
SaaS Sales Players
By Jesse Woodbury
Interviews with the SaaS industry's top performing sellers. SaaS Sales Players breaks down the mindset, habits and processes used by software's most successful revenue producers to crush quota and make bank.

Sales & Prospecting Insights from a Lawyer Turned SaaS Founder with Andy Cabasso of Postaga
Sales & Prospecting Insights from a Lawyer Turned SaaS Founder with Andy Cabasso of Postaga
SaaS Sales PlayersJan 11, 2022
00:00
43:10

December Recap, New Year & Updates
December Recap, New Year & Updates
Jesse shares why there were no episodes in December & speaks briefly about the state of SaaS.
Reach out at: jesse@jessewoodbury.com
If you enjoyed this episode, please rate, review & share
Jan 09, 202309:32

Making an Impact as a First-In or Early Sales Hire
Making an Impact as a First-In or Early Sales Hire
Jesse shares ideas for making an impact quickly in a startup, drawing from his days as a first-in & early sales hire. With large-scale layoffs at Big Tech firms, we're likely to see more SaaS launches & more opportunities to join as a first-in or early rep.
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Nov 30, 202223:55

How To Recession Proof Your Message & Pitch
How To Recession Proof Your Message & Pitch
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?
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 performance & career coaching with Jesse? DM on LinkedIn or email jesse@jessewoodbury.com
Nov 18, 202205:51

Retiring the Hawaiian Shirt Headshot, Ratings & Reviews, Slack Channel & Other Updates
Retiring the Hawaiian Shirt Headshot, Ratings & Reviews, Slack Channel & Other Updates
Jesse shares a few quick updates about the podcast cover, private Slack Channel & asks for a review or rating of the show.
Interested in 1:1 coaching with Jesse? DM on LinkedIn or email jesse@jessewoodbury.com
Nov 18, 202204:36

Sell with Swagger with Tim Zielinski of Dynatrace
Sell with Swagger with Tim Zielinski of Dynatrace
Tim Zielinski is the RVP of Strategic Acquisition Sales at Dynatrace & the author of Sell with Swagger (Amazon Link). Tim shares his career story of transitioning from Java developer to SaaS Sales leader. He also shares actionable highlights from his book & career.
Connect with Tim on LinkedIn: https://www.linkedin.com/in/tim-zielinski-b32ab71/
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM on LinkedIn or email jesse@jessewoodbury.com
Nov 03, 202238:07

Improving Your Executive Presence
Improving Your Executive Presence
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.
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Nov 03, 202216:49

Why You Shouldn't Let Your Career Destroy Your Health
Why You Shouldn't Let Your Career Destroy Your Health
Jesse talks about toxic managers, "Sunday Scaries" & why you shouldn't let your job, boss or quota destroy your physical & mental health.
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Oct 31, 202209:20

Challenger Selling? In this Economy?!? With Jen Allen of Challenger™
Challenger Selling? In this Economy?!? With Jen Allen of Challenger™
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.
Follow Jen on LinkedIn: https://www.linkedin.com/in/jenniferallen1121/ Winning the Challenger Sale Podcast: https://www.challengerinc.com/podcast/
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Oct 24, 202253:12

Key Insights from a Sales Enablement Leader with Lauren Flannery of Whoop
Key Insights from a Sales Enablement Leader with Lauren Flannery of Whoop
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.
Connect with Lauren https://www.linkedin.com/in/lauren-flannery/ Whoop: https://www.whoop.com/
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Oct 13, 202201:08:31

Common Reasons Your SaaS Deals Stall & How You Can Fix It
Common Reasons Your SaaS Deals Stall & How You Can Fix It
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.
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Sep 24, 202231:20

Improving Outbound & Growing Your Sales Pipeline with Christian Banach
Improving Outbound & Growing Your Sales Pipeline with Christian Banach
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 & troubleshooting when your outreach is now working.
Christian's Website: https://christianbanach.com/
Connect on LinkedIn: https://www.linkedin.com/in/christianbanach/
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Sep 14, 202255:51

From Entrepreneur & Small Business Owner to High Performance SaaS Seller with Chase Barmore of WhatConverts
From Entrepreneur & Small Business Owner to High Performance SaaS Seller with Chase Barmore of WhatConverts
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.
How to contact Chase:
IG: https://www.instagram.com/mrlifebar/
Linkedin: https://www.linkedin.com/in/chase-barmore-78960418/WhatConverts.com
Sign-up for a free 14 day trial here: https://app.whatconverts.com/sign-up-trial or book a demo with Chase https://calendly.com/chase-barmore/30min
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Sep 01, 202201:12:07

