In one line
Jason Walker went from winning AE of the Year at e-learning company Go1 to being unexpectedly let go days before President's Club — and turned that week into the launch of his travel app Keepsake, recorded live at the 2022 Sales Success Summit as a self-described "accidental entrepreneur." His playbook: shrink the time to transparency, treat context as king, and know the problem better than the customer does.
Who is Jason Walker?
Jason Walker is a sales leader and first-time tech founder based in Utah. He was the longest-standing and top-performing enterprise sales rep at Go1, an Australian software company that aggregates e-learning content into one place ("what Spotify did for music," but for corporate training) — where he grew from ~$80K in a debut year with no real product to sell (against a ~$480K quota) to 156% of quota and a President's Club qualification, before being let go right after winning AE of the Year. Earlier in his career he sold golf balls back to golfers, upsold car washes, and did solar, TV, and high-technical enterprise sales for SolarWinds (IT monitoring software). An idea that "wouldn't leave" became Keepsake, a travel app that automatically crowdsources and centralizes a trip's photos and memories — which he pivoted toward B2B event engagement and demoed live at the Summit the week he was laid off.
Key questions answered
What are the top three things Jason Walker attributes his sales success to? Per Jason Walker, on Sales Success Stories, the three are: (1) time to transparency — how fast you can earn a customer's trust in a sincere way so their feedback is authentic; (2) context is king — understanding who you're talking to and explaining your solution in a way they can grasp and re-explain internally; and (3) know the problem your product solves better than the customer does, so you can come in as an expert and provoke new ways of thinking. 0:07:34
Why did Jason Walker leave a sales job he loved to start Keepsake? Per Jason Walker (Keepsake), he had loved his Go1 job and was good at it, and the hardest thing was deciding when to actually commit to a venture he wasn't "educated in" while supporting a family. What decided it was regret: if he'd seen his own idea on the market having not built it, "I would have regretted that my entire life." A layoff right after qualifying for President's Club forced the timing. 0:19:42
How do you sell a product that isn't fully built yet without selling vaporware? Per Jason Walker, on Sales Success Stories, "one of the most powerful things you can do is own what you're not, and own it," because either you're selling to the wrong customer or they're the right customer and don't care what you don't do — "roadmap selling, future selling is just a disaster." Owning what you do and don't do makes deals cleaner and customers happier. 0:21:27
When should a salesperson share pricing with a buyer? Per Jason Walker, if a buyer asks for a price, give them pricing (with context) rather than hiding it: refusing to share until "I got to have this conversation first" reads as a red flag — "this guy just wants me for all my money" — and once you lose that trust, you lose it forever. 0:22:27
What is Jason Walker's origin story — how did he get into sales? Per Jason Walker, on Sales Success Stories, he's an ADD "thinker" who was "forced into sales by default" because he likes to talk to people and problem-solve. He sold found golf balls back to golfers for $2 apiece, upsold car washes, then moved through solar sales, TV sales, and enterprise IT-monitoring sales at SolarWinds, into learning & development at Go1, and finally to founding his own company. 0:23:59
How did Jason Walker stay grounded going from #1 rep to being let go? Per Jason Walker, it came down to balance and confidence: his first thought was "you guys are stupid" because he knew he could pivot to a competitor if needed, so he wasn't worried about himself. Having worked through real personal challenges, "if I fail at this, who cares? We have skills as salespeople where we will never not have a job." 0:32:05
Frameworks & concepts
- Time to transparency — the speed at which you can earn a customer's sincere trust; minimize it and, per Jason, "competition doesn't really stand much of a chance." He aims for the sale to feel like "hanging out with a friend" so customers are excited to show up.
- Context is king — a "full-circle thing": understand the customer's problem well enough to solve it meaningfully, and explain your solution so they can re-explain it to others internally, connecting dots buyers don't yet have.
- Own what you're not — transparently stating what your product does and doesn't do; "roadmap selling, future selling is just a disaster," so owning the gaps yields cleaner deals and happier customers.
- Co-selling / partner selling — pairing with a complementary rep (here, Alex Smith, whose product Jason's content "sits inside of") to present a single, stronger solution on the same call; Jason maintains 7–8 active partner relationships, investing most in the ones open to collaboration.
- Consensus / internal-collaboration selling — addressing the "holes in sales processes" around how a champion influences the stakeholders they don't directly control on the customer side.
- Curiosity as the core sales skill — "curiosity is your most important thing you can have in sales," because the more questions you ask, the more you understand the real challenges behind a buyer's role.
Notable claims
- Per Jason Walker, in his first year at Go1 he sold about $80K against a roughly $480K quota with essentially no product to sell, then reached 156% of quota in year two once the product and his understanding of the customer improved.
- He was let go from Go1 right after winning AE of the Year and after qualifying for President's Club — the layoff freed his calendar to attend the Summit and demo Keepsake.
- He maintains 7 to 8 active co-selling partner relationships and credits partner selling (with Alex Smith) as a major driver of his quota attainment.
- Per Jason, Keepsake reached a first working beta version the day before the Summit; its B2B pivot crowdsources event photos into one place and sends real-time feedback prompts for social-selling use.
