Jesse Woodbury
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.
Author
Jesse Woodbury
Category
Podcast website
Latest episode
Oct 17, 2025
Where to listen?
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Episodes
How Sellers Can Improve Their Executive Presence 03.11.2022 17:49
After a 3-mile night walk, Jesse logs in at 10pm to share some thoughts around improving your executive presence and why that matters in your career. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ssp CONNECT WIT...
Why You Shouldn't Let Your Tech Career Destroy Your Health 31.10.2022 10:20
Jesse talks about toxic managers, "Sunday Scaries" & why you shouldn't let your job, boss or quota destroy your physical & mental health. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ssp CONNECT WITH JE...
Challenger Selling? In this Economy?!? with Jen Allen-Knuth 24.10.2022 55:00
Jen Allen is the Chief Evangelist at Challenger™ & Host of Winning the Challenger Sale Podcast. Jen shares actionable & easy to implement tactics based on The Challenger™ Sale to continue winning in B2B Sales even in tough economic times. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discoun...
Key Insights from a Sales Enablement Leader with Lauren Flannery of Whoop 13.10.2022 1:09:32
Lauren Flannery is the Senior Manager of Enablement at Whoop. Lauren shares how she transitioned from hospitality to SaaS starting as an SDR & moving into sales enablement leadership. Lauren shares ideas for empowering women in SaaS sales. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount o...
Common Reasons Your Deals Stall & How You Can Fix It 24.09.2022 32:20
Jesse shares some common scenarios that cause SaaS deals to stall in the buying process. With suggestions for why it might be happening & how you can fix it. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ssp...
Improving Outbound & Growing Your Sales Pipeline with Christian Banach 14.09.2022 56:51
Christian Banach is the Principal & Chief Growth Officer of Christian Banach LLC , a leading strategic new business development advisory for marketing service firms in growth mode wanting to land 6 and 7-figure opportunities predictably. Christian shares lessons from his work with clients on the topics of content creation, writing a weekly newsletter, prospecting sequences & troubleshootin...
From Entrepreneur & Small Business Owner to High Performing SaaS Seller with Chase Barmore of WhatConverts 01.09.2022 1:13:07
Chase Barmore is a Business Development Representative at WhatConverts . Prior to breaking into SaaS Sales he was a serial entrepreneur & small business owner, starting & operating Life Bar & Ready Valet. Chase shares how he transitioned into SaaS Sales. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSUR...
Prospecting & Prioritizing Mental Health, Mindset, and Wellness from an SDR Turned AE with Anthony Natoli 24.08.2022 40:48
Anthony Natoli is a former SDR turned AE. He helps SDRs and AEs in B2B SaaS prospect with intention to book more quality meetings without burning out. He's an advocate for prioritizing mental health, mindset, and wellness for SaaS sales professionals based on his own journey. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo c...
You're Probably More Valuable Than You Think... 12.08.2022 14:27
Jesse powers through a Friday evening monsoon storm and shares thoughts about your value as a SaaS revenue player. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ssp EPISODE LINKS: • Blog by Cory Bray: https://www...
Sales Secrets from a $100M Sales Rep with Brandon Bornancin of Seamless.AI 28.07.2022 55:25
Brandon Bornancin is the #1 best-selling author of 3 books, a serial salesperson (sold over $100M in sales), eight-figure entrepreneur (2x), inventor of Seamless. AI, and motivational speaker who is obsessed with helping you maximize your success. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discoun...
The Importance of Being Brief in SaaS Sales 07.07.2022 13:20
Jesse shares ideas for being more brief in your communication with buyers. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ssp CONNECT WITH JESSE: • Linkedin: https://www.linkedin.com/in/jessewoodbury/ • Twitter:...
Layoffs in Tech & What to Do If You're Impacted 09.06.2022 25:42
Jesse shares what he did to get back on track in his career after sudden unemployment a few years ago. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ssp CONNECT WITH JESSE: • Linkedin: https://www.linkedin.com/i...
Do You Have a Highlight Reel for Your SaaS Sales Career? 20.05.2022 11:57
Jesse nerds out on all of the data he tracks around prior sales results & shares why you should have a SaaS sales highlight reel of your own. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ssp CONNECT WITH JES...