Prospecting & Prioritizing Mental Health, Mindset, and Wellness from an SDR Turned AE with Anthony Natoli of Lattice
Prospecting & Prioritizing Mental Health, Mindset, and Wellness from an SDR Turned AE with Anthony Natoli of Lattice
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.
Subscribe to Anthony's newsletter for high-quality and actionable prospecting tips delivered directly to your inbox every week: https://anthonynatoli.me/
Connect with Anthony on LinkedIn: https://www.linkedin.com/in/anthony-natoli/
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Aug 24, 202239:48

You're Probably More Valuable Than You Think
You're Probably More Valuable Than You Think
Jesse powers through a Friday evening monsoon storm & shares thoughts about your value as a SaaS revenue driver.
Article & post mentioned in the episode:
Blog by Cory Bray: https://www.linkedin.com/pulse/early-stage-startup-sales-rep-equity-usually-rip-off-cory-bray/
Post by Ryan Walsh: https://www.linkedin.com/posts/ryancwalsh_sales-metrics-attrition-activity-6963475640775802880-pwLt?utm_source=linkedin_share&utm_medium=member_desktop_web
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Aug 12, 202213:26

On Doing Whatever It Takes, Sales Secrets from a $100M Sales Rep with Brandon Bornancin of Seamless.AI
On Doing Whatever It Takes, Sales Secrets from a $100M Sales Rep with Brandon Bornancin of Seamless.AI
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.
linktr.ee/brandonbornancin
Career opportunities at Seamless.AI: https://www.seamless.ai/about/careers
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Jul 28, 202254:25

The Importance of Being Brief in SaaS Sales
The Importance of Being Brief in SaaS Sales
Jesse shares ideas for being more brief in your communication with buyers.
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Jul 07, 202211:32

Layoffs in Tech & What to Do If You're Impacted
Layoffs in Tech & What to Do If You're Impacted
Jesse shares what he did to get back on track in his career after sudden unemployment a few years ago.
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
Jun 09, 202224:42

Do You Have a Highlight Reel for Your SaaS Sales Career?
Do You Have a Highlight Reel for Your SaaS Sales Career?
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.
If you enjoyed this episode, please rate, review & share.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
May 20, 202210:57

A Prospecting Campaign Idea to Help You Get Intro'd To The Right Stakeholders
A Prospecting Campaign Idea to Help You Get Intro'd To The Right Stakeholders
Jesse shares a prospecting play you can run to use Procurement contacts to get in the door at a large enterprise.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
If you enjoyed this episode, please rate, review & share.
May 13, 202211:44

What Happens If I Miss My Quota in SaaS Sales?
What Happens If I Miss My Quota in SaaS Sales?
Jesse's musings about SaaS quota achievement.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
If you enjoyed this episode, please rate, review & share.
Apr 29, 202214:16

The Secret to Scaling SaaS Companies From Someone Who's Done It Many Times Over with Patrick Parker of SaaS Partners
The Secret to Scaling SaaS Companies From Someone Who's Done It Many Times Over with Patrick Parker of SaaS Partners
Patrick Parker is the CEO of SaaS Partners (saaspartners.io). Patrick has has led the creation, go-to-market & scale of 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.
Connect with Patrick: https://www.linkedin.com/in/patrickbparker/
Patrick & team are ALWAYS hiring. email: hello@saaspartners.io for more info.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
If you enjoyed this episode, please rate, review & share.
Apr 14, 202236:06

Announcement! - First Ever SSP Happy Hour & Meetup in Austin, Texas
Announcement! - First Ever SSP Happy Hour & Meetup in Austin, Texas
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
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
If you enjoyed this episode, please rate, review & share.
Mar 30, 202202:31

Knowing Your On Track in Your SaaS Sales Journey
Knowing Your On Track in Your SaaS Sales Journey
Jesse shares some career milestones, that put him on track for success.
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
If you enjoyed this episode, please rate, review & share.
Mar 24, 202229:10