- He worked with startup-coaching company TackleBox (host Brian Scordato, podcast Idea to Startup) to validate the idea before going all in.
Companies, tools & books mentioned
Companies & organizations: Keepsake, Go1, SolarWinds, TackleBox, Sales Success Summit.
Tools & platforms: LinkedIn, Zoom, Spotify (referenced as an analogy), 10-Ks and news reports (research inputs).
Podcasts mentioned: Idea to Startup (Brian Scordato / TackleBox).
People referenced (past Sales Success Stories guests): Alex Smith (co-selling partner), David Weiss (recession-proofing-your-career panel), Chris McNeill (partner selling), Jheryn Kenney.
Connect with Jason Walker: LinkedIn · Keepsake.
Quotes
"I've been a sales guy. I've been a sales guy my whole life. 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 ideas sometimes don't leave. And if they don't leave, they can turn into something different." — Jason Walker 0:03:24
"Context is a full circle thing. It's context, understanding their problem well enough to be able to solve their problem in a meaningful way, but also making sure you're explaining your things in a way." — Jason Walker 0:08:38
"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. Because roadmap selling, future selling is just a disaster." — Jason Walker 0:21:27
"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. ... If I fail at this, who cares? We have skills as salespeople that we will never not have a job, in my opinion. So go try." — Jason Walker 0:25:40
"Your network is everything. Your network dictates your success, because if you have a good network like this, you hit a bump in the road, there's like 100 people to fall on." — Jason Walker 0:35:10
0:08 Scott Ingram: You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights and strategies to help you improve. To learn more, visit us at top1.fm. Here's your host, Scott Ingram.
0:24 Scott Ingram: So today on the Sales Success Stories podcast, we have got a really, really interesting, unique, never happened before type of conversation. And to make it more fun, we're live at the 2022 Sales Success Summit. Awesome. And I'm with Jason Walker. And Jason and I had an interview scheduled together last Friday, a week ago Friday.
0:52 Jason Walker: Yeah.
0:53 Scott Ingram: And Jason was the top performer in his company. And we were going to talk about that like many times over. Incredible track record. I couldn't wait to dig into this interview. And we started that interview. I think we might have had a miss, like we had to reschedule. So we finally get together, we start this conversation, and I'm just kind of checking in, right? A little pregame. What's going on? I'm going to let you kind of take it over from there. Like, what happened? What kept us from actually doing an interview that day?
1:19 Jason Walker: Well, it's complicated to say the least, but to simplify things for time's sake is I was let go from my job unexpectedly right after winning AE of the Year or whatever you want to call it. And I still am at a loss for what I, you know, where to go from here. But similar to David, the network, you know, opportunities are already there. Yeah.
1:42 Scott Ingram: So anyway, so the most interesting part of this, so we're talking through this, I mean, it becomes like, okay, forget this interview thing. Like, let's just kind of unpack this and talk this through and, you know, what happened and where are you at and how do we help and All of this kind of stuff. What then transpired is like, well, I've been doing kind of this thing on the side. It's kind of funny the timing and the way this worked out. At the same time, I'm going to give away probably too much, but I'll let you give the backstory of kind of what you were working on. We were kind of finalizing the contracts and the structure for the production of this event. And one of the things I was trying to make a decision on that I've always kind of missed Some of you might know the story from last year. Spent a lot of money to do kind of all of the B-roll footage for the event, 'cause it's so hard to articulate the value of what this is, right? I was trying, we were trying really hard to show it. And so we did all of that and man, we had lots of great interviews and just all this capture and all this great footage. And all of that was filmed with a camera that was rented. And it was just a very busy time in the land of production. There was a lot going on in the world. That camera got returned with the memory card in it. And the process of the rental company who immediately turned the camera around is they delete all of those, that footage. So we lost 3 days worth of content. But what I was debating, I was like, you know, I've always invested in the video side of this, but we should get some photography and some footage of this too. And so we're talking about, you know, do we hire a photographer? It's kind of a pricey proposition. I was literally in the middle of that debate, and Jason tells me, oh, I've been working on this other thing on the side. So I'll let you pick it up from there.
3:24 Jason Walker: Yeah, this is actually very interesting, and probably where you want to go with this is I've been a sales guy. I've been a sales guy my whole life. 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 ideas sometimes don't leave. And if they don't leave, they can turn into something different. Different. And so I don't know if you want to go into like backstory from a time perspective, but we'll say from a high level, have you ever gone on a vacation with the people that you love, people that you experience things with, and try to recreate those memories or experience those memories after the fact conversationally with whatever, and you don't remember the things that other people went with you? This is hard to explain live, just realized. But anyway, You know, what my app is designed to do is memories make connections with the people that you love. Not remembering the things that you do with people you love create disconnection. And so what my app does is it takes… it's a travel app that allows you to go on a trip with your friends or your family, and it automates the process of taking all your photos, interactions, and it puts it all into one place automatically for you. It allows you to kind of crowdsource your vacations, kind of and centralize them. But that's kind of where the idea came from. You know, that's the conception. But where it comes into play here is what my technology has allowed me to do is kind of pivot into B2B. And that's why this technology allows us to crowdsource all the photos from here into one place. And what it's supposed to do, which I didn't get a test here, is create engagement where it's going to send you notification questions to get your real-time feedback of this vacation or this event for the organization. They'll use and control the photos, which you can share on social media for social selling purposes.
