Sales Players

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.

EPISODE 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 Sl...

Jesse breaks down the exact numbers he tracks to stay on target and outperform quota.

EPISODE LINKS:

• 1:1 Coaching Intro: 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....

Jesse sits down with his former sales leader Vince Beese, the only exec he’s ever seen cold call procurement to get a deal done. They break down Vince’s new book Red Zone Selling, including tactical plays for managing late-stage deals, building mutual action plans that actually work, and why enterprise sales is more like football than most reps realize. If you're selling big deals in a competitive market, this one's a masterclass.

E...

Jesse shares 20 proven sales plays he turns to when deals stall, pipeline dries up, or nothing seems to be working. These are high-leverage, momentum-building activities that have helped him bounce back from slumps and close big deals.

EPISODE LINKS:

• https://www.salesplayers.co/posts/20-high-leverage-sales-activities

CONNECT WITH JESSE:

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

• Website: https://jessewoodbury.com/

HELP...

Jesse (who is not giving financial or investment advice) shares why tech sellers have a huge advantage when it comes to building wealth and financial security. He shares a few things you can do to develop financial security which will enhance your selling career.

CONNECT WITH JESSE:

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

• Website: https://jessewoodbury.com/

HELP GROW SP:

• Join Sales Players Slack Community: https://...

Jesse sits down with "Fidel Cache Flow," an anonymous tech seller who’s built a cult following on Sales Twitter with unfiltered takes on career growth, wifi money, and escaping the W2 grind. Fidel runs Desperados, a fast-growing private community for sellers looking to build income beyond quota. In this episode, they dive into contract stacking, virtual assistants, building while employed, and why aiming for #1 on the leaderboard m...

Jesse breaks down 23 hard-earned truths about enterprise sales that every seller should know

SPONSORS:

• ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp

EPISODE LINKS:

• Read the 23 Truths: https://www.salesplayers.co/posts/23-absolute-truths-about-enterprise-selling

• Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview

CONNECT WITH J...

The best candidates don’t just show up, they sell themselves at every step. In this episode, Jesse shares the high-leverage interview plays that get offers in today’s brutal job market.

SPONSORS:

• ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp

EPISODE LINKS:

• Join the FREE Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free

• Book FREE 1:1 Coachi...

Jesse breaks down the 10 traits that separate good reps from top-performing enterprise and mid-market sellers. After a decade in tech sales and five years interviewing the best in the game, he shares what it really takes to sell at the highest level.

SPONSORS:

• ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp

EPISODE LINKS:

• Read: https://www.salesplayers.co/posts/top-tech-selle...

Jesse shares the unfiltered story of his time as the founding AE at a seed-stage startup. From landing the role on a mountain bike trail to building sales ops from scratch, it's a raw look at what early-stage startup life is really like.

SPONSORS:

• ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp

EPISODE LINKS:

• Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/j...

Jesse breaks down the exact cold call routine he uses daily to drive pipeline.

SPONSORS:

• ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp

EPISODE LINKS:

• Want to get better at cold calls? 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://...

Jesse reminds sellers why understanding the product matters, especially when selling to IT buyers.

SPONSORS:

• Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury

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.c...

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

SPONSORS:

• Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury

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://...

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

SPONSORS:

• Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury

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/jesse...

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

SPONSORS:

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

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...

Jesse shares his basic process for negotiating compensation as a tech seller.

SPONSORS:

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

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 Communi...

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

SPONSORS:

• Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury

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/...

Jesse shares ideas for how you can become a more fierce competitor in your 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/salesplayers

EPISODE LINKS:

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

• Book FREE 1:1 Coa...

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:

• Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury

• Fathom (#1 AI ...