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:

[email protected]
ALL Enterprise Sales Episodes
ALL Sobriety Inspirational Episodes
ALL SDR Episodes
2022 Sales Success Summit
Jason Walker on LinkedIn
Keepsake
Keepsake on Instagram
Keepsake on LinkedIn

Podcasts Mentioned:

Idea to Startup

Jeff Bajorek is taking over the Sales Success Stories Podcast during the 2022 Sales Success Summit.

In today’s bonus episode of the Sales Success Stories Podcast, I’ve got something unique for you. This is an episode that Carson Heady shared on his own Salesman on Fire podcast where he talked through some of the ins and out of both creating and working through a 9-Figure deal. I asked him if I could share this with you here, because there are so many great insights within this particular Sales Success Story. I’ll also mention this again at the end, but if you’d like to listen to my original conversation with Carson here on this podcast you’ll want to go back and look for episode 54 OR you can just point your browser at top1.fm/54 and that’ll take you straight there.

For more, be sure to check out Carson’s Salesman on Fire podcast and our original interview here on Sales Success Stories in episode 54 and of course, top1.fm/54 will take you straight there. Thanks for listening and I’ll talk to you next week.

Anatomy of a 9-Figure Deal That Started on LinkedIn – Carson Heady with Tom Burton from Salesman on Fire

Everyone has a superpower. Lisa Palmer is that she’s an “outside-in thinking” strategist who leads executive peers to envision and surface business value from technology investments. She does this through the intersection of her four primary lenses: Seasoned IT Practitioner, Enterprise Software Leader, Executive Advisory, AI for Enterprise Researcher. Lisa is a Continue Reading …

Until Tom Barnes very recently stepped into a new Head of Sales role at Praxis Labs, he was the number one Enterprise Sales Director at Humu, an organization with a mission to make work better with science and machine learning. Tom has the Continue Reading …

I don’t know about you, but I’m constantly on the lookout for every possible competitive advantage I can find to try to improve myself and my results. It’s a huge reason why I started this show. Selfishly it allows me to build relationships with and learn from the best of the best in sales today. Unselfishly I record those conversations so you can listen in and learn alongside me.

In addition to listening to these stories and gleaning the insights from top performers, one of the most powerful performance enhancers I’ve found isn’t illegal or even unethical. I think of them as Performance Enhancing Events

Of course, I’m talking about the Sales Success Summit where I’m able to bring many of these top performers who you’ve heard on this show together so that you too can meet them, talk with them and learn from them. The most fun part is that they’re just engaged as you are, because they’re taking advantage of the opportunity to learn and network to further improve their own results.

How do you think they got to be top performers in the first place?

Last week I was able to round out the speaker lineup to address some critically important topics like team selling, prospecting, and one of the most important differentiators I’ve found in top enterprise sellers that I don’t believe is adequately addressed in any sales book out there, and that’s how to manage the internal sale inside your organization.

As I record this we still have tickets available and you can be in the room and be a part of this rather intimate Performance Enhancing Experience where the content is killer, but it’s not even the most important thing. The connections and conversations you’ll have can be way more impact if you really get engaged and involved in the event and to help with that Jack Wilson and Chris Watson are helping me develop the best after-party experience yet in addition to all of the time you have to connect over breakfast tacos, bbq and potentially even some special milkshakes.

Do yourself a favor and click over to Top1Summit.com to make that investment in yourself and grab your ticket. Now if you just can’t make it out, thanks to Outreach and Gong you can still get access to the videos of the presentations for FREE. The registration for those is on the same page at Top1Summit.com. That’s T-O-P the Number 1, S-U-M-M-I-T dot com.

Now those of you who are already on the listener list and got my email on Sunday, because I always try to give those subscribers a little bit of a head start and a sneak peek. They know that I promised something a little special in today’s episode. Here’s what I’d like to do, because the secret ingredient at the Summit is the quality of attendees. My being able to put the best, most committed, and motivated people I can find together in the same room is what creates the real magic.