5:06 Scott Ingram: Yeah. So it's a lot to explain. The way this conversation goes though, I'm not quite sure how we got to the app. I think I was just asking like, what's next? Where do you go from now? And this was like real time. It had happened the day before or that morning. So I'm like, I get you're processing.
5:19 Jason Walker: Yeah.
5:19 Scott Ingram: But you know, let's just kind of talk this through. And he's like, well, I just finished developing and we released the first version. Nobody's even seen this. Like nobody had seen it.
5:28 Jason Walker: Yeah, I have the first working beta version. Yeah. Today.
5:32 Scott Ingram: So he's like, I just…
5:33 Jason Walker: it's that new.
5:33 Scott Ingram: I just got this. And I was thinking about making this transition, so maybe this is a sign. And he's walking me through what it is and talking about sort of, oh, it's for families and vacations and things like that. I'm like, yeah, but what if it was for a conference? What if we used it at the summit like next week? And so that's what happened. So you guys saw that ask. I said, you know what? Get on a plane. Well, you had thought about coming to the summit.
5:57 Jason Walker: I was already coming to… better part of the story, sorry. I had qualified for President's Club, which is scheduled for this week. I had tickets to this previously. I had to let Scott know that I couldn't come a while ago. And so you oddly reached out to me through the podcast right after I had realized that I had the free time to come here and test my app conveniently.
6:18 Scott Ingram: Right. You're like, hey Scott, I can't go to the summit. I've got to go to President's Club. Pretty good excuse.
6:22 Jason Walker: Yeah.
6:22 Scott Ingram: Get laid off, no President's Club, free to come to the summit.
6:25 Jason Walker: Yep.
6:25 Scott Ingram: Like, you need to come back. You need to come back. We're gonna play with this app. We're gonna do this whole thing. And I always intentionally leave this spot open, right? I leave a time on the afternoon of the second day because something's gonna happen. Something relevant is going to come about. And what we're experiencing right now is just all kinds of weirdness with people getting laid off, with the economic situation and everything else. So I'm like, this could not possibly be any more relevant and any more timely. We'll allude to the panel conversation that nobody outside of this room will ever get to hear because of the places that we went. But David was talking about, David Weiss was talking about how to recession-proof your career. And it makes sense to have kind of other projects and things that you're working on so that you have other angles and other places you can go. And so just the real-time nature of this experience was absolutely wild. So that's the backstory. Let's do a little bit of contextualizing.
7:23 Jason Walker: Yes.
7:23 Scott Ingram: Just in terms of what you were doing. So the first place I always go with these interviews is immediate value. Give us the top 3 things that have contributed the most to your success in sales.
7:34 Jason Walker: Yeah, I had a really hard time actually narrowing it down to 3, but my number one thing that I've learned over my sales career is time to transparency. Is how fast can you gain your customer's trust in a sincere way where when you get a question, you're gonna get authentic feedback. And if you can find a process or a way to do that as fast as possible, competition doesn't really stand much of a chance unless your product blows, which maybe some of you guys deal with. Some of us have in the past for sure.
8:04 Scott Ingram: So, all right, we're going deeper on that, but give us number 2 and 3.
8:07 Jason Walker: So number 2 is context is king. Your customers talk to a lot of vendors. They talk about a lot of problems and you're probably solving one of them. And so understanding who you're talking to, explaining it to them in a way that they can understand it and a way that allows them to solve the problem to other people is extremely important, I guess, because that's where the loss is in the details or in the lack of understanding or the miscommunication or all the millions of different things.
8:33 Scott Ingram: So is that really just about understanding them? Like this is the what's in it for me kind of piece and connecting those dots?
8:38 Jason Walker: Context is a full circle thing. It's context, understanding their problem well enough to be able to solve their problem in a meaningful way, but also making sure you're explaining your things in a way… because when we pitch our products, we know it, we talk about it all the time. And so when we pitch our product, we assume that they understand this normal line of thinking that they probably don't have. And so we have to help them connect dots, and you have to confirm that so you can move the deal along in a more meaningful way. You don't waste your time on deals that don't make sense.
9:06 Scott Ingram: Nice. Third thing.
9:07 Jason Walker: Third thing is know more about what your product does or the problem your product fixes or solves better than they do. So what I mean by that is if you can come in as an expert, somebody that 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 strategic way.
9:33 Scott Ingram: Nice. I guess that, I think, interestingly kind of ties back to what Jheryn was talking about earlier in terms of the brand and the roll out the red carpet before you arrive, right? If you have that reputation of being somebody that facilitates really valuable conversations, right? Because I can connect those dots for you, I can facilitate value. So let's now get some of the context, and then I really want to come back to your process around kind of getting to trust. I think that's a really interesting topic for us. And then we're gonna start a line and I'm gonna make this a really easy interview for me. You all ask all the questions, but I mean, talk about whether you wanna name the company or not, but talk about kind of what you've been up to, what the results have been, and what the recent experience has been until the inexplicable event.