Data Security, Compliance & Selling to Technical Buyers with Girish Redekar of Sprinto
Data Security, Compliance & Selling to Technical Buyers with Girish Redekar of Sprinto
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 deals.
Connect with Girish: https://www.linkedin.com/in/girishredekar/
Learn more about Sprinto: https://sprinto.com/
Interested in 1:1 coaching with Jesse? DM me on LinkedIn or email jesse@jessewoodbury.com
If you enjoyed this episode, please rate, review & share.
Mar 17, 202238:27

How to Transform Your Mindset, Manage Stress, Anxiety & Addiction & Become an Elite SaaS Seller with Ian Koniak
How to Transform Your Mindset, Manage Stress, Anxiety & Addiction & Become an Elite SaaS Seller with Ian Koniak
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, mental & physical health.
Learn more about Ian's coaching program: https://iankoniak.com/
Connect/Follow Ian on LinkedIn: https://www.linkedin.com/in/iankoniak/
Mar 04, 202255:32

Breaking Down Common Acronyms in the SaaS Business (While Drinking Tequila)
Breaking Down Common Acronyms in the SaaS Business (While Drinking Tequila)
Jesse goes through a list of common acronyms you'll hear in SaaS, while sipping a Paloma.
Full list of acronyms to be published...
Feb 19, 202226:47

A Stanford Ph.D's Approach to Selling & The Value-Driven Growth Methodology with Brent Keltner of Winalytics
A Stanford Ph.D's Approach to Selling & The Value-Driven Growth Methodology with Brent Keltner of Winalytics
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 Fit.
Connect with Brent on LinkedIn: https://www.linkedin.com/in/bkeltner/
Work with Winalytics: https://info.winalytics.com/free-winalytics-growth-assessment-and-consultation
Feb 14, 202245:07

A Simple Formula to Estimate the Annual Revenue & Burn Rate of any SaaS Startup
A Simple Formula to Estimate the Annual Revenue & Burn Rate of any SaaS Startup
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.
The original blog post I first learned this formula from: https://www.saastr.com/how-to-figure-out-your-competitors-revenues-in-about-70-seconds/
Feb 08, 202203:54

Mastering Your Pitch with Rajiv 'RajNATION' Nathan
Mastering Your Pitch with Rajiv 'RajNATION' Nathan
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.
For SaaS Sales Players Only: https://www.startuphypeman.com/ssp
Connect with Raj on LinkedIn: https://www.linkedin.com/in/rajivnathan/
Feb 03, 202259:09

The 7 Steps to 7 Figures in SaaS Sales with Brandon Fluharty
The 7 Steps to 7 Figures in SaaS Sales with Brandon Fluharty
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.
Subscribe to Be Focused, Live Great & Get Early Access to 7 Steps to 7 Figures: https://brandonfluharty.com/
Connect & Follow Brandon: https://www.linkedin.com/in/brandonfluharty/
Jan 30, 202245:16

Knowing Your Tech Stack, Marketplace & Transitioning from Contributor to Leader with Asa Hochhauser of McGaw.io
Knowing Your Tech Stack, Marketplace & Transitioning from Contributor to Leader with Asa Hochhauser of McGaw.io
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.
Connect with Asa on LI: https://www.linkedin.com/in/asahoc/
Jan 20, 202244:48

The Simple Cadence I'm Using for my Prospecting
The Simple Cadence I'm Using for my Prospecting
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-playbook
This 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/ed40ca34ed45939cc97631414e8b70/Image-from-iOS-2-.jpg
(Seriously though, buy the damn book, you'll be glad you did.)
Jan 20, 202211:60

Sales & Prospecting Insights from a Lawyer Turned SaaS Founder with Andy Cabasso of Postaga
Sales & Prospecting Insights from a Lawyer Turned SaaS Founder with Andy Cabasso of Postaga
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.
Connect with Andy on LinkedIn: https://www.linkedin.com/in/andrewcabasso/
Jan 11, 202243:10

Quick Time Management Tip for SaaS Sellers
Quick Time Management Tip for SaaS Sellers
Jesse shares a quick tip for managing money making activities, prep & breaks on your calendar to improve productivity. Simple & effective.
Here's the link to the original post by Morgan J. Ingram: https://www.linkedin.com/posts/morganjingram_color-code-your-calendar-here-is-a-starter-activity-6754761555432230912-VDvj
Jan 08, 202206:03

Career Transitions, Startups, Research & Streamlining Results with David Nakano of Airkit
Career Transitions, Startups, Research & Streamlining Results with David Nakano of Airkit
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.
Connect with David on LinkedIn: https://www.linkedin.com/in/david-nakano/
Jan 06, 202201:12:12

