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
Becoming a Category Expert & Humanizing Your Sales Cycles with Andy Teipen 20.07.2023 50:05
Andy Teipen has led sales for several early-stage SaaS companies and he's coached numerous reps to success throughout his leadership career. Andy shares insights around his career success and some ideas for becoming an expert in your industry. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=jesse-woodbury use this link with promo code JWSURFE5 f...
Part III - Closing Your First (Or Next) $100K+ SaaS Deal 12.07.2023 14:17
Part 3/3 on closing your first (or next) $100K deal. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=jesse-woodbury 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 onb...
Part II - Closing Your First (Or Next) $100K+ SaaS Deal 07.07.2023 16:23
Part 2/3 on closing your first (or next) $100K deal. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=jesse-woodbury 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 onb...
Part I - Closing Your First (Or Next) $100K+ SaaS Deal 05.07.2023 14:03
Part 1/3 on closing your first (or next) $100K deal. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=jesse-woodbury 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 onb...
Building the Future of Manufacturing with SaaS with Renan Devillieres of OSS Ventures 28.06.2023 25:59
Renan Devillieres is the Founder & CEO of OSS Ventures, a Paris-based startup studio that is building & investing in the future of Manufacturing operations. Renan shares insights into the massive opportunity at hand in disrupting this vertical with SaaS. If you're interested in opportunities with OSS Ventures and it's portfolio companies, use the links in the episode notes below to...
Growing Your Online Network and the Future of Selling with Scott Leese 21.06.2023 41:41
Scott Leese has over 20 years of experience building and scaling sales organizations, advising over 100 startups, and achieving two 9- and 10-figure exits. He also built his consulting firm from scratch to $5M+ in revenue. Scott has founded three startup communities with a combined membership of 5,000+, making him one of the most experienced community builders in tech. SPONSORS: • Surfe (Connect y...
A Day in the Life of a SaaS CEO with Jennifer Smith of Scribe 12.06.2023 41:54
Jennifer Smith is the CEO & Co-Founder of Scribe, A screen capture tool that turns any process into a step-by-step guide. Jennifer shares a day in the life of a tech CEO, how she came up with the idea for Scribe and insights on Product-Led Sales. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=jesse-woodbury use this link with promo code JWSURFE...
Steal My Value Drivers Template to Improve Your Messaging & Pitch 09.06.2023 7:09
Jesse walks through Value Drivers, how to define them and shares examples. Template link available below in the show notes. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=jesse-woodbury 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....
The Intersection of AI & Sales with Wissam Tabbara of Truebase 05.06.2023 40:19
Wissam Tabbara is the Founder & CEO of Truebase. He's a 3X Founder with 2 Exits. His company Truebase (truebase.io) simplifies and automates prospecting to quickly discover potential customers with high conversion likelihood. He shares his views on how AI will impact prospecting and sales. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=jess...
How to Find the Right Path in Your Sales Career with Chris Dankowski 31.05.2023 58:00
Chris Dankowski is a Revenue Strategist at Salesloft by day. Career Advisor for sales reps by night. - Former AE at top companies such as: Evernote, HubSpot, and Outreach. Today Chris shares insights on Sales careers from landing a role at a top tech company to pivoting out of sales into another role. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=...
Proposing Next Steps and Implementing a Mutual Action Plan to Improve your Odds of Closing the Deal 26.05.2023 5:54
Following a Slack conversation with a close colleague, Jesse shares 2 ways to improve your odds of moving a deal from product demo to signed order form. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=jesse-woodbury use this link with promo code JWSURFE5 for a 5% discount on your first year • Overloop (Run multi-channel outbound campaigns, from a si...
Are You Selling a Vitamin or a Painkiller? 19.05.2023 7:28
Jesse shares his response to a question that came up during an SSP meetup about selling a must have (painkiller) app v. selling a nice to have (vitamin) app. Here's two things you can do if you find yourself at a vitamin SaaS company: 1. Learn all you can about your buyer and their industry so you can be a partner and consultant to their business 2. Truly understand WIIFM... What's in it f...