10:15 Jason Walker: Yeah.
10:16 Scott Ingram: Inexplicable.
10:17 Jason Walker: I like that. So I was working for a software company called Go1, which to simplify is doing what Spotify did for music and aggregating all the music into one central place. It does that with e-learning content for organizations. So it gives you one place to have every piece of training. Anyway, so I've been there since it was brought to the United States because it's an Australian-based company. I was there as their second cohort in the US. The first cohort was let go very, very quickly. And so I've been the longest-standing sales rep there for a long time. The first year I was there, we didn't really have a product to sell and I sold about $80K. Not great. My quota was like $480K. Not a good thing. Year 2, quotas went up, product got better, understood the product, how to sell it, and figure out who our customer was and why our product mattered. That got me to year 2, 156% of my quota, a top-performing rep. Year 3 is where I met Alex Smith, and he's the sole reason why I hit quota. No, I work with Alex Smith as a… we work together. He works at another… but yeah, he works for an LMS or a learning management system, and so we jump on calls together and we sell together. So understanding the value of partner relationships, understanding how if I provide Alex Smith the value I provide my customers, he's gonna wanna work with me more than not work with me. And I think it would be valuable to have a conversation with Alex Smith and myself at some point, 'cause I just think that channel and relationships on every level, not only from a strategic selling perspective, but just customers that value you and trust you will come back to you. Also stay in the same vertical as much as you can.
11:48 Scott Ingram: Yeah, great, great stuff. I mean, Tom called out earlier, like, we just overlook referrals. And I've been saying that forever too. Like, we go after the coldest, hardest thing. Like, wait a minute, you already know somebody that can introduce you, right? There's somebody else in that organization. That goes for whether you're looking for a job, you're looking to get introduced to an executive in a new opportunity. I mean, there's just so much of that stuff. So where am I going? Why isn't there a line? There's got to be a question. Alex Smith is going to come save us.
12:15 Jason Walker: I got water now, so I'm fine to talk.
12:18 Scott Ingram: Okay, so I want to come back to the idea around kind of developing that trust. You said that there's a process, like getting to trust quickly. What is that process? Because I imagine that's not just those customer conversations, it's with a potential partner conversation.
12:31 Jason Walker: Yeah, I mean, it's hard to say. It's authenticity, I guess. It's my desire to have a transparent and safe environment. For my customers. So what I try to do is I bring transparency, I bring humor, a lot of it, and I go out, I was like, I don't care if I earn your business or not. I just want the chance to show you what we have or to understand your problem. And by the questions I ask, and the more curious I get, the more trust I get, I guess. It's really hard to answer as a singular process 'cause I may talk to a person that doesn't wanna deal with my jokes. And so I have to tone it down as much as I can, which is not a lot, but I have to adapt to my customer to get them to feel safe and want to have fun with me on the call. So they want to show up to my calls and like, you know, I've had breakup calls, but they want to show up to do it, which is good, I think. Yeah.
13:19 Scott Ingram: My style is similar. Like, I enjoy the humor. What I watch for is if I get the same looks from my jokes that I get from my kids. Okay, time to tone it down. Grace, what do you got for us?
13:30 Jason Walker: That's probably a good reference point. When you start getting looks similar to the way your kids look at you when you make a dad joke. I got dad jokes for days. Comes with the territory, from what I'm told. So my question is, so for Jason, we all most of the time have ideas. And for you, there was an event that went, okay, I'm gonna step off and I'm gonna take the risk and do this thing full-time. And that's not always the case. And so what was the inflection point for you of, okay, this idea won't leave. But I'm gonna keep doing what I'm doing and it won't leave and I now need to do something about it. Yeah, it's a hard thing to answer because, at least for me, I didn't know what to do with the idea I couldn't stop thinking about. Yeah. The most consistent advice I've heard is find mentorship, find coaching, find someone that's done it and let them teach you. Don't try to figure it out on your own. So I went to a company called TackleBox. He has a podcast, his name is Brian Scordato. I'll plug him here. And his podcast is called Idea to Startup. And the whole concept is taking an idea, validating it, talking to people to see if it's a real problem, and leveraging that. And as you kind of go through that process, you feel more confident in it. And then you get fired, and then you're forced to do it. So that's how it works.
14:47 Scott Ingram: There you go.
14:48 Jason Walker: Yeah, that's my experience at least. Good question. Thanks.
14:51 Scott Ingram: Tamina.
14:52 Jason Walker: Hey, Jason. Kind of to follow on that same thread, What has been the hardest part for you? I know it's not been very long, but what has been the hardest part, or what do you anticipate being difficult for you as you step into a founder position and move into being an entrepreneur and not solely focused on sales? Terrified for my life. I can give more context, but that would be the overall feeling. I mean, I don't know what I'm doing, right? I'm a sales guy. I'm in software. And this is something I would challenge everybody that maybe has interest is you as software people understand how software works. Or problems that software doesn't fix. And that's how I started thinking about this idea as I leveraged my software experience, I guess, and put that into like this idea. And now the way that it operates is based off of like my understanding of how LMSs work. Does that make sense?
