aug '25 Only Coaching Promo ($99 Sessions) Book at: https://calendly.com/jessewoodbury/paid-coaching-sessionCONNECT 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 showGUEST 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

Sriharsha (Sai) Guduguntla is the Co-Founder of Hyperbound, an AI Sales Coach. He joins Jesse to share insights into how sellers can use AI to improve their craft. SPONSORS:ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnershipEPISODE LINKS: • Connect with Sai: https://www.linkedin.com/in/sguduguntla/ • Get Hyperbound: https://www.hyperbound.ai/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 showGUEST 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 numbers he tracks to stay on target and outperform quota.SPONSORS:ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnershipEPISODE LINKS: • 1:1 Coaching Intro: https://calendly.com/jessewoodbury/1-1-coaching-overviewCONNECT 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 showGUEST 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