If you’re one of those people and you don’t have a ticket yet. I want you to sell me on why you need to be at this year’s Summit. I’m not going to tell you how to pitch me. It’s up to you to figure out the right channel, the right tools, and the right message. But if you put in that little bit of effort and impress me. I might be willing to do something special for you to make it that much easier for you to join us at the Summit.

You’ve gotta do the work, and I can’t wait to see your approaches and creativity.

I’ve got one other idea. Referrals and recommendations are powerful things. If you have a friend that’s one of us. They’re committed to sales as their career, as a true profession, they’re constantly learning and trying to improve and they need to be in this room. Nominate them. Tell me why they need to be a part of the most impactful part of the Sales Success Community. Don’t forget to let me know how I can get in touch with them.

The last suggestion I’ll make is for sales leaders. If you are committed to your team and you want to see them succeed. Consider bringing at least a couple of your top performers, or those who are working the hardest on the inputs who really deserve a reward.

Next week you’ll get to hear my interview with Tom Barnes. It’s a great one and I can’t wait to share it with you. He tells the story of how Paul DiVincenzo brought his team to the Summit last year. Now Paul’s been on this podcast and attended multiple Summits and knew the value and Tom was a member of Paul’s team. Tom walked out of that event just a few months into his role as an Enterprise Sales Director at Humu and went on to become their #1 top seller himself this year. He’s since accepted a Head of Sales job at an early-stage startup and is bringing his own team to the Summit this year.

If that’s not the best testament to how powerful this event is, I don’t know what is. So consider bringing at least a portion of your team to help them achieve new levels of performance. Don’t worry, we’ll provide the oxygen to help them get there.

That’s it for today. Your only task right now is to go to Top1Summit.com. Hopefully, you’ll buy a ticket and join us, but at the very least make sure you register to get access to the videos.

Then make sure you’re subscribed to the podcast because Tom’s story that will release next Tuesday is one that you don’t want to miss.

Thanks for listening!

Sebastian Amaya is the top seller at IBISWorld, an organization that provides trusted industry research on thousands of industries worldwide. In his role, Sebastian leverages his experience and acumen to provide businesses with market insights and strategic outcomes. Sebastian is an Continue Reading …

Steve Reed is the Creator of Experiences and top seller for the Minnesota Vikings. In his role, Steve provides the very best experience in sports for client entertainment by offering the complete package, including food, drinks, a spectacular view of the action and so much more. Growing up as a superfan of the Vikings, Continue Reading …

And now for something completely different. I sent a newsletter out a couple of weeks ago that wasn’t really directly related to sales at all.

Instead, I was talking about a couple of books that I was reading on macro economics and what the future of the world might look like. It prompted some really interesting conversations and feedback. And one of those bits of feedback was that it was nice to get away from the pure sales content sometimes.

I thought I’d lean into that a bit as we start to wrap up the summer and wanted to share my favorite recent non-fiction read, and by “read” I actually mean listen on Audible. This was “Project Hail Mary” by Andy Weir. You may recognize the author as the author of “The Martian” which was another book I absolutely loved.

Now, he did a book in between called “Artemis” not my favorite, but “Project Hail Mary” is amazing. I highly highly recommend it. And I’d also love to hear what you’re reading, or your favorite recent reads. I might even include some of those in a future newsletter.

You can email me at [email protected] or feel free to send me a note on LinkedIn, and if you’re not already on the listener list and receiving these newsletters. Click over to top1.fm and drop your name and email address into one of the forms.

Thanks for listening, enjoy the rest of your Summer and make sure you’re subscribed to the podcast so you don’t miss my next interview with a top-performing sales professional.

Mike Anderson is the Top Strategic Account Manager at Terryberry out of Chicago, Illinois. Mike strives for excellence and aims to meet all of his customers’ needs. For Mike, sales is an adventure, one that should be joyous and fun. Today, Mike talks about his Continue Reading …