Best SP Pod Podcasts (2025)

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SP Pod #381: Pike Week 1:33:25

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4d ago1:33:25

1:33:25

Ian and Chris (remember him?) got back together with the season drawing to a close. The MLB club can't hit outside of minor league ballparks, but still seems to be in decent shape in the AL playoff picture. The guys discussed the end-of-season outlook in MLB and whether, just maybe, Luis Perales has a shot at contributing this season. Plus, your em…

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Lessons on Building a Personal Brand from 5 Years of Podcasting 15:12

5d ago15:12

15:12

Lessons on (personal) brand building from 5 years of hosting this podcast. SPONSORS: ChatAE: https://www.chatae.ai/ EPISODE 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-overview CONNECT WITH JESSE: • LinkedIn…

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20 Questions I Use to Stress-Test My Deals 13:13

7d ago13:13

13:13

Jesse shares 20 go-to questions for introducing friction in your deals. SPONSORS: ChatAE: https://www.chatae.ai/ EPISODE 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-overview CONNECT WITH JESSE: • LinkedIn: h…

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SP Pod #380: Connelly Early is here and AFL rosters are out 1:13:09

11d ago1:13:09

1:13:09

Ian is flying solo again this week as he discusses another notable starting pitcher debut! He starts off by breaking down what he saw from Connelly Early against the Athletics and then the Red Sox debut of Kyle Harrison. He also touches on Payton Tolle’s struggles and how he fits in the rotation the rest of the year. After that, he breaks down the …

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What I’m Hearing: Sales Trends Shaping Tech in 2025 15:21

14d ago15:21

15:21

Jesse shares insights on trends he's hearing about from conversations with sales leaders, founders, and recruiters etc. EPISODE LINKS: • Schedule 1:1 Coaching Consult: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ HELP GROW SP: • Join Sales Players Slack Community…

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SP Pod #379: Rolling with Tolle 59:20

22d ago59:20

59:20

Ian is joined by Geoff Pontes of Baseball America to breakdown all things Payton Tolle! They do a deep dive into Tolle’s journey to the majors and his MLB debut and after that discuss what the future looks like for him and where he ranks on the list of top left-handed pitching prospects in all of baseball. Finally, Ian wraps the show up by going th…

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How I Re-Engage Closed-Lost Opportunities 5:24

26d ago5:24

5:24

Jesse shares his approach to building pipeline from the closed-lost deals in your territory. EPISODE LINKS: • Re-engagement Email Template: https://www.salesplayers.co/posts/copy-my-re-engagement-email-template CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • 1:1 Coaching: https://calendly.com/jessewoodbury/paid-coaching…

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SP Pod #378: Taking stock of the Red Sox pitching depth in Worcester 1:08:43

1M ago1:08:43

1:08:43

Ian is flying solo this week after spending another week in Worcester. He starts off by discussing the latest roster moves by the Red Sox, including the Nate Lowe signing and Jhostynxon Garcia’s promotion to the major leagues. He then breaks down the candidates to replace Walker Buehler in the rotation and makes the case for and against Payton Toll…

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5 Habits That Close More Deals 12:02

1M ago12:02

12:02

Jesse shares five simple but powerful habits that increase your chances of closing more deals. EPISODE LINKS: • Aug '25 Coaching Promo ($99 Sessions) Book at: https://calendly.com/jessewoodbury/paid-coaching-session CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP GROW SP: • Join …

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Your Network Is Doing More for Your Sales Career Than You Think 12:59

1M ago12:59

12:59

Jesse shares ideas for getting yourself out there and building your network. EPISODE 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-session CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewood…

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SP Pod #377: All the Anthony That Money Could Buy 2:01:36

1M ago2:01:36

2:01:36

Roman Anthony got paid, and the boys predictably think it was... a nice piece of business. Ian and Chris discuss the extension, then talk about Ian's extended look at the Worcester Red Sox, including the latest on Kristian Campbell and Payton Tolle, among many others. Plus, your emails! Got something to say? We love talking about what you want to h…

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5 Ideas for Turning Your Sales Skills Into Extra Income 22:19

2M ago22:19

22:19

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. EPISODE LINKS: • Aug '25 Only Coaching Promo ($99 Sessions) Book at: https://calendly.com/jessewoodbury/paid-coaching-session CONNECT WI…

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SP Pod #376: May, Matz, and Prospects on the Move 2:05:56

2M ago2:05:56

2:05:56

Ian and Chris have a lot to say about the little that the Red Sox did at the Trade Deadline. Plus, news breaks during the recording, the guys discuss the latest promotions and players most likely to come up to help the MLB club, our updated rankings, and your emails! Got something to say? We love talking about what you want to hear about. Make sure…