Pt. III Accelerating Your SaaS Selling Results & Career in 2022 - Ideas for Owning Your Career Path
Pt. III Accelerating Your SaaS Selling Results & Career in 2022 - Ideas for Owning Your Career Path
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.
Dec 31, 202124:57

Pt. II Accelerating Your SaaS Selling Results & Career in 2022 - Breaking into SaaS Sales
Pt. II Accelerating Your SaaS Selling Results & Career in 2022 - Breaking into SaaS Sales
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.
Dec 30, 202125:11

Pt. I Accelerating Your SaaS Selling Results & Career in 2022 - Earning A Record W2
Pt. I Accelerating Your SaaS Selling Results & Career in 2022 - Earning A Record W2
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
Dec 28, 202118:42

How to Sell Without Selling Out with Andy Paul
How to Sell Without Selling Out with Andy Paul
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 Sales Experts and has consulted some of the biggest businesses in the world including: Square, Philips, Grubhub and more. He's one of the leading voices in the sales industry today.
Website: andypaul.com
LinkedIn: https://www.linkedin.com/in/realandypaul/
Pre-Order Sell Without Selling Out: https://www.andypaul.com/#pre-order-now-ap
The Sales Enablement Podcast: https://podcasts.apple.com/us/podcast/sales-enablement-podcast-with-andy-paul/id1046045197
Dec 21, 202144:19

My Top 10 Must-Read Books for Business & Sales
My Top 10 Must-Read Books for Business & Sales
Jesse shares 10 influential business books that shaped his life & career.
The Books (Links to be added later):
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 Hard Thing About Hard Things by Ben Horowitz
Steve Jobs by Walter Isaacson
High Output Management by Andy Grove
Measure What Matters by John Doerr
Dec 01, 202113:21

From Bankrupt Small Business Owner to Top SaaS Seller With Chris Dankowski of Sapper Consulting
From Bankrupt Small Business Owner to Top SaaS Seller With Chris Dankowski of Sapper Consulting
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.
Connect with Chris on LinkedIn: https://www.linkedin.com/in/chrisdankowski/
Nov 17, 202156:31

How to Master a Salary Negotiation in SaaS
How to Master a Salary Negotiation in SaaS
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
Resources:
https://www.glassdoor.com/index.htm
https://www.linkedin.com/salary
https://www.bridgegroupinc.com/inside-sales-resources
https://www.repvue.com/
Nov 10, 202126:08

Managing Your SaaS Sales Career with Christine Rogers of Aspireship
Managing Your SaaS Sales Career with Christine Rogers of Aspireship
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.
Website: https://aspireship.com/
Christine's LinkedIn: https://www.linkedin.com/in/christinerogers2/
Oct 29, 202157:35

Meeting Your Prospects Where They Are Using Social Selling with Ryann Dowdy of Social Sellers Academy
Meeting Your Prospects Where They Are Using Social Selling with Ryann Dowdy of Social Sellers Academy
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.
Connect with Ryann on LinkedIn: https://www.linkedin.com/in/ryanndowdy/
Check out her podcast: https://dailysalesondemandforceos.com/300f0-web-agency-portfolio-single/
Oct 26, 202147:39

5 Tips for Better Discovery Conversations
5 Tips for Better Discovery Conversations
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.
Please share your process and ideas: jesse@jessewoodbury.com
Oct 24, 202116:46

Sales Transformation, Podcasting & Startup Sales with Collin Mitchell of Salescast
Sales Transformation, Podcasting & Startup Sales with Collin Mitchell of Salescast
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.
Book a podcast strategy session with Collin: https://meetings.hubspot.com/collin30/podsesh
Podcast: https://www.salestransformation.fm/
Collin's LinkedIn: https://www.linkedin.com/in/collincmitchell/
Oct 20, 202137:16

How to Find Great Opportunities in SaaS Sales with Amanda Jones
How to Find Great Opportunities in SaaS Sales with Amanda Jones
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.
LinkedIn: https://www.linkedin.com/in/amandaharknessjones/
Website: https://www.amandadianeconsulting.com/
Oct 14, 202134:27