How to Self-Source the Right Buyer at the Right Time with the Right Message with Jamie Shanks of Pipeline Signals 11.05.2023 40:10
Jamie Shanks is the CEO of Pipeline Signals , a Toronto-based company designed to help sellers get more "at-bats" by enabling reps to self-source pipeline at scale. Today Jamie shares insights from his work with clients around account targeting and using sales intelligence to improve pipeline generation and close rates. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - h...
From Personal Banker to SaaS CEO, Customer Led Growth & Sales Automation Insights with Rafael Figueroa of Overloop 04.05.2023 50:35
Rafael "Rafa" Figueroa is the CEO of Overloop . In this episode he shares his journey from being a Personal Banker to the CEO of Overloop. We talk customer success, growth and he shares his insights on SaaS sales and the tools that will power the revenue behind next round of amazing companies. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_l...
Building & Scaling Profitable SaaS & Services Companies with Phil Alves of DevStats/DevSquad 27.04.2023 40:46
Phil Alves is the CEO of DevSquad & DevStats and the Host of the SaaS Origin Stories Podcast. He shares his journey from starting and selling his first company, moving from Brazil to Utah and gives some tips for founders and revenue hires for quickly scaling revenue. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code J...
How to Negotiate a Signing Bonus for Your Next Role 25.04.2023 10:46
Signing bonus are an open secret in the software industry. When negotiated correctly, AEs/SDRs can secure $5K - $25K+ in upfront bonuses paid out with your first check in a new role. In this episode, Jesse shares his process and talk track for getting a signing bonus. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSU...
10 SaaS Sales Predictions 14.04.2023 26:17
Jesse drops 10 predictions for changes coming to SaaS Selling. 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 onboardi...
Networking, Negotiating & Winning SaaS Deals Quickly with Chase Barmore of WhatConverts 06.04.2023 1:09:12
Chase Barmore is an Account Executive at WhatConverts . He was previously a serial entrepreneur and small business owner, starting and operating Life Bar and Ready Valet. Chase shares his playbook for networking, building pipeline and closing deals quickly. 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...
How I Nurture Prospects Without Sending Annoying “Check-in” Emails 01.04.2023 25:16
Jesse shares some ideas for how to add value to you buyers over the long-term and to eliminate the dreaded "checking in" emails. 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....
A Recruiter's Perspective on Growth, Interviewing & Evaluating Opportunities with Christine Kull 22.03.2023 56:14
Christine Kull is one of the top recruiters and executive headhunters in the industry. She shares the story of her career, insights on hiring, interviewing and evaluating opportunities and shares how networking and picking up the phone can open doors. 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% dis...
December Recap, New Year & Updates 09.01.2023 10:32
Jesse shares why there were no episodes in December & speaks briefly about the state of SaaS. 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/jess...
Making an Impact as an Early Sales Hire 30.11.2022 24:55
Jesse shares ideas for making an impact quickly in a startup, drawing from his days as a first-in and early sales hire. With large-scale layoffs at Big Tech firms, we're likely to see more SaaS launches and more opportunities to join as a first-in or early rep. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURF...
4 Tips to Recession-Proof Your Message & Pitch 18.11.2022 6:51
Jesse shares 4 areas you need to emphasize in your pitch to resonate with prospects during a challenging economic environment: 1. How does your SaaS lower costs for your buyer? 2. How does your SaaS help buyers do more with less? 3. How does your SaaS mitigate risk for your buyer? 4. How does your SaaS enable your buyer to consolidate tech, systems, processes or teams? SPONSORS: • Surfe (Connect...
Retiring the Hawaiian Shirt Headshot, Ratings & Reviews, Slack Channel & Other Updates 18.11.2022 5:36
Jesse shares a few quick updates about the podcast cover, private Slack Channel & asks for a review or rating of the show. 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: ht...
Sell with Swagger with Tim Zielinski of Dynatrace 03.11.2022 39:07
Tim Zielinski is the RVP of Strategic Acquisition Sales at Dynatrace & the author of Sell with Swagger . Tim shares his career story of transitioning from Java developer to SaaS Sales leader. He also shares actionable highlights from his book & 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...
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