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.

Last refreshed: June 30th, 2025 at 10:18 AM ⓘ

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Episodes

On Succeeding as the First Sales Hire with Luke Bivens of Gatsby

Luke Bivens tells how he made his way into software sales and shares strategies on being successful as the first sales hire in a software startup. Luke also shares how to position your offering, utilize internal resources and meet your buyers where they are. 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 • Overloop (Run multi-channel outbound campaigns, from a single plat...

Jan 05, 2021•1 hr 5 min

Finding Your First Opportunity in SaaS Sales - Pt. III

Jesse shares a few strategies for interviewing and closing the deal on your first software sales role. 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 • Overloop (Run multi-channel outbound campaigns, from a single platform) - https://get.overloop.com/ssp use this link for an extended trial and additional onboarding hours • Close (The CRM Built for Growth) - https://refer....

Jan 05, 2021•12 min

Finding Your First Opportunity in SaaS Sales - Pt. II

Jesse outlines criteria for evaluating the right SaaS opportunity for you. Account Executive vs. Sales Development Representative and how to decide which place to start. 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 • Overloop (Run multi-channel outbound campaigns, from a single platform) - https://get.overloop.com/ssp use this link for an extended trial and additional o...

Dec 19, 2020•16 min

Finding Your First Opportunity in SaaS Sales - Pt. I

Jesse shares a few considerations for finding your first opportunity 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 on your first year • Overloop (Run multi-channel outbound campaigns, from a single platform) - https://get.overloop.com/ssp use this link for an extended trial and additional onboarding hours • Close (The CRM Built for Growth) - https://refer.close.com/ssp EPISO...

Dec 09, 2020•18 min•Ep. 11

Getting After It with Leigh Kindley of 6sense

Leigh Kindley shares her origin story and talks about the importance of using creativity and data to become a master at selling to enterprises. 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 • Overloop (Run multi-channel outbound campaigns, from a single platform) - https://get.overloop.com/ssp use this link for an extended trial and additional onboarding hours • Close (T...

Nov 28, 2020•57 min

Breaking Up (Disqualifying) Prospects That Aren't a Fit

Jesse shares a few ideas for how to politely disqualify a prospect without sounding like a gatekeeping asshole. 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 • Overloop (Run multi-channel outbound campaigns, from a single platform) - https://get.overloop.com/ssp use this link for an extended trial and additional onboarding hours • Close (The CRM Built for Growth) - https...

Nov 20, 2020•10 min

How to Multi-Thread Your Deals

Jesse shares the importance of having multiple contacts and stakeholders involved in large deal cycles. 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 • Overloop (Run multi-channel outbound campaigns, from a single platform) - https://get.overloop.com/ssp use this link for an extended trial and additional onboarding hours • Close (The CRM Built for Growth) - https://refer...

Nov 19, 2020•11 min

Being Authentic and Asking the Right Questions with Zachary Ballenger of Casted

Zachary Ballenger shares advice on being genuine, having a close plan and he also talks about being a nerd and shares some thoughts on mixing politics and business in order to be your authentic self. Zachary has been a top sales player and also knows a thing or two about scaling revenue teams. 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 • Overloop (Run multi-channel ou...

Nov 04, 2020•1 hr 27 min

Call CFOs

Jesse shares one straight from his own playbook: How calling on CFOs might get you your next deal even if you don't sell to finance teams. 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 • Overloop (Run multi-channel outbound campaigns, from a single platform) - https://get.overloop.com/ssp use this link for an extended trial and additional onboarding hours • Close (The CR...

Oct 22, 2020•8 min

How to Make "No" Work for You

Jesse geeks out on a tactic from the book Never Split the Difference : Using "NO" to your advantage. 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 • Overloop (Run multi-channel outbound campaigns, from a single platform) - https://get.overloop.com/ssp use this link for an extended trial and additional onboarding hours • Close (The CRM Built for Growth) - https://refer.cl...

Oct 09, 2020•7 min

How to Win Big Deals and Influence Customers with Dustin Brown of Outreach.io

Dustin Brown takes a quick break from sending multi-six-figure order forms to share how he builds lifelong relationships with his customers and how doing so has helped him achieve amazing results while also finding deep satisfaction and fulfillment in the journey. Dustin also shares some pro-tips for Outreach users and speaks to how you can stand out from the crowd. SPONSORS: • Accord (Deal Execution Platform Designed to Enforce Execution Excellence) - ⁠https://hubs.la/Q02wP0ZM0⁠ • Leadfeeder (t...

Oct 08, 2020•1 hr 5 min•Ep. 5

Take on Complexity for your Customers

Jesse discusses a mindset change that's made a big impact on both his pipeline and career fulfillment. SPONSORS: • Accord (Deal Execution Platform Designed to Enforce Execution Excellence) - ⁠https://hubs.la/Q02wP0ZM0⁠ • Leadfeeder (turn pageviews into pipeline) - ⁠https://www.leadfeeder.com/?utm_source=podcast&utm_medium=body&utm_campaign=salesplayers⁠ SP fans use this link for an extended, 21-day free trial • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/...

Oct 02, 2020•6 min•Ep. 4

Do the Hard Thing

Jesse share's how effective it can be to roll up your sleeves and do the "hard thing." SPONSORS: • Accord (Deal Execution Platform Designed to Enforce Execution Excellence) - ⁠https://hubs.la/Q02wP0ZM0⁠ • Leadfeeder (turn pageviews into pipeline) - ⁠https://www.leadfeeder.com/?utm_source=podcast&utm_medium=body&utm_campaign=salesplayers⁠ SP fans use this link for an extended, 21-day free trial • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=jesse-wo...

Sep 29, 2020•5 min•Ep. 3

How to Ramp 80% Faster with Amanda Jones of Chorus.ai

Amanda Jones shares how she broke into SaaS, how she's landed at some of the industry's hottest companies and how she managed to close a deal in her first 24 days in a new role. SPONSORS: • Leadfeeder (turn pageviews into pipeline) - https://leadfeeder.partnerlinks.io/rsscjriylqgb • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Connect with Amanda on LinkedIn: https://www.linkedin.com/in/amandaharknessjones/ CONNECT WITH JESS...

Sep 25, 2020•1 hr 2 min•Ep. 2

Trailer

Sales Players - On a mission to help reps, founders and operators generate more pipeline, close more deals and build wealth in tech sales. 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: • LinkedIn: https://www...

Sep 20, 2020•24 sec•Ep. 1

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