15:40 Scott Ingram: Yeah.
15:41 Jason Walker: I don't know if that answered your question directly, but… So you feel like because you have experience with the software and the space, you have more confidence moving forward? You're gonna see a lot differently. Yeah, your experience provides a very, very unique way to look at the world. And so that software experience allows you to see aggregation from a much different perspective, aggregating content. So that's why my idea is centered around aggregating, because I get how that works and how much that simplifies lives for organizations I work with. So how do I apply that in another industry, or how do I look at another problem and just let it ideate for a while? And you'll start just noticing things. Awesome. Thank you.
16:16 Scott Ingram: Really not that helpful.
16:16 Jason Walker: Appreciate it.
16:17 Scott Ingram: Well, you've been a founder for a week, so, you know. Yeah. Yeah.
16:22 Jason Walker: They call me an expert.
16:24 Scott Ingram: All right. Come a long way.
16:25 Jason Walker: Yeah.
16:27 Scott Ingram: Like, I can just, you know, attest to the fact of when you said context is king, how you present and do it in a very concise way of 5 minutes. I would bring you in on calls and in 5 minutes he could kind of go through just specifically what this solution is going to do for the customer and open up conversations and to give context. You would not just say this is the Spotify for learning, but you would be like, you know when you would get kind of those Britney Spears songs, like one, you had to go to Tower Records and just buy that. To get that one song, you had to buy the whole CD. And like you, when you bought your Backstreet Boys songs in the '90s, instead of buying them one-off, you could just get… Spotify changed that by just making it really easy to pay a subscription fee. My question to you is, how do you think about… I think context is so, so key. How do you think about crafting your pitch in a way that really, like, lands on the person differently? Because it's not just the same pitch. I hear you deliver it differently to the person. So how do you think about it or really make it your own?
17:28 Jason Walker: It's a complicated question, actually, because I think it comes down to, for me, and what you've seen is expertise and my ability to know enough to know what to do with different customers and how to talk to them. Right? But it really is all going to come down to your questions, your discovery, and understanding the person you're talking to so that you can intuitively know how to talk to them. And that's the best way to explain it, I guess, because it's not really a tactical thing like an A plus B equals C thing. It's very nuanced. And as you've seen it, I adapt as much as I need to, but I couldn't tell you like the methodology behind it. Does that make sense? It does. I like it. Now actually answer your question again.
18:04 Scott Ingram: Jason, how are you like developing that expertise? Because again, you're sort of suggesting that you're to a place where it's a little bit unconscious competence type of thing, right? I don't have to think about this, I do it. How do you get to that place?
18:16 Jason Walker: Discovery. Again, it's understanding your problem, the problem you're solving better than your customer. Educating yourself on the space, what challenges they experience. The way I like to look at, especially I sell into learning and development, and something if you sell into that space, those are people people. They love people. And so usually they get into an HR role is to help people, like they're passionate about it, but they're bogged down by all these little processes and procedures and things that don't let them do the thing they want to do. So I spend time understanding that problem. And that is pretty common theme across all of the people I talk to in different forms, right? But if I can understand what lights them on fire and what challenges are preventing that fire from being lit, and I can pull some of those away, that's gonna make me stand out significantly more, and it's gonna allow me to…
19:04 Scott Ingram: Brilliant.
19:05 Jason Walker: Does that make sense?
19:05 Scott Ingram: Yeah.
19:06 Jason Walker: What's up, Jason? Hey.
19:08 Scott Ingram: I'm curious, as a sales rep to founder, someone who did this a little over a year ago, what drove that decision, and specifically around the timing?
19:17 Jason Walker: I was scared in the sense where I wanted to prove out the model before I ended up leaving and have a certain income that could at least surpass or replace.
19:27 Scott Ingram: So it was easy and confident, but knowing kind of where you were, and I'm just curious your thought process around why leave versus why do it on the side and prove it out and kind of where you're at with that. What drove you to just go all in right now at this point?
19:42 Jason Walker: Well, I loved my job a lot and I was really good at it. And that was the biggest thing I didn't want to face over the last year is like, when do I actually commit? And move forward and leave this other thing that I love behind that I know I'm good at and I know is going to bring my money in and I know is going to support my family and I know it's not that risky to do this thing that I am not educated on in. Like, I'm not a founder over and over again. I've done sales and I understand that really, really well. There's a lot of part of this I don't understand, and that's scary when you have family and kids. And I guess just to elaborate on the question, you talk about the idea won't leave, but just talk about the calling In other words, if you died tomorrow, would you have regret of not going for this? Was that part of the decision of doing this all in on your own business? Yes, that was the biggest reason. Sorry, thanks for clarifying. That was my question. Yes, thank you. 100% regret. I didn't want it. I had something. I didn't know if it was great, but if I would have saw that on the market, I would have regretted that my entire life. And it's not worth the risk. And getting something developed is not as expensive as you think either.
20:47 Scott Ingram: Just fun fact. For those of you in the room, this is the reason why we need to take lots of pictures tonight. And I think there's going to be lots of stuff to take pictures of. So that'll be exciting. For those who are listening on the podcast, hopefully we'll have something to show. We'll actually be able to do a little bit of a demo and hopefully kind of show off what that summit experience looks like because we've crowdsourced your images and how much fun you've had. So yeah, this is going to be some fun.