Deconstructing the Challenger Sale with Jennifer Allen of Challenger
Deconstructing the Challenger Sale with Jennifer Allen of Challenger
Jen Allen 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.
Winning the Challenger Sale Podcast: https://podcasts.apple.com/us/podcast/winning-the-challenger-sale/id1559020842
Jen's LinkedIn: https://www.linkedin.com/in/jenniferallen1121/
Oct 06, 202144:25

Authentic Persuasion & Going From Order Taker to Quota Breaker with Jason Cutter
Authentic Persuasion & Going From Order Taker to Quota Breaker with Jason Cutter
Jason Cutter shares his playbook for Authentic Persuasion in Sales.
Connect with Jason on LinkedIn: https://www.linkedin.com/in/jascut/
Get a copy of the Scalable Sales Success Iceberg & Checklist -
DM, email (jason@cutterconsultinggroup.com) or call/text – (206) 234-1848
Oct 01, 202101:00:08

How to Be Focused, Live Great AND Make 7 Figures in SaaS Sales with Brandon Fluharty
How to Be Focused, Live Great AND Make 7 Figures in SaaS Sales with Brandon Fluharty
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.
Follow Brandon on LinkedIn & check out his newsletter: Be Focused. Live Great.
Connect on LinkedIn: https://www.linkedin.com/in/brandonfluharty/
Website/Newsletter Sign Up: https://brandonfluharty.com/
https://befocusedlivegreat.com/
Sep 20, 202146:48

Death to Fluff in Sales & the Mic Drop Method for Cold Calling with Belal Batrawy
Death to Fluff in Sales & the Mic Drop Method for Cold Calling with Belal Batrawy
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.
Belal's LinkedIn: https://www.linkedin.com/in/belbatrawy/
Belal's Mic Drop Method for Cold Calling: http://forms.peek.link/28dB
Newsletter: https://deathtofluff.substack.com/
Sep 07, 202148:49

Sales Lessons from a Veteran Entrepreneur with Patrick Baynes of NerdWise
Sales Lessons from a Veteran Entrepreneur with Patrick Baynes of NerdWise
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.
Nerdwise: https://www.nerdwise.com/
Connect with Patrick's LinkedIn: https://www.linkedin.com/in/baynes/
Sep 01, 202158:51

How to Maintain a Positive Mindset When Things Aren’t Going Well
How to Maintain a Positive Mindset When Things Aren’t Going Well
Jesse shares 3 things you can work on to remain positive and control your mindset.
Don't forget to join the 6-figure Close Plan Training Course. I'm closing it down at the end of August. Don't miss an opportunity to learn the framework for managing large SaaS deals: https://www.saasplayers.com/closeplan
Aug 21, 202116:13

Using LinkedIn Sales Navigator to Build Credibility, Find Buyers & Create Org Charts
Using LinkedIn Sales Navigator to Build Credibility, Find Buyers & Create Org Charts
Jesse shares how he's currently using LinkedIn in his prospecting and sales process.
Don't forget to check out the 6-Figure Close Plan: https://www.saasplayers.com/closeplan
Aug 11, 202108:38

On Being a Rainmaker, "LinkedIn Rapper" & Highly Competitive Seller with Jaime Safianow of Quantum Metric
On Being a Rainmaker, "LinkedIn Rapper" & Highly Competitive Seller with Jaime Safianow of Quantum Metric
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 prospecting. Jaime has been a friend for nearly a decade and she's one of the top sellers I've worked with in my career.
Connect with Jaime on LinkedIn: https://www.linkedin.com/in/jaimesafianow/
Aug 02, 202149:30

6-Figure Close Plan (Program Launch Announcement)
6-Figure Close Plan (Program Launch Announcement)
Jesse shares an exciting announcement about the release of an upcoming virtual training program & Slack community.
Learn more about the virtual training and Slack group at www.saasplayers.com
Or email support@jessewoodbury.com
Aug 02, 202103:08

Is SaaS Sales a Career or a Lifestyle?
Is SaaS Sales a Career or a Lifestyle?
Jesse shares thoughts on managing work life balance as a seller and whether this profession is... well a profession or a lifestyle.
Jul 27, 202108:51

Mastering The Cold Call With Chris Beall of ConnectAndSell
Mastering The Cold Call With Chris Beall of ConnectAndSell
Chris Beall of ConnectAndSell stops by to share some wisdom about sales, business, cold calling and life in general.
Connect with Chris on LinkedIn: https://www.linkedin.com/in/chris-beall-7859a4/
Check out ConnectAndSell: https://connectandsell.com/
Read Five Sentences That Will Change Your Life Pt. I: https://connectandsell.com/five-sentences-will-change-life-part-1/
Read Five Sentences That Will Change Your Life Pt. II: https://connectandsell.com/five-sentences-will-change-life-part-2/
Jul 07, 202101:06:42

