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Disrupting SaaS Sales Approach - Jesse Woodbury- Episode # 031

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Our guest today, Jesse Woodbury is a disruptor in SaaS sales and a host of a successful podcast show SaaS Sales Players.  

High dollar SaaS sales tend to involve at least half a dozen stakeholders with crazy competition and them being educated about the industry. Enter Jesse Woodbury, he has created 2 frameworks that help providers close over 7 figures in ARR. 

  Key Takeaways:   

  • The SaaS market currently growing by 18% each year and is expected to grow to 22% by end of 2022 and is being considered to transform the IT industry from a cost centre to a value centre.  
  • SaaS adaption in the Health care industry is growing at the rate of 20% per year.    
  • The main ingredient for disruption is being a thought leader while creating and putting out content regularly which roughly equates to making 100 cold calls or sending 100 emails a day.    
  • Content can be repurposed and packaged up in a way that your buyers consider you a thought leader in their industry.     
  • He also changes his mind-set and considered being a consultant or a partner instead of a salesperson as the main prospects are executive-level buyers like CEO, COO, CTO, CFO etc. which in turn increased the deal sizes and time.    
  • Tips for frontline SaaS salesperson – read and compile relevant articles to your industry and take snippets that might be relevant to your buyers. Package and share them with your potential clients, even in the middle of buying/deal cycles. This helps you build credibility, and value and position yourself as a partner in their business. 
  • Status Quo of SaaS Sales – One had to fix an appointment and sell the hardware or servers on company premises, usually a large multi-million dollar complex deal.    
  • With a lot of market automation techniques and more than 20,000 SaaS companies trying to sell their services, there is a lot of noise. Executives aren’t sure which tool is valuable and supports their business.      
  • Being in SaaS sales is an incredibly lucrative game if you play the game right. The best sellers have been figured from implementing content.   
  • Being a sales rep in a high ticket SaaS company, the role is to create valuable content for buyers. It can be specific about which tackles/handle a problem.    
  • With the current status quo, the average tenure for a Sales VP in SaaS companies is 18 months, and even shorter tenure with frontline reps, resulting in huge financial losses and potential revenue. 
  • Even if you have a small subset of your reps posting relevant content to your buyers, word gets around that they are available to partner with your business and solve problems.    
  • Jesse's advice to the sales rep is to “find the medium, platform or channel that works best for you, some people that are tweeting, for others it may be LinkedIn. As for me, I like recording podcasts. I know a lot of reps who have found success with video content.”   
  • The status quo was to update your name and numbers in the sales force and inform your manager about the next steps to close the deal. Jesse suggests making the deal more conversational and collaborative, that’s how you know make your deals more predictable and have more span of control.       

Quote of the show: 

18:40 – 19:12   “Being in SaaS is an incredibly lucrative game if you play the game right, but if you’re not playing the game effectively. Sales is the highest and the lowest paying job in the planet. Sales is very much what you kill and if you can’t do that because you’re sticking to the status quo, then how you do continue hitting you’re numbers and continue on with the profession. So that’s been the challenge and that’s why the shift has to happen more broadly” 



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