21:11 Jason Walker: Yeah. Yeah. Yeah. So actually on that point, Connect with me on LinkedIn so we can connect so I can get you access to provide the photos for this. Hey, Jason. Hey.
21:20 Scott Ingram: As sales reps, we often feel really handcuffed by our product, what it has, what it doesn't have.
21:27 Jason Walker: You mentioned that at your last company you started when it was pretty bare bones. Obviously, you're founding your new company now when it's just getting started. How do you navigate that selling motion without selling vaporware? And how did those conversations change as the product develops? It's a really hard question to answer in terms of how you approach that, you know, because what I've learned as we've kind of gone through this process of going from a startup to a full-fledged business is 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. Because roadmap selling, future selling is just a disaster and very hairy, very hairy. Like, if you can own what you do And what you don't do, your deals will be cleaner, your customers will be happier, and you'll, you hopefully more revenue will come into the business and better development and better stuff to sell.
22:17 Scott Ingram: Well, and that's part of that trust, right? When you can talk about those things transparently, you're like, we suck at this. We're not the right solution for that, but we're great at that.
22:25 Jason Walker: Right.
22:25 Scott Ingram: People aren't used to hearing that.
22:27 Jason Walker: Exactly. But if someone asks me a price, I'm going to give them pricing if I can with context. You know, like pricing doesn't matter because I don't know your solution. So this is pointless to look at. But we can talk about it if you want to see it. But I don't want to hide it because that, you know, even it's like, well, I got to have this conversation before I can give you a price. Just says red flag. This guy just wants me for all my money. I lose that once, I lose it forever. And it's not worth it.
22:48 Scott Ingram: Say more about that, right? Because this is a whole topic in and of itself, right? This idea of at what point do you share price? What if you don't know enough? You know, just having that context, it sounds like you're on the side of, hey, the buyer wants to know price. Let's give them an idea.
23:02 Jason Walker: Yeah, well, how many times have we heard this week or during the conference that somebody closed a deal significantly higher than the original quote was? Because you understood the problem and were able to produce way more value.
23:16 Scott Ingram: Yeah.
23:17 Jason Walker: And I don't know if it's applicable for everybody, but also there's a huge, huge need in, or a lot of holes in sales processes around consensus selling and internal collaboration on the Customer side, understanding how do I influence those I don't have the ability to influence.
23:33 Scott Ingram: The Harry Deal Man himself. Oh, I hope that's my moniker from now on. Should be.
23:38 Jason Walker: Gotta grow your hair out though.
23:39 Scott Ingram: Hey Jason, I'm gonna ask you a question that Scott usually asks, but he hasn't asked yet, which is what's your origin story and how did that, you know, your family, your friends, your background, how did that contribute to your sales journey?
23:52 Jason Walker: Happy to answer that. Do you wanna save that or do you want me to answer that?
23:54 Scott Ingram: No, answer. He asked the question.
23:56 Jason Walker: Just making sure.
23:56 Scott Ingram: I love it that you guys ask all the rest of my questions.
23:58 Jason Walker: Yeah.
23:58 Scott Ingram: I'm gonna see it.
23:59 Jason Walker: They really don't want me on again. We know him by heart by now. So my origin story is, from a sales perspective at least, like, I grew up in Utah, still there. If you can't tell, I'm an ADD individual, which has forced me into sales by default, I guess, because I like to joke, I like to talk to people, and I like to problem solve. So I've realized that over the last little bit is that's why I'm here. But I've kind of evolved through, you know, I used to go find golf balls on a golf course and I would sell those right back to the golfers for twice, you know, $2 a pop or whatever. You know, I used to, you know, upsell people a car at a car wash. You know, then I've done solar sales, I've done TV sales, you know, then I've done enterprise, really, really high technical sales for, you know, SolarWinds, which is IT monitoring software, down to L&D to starting my own company. That's kind of my journey at a high level. I mean, there's just so much in there. I got 3 kids? I just found out…
24:53 Scott Ingram: oh, sorry.
24:53 Jason Walker: No, no. Hold on. Hold on. I just found out today I'm having a kid. Yeah. You can't release this until my wife tells people. No, I'm just kidding. Jeez.
25:05 Scott Ingram: The pressure.
25:06 Jason Walker: I know.
25:07 Scott Ingram: The editing. Oh.
25:10 Jason Walker: No pressure.
25:12 Scott Ingram: Anyway, this is all the rest of my interviews. Like, I'm retiring from asking questions. I'm going to let you all do it. Hey Jason, that was actually perfect. It teed up my question. What I really admire about you stepping into this new chapter is that it shows that you've really cultivated a lot of trust and belief in yourself. And I'm curious, along those moments in the journey and what you've accomplished so far, what were those key moments that have allowed you to cultivate and build that trust in yourself to take this step?
