BC Startup Sales Podcast — Outbound 3.0 with Jason Bay (Blissful Prospecting)

This week we were joined by Jason Bay, Co-Founder and CRO of Blissful Prospecting, to discuss the evolution of prospecting and outbound, as well as best practices for how to prospect in today’s era of Outbound 3.0.

Jason’s sales experience dates back to 2008. At 19, he ran his first six-figure business painting houses while attending school at Oregon State University. He’s worked with hundreds of sales reps and personally closed millions of dollars in revenue during his career. At Blissful Prospecting, he’s in charge of growing the company through marketing and sales efforts. In his free time, Jason also enjoys stand up comedy, reading, traveling, hiking, and geeking out on productivity tips.

We start the podcast learning some SaaS sales lessons from Jason’s early days building a painting business. We then get into how to determine whether to outsource your outbound efforts or hire a full-time SDR as an early-stage startup (TLDR: have you already figured out your messaging/product market fit? If no, don’t outsource). Jason sheds light on this new concept of Outbound 3.0 – the next evolution of outbound that requires companies to cut through the clutter. There are three components to do this effectively: i) identify good fit accounts and contacts, ii) engage them with simple conversation starters, and iii) convert them to opportunities and move them through the sales funnel. There’s a distinct shift from mass blast to quality and from product-centric messaging to buyer-centric messaging. Companies can excel in this new era of outbound 3.0 through content, thoughtful multi-channel/multi-touch outreach cadences, and using conversational messaging.

We discuss how to determine the level of personalization in your outbound efforts based on ACV. Next, we get into how to balance customization with volume and specific tactical suggestions around your cadences, segmentation, subject lines, and calls to action. When it comes to your cadences, Jason suggests 12 to 15 touches over 30-45 days with messaging spread out over 2-3 distinct value props. Jason also breaks down how to think about your sales tech stack in the early days (he’s a big fan of Apollo.io). For subject lines, Jason suggests you keep it short, use the prospect’s first name, or try using three words that are relevant but seemingly unrelated to pique their interest (“Initiative, 2020, Company Name”). When it comes to the call to action, a big mistake SDRs make is asking for a meeting too early – can I have 30min of your time? Jason suggests slowing down and making your email easier to respond to: is this something worth chatting about; is this a challenge you’re having right now; is this something that is on your radar?

Jason shares some of the top mistakes outbound teams make in the early days and how to avoid them. These include buying the wrong tools (and too early), lack of coaching and training, lack of collaboration (especially around messaging), and lack of outsourcing (list building, prospect research, etc. – he recommends TaskDrive). Jason sees outbound teams being too assumptive today about what a prospect is focused on and what a prospect cares about. Another common mistake is that SDRs will start with a personalized sentence or two, but then won’t connect it to the rest of the email. It is important to tie it all together to make it relevant and genuine.

Another topic we discussed is setting the right goals for your outbound efforts. Jason advises you should aim to set up a meeting with 3-6% of the accounts you are reaching out to and work backwards from there (reply rates of 5%+ and open rates of 50-60%+).

Lastly, Jason created a framework called the REPLY method to help create a 5-step process for writing cold emails/cold call scripts, and he put together an easy one-page cheatsheet that you can access here. His biggest tip on how to prospect effectively? Lead with curiosity and don’t be assumptive about what the prospect wants or cares about.

If you liked “Outbound 3.0” and want to read more content from the Bowery Capital Team, check out other relevant posts from the Bowery Capital Blog. If you haven’t already, subscribe to the podcast to get all our new content each week!