Jesse Woodbury

Sales Players

Business EN ↓ 205 episodes

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

Business

Podcast website

www.salesplayers.co

Latest episode

Oct 17, 2025

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Episodes

Knowing Your Tech Stack, Marketplace & Transitioning from Contributor to Leader with Asa Hochhauser of McGaw.io 20.01.2022

Asa Hochhauser is the VP of Sales at McGaw.io. Asa shares his story, transition to Sales leadership, perspectives in selling at a product led growth company & how to keep a pulse on your market.  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...

The Simple Cadence I'm Using for my Prospecting 20.01.2022

Jesse shares a really simple, 15-day prospecting & outreach cadence by Trish Bertuzzi in her book The Sales Development Playbook: https://www.bridgegroupinc.com/sales-development-playbookThis was a great book & one that helped me gain a new perspective on this business & level up significantly. Pic of the cadence from the book: https://images.clickfunnels.com/c6/ed40ca34ed45939cc976314...

Sales & Prospecting Insights from a Lawyer Turned SaaS Founder with Andy Cabasso of Postaga 11.01.2022

Andy is the co-founder at Postaga , a new all-in-one platform for link building and email outreach. Recently featured on Product Hunt as #1 product of the day. Andy shares how he went from Law Student to entrepreneur & how sales & marketing helped him secure Postaga's early customers & funding. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr...

Quick Time Management Tip for SaaS Sellers 08.01.2022

Jesse shares a quick tip for managing money making activities, prep & breaks on your calendar to improve productivity. Simple & effective. 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:...

Career Transitions, Startups, Research & Streamlining Results with David Nakano of Airkit 06.01.2022

David Nakano is an Account Executive at Airkit. David shares his career transition story, SaaS opportunity framework & some ideas for building rapport, building pipeline, researching companies & putting your SaaS career on the fast track. 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...

Pt. III Accelerating Your SaaS Selling Results & Career in 2022 - Ideas for Owning Your Career Path 31.12.2021

Jesse shares a few examples of how you can take control of your SaaS Sales career path, standout from your peers & practice consistency, predictability & control.  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.clos...

Pt. II Accelerating Your SaaS Selling Results & Career in 2022 - Breaking into SaaS Sales 30.12.2021

Jesse shares ideas around how he'd approach breaking into SaaS Sales if he had to start over again today, but knowing what he knows now about the industry. 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 CONNEC...

Pt. I Accelerating Your SaaS Selling Results & Career in 2022 - Earning A Record W2 28.12.2021

Jesse shares a few ideas for how to make 2022 a record earnings year & W2 for yourself. If you'd like a copy of my capacity planner email me at: jesse@jessewoodbury.com 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.clo...

How to Sell Without Selling Out with Andy Paul 21.12.2021

Andy Paul host of the Sales Enablement Podcast shares insights, stories & some hot takes on the state of SaaS selling. In addition to his podcast (which was acquired by Revenue.io in 2020) he's the author of two award-winning sales books, "Zero-Time Selling" and "Amp Up Your Sales" with a third book on the way: "How to Sell Without Selling Out." He's #8 on LinkedIn's list of Top 50 Global Sale...

My Top 10 Must-Read Books for Business & Sales 01.12.2021

Jesse shares 10 influential business books that shaped his life & career.   The Books: Never Split the Difference by Chris Voss  The Four-Hour Work Week by Tim Ferris  From Impossible to Inevitable/Predictable Revenue by Aaron Ross & Jason Lemkin  Selling Above & Below the Line by Skip Miller  The Sales Development Playbook by Trish Bertuzzi  Think & Grow Rich by Napoleon Hill  The...

From Bankrupt Small Business Owner to Top SaaS Seller with Chris Dankowski of Sapper Consulting 17.11.2021

Chris Dankowski of Sapper Consulting shares his career journey from small, bankrupt business owner to SaaS AE at some of the industries top companies. Chris also digs into insights around effective prospecting & shares how to land great opportunities in SaaS.  SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5...

How to Master a Salary Negotiation in SaaS 10.11.2021

Jesse shares ideas, tips, resources & learnings for effective salary negotiation for SaaS sales positions. Please reach out if I can be a resource: jesse@jessewoodbury.com 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....