Developing Winning Habits & Using Your Resources to Find Success in Software Sales with Scott Milener of IntroSnap
Developing Winning Habits & Using Your Resources to Find Success in Software Sales with Scott Milener of IntroSnap
Scott Milener is a veteran technology sales rep, leader & founder. Scott is the CEO of IntroSnap, which connects buyers and sellers by supporting charitable giving to the organization of the buyer's choice. Scott shares tips and insights for success that he's gained during his technology career working with both large companies & early stage startups.
Connect with Scott: https://www.linkedin.com/in/milener/
https://www.introsnap.com/
Scott's book recommendation: https://survivaltothrival.com/
Jun 25, 202157:09

5 Things to Look For When Interviewing for your Next SaaS Sales Role
5 Things to Look For When Interviewing for your Next SaaS Sales Role
Jesse shares a list of things you can vet for before accepting your next software sales role, regardless of whether your an SDR, AE or other.
-A strong product offering, product market fit, clear value proposition & value drivers, legit happy customers and documented success stories
-Quality leadership, particularly sales leadership - Do they have any LinkedIn recommendations?
-Well documented rep/team success & results - In general, are reps achieving their goals? What is the top performer specifically doing?
-Rep investment - How do they train, enable and advance reps to career & financial success?
-Do they respect boundaries, provide & receive feedback?
Jun 05, 202125:43

What Sales Can Learn from Special Operations Forces (SOF) with John Wood
What Sales Can Learn from Special Operations Forces (SOF) with John Wood
John Wood shares his learnings from a 6-year military career in the 75th Ranger Regiment (Special Operations Forces).
5 SOF Truths:
1. Humans are more important than Hardware.
2. Quality is better than Quantity.
3. Special Operations Forces cannot be mass produced.
4. Competent Special Operations Forces cannot be created after emergencies occur.
5. Most Special Operations require non-SOF assistance
Connect with John on LinkedIn: https://www.linkedin.com/in/john-wood-85038066/
May 19, 202101:11:07

4 Things I'm Proud of in My SaaS Sales Journey
4 Things I'm Proud of in My SaaS Sales Journey
Jesse shares 4 things he's proud of in his SaaS selling career so far.
Connected with great mentors
Invested in himself to improve his craft
Developed and nurtured a strong network of peers, leaders & customers
Made moves at the right time (leaving when it's time to go or sticking it out when he felt like quitting)
May 12, 202120:42

3 Things I Would Have Done Differently In My SaaS Sales Journey
3 Things I Would Have Done Differently In My SaaS Sales Journey
Jesse shares the 3 things he would have done differently in his SaaS selling career to personally scale faster.
Think Bigger, Aim Higher & Master Mindset
Ask for Help, Feedback & Utilize Leaders & Other Resources
Think Like a Partner or Consultant to Prospects
Apr 30, 202118:11

How Having a "Close Plan" Will Help You Improve Forecasting & Conversions
How Having a "Close Plan" Will Help You Improve Forecasting & Conversions
Jesse's been AWOL for too long... He comes up for air after a crazy busy month & sales quarter to share how he designed close plans, mutual action plans, mutual milestones... or whatever the hell you want to call them.
Implementing a plan will help you build credibility, improve forecasting & close more deals.
If you'd like a copy of Jesse's template email: jesse@jessewoodbury.com
Apr 07, 202111:33

Quick Podcast Update
Quick Podcast Update
With 20 episodes completed, Jesse says thanks to the guests and listeners who've made the show possible. If you or someone you know would like to be a guest on the show or if you have feedback (positive or negative) please reach out to me on LinkedIn or at jesse@jessewoodbury.com
A companion website to the podcast will be coming soon! Thank you.
-Jesse
Mar 03, 202105:38