25:40 Jason Walker: I don't know if I'll be able to get through this. A lot of healing, a lot of experience. A lot of challenges. I grew up in a really religious community. That has challenges on its own. You know, I got married semi-young, had 2 kids, got divorced, had an addiction problem, got over that. 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. You just trust yourself because I've gone through, you know, a lot of stuff, as everybody here probably has. And 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? You know, we have skills as salespeople that we will never not have a job, in my opinion. So go try. Hey, Jason. Awesome stuff. It's cool to hear your story. One thing that really popped up to me when you were speaking was reducing the time to transparency. And I've learned That you have to give a lot more before you can take. So I was just interested to hear about your processes or some of your strategies to give in order to be able to take down the line. Yeah, I like to use Zoom as an example. How many of our customers spend a ton of time on Zoom? How many of our customers want to join a call with you on Zoom? No, they don't. But what if they did? I want them to be excited that they have a call with me so they show up. That's the type of relationship that this space… like, I want me selling my product to be a break. That's what transparency should feel like. I'm hanging out with a friend, I have a problem, we're talking about it kind of a thing. And then it creates just a bond and a trust factor that allows you both to be free on a phone call kind of a thing. I don't know if that's a good example.
27:19 Scott Ingram: It's good. It's good.
27:19 Jason Walker: Thank you.
27:20 Scott Ingram: Yeah. Tamina's back for more.
27:22 Jason Walker: Hey, I'm back. So I thought it was really interesting how you mentioned that you and Alex were co-selling, and I want to understand a little bit more about that. Is that a scenario where you're both on Zoom with a customer or a prospect that you're both going after, or what does that look like? So do you want to tell them? I mean, because you bring me in, that's why I'm asking. But anyway, so Alex sells a product where what I sell sits inside of. When he's selling that, if he doesn't have something to sit inside of it, it makes his product not as strong, right? Because there might be a product that does both of them at the same time. So we can co-sell together on a call where we can kind of show them a singular solution, just like the competitor that's way stronger because he has a competitor that focuses on one thing and he does one thing and they're super strong together. Right. Anyway, go ahead. So that's really interesting to me because my product has a lot of integrations. And I'm curious, is that partnership something you two built outside of the leadership at your organization, or is that something that leadership had to be sold on to say, yeah, join these calls together, that's a great idea? I forced him. That's true. I didn't give him a choice, really. But it really is a choice on the rep, really, and the value that they get from somebody like me. And so he'd be a better person to ask that question to.
28:35 Scott Ingram: Okay.
28:35 Jason Walker: But I bring a lot of value, and I can sell content better than he can in this scenario. So he'd be stupid not to bring me in.
28:42 Scott Ingram: Jason, how many of those types of relationships do you have? Like, how many other reps for how many other organizations? Like, what is that landscape for you?
28:50 Jason Walker: Oh man, there's so many. Actively, I would say 7 to 8 partners.
28:55 Scott Ingram: And do you have… I'm totally leading the witness here because I have a thought… but do you have a way of kind of determining who the people that you really want to continue to invest the time with are?
29:05 Jason Walker: Yeah, I think it's pretty clear. The ones that are open, open to collaborating, allowing me to do what I do well so they can do what they do well. There's a lot that, you know, reps which I get as a co-seller You're trusting somebody you don't know with your deal, which is terrifying. So I get the hesitation to want to co-sell, but if you can trust me and I can do what I do all the time for you, it makes you be able to do your job way better because I've done half of the heavy lifting for you. Yeah, hopefully a little bit better than you would, or a lot better.
29:34 Scott Ingram: Yeah, I mean, Chris McNeill does this real well. We've done that on some deals in the past. You know, I… for me, it always comes down to… I mean, it's kind of those referral relationships. You find the ones that it actually works, right? Like, hey, we actually have this partnership because they're kind of hard to find, right? It's the minority that really work out. And then once you find those partners, like, game on, game on, right? Because then you can really go at it together. And I think there's a ton of value in that, man.
29:59 Jason Walker: You can't stress that enough. Like, the thought of I have somebody like Alex who's amazing at his job selling deals on my behalf while I'm closing other business, you can't ask for a better scenario than that.
30:08 Scott Ingram: Yeah.
30:08 Jason Walker: And that's how you get those big paychecks. Yeah.
30:10 Scott Ingram: We've only been saying Alex the whole time, so let's give him a full shout out. We're talking about Alex Smith.
30:14 Jason Walker: Alex Smith.
30:15 Scott Ingram: Sorry.
30:15 Jason Walker: He's just right there. I can see him.
30:17 Scott Ingram: Dan.
30:19 Jason Walker: Jason, this is great. So if I'm assuming one of your superpowers is knowing the persona that you sell to and what they care about, you talked about your year 1, $80K, year 2, $150K, whatever percent. And clearly you've done this in different roles. Aside from discovery and having a fun environment or meetings that people want to attend, obviously you're asking questions and finding out what's important to them. Do you have any other tips, tricks along the way that you've found to really, I guess, accelerate or be effective in understanding the personas? I don't know if this is the right answer, but I would say understanding the competitive landscape is really extremely valuable to kind of continue that, I guess, because if you have an understanding of the competitive landscape, you have the ability to ask thought-provoking questions that may or may not poke holes in the story they've been told or whatever. Would you say most of where you're getting that understanding is just from your conversations then with those people? Yeah, it goes back to one of my 3, which is know more than the customer about the problem you solve or be an expert. That's basically… And you know more by just asking the different customers and finding the competitors and just putting yourself in their shoes? Yeah, just understanding the real challenges or what challenges are getting in the way of why they're actually in the job that they're in. Understanding that gap. That's awesome.
