Sales Players

Jesse shares ideas for how you can become a more fierce competitor in your deals. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Mutual Action Plan: https://docs.google.com/presentation/d/1br4CrpdOq-3ToypxCTWQ75Ea9DbKtpWSU_bTcKK_TiE/edit#slide=id.p • Book FREE 1:1 Coaching Intro with...

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: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm...

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 bet...

Jesse shares the 10k play for developing a PoV when reaching out to executives at public companies. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https:/...

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: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-...

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: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-ov...

Jesse shares some ideas for choosing a winning startup by drawing from his own experience working in early startups as a seller. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Books Mentioned: Play Bigger, Crossing the Chasm CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in...

Jesse shares insights on the current state of tech sales hiring with ideas for how to ace your next interview. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • Linked...

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: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Connect with Amanda: https://www.linkedin.com/in/amandamcrooks/ • BlinkMetrics: ht...

Jesse shares some tips for getting the most out of your sales meeting recordings tool (Gong, Chorus etc.) SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Get Fathom: Get Fathom: https://fathom.partnerlinks.io/salesplayers CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jes...

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: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2...

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: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Web...

*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: ChatAE (AI Account P...

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...

Morgan J. Ingram is the Founder & CEO of AMP Creative. Morgan is a force to be reckoned with in the B2B Sales Community. He initially gained traction as the creator and host of The SDR Chronicles and has since gone on to build an amazing career as a subject matter expert, keynote speaker and advisor. He joins the Sales Players to share how sellers and leaders can build their subject matter exp...

Dustin Beaudoin is the Founder of ChatAE, a copilot built for pre- and post-call tasks. Built to prep for calls, write recap emails, and plan next steps while coaching you to become an elite seller. Dustin joins SP to share ideas for leveraging AI in your sales process. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - https://dash.partnerstack.com/leadfeeder/links⁠ - SP fans use this link...

Kevin McIntyre is the CRO of Dealfront. In this episode he joins the Sales Players to share insights from his career journey to CRO. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - ⁠⁠⁠⁠⁠⁠⁠⁠ https://leadfeeder.partnerlinks.io/rsscjriylqgb this link for an extended, 21-day free trial • Salesblazers (Free Sales Networking Community) - https://www.salesforce.com/blog/sales/salesblazer-communi...

Paul M. Caffrey is a Dublin-based Author, Speaker & Sales Performance Coach. He joins the Sales Players to share insights from his work as an AE coach and author of the book: The Work Before the Work: The Hidden Habits Elite Sales Professionals Use to Outperform the Competition. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - ⁠⁠⁠⁠⁠⁠⁠⁠https://leadfeeder.partnerlinks.io/rsscjriylqgb - S...

Jeb Blount is the author of 15 books, including Fanatical Prospecting , a staple in the modern tech sales world. Jeb is a coach and advisor and founded Sales Gravy to help sales organizations, sales leaders, and sales professionals sell more. Jeb joins the Sales Players to share ideas for mastering sales conversations, building discipline in prospecting and using AI to enhance productivity. SPONSO...

Mike Simmons is the Founder of Catalyst A.C.T.S which helps technical SaaS founders and team leaders scale their organizations from $2M - $80M ARR using design thinking. Mike is based in Phoenix, AZ and joins the Sales Players to share insights around process, people, communication and leadership. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - ⁠⁠⁠⁠⁠⁠https://leadfeeder.partnerlinks.io/rss...

Egan Montgomery is the Co-Founder of Backstroke, a GenAI email platform marketers. Based in Indy, Egan joins the Sales Players to share lessons learned from his career journey from Intern to Founder. 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...

Corey Kossack is the Founder & CEO of Aspireship a career acceleration platform built for the modern workforce. Corey's based in Scottsdale, Arizona and he joins the Sales Players to share his perspective on the current state of the job market while sharing lessons on career growth, transition and re-invention. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - ⁠⁠⁠⁠https://leadfeeder...

Shimmy Savitsky is the Founder of Esek, an automation consulting agency that specializes in helping salespeople. Shimmy joins the Sales Players to share some ideas for incorporating more automation into the sales process. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - ⁠⁠⁠https://leadfeeder.partnerlinks.io/rsscjriylqgb⁠⁠⁠ - SP fans use this link for an extended, 21-day free trial • evyAI...

A replay from our most recent SP virtual meetup. Join us in Slack to get notified about the next one: https://www.launchpass.com/saas_sales_players SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - ⁠⁠⁠https://leadfeeder.partnerlinks.io/rsscjriylqgb⁠⁠⁠ - SP fans use this link for an extended, 21-day free trial • evyAI (AI Content Assistant for LinkedIn) - ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://evyai.com/?via=sale...

Phil Putnam is a speaker, author, coach & workshop leader helping leaders get top team performance and extend employee tenure. He joins the Sales Players to share insights into staying motivated in sales. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - ⁠⁠https://leadfeeder.partnerlinks.io/rsscjriylqgb⁠⁠ - SP fans use this link for an extended, 21-day free trial • evyAI (AI Content Ass...