The Fundamentals of SaaS Selling with Jeroen Corthout of Salesflare
The Fundamentals of SaaS Selling with Jeroen Corthout of Salesflare
Jeroen Corthout is the Co-Founder of Belgium-based Salesflare. Jeroen shares his journey from product to marketing to manageing SaaS sales and growth for Salesflare. He shares his strategy for building trust with customers, improving pipeline conversion and managing time and efficiency. Resources discussed in the episode can be found below:
Salesflare website: https://salesflare.com/
SaaS Sales Fundamentals Blog Post: https://blog.salesflare.com/saas-sales
Connect with Jeroen on LinkedIn: https://www.linkedin.com/in/jeroencorthout/
Feb 18, 202150:29

The Number One Question To Ask When Discussing Pricing
The Number One Question To Ask When Discussing Pricing
Jesse shares a go-to question that will help prompt feedback from your prospects on your pricing proposal.
Feb 08, 202103:29

The Secret to Closing $10MM+ Mega Software Deals with Jamal Reimer
The Secret to Closing $10MM+ Mega Software Deals with Jamal Reimer
Jamal Reimer shares his incredible story of transformation from average rep, who was let go for low performance, to learning 5 key skills that helped him close his first $10 million dollar mega software deal. Jamal has since secured multiple $50 million dollar deals and has closed more than $160 million in his career. Jamal shares how to master mindset, working with executives and how to position yourself for victory in an RFP process. If you're looking to dramatically increase your average deal size, follow Jamal on LinkedIn and check out his mentoring program and masterclasses.
Jamal's Website: https://www.megadealsecrets.com/
Connect with Jamal on LinkedIn: https://www.linkedin.com/in/jamal-reimer/
Feb 01, 202151:47

"Can You Send Me Some More Info?"
"Can You Send Me Some More Info?"
How to handle the very common "Can You Send Me Some More Info?" objection.
Jan 27, 202109:51

How to Double Your Income This Year In Software Sales with Ian Agard of Clio & Grind
How to Double Your Income This Year In Software Sales with Ian Agard of Clio & Grind
Ian Agard spends his Friday evening sharing how he broke into his software sales career after working as an actor. He shares how his mindset, goal setting and commitment to discipline helped him double his income in under a year. Ian also discusses his side project, Grind, a community built to help SaaS sellers level up.
Connect with Ian on LinkedIn: https://www.linkedin.com/in/ianagard/
Grind: http://www.grindsaas.com/
Jan 16, 202101:03:53

On Succeeding as the First Sales Hire with Luke Bivens of Gatsby
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.
Connect with Luke on LinkedIn: https://www.linkedin.com/in/luke-bivens-50054641/
Jan 05, 202101:05:05

Finding Your First Opportunity in SaaS Sales - Pt. III
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.
Jan 05, 202110:21

Finding Your First Opportunity in SaaS Sales - Pt. II
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.
Dec 19, 202014:06

Finding Your First Opportunity in SaaS Sales - Pt. I
Finding Your First Opportunity in SaaS Sales - Pt. I
Jesse shares a few considerations for finding your first opportunity in SaaS Sales.
https://gregslist.com/
Dec 09, 202016:11

Getting After It with Leigh Kindley of 6sense
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.
Connect with Leigh on LinkedIn
Nov 28, 202055:07

Breaking Up (Disqualifying) Prospects That Aren't a Fit
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.
Nov 20, 202008:14

The Importance of Multi-Threaded Deals
The Importance of Multi-Threaded Deals
Jesse shares the importance of having multiple contacts and stakeholders involved in large deal cycles.
Nov 19, 202009:46

Being Authentic and Asking the Right Questions with Zachary Ballenger of Casted
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.
Connect with Zachary on LinkedIn
Nov 04, 202001:25:49

Call CFOs
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.
Oct 22, 202006:45

How to Make "No" Work for You
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.
Oct 09, 202005:00

How to Win Big Deals and Influence Customers with Dustin Brown of Outreach.io
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.
Connect with Dustin on LinkedIn
Dustin's Book Recommendations
Oct 08, 202001:03:52

Take on Complexity for your Customers
Take on Complexity for your Customers
Jesse discusses a mindset change that's made a big impact on both his pipeline and career fulfillment.
Oct 02, 202003:54

Do the Hard Thing
Do the Hard Thing
Jesse share's how effective it can be to roll up your sleeves and do the "hard thing."
Sep 29, 202003:07

How to Ramp 80% Faster with Amanda Jones of Chorus.ai
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.
Connect with Amanda on LinkedIn
Read the Blog Article
Sep 25, 202058:41

Trailer
Trailer
Jesse shares why he's creating yet another sales podcast.
Sep 20, 202000:49