31:34 Scott Ingram: Yeah. All right, so I'm gonna let Mike ask a question. Way easier than what I had in mind. I was hesitant to ask this. Perfect. I don't know if it's too personal or not, but you kind of scooted over, hey, I was number 1 and then I was let go. I don't know if you're kind of still unpacking that or what, but you seem to be in a good headspace. Not asking you to indulge us on what went down, but more of your mindset. And how you got to going from, hey, I'm going to President's Club to I don't even have a gig anymore, they let me go. And kind of what was that mindset?
32:01 Jason Walker: What was that process?
32:03 Scott Ingram: Maybe elaborate a little bit on that.
32:05 Jason Walker: Yeah, it goes back to balance in my life and it goes back to confidence in myself, I guess. Like, they let me go, my first thought is, you guys are stupid. Like, I can get a sales job with the competitor or whatever I need to do, right? So I'm not worried about myself. So I wasn't worried about being let go. I could pivot. Does that make sense? Yeah.
32:26 Scott Ingram: I mean, do you fight back on that a little bit? Or because you were like, I'm number 1, what's going on? Or do you, do you dig into that with leadership?
32:32 Jason Walker: Do you go above your boss? Yeah. Yeah. On the side, yes. I'm exploring my rights on that. Is that what you're referring to?
32:38 Scott Ingram: Like, I mean, just like, do you just say, I imagine you didn't go, oh, okay, thanks for the time. I'll see you guys later. I imagine you're probably trying to figure out, you know, I need answers. I need reasoning, you know, I need to get better professionally. So if there's something I can learn from this, yes, all of those things.
32:54 Jason Walker: But the problem that I ran into with mine is I wasn't given any of those opportunities. I got a one cut out, cut off from everything. So I didn't get a chance to get that feedback. And the information provided to me was not concrete or specific. So it's really hard to process. But when it comes to leadership, and understand when you have bad leadership, it's not a hard thing to realize that People are lazy with the choices that they make. But that's a personal opinion directed at nobody, probably.
33:20 Scott Ingram: I'm gonna tap dance while Grace runs up here.
33:22 Jason Walker: So my question is, being in a partnership sale role or being in enterprise, there is deep work, there is research, there's a very clear understanding of your ICP, as you alluded to and have talked about. There are so many places to pull information. There are so many places to look. There's such incredible rabbit holes that you can go down that may or may not actually be helpful in kind of formulating that point of view and formulating that understanding. How did you, or how do you navigate that? Do you sort of, okay, I'm gonna look at X number of resources, I'm going to, like, what does that process look like? And you're talking about how I get my expertise? Yeah, basically, 'cause you've got community, you've got LinkedIn, you've got news reports, you've got 10-Ks, you've got all these different places to go, so. I mean, a lot of it's gonna come down to time. Yeah, the hours, understanding the problems enough. There's so many different ways to look at the problems that they have. So I would say taking the time to ask really, really good questions and curiosity is your most important thing you can have in sales. Because the more questions you ask, the more you understand. But LinkedIn, understanding what people are talking about and engaging, putting your own thoughts out there and kind of seeing what feedback you get. It might not be great, but it helps you understand the way people are thinking about things too. Yeah, and probably where your own blind spots are too, of sharing an opinion, having someone say, you know, hey, here's a piece that you're missing, or here's another angle, or having that become more of an in-depth conversation. It's pressure checking your view of the world or your narrative, making sure that you're not an insane person, which is why I'm afraid to post my own content. That's why all of us are.
34:52 Scott Ingram: It's okay. So we're basically at the end of the core content for this. I'm really curious, you know, you bring to this a very, very, very different perspective than you would have had with your initial plan when you signed up for the summit. What's your biggest takeaway? Like, what's resonating with you most these last couple of days here?
35:10 Jason Walker: Man, is that your network is everything. Your network dictates your success because if you have a good network like this, you hit a bump in the road, there's like 100 people to fall on. Easily the biggest takeaway for me as a newbie.
35:25 Scott Ingram: That's about the best setup for a break and some networking I've ever heard.
35:28 Jason Walker: Thanks, Jason. Perfect. Thank you. It was awesome.
35:32 Scott Ingram: Thank you. Make sure you're subscribed to the podcast so you don't miss my follow-up interview with Jason. You'll also find an interview with a top channel partner seller coming soon as well. As for the summit, it was our best one yet. Again, the first survey question I asked was, was this the best sales event you've ever attended? 91% said yes, and 100% of those that said no still gave it 5 stars. To learn more about what's coming in 2023 and to get involved in the community, click over to top1.fm/2023 for details.
36:09 Jason Walker: Thanks for listening to the Sales Success Stories podcast. To be sure you never miss an episode and for an invitation to our Sales Success Community powered by Influitive, subscribe to our newsletter at top1.fm.

