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 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/ss...
Nov 17, 2021•58 min
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.close.com/ssp EPISODE LINKS: • https://www.glassdoor.com/index.htm • https://www.linkedin.com/salary...
Nov 10, 2021•27 min
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 code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer....
Oct 29, 2021•59 min
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 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount o...
Oct 26, 2021•49 min
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 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on y...
Oct 24, 2021•18 min
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 JWSURFE5 for a 5% discount on your first year • Overloop (Run multi-channel outbound campaigns, from a sin...
Oct 20, 2021•38 min
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 campaigns, from a single platform) - https://get.overloop.com/ssp use this link for an extended trial an...
Oct 14, 2021•35 min
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 promo code JWSURFE5 for a 5% discount on your first year • Overloop (Run multi-channel outbound cam...
Oct 06, 2021•45 min
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 onboarding hours • Close (The CRM Built for Growth) - https://refer.close.com/ssp EPISODE LINKS: • Conn...
Oct 01, 2021•1 hr 1 min
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 multi-channel outbound campaigns, from a single platform) - https://get.overloop.com/ssp use this li...
Sep 20, 2021•48 min
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 LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% disc...
Sep 07, 2021•50 min
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 in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% disco...
Sep 01, 2021•1 hr
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 and additional onboarding hours • Close (The CRM Built for Growth) - https://refer.close.com/ssp CONNEC...
Aug 21, 2021•16 min
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 trial and additional onboarding hours • Close (The CRM Built for Growth) - https://refer.close.com/ssp CONN...
Aug 11, 2021•9 min
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 ...
Aug 02, 2021•49 min
Jesse shares an exciting announcement about the release of an upcoming virtual training program and Slack community. 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) - ...
Aug 02, 2021•3 min
Jesse shares thoughts on managing work life balance as a seller and whether this profession is... well a profession or a lifestyle. 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...
Jul 27, 2021•9 min
Chris Beall of ConnectAndSell stops by to share some wisdom about sales, business, cold calling and life in general. 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) - ...
Jul 07, 2021•1 hr 7 min
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. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 fo...
Jun 25, 2021•57 min
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 perfor...
Jun 05, 2021•26 min
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 SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp u...
May 19, 2021•1 hr 11 min
Jesse shares 4 things he's proud of in his SaaS selling career so far. Connected with great mentors Invested in myself to improve my craft Developed and nurtured a strong network of peers, leaders and 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, 2021•21 min
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 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...
Apr 30, 2021•18 min
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. 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 • Overl...
Apr 07, 2021•12 min
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. 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) -...
Mar 03, 2021•6 min
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. 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 ...
Feb 18, 2021•50 min
Jesse shares a go-to question that will help prompt feedback from your prospects on your pricing proposal. 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://re...
Feb 08, 2021•3 min
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...
Feb 01, 2021•55 min
How to handle the very common "Can You Send Me Some More Info?" objection. 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 CONNECT WITH J...
Jan 27, 2021•10 min
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. 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 • Ov...
Jan 16, 2021•1 hr 4 min