A Prospecting Campaign Idea to Help You Get Intro'd To The Right Stakeholders 13.05.2022 13:30
Jesse shares a prospecting play you can run to use Procurement contacts to get in the door at a large enterprise. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ssp CONNECT WITH JESSE: • Linkedin: https://www.link...
What Happens If I Miss My Quota? 29.04.2022 16:07
Jesse's musings about SaaS quota achievement. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ssp CONNECT WITH JESSE: • Linkedin: https://www.linkedin.com/in/jessewoodbury/ • Twitter: https://twitter.com/jessewood...
The Secret to Scaling SaaS Companies From Someone Who's Done It Many Times Over with Patrick Parker of SaaS Partners 14.04.2022 37:51
Patrick Parker is the CEO of SaaS Partners . Patrick has led the creation, go-to-market & scale for a handful of SaaS startups. He shares examples of consistent processes that lead to revenue growth, while also sharing resources for sellers looking to understand the elements of scaling a SaaS business. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr...
Announcement! - First Ever SSP Happy Hour & Meetup in Austin, Texas 30.03.2022 3:31
Jesse shares deets about the upcoming SaaS Sales Players Meetup & Happy Hour in ATX. This is a chance to meet Jesse, fellow fans of the show & likely a few of the guests who have been on the show. Please RSVP here: https://www.eventbrite.com/e/309092342517 SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5...
Knowing Your On Track in Your SaaS Sales Journey 24.03.2022 30:10
Jesse shares some career milestones, that put him on track for success. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ssp CONNECT WITH JESSE: • Linkedin: https://www.linkedin.com/in/jessewoodbury/ • Twitter: htt...
Data Security, Compliance & Selling to Technical Buyers with Girish Redekar of Sprinto 17.03.2022 39:27
Girish Redekar is the Co-Founder of Sprinto, a SaaS designed to help enterprises with compliance & security. Girish joins us after midnight IST to share the importance of compliance & data security for modern companies & how you as a seller can prepare for security evaluations. Girish also shares best practices for working with a technical buyer, decision maker or influencer in your de...
How to Transform Your Mindset, Manage Stress, Anxiety & Addiction & Become an Elite Seller with Ian Koniak 04.03.2022 56:32
Ian Koniak is the Founder & President of Ian Koniak Sales Coaching . Before starting his coaching business, he spent 9 years as a high performing, Strategic Rep at Salesforce. Ian shares how he transitioned from hardware to software sales - landing a top role at Salesforce. Ian also opens up about the pressures of being a top performer & how sellers can maintain control of their mindset, m...
Breaking Down Common Acronyms in the SaaS Business (While Drinking Tequila) 19.02.2022 27:47
While sipping an ice-cold "Paloma," Jesse reads through a list of common acronyms you'll hear while working in tech sales. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ssp EPISODE LINKS: • I had planned to publi...
A Stanford Ph.D's Approach to Selling & The Value-Driven Growth Methodology with Brent Keltner of Winalytics 14.02.2022 46:08
Brent Keltner is the President of Winalytics’ and creator of the value-driven growth methodology. Brent has over 10 years of experience as a revenue leader in enterprise to early stage companies and 10 years as a Ph. D. social scientist at Stanford and the RAND Corporation. Brent’s clients have included among others AdmitHub, Ascend Learning, Credo Reference, DealerRater, Lexmark, Mursion and True...
A Simple Formula to Estimate the Annual Revenue & Burn Rate of any SaaS Startup 08.02.2022 5:40
Jesse shares an easy formula he learned years ago to estimate ARR & burn rate for Pre-IPO, VC-backed SaaS startups. # of employees on LinkedIn x $200,000. Give it a try. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.c...
Mastering Your Pitch with Rajiv 'RajNATION' Nathan 03.02.2022 1:00:09
Rajiv 'RajNATION' Nathan is a chief pitch artist, rapper & the founder of Startup Hypeman. He shares his Que Pasa elevator pitch method & ideas for improving your pitch, telling better stories & improving your posturing. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first...
7 Steps to 7 Figures in SaaS Sales with Brandon Fluharty 30.01.2022 46:17
Brandon Fluharty is back to share details about his upcoming eBook: 7 Steps to 7 Figures. Brandon is a VP of Strategic Account Solutions at LivePerson & Author of Be Focused, Live Great a newsletter about Brandon's operating system for earning 7-figures in SaaS sales without hustle & burnout. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp...
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