Managing Your SaaS Sales Career with Christine Rogers of Aspireship 29.10.2021

Christine Rogers is the President & COO of Aspireship . She shares insights from her 15-year career in SaaS sales, leadership & entrepreneurship. Aspireship is a very exciting startup working to level the playing field for professionals aspiring for a career in SaaS.  SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo c...

Meeting Your Prospects Where They Are Using Social Selling with Ryann Dowdy of Social Sellers Academy 26.10.2021

Ryann Dowdy helps high-achieving women leave their 9-5 and build a 6-figure business by teaching them how to master sales conversations and the mindset work required to make a total identity shift. Ryann has mentored, managed, and trained thousands of sales reps. Ryann focuses on the art of building relationship and human to human connection. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60...

5 Tips for Better Discovery Conversations 24.10.2021

Discovery is extremely important in the sales process. When done right, it builds trust, improves close rate and can help deals close faster. Jesse shares a few things he has seen improve the discovery process. Mastering discovery is an ongoing pursuit and even the most elite sellers still invest in learning and practicing great discovery.  SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 s...

Sales Transformation, Podcasting & Startup Sales with Collin Mitchell of Salescast 20.10.2021

Collin Mitchell is the host of Sales Transformation and CRO of Salescast. Collin shares his sales story and journey as an entrepreneur and podcaster. Collin also shares his insight into how podcasting can be used as a channel for sellers to reach their ideal buyers.  SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSUR...

How to Find Great Opportunities in SaaS Sales with Amanda Jones 14.10.2021

Amanda Jones returns to the podcast to share details around the launch of her sales consulting business. She also shares some tips on how to land an opportunity at a top SaaS company. 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 camp...

Deconstructing the Challenger Sale with Jennifer Allen-Knuth of Challenger 06.10.2021

Jen Allen-Knuth is a Key Account Executive at Challenger & the Host of the Winning the Challenger Sale Podcast. Jen is an expert in B2B sales strategy and the Challenger methodology. Connect with her on LinkedIn and be sure to subscribe to the Winning the Challenger Sale Podcast. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with...

Authentic Persuasion & Going From Order Taker to Quota Breaker with Jason Cutter 01.10.2021

Jason Cutter shares his playbook for Authentic Persuasion in 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 onb...

How to Be Focused, Live Great AND Make 7 Figures in SaaS Sales with Brandon Fluharty 20.09.2021

Brandon Fluharty is one of the top minds in the SaaS Sales industry today. He was kind enough to share insights into his personal operating system that yielded him 8 figures in SaaS revenue & a 7-figure W2.  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...

Death to Fluff in Sales & the Mic Drop Method for Cold Calling with Belal Batrawy 07.09.2021

Belal Batrawy is the creator of DeathtoFluff . He's an amazingly talented seller who's spent much of his career driving revenue for early stage SaaS startups. Belal is one of the top minds in the industry and spends his time advising startups with their go-to-market efforts and helping reps improve their pitch with his Mic Drop Cold Call framework.  SPONSORS: • Surfe (Connect your CRM with LinkedI...

Sales Lessons from a Veteran Entrepreneur with Patrick Baynes of NerdWise 01.09.2021

Patrick Baynes is the CEO of Nerdwise, a Philly-based startup that enables sales teams to accelerate each stage of the buying process from prospect discovery to outreach and acquisition. Patrick shares how to level up professionally, approach prospecting and pipeline generation with strategy & data and how to thoughtfully serve your customers.  SPONSORS: • Surfe (Connect your CRM with LinkedIn...

How to Maintain a Positive Mindset When Things Aren’t Going Well 21.08.2021

Jesse shares 3 things you can work on to remain positive and control your mindset.  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 an...

Using LinkedIn Sales Navigator to Build Credibility, Find Buyers & Create Org Charts 11.08.2021

Jesse shares how he's currently using LinkedIn in his prospecting and sales process.  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 tr...

On Being a Rainmaker, "LinkedIn Rapper" & Highly Competitive Seller with Jaime Safianow of Quantum Metric 02.08.2021

Jaime Safianow who Manages Sales Development at Quantum Metric, takes some time on a Friday evening to share her playbook for success in the software industry. Jaime is an expert at making a splash with social selling, famous for her viral LinkedIn videos where she Raps about her product and solution. Jaime shares how to stand out in a crowded category and how to leverage LinkedIn for effective pr...

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