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Why Reps Are Ditching Managers for AI Roleplay with Sriharsha (Sai) Guduguntla of Hyperbound 39:36

2M ago39:36

39:36

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/jesse…

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SP Pod #375: Trade Deadline Preview 1:41:38

2M ago1:41:38

1:41:38

Ian and Chris recorded a rare weekend episode to make sure they got this in before the hot stove really turned up before the trade deadline! Where will the Red Sox add? What will it cost? Who might be on the block? And how does the Marcelo Mayer injury play into it? All that, plus a look back on the FCL season, which ended on Thursday, in this epis…

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SP Pod #374: Draft Review with MLB.com's Jim Callis 1:39:03

2M ago1:39:03

1:39:03

This episode goes to eleven, as our friend Jim Callis from MLB.com makes his record-regaining eleventh appearance on the show! Ian and Chris got Jim's thoughts on Boston's incoming draft class, the state of the Red Sox system as it enters the post-Big Three era, and even responded to some of your emails! Got something to say? We love talking about …

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The Metrics That Matter Most in Tech Sales 15:19

2M ago15:19

15:19

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…

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SP Pod #373: Draft Day 2 Run-Through 1:20:33

2M ago1:20:33

1:20:33

After 21 picks, it's clear the Red Sox have a thing for big pitchers out of the SEC. But what else is there to know about the Red Sox' 21-member draft class? Ian and Chris break it all down from rounds 4 to 20. Got something to say? We love talking about what you want to hear about. Make sure to email us at [email protected]. Social Media Li…

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SP Pod #372: Draft Night 1 Speed Run 45:19

2M ago45:19

45:19

Kyson Witherspoon. Marcus Phillips. Henry Godbout. Anthony Eyanson. Meet the newest Red Sox draftees! Ian and Chris broke down the group with scouting reports, their takes, and potential rankings landing spots for all four, and looked ahead to day 2 of the draft. Got something to say? We love talking about what you want to hear about. Make sure to …

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SP Pod #371: July rankings discussion with Mike Andrews 1:11:34

2M ago1:11:34

1:11:34

Ian is joined by SoxProspects Editor-In-Chief Mike Andrews this week to break down the new July rankings. They discuss why Payton Tolle jumped to third in the system, why several FCL players are rising and the notable players who’ve fallen in the rankings as well. They also briefly discuss the Red Sox now that Alex Bregman and Masataka Yoshida are …

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SP Pod Ep. #370: Check-in with Alex Speier 1:26:02

3M ago1:26:02

1:26:02

In our second episode of the holiday week, Ian is joined by Alex Speier of the Boston Globe to break down everything going on with the Red Sox right now. They start off by talking about the Red Sox pitching depth, what’s going on with Tanner Houck, and how Kyle Harrison is adjusting to the Red Sox pitching development program. They then move over t…

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SP Pod #369: MLB Draft Preview with Geoff Pontes of Baseball America 49:44

3M ago49:44

49:44

Special episode this week as Ian is joined by Geoff Pontes of Baseball America to preview the upcoming MLB Draft! We hit on a range of draft topics including the strengths and weaknesses of the class, how it compares to last year and who could fall from the top 10 to the Red Sox. Geoff also discussed why former Red Sox draftee Gavin Kilen is an int…

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What My Former Sales Leader Taught Me About Red Zone Selling with Vince Beese 48:36

3M ago48:36

48:36

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 rea…

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20 Sales Plays I Run When Nothing Else Is Working 8:49

3M ago8:49

8:49

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: • LinkedI…

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SP Pod #368: Devers fallout, and Back to Business 1:47:59

3M ago1:47:59

1:47:59

With a few more days gone by, Ian and Chris had a few more thoughts on the Rafael Devers trade fallout. With that out of their systems, there was plenty of other discussion on Kristian Campbell being optioned back to Worcester, some other minor league news, and another big crop of emails Got something to say? We love talking about what you want to …

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SP Pod #367: RAFAEL DEVERS TRADE EMERGENCY POD 1:07:47

3M ago1:07:47

1:07:47

Rafael Devers has been traded. 'Nuff said. Got something to say? We love talking about what you want to hear about. Make sure to email us at [email protected]. Social Media Links: IG: @SoxProspects @SPChrisHatfield @IanCundall @SoxProspects (All 3 are the same on Bluesky as well) Love the show? Want to help us out while also getting exclusiv…

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Building Financial Security as a Tech Seller 25:47

3M ago25:47

25:47

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: …

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SP Pod #366: Roman, Reports, Rankings 1:39:43

3M ago1:39:43

1:39:43

It's an action-packed episode. Roman Anthony is finally in Boston. Ian traveled to Greenville and Portland and has some reports. We updated the rankings. Today's episode is brought to you by the letter "R". Plus, it's the SoxProspects Donation Drive! Show your support for the show by heading to our Donations page or joining our Patreon! Donations p…

