Perspective is everything, and nobody knows that more than today’s guest, Jason Walker. That’s because Jason recently went from President’s Club to being let go by his company, an event that would rock most people’s worlds. Instead of letting it get him down, Jason took this moment as an opportunity to pursue an idea that he’s had for a very long time. Hence, Jason’s self-described title of ‘Accidental Entrepreneur.’
Jason is a sales leader and tech founder who is commercially astute and vision-driven. He has over ten years of sales pipeline management, and operational strategy experience across a breadth of sectors – from renewables & environment through computer software, to e-learning. Jason is widely regarded for his propensity in leading business growth solutions, and today he joins the show to share his sales origin story, his journey to entrepreneurship, and challenges he anticipates facing as a first-time founder. Jason shares the top three things he attributes to his sales success, including gaining customer trust in a sincere way, understanding that context is king, and knowing the most about his product.
Jason gets specific, answering audience questions about how he thinks about crafting his pitch, what he thinks about developing competence and expertise, and what drove him to go ‘all-in’ on his idea. Jason speaks to navigating the sales process during product development, knowing when to share pricing with customers, and strategies for co-selling. Finally, Jason talks about the competitive landscape, the intentionality of spending more time with collaborators, and what has resonated with Jason the most throughout his time at the Sales Success Summit.
What We Covered:
00:24 – Scott introduces today’s guest, Jason Walker, who joins the show to share his unique journey from Sales to Entrepreneurship
07:20 – The top three things Jason attributes to his success
07:37 – Number One: Time to transparency – Gaining customer trust in a sincere way
08:06 – Number Two: Context is King
09:05 – Number Three: Know more about your product better than anyone else does
10:05 – Jason details his journey to entrepreneurship
12:17 – The process of getting to trust quickly
13:39 – The inflection point that led Jason to launch Keepsake
14:51 – Challenges Jason anticipates as a first-time founder
16:25 – How Jason thinks about crafting his pitch
18:01 – Developing competence and expertise
19:06 – What drove Jason to go ‘all-in’ on launching his own company
21:17 – Navigating the sales process during product development
22:46 – Knowing when to share pricing
23:38 – Jason’s sales origin story
25:18 – Healing, experience and challenges
26:25 – Strategies Jason employs to minimize the time to transparency
27:20 – The co-selling process, explained
28:40 – Choosing to spend more time with collaborators
30:16 – Understanding the competitive landscape
31:36 – Jason’s mindset going from President’s Club to being let go
33:19 – Why curiosity is the most important trait to have
34:53 – What has resonated the most with Jason throughout his time at the Sales Success Summit
35:29 – Scott encourages listeners to subscribe to the podcast for his follow-up interview with Jason Walker
Tweetables:
“I’ve been a ‘Sales Guy’ my whole life. I had no intentions of being an entrepreneur in any way, shape, or form. But, ideas happen and, if you’re like me, I’m a thinker, and sometimes ideas don’t leave. And if they don’t leave, they can turn into something different.” (03:27)
“Context is a full-circle thing. Context is understanding the problem well enough to be able to solve that problem in a meaningful way, but also making sure you’re explaining your things in a certain way.” (08:37)
“If you can come in as an expert – someone who knows this way better than them – you have the ability to provoke new thoughts, new lines of thinking, and new ways of thinking about the problem, which allows you to position your product in a much more unique and strategic way.” (09:17)
“One of the most powerful things you can do is own what you’re not. And own it, because either A.) you’re trying to sell to the wrong customer, or B.) they’re the right customer and they don’t care what you don’t do. Roadmap selling, future selling is just a disaster.” (21:50)
“So, going through these challenges and being forced to look in the mirror and understand who you are, and what you’re about, and really what lights you on fire, it’s a byproduct of that. . Once you’ve taken the time to understand the learnings you’ve gained from that, how strong you are, and what you’re capable of, if I fail at this, who cares? We have skills, as salespeople, where we will never not have a job in my opinion.” (25:53)
Links Mentioned:
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2022 Sales Success Summit
Jason Walker on LinkedIn
Keepsake
Keepsake on Instagram
Keepsake on LinkedIn