

Sales Players
Jesse Woodbury
The #1 resource for top players in Tech Startup Sales. Hosted by Jesse Woodbury, an expert in early-stage startup selling, Sales Players features weekly, actionable ideas for reps, founders, and operators by exploring the mindset, skills, and tools high performers use to generate pipeline, close deals, and build wealth in Tech Sales.
Episodes
Mentioned books

Oct 17, 2025 • 11min
Making the Most of Your Tech Sales Career
 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 

Sep 19, 2025 • 15min
Lessons on Building a Personal Brand from 5 Years of Podcasting
 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 

Sep 17, 2025 • 13min
20 Questions I Use to Stress-Test My Deals
 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 

Sep 10, 2025 • 15min
What I’m Hearing: Sales Trends Shaping Tech in 2025
 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 

Aug 28, 2025 • 5min
How I Re-Engage Closed-Lost Opportunities
 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 

Aug 19, 2025 • 12min
5 Habits That Close More Deals
 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 

Aug 13, 2025 • 13min
Your Network Is Doing More for Your Sales Career Than You Think
 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 

Aug 9, 2025 • 22min
5 Ideas for Turning Your Sales Skills Into Extra Income
 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 

Jul 31, 2025 • 40min
Why Reps Are Ditching Managers for AI Roleplay with Sriharsha (Sai) Guduguntla of Hyperbound
 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 

Jul 19, 2025 • 15min
The Metrics That Matter Most in Tech Sales
 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 


