
Sales Players
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.
Latest episodes

Mar 29, 2025 • 16min
Why It's Important to Find Your Niche in Tech Sales
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:• Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury• Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayersEPISODE LINKS:• Book FREE 1:1 Coaching Intro with Jesse: 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 • 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© Sales Players, LLC

Mar 24, 2025 • 26min
Improving Your Close Rate & Driving Predictability in Your Pipeline & Deals
Jesse shares a checklist of ideas for de-risking your deals to increase your close rate and drive more predictability in your pipeline and deals.SPONSORS:• Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury• Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayersEPISODE LINKS:• Book FREE 1:1 Coaching Intro with Jesse: 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 • 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© Sales Players, LLC

Mar 20, 2025 • 30min
How to Pick a Winning Startup as a Seller
Jesse shares some ideas for choosing a winning startup by drawing from his own experience working in early startups as a seller. SPONSORS:• Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury• Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayersEPISODE LINKS:• Books Mentioned: Play Bigger, Crossing the ChasmCONNECT 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 • 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© Sales Players, LLC

Mar 6, 2025 • 28min
How to Ace Sales Interviews & Be the Top Candidate
Jesse shares insights on the current state of tech sales hiring with ideas for how to ace your next interview. SPONSORS:• Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury• Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayersEPISODE LINKS:• Book FREE 1:1 Coaching Intro with Jesse: 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 • 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© Sales Players, LLC

Feb 26, 2025 • 48min
Lessons from the Startup Trenches with Amanda Crooks of BlinkMetrics
Amanda Crooks is the Founding Director of BlinkMetrics. In this episode, she joins Jesse to share lessons from selling software in a bootstrapped startup. SPONSORS:• Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury• Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayersEPISODE LINKS:• Connect with Amanda: https://www.linkedin.com/in/amandamcrooks/• BlinkMetrics: https://blinkmetrics.com/• From Chaos to Clarity: https://youtube.com/playlist?list=PLeVK0fSurSGX9V65blWffe3B1HGEq9Fpf&si=afRV-sS6Y3eKXMbfCONNECT 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 • 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© Sales Players, LLC

Feb 19, 2025 • 23min
7 Tips for Getting the Most Out of Your Meeting Recording Tool
Jesse shares some tips for getting the most out of your sales meeting recordings tool (Gong, Chorus etc.)SPONSORS:• Surfe (LinkedIn Prospecting Streamlined) - SP Discount link: https://www.surfe.com/?kfl_ln=jesse-woodburyEPISODE LINKS: • Get Fathom: Get Fathom: https://fathom.partnerlinks.io/salesplayersCONNECT 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 • 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© Sales Players, LLC

Feb 12, 2025 • 55min
Winning an Electric Car as a Sales Spiff and Other Crazy Career Stories with Chris Dankowski
Chris Dankowski is a Sales Strategy Consultant and Coach to Sellers and Founders in tech. Based in Austin, Texas, Chris has previously sold at top companies like: Evernote, Outreach and HubSpot. In this episode, Chris shares insights on managing your tech sales career.SPONSORS:• Surfe (LinkedIn Prospecting Streamlined) - SP Discount link: https://www.surfe.com/?kfl_ln=jesse-woodburyEPISODE LINKS: • Connect with Chris: https://www.linkedin.com/in/chrisdankowski/ • Website: https://www.dankow.ski/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 • 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© Sales Players, LLC

Feb 7, 2025 • 32min
Why Your Buyers Don't Take You Seriously + Show Update & Re-Intro
Jesse shares an update on the future of Sales Players, re-introduces his background and shares an important mindset shift that will help your buyers take you more seriously.
SPONSORS:
• Surfe (LinkedIn Prospecting Streamlined) - SP Discount link: https://www.surfe.com/?kfl_ln=jesse-woodbury
CONNECT WITH JESSE:
• LinkedIn: https://www.linkedin.com/in/jessewoodbury/
• Website: https://jessewoodbury.com/
HELP GROW SP:
• Join: 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
© Sales Players, LLC

Jan 16, 2025 • 32min
Outcome of 7-Figure Deal: Increase in Customer Stock Price - Pod Swap with How the Deal Was Done
*Pod Swap - Jesse's interview on the How the Deal Was Done podcast: Jesse Woodbury shares his journey of converting a small proof of concept into a seven-figure deal with a B2C Home Services Company. A deal so impactful it raised the buying company’s share price. This deal is a perfect example of the power of internal champions and genuine customer relationships.
SPONSORS:
• Leadfeeder (Turn Page Views into Pipeline) - https://leadfeeder.partnerlinks.io/rsscjriylqgb - SP fans use this link for an extended, 21-day free trial
• Salesblazers (Free Sales Networking Community) - https://www.salesforce.com/blog/sales/salesblazer-community-sign-up/?utm_campaign=amer_sfpartners&utm_medium=offline_promo&utm_source=podcast&utm_content=salesblazer_thesalesplayers
EPISODE LINKS:
• How the Deal Was Done Podcast: https://www.dealstoriespodcast.com/episodes/ep-29-outcome-of-7-figure-deal
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
• 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

Jan 6, 2025 • 48min
Building Your Professional Network Via Slack with Kaela Altman of Salesforce, Salesblazers
Kaela Altman is the Community Manager for the Salesforce, Salesblazers sales networking community. Based in New York, she brings 15+ years of building, managing, and growing communities for enterprise tech. She joins the Sales Players to share details about growing and managing the Salesblazers Slack community.
SPONSORS:
• Leadfeeder (Turn Page Views into Pipeline) - https://leadfeeder.partnerlinks.io/rsscjriylqgb - SP fans use this link for an extended, 21-day free trial
• Salesblazers (Free Sales Networking Community) - https://www.salesforce.com/blog/sales/salesblazer-community-sign-up/?utm_campaign=amer_sfpartners&utm_medium=offline_promo&utm_source=podcast&utm_content=salesblazer_thesalesplayers
EPISODE LINKS:
• Connect with Kaela: https://www.linkedin.com/in/kaelaaltman/
• Join Salesblazers: https://sforce.co/thesalesplayers
CONNECT WITH JESSE:
• LinkedIn: https://www.linkedin.com/in/jessewoodbury/
• Website: https://jessewoodbury.com/
CONNECT WITH CHASE:
• LinkedIn: https://www.linkedin.com/in/chase-barmore
• Website: https://chasebarmore.com
HELP US GROW SP:
• Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players
• Subscribe!
• Leave a rating, write a review, and share
• Check out the above sponsors, it's the best way to support the show
PAST 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