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The Anonymous Tech Seller Who Built a 6-Figure Side Hustle with "Fidel Cache Flow" 39:29

4M ago39:29

39:29

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, vi…

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23 Absolute Truths About Enterprise Selling 4:25

4M ago4:25

4:25

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 …

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SP Pod #365: Time for a Rant 1:54:30

4M ago1:54:30

1:54:30

It's June and the guys have some things to get off their chests about the roster decisions in MLB and Roman Anthony still being in Triple-A. Plus, a bumper crop of emails includes questions about Blaze Jordan, development at the MLB level, and more. Got something to say? We love talking about what you want to hear about. Make sure to email us at po…

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What Top Tech Sales Candidates Do Differently 10:18

4M ago10:18

10:18

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 Sl…

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Top Tech Sellers Share These 10 Traits 4:27

4M ago4:27

4:27

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://tr…

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What I Learned (the Hard Way) as a Founding AE 20:27

4M ago20:27

20:27

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.co…

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SP Pod #364: Singing a New Song 1:17:32

4M ago1:17:32

1:17:32

Plenty of news on the farm for the guys to discuss: The Password leads a set of promotions while his brother is among a set of players starting rehab assignments, there's evidence that the promotions of Roman Anthony and/or Marcelo Mayer may be approaching, and oh yeah... Noah Song is back again. Your emails led the conversation as well. Listen in!…

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This Is Exactly How I Approach Cold Calls Every Day 9:39

4M ago9:39

9:39

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 CONNE…

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SP Pod #363: Very Mid May 1:48:54

4M ago1:48:54

1:48:54

The Red Sox are mid again. Why? Ian and Chris examine what's up with the MLB club, then dive into our latest rankings update, spiced up with some reports from Ian's week in Portland, where yes, they did play SOME of their scheduled games. Listen in! Got something to say? We love talking about what you want to hear about. Make sure to email us at po…

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Want Bigger Deals? Learn the Product 9:32

4M ago9:32

9:32

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: •…

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A Week in My Life: Tech Sales, Family, Fitness & Side Projects 17:48

5M ago17:48

17:48

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 CONNEC…

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Why You're Still an SDR (and What to Do About It) 20:14

5M ago20:14

20:14

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-…

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SP Pod #362: First Base First 1:18:42

5M ago1:18:42

1:18:42

Triston Casas's season-ending injury is on everyone's mind, and Ian and Chris are here to break down the team's options. Is it as simple a situation as it seems like it should be? Meanwhile, we've got another set of promotions to discuss, the Florida Complex League season has begun, and of course, your emails round out this episode Got something to…

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SP Pod #361: April Live Looks 1:23:33

5M ago1:23:33

1:23:33

Ian and Chris have been out to the fields and have reports from Worcester, Portland, and Salem. Plus, the guys break down the season's first promotions of Franklin Arias, Brandon Clarke, and Hayden Mullins. (Note: This episode was recorded before Triston Casas' knee injury on Friday night. We'll discuss that next episode.) Got something to say? We …

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Why You Should Hold Off on Going Fully Remote in Your Career 6:30

5M ago6:30

6:30

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://ww…

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Comp Negotiation Fundamentals for Tech Sales 10:27

5M ago10:27

10:27

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/jessewoodb…

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SP Pod #360: Everybody's Thinking About the Roman Empire 1:22:46

5M ago1:22:46

1:22:46

Old reference? Sure, but in the case of Roman Anthony (and Marcelo Mayer), it seems true these days. Ian and Chris discussed when the game's top minor league prospect might finally get the call to the Bigs. Plus, some MLB pitching talk and your emails! Got something to say? We love talking about what you want to hear about. Make sure to email us at…

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Key Mindset Shifts for Long-Term Success in Tech Sales 16:47

5M ago16:47

16:47

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/jes…

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Are You Staying Competitive in Deals? 12:09

5M ago12:09

12:09

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/pres…

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SP Pod #359: Breaking down the Quinn Priester trade and early season impressions 53:31

6M ago53:31

53:31

Ian is joined by Chris Clegg of the Dynasty Dugout to talk about the Quinn Priester trade with Milwaukee and Hunter Dobbins major league debut. After that, they discuss the noteworthy performances in Salem and Worcester so far including Franklin Arias, Blake Aita, Roman Anthony and Marcelo Mayer. They also discuss what they saw first-hand in Greenv…

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Using AI to Build The "R" in your CRM with Rachit Kataria of Centralize 49:08

6M ago49:08

49:08

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 Streamli…

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Dealing with Uncertain Times as a Tech Seller (& I Need YOUR Feedback) 16:16

6M ago16:16

16:16

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 [email protected] 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 m…