5 Memorable Sales Insights From SaaStr Podcast Episodes

A few weeks back, I binge consumed a lot of SaaStr podcast episodes.
And after reflecting back on my notes (I tend to be pretty bullish on note taking), there was 5 startup sales insights from the episodes I listened to that were particularly memorable and stuck with me that I wanted to share.
1. Relationship Between Product & Sales People
— From Episode 87 with Michael Driscoll (Michael E. Driscoll)
Context: Harry Stebbings, the host (& my favorite podcast host I might add), asked a thoughtful question about “harmonizing the engineering and sales culture under one roof.”
“Engineers fundamentally don’t just want to build software, they want to build software that has an impact on the world and in a commercial organization, the people that drive that impact principally are the sales folks.” -Michael Driscoll
Quick Commentary:
Provides an insightful macro perspective on the relationship between sales people and product people that is easy to forget.
Really highlights the importance of a collaborative relationship and the importance of the sales team having an open dialogue with the product team as the sales folks are really the one’s working closest with the customers and are in a position to obtain valuable data and input for the product team.
2. First Sales Hire
— From Episode 119 with Mark Roberge & Michele Law (Mark Roberge)
Context: A hypothetical was proposed: you are an early stage startup with a bunch of engineers and things are going well and now it’s time to hire your first sales person. Who do you hire? The big VP at your competitor? A star rep in your industry? Who is it?
“What you need are a couple characteristics. You need somebody who knows how to sell. But equally important knows how to listen because you are still testing your product market fit, you dont know what the sales playbook is…you need somebody who can wear multiple hats…who can sell but also can help you connect the dots both for the product and the customer, for the sales playbook, for the go-to market, for everything…” -Michele Law
“Think about in the early phases of your business, what is more valuable from those first 100 dials you do: is it the customers and revenue or is it the feedback? And what is the sales person that is going to enable that learning and feedback” -Mark Roberge
Quick Commentary:
This episode was loaded with sales insight. Fascinating episode.
This particular topic on early stage sales hires highlighted that sales hires need to be made with close consideration for the exact role you are looking to hire for.
For instance, the skills needed to be successful in an early stage sales role are much different than the skills needed to be a successful VP at a large organization.
Mark effectively highlighted this point by touching on the importance of considering whether revenue is your sole focus or if customer learning and acquiring valuable feedback is the main focus.
3. Different Types of Sales People
— From Episode 86 with Auren Hoffman (Auren Hoffman)
Context: Auren Hoffman, speaking at Saastr Annual 2016, shared 5 core lessons that he learned as the CEO at LiveRamp, one of them being on the 2 types of sales people out there.
“There are basically 2 types of sales people: there are product oriented sales people and there are relationship oriented sales people. And you need to figure out what type of company you are..because it’s really going to change the type of sales people you need. The relationship oriented sales people are the typical sales person you find…they are outgoing, they are extroverted, they are your friend…they will talk to you when you are on the airplane…they are the life of the party. If you are selling a product with a lot of competition and not as differentiated, that relationship oriented sales person will be very valuable. The product oriented sales person…when the cocktail hour comes they go to their hotel room and shoot off like 50 emails, they are just as competitive as the relationship oriented sales person….much more into the weeds of the product and much more technical…if you have a product that is really different, then you want the product oriented sales person “-Auren Hoffman
Quick Commentary:
Auren did preface this segment by acknowledging that this perspective is “controversial”. But I found this perspective very insightful and made a ton of sense to me.
To me, it really highlights the importance of sales professionals taking an honest inventory of who they are and ensuring that they best position themselves for success by pursuing a role that is in line with their personality and strengths/desired strengths.
Being sold on the product you are selling is a prerequisite in my view, but it’s also important to think critically about how the product you are selling and the skills required to succeed with such product aligns with your strengths and personality.
He went on to say that one of his biggest mistakes as a founder was hiring extroverted people to sell differentiated products. Highly recommend listening to the entire segment.
4. Asking Great Questions
— From Episode 88 with John Barrows (John Barrows)
Context: John Barrows is a leader in the sales industry. He trains sales professionals at many tech companies including Salesforce, Twitter, Box, & LinkedIn.
“If I can’t tie my solution to one or two of the top priorities that you have as a business, then the likelihood of me selling anything is not high. I try to walk in with knowledge about that person, about their role, and things that are going on with their business so that I can ask more educated questions to uncover what those true priorities are…if you ask a dumb question you are going to get a dumb answer” — John Barrows
Quick Commentary:
This episode was full of practical and actionable sales insight. I particularly found a lot of value in John’s insight on the importance of understanding your prospects’ top priorities and being crafty in finding ways to uncover these true priorities.
I think the most important insight that this line highlights is the value and importance of being really good at asking questions.
I also appreciated how he tied his line about dumb questions leading to dumb answers to how young sales reps often reach out to him for advice and start off the conversation by asking him to share his background (information that is easily accessible on his LinkedIn profile).
I jokingly asked him on twitter if I could hop on a call with him so that I could ask about his background and we ended up actually having a great conversation. John is full of great insight and I highly recommend listening to the entire episode.
5. The Future of Sales
— From Episode 84 with Alex MacCaw (Alex MacCaw)
Context: Alex is the cofounder & CEO of Clearbit and was answering Harry’s question about the inefficiencies in sales teams and ways that smart companies make the process more special for the customer.
“A lot of people try to do lead qualification manually which is a mistake. It’s a waste of time. You have to look at the sales process holistically and try to optimize each step of the funnel. “
Alex then went on to discuss a very important point:
“Personalization is the future of sales. As it stand now, every customer gets the same experience. They see the same website, the same signup form, the same backend product and often get the same scripted sales call. People are different and they like to be treated differently. Now the only way you can do personalization at scale is to have more data essentially.” -Alex MacCaw
Quick Commentary:
With the incredible innovation taking place and all of the new use cases of AI & ML, I found a lot of value in hearing Alex’s perspective on the future of sales.
Have done a deep dive on this topic and think his point about personalization being the future of sales is a very important one to consider for companies and for sales people.
Currently it seems like personalization with sales is associated with fairly inefficient practices like additional manual lead qualification and significant due diligence on prospects before reaching out even in volume centric sales.
But with the rise of chat bots, personalized email software tools, and other impressive AI that is able to create a more automated personalized experience at scale that is going to continually improve, it requires sales reps to be proactive with the disruption that is continuing to take place.
And to me a proactive approach would be focusing on investing in skills that technology has a tougher time doing such as being industry experts and a trusted resource that helps people gain a better understanding for their specific situation given the massive amount of information available to people.
