Sales Players

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

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• 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.

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• 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.

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• 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.

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• 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.

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• 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

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

• Website: https://...

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

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• 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.

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• 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.

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• 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.

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• 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.

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• 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.

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• 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.

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

• Fathom (#1 AI ...

Jesse shares how he is planning to navigate the uncertain times ahead and asks for feedback on what direction to take the show. Please reach out on Slack, InMail, or email jesse@salesplayers.co to share: #1 What keeps you coming back to the show? #2 What topics would you like to hear more about? For a few of you, I'll pay you for your time giving me feedback on how I can make Sales Players better. Thank you!

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• Surfe (Linked...

Jesse shares the 10k play for developing a PoV when reaching out to executives at public companies.

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:

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

CONNECT WITH JESSE:

• L...

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/salesplayers

EPISODE LINKS:

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

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/salesplayers

EPISODE LINKS:

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

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/salesplayers

EPISODE LINKS:

• Books Mentioned: Play Bigger, Crossing the Chasm

CONNECT WITH JESSE:

• LinkedIn: https://ww...