The secret sauce to your sales success? It’s what happens before the sale. It’s the planning, the strategy, the leadership. And it’s more than demo automation. It’s the thoughtful work that connects people, processes, and performance. If you want strong revenue, high retention, and shorter sales cycles, the pre-work—centered around the human—still makes the dream work. But you already know that.
The Unexpected Lever is your partner in growing revenue by doing what great sales leaders do best. Combining vision with execution. Brought to you by Vivun, this show highlights the people and peers behind the brands who understand what it takes to build and lead high-performing sales teams. You’re not just preparing for the sale—you’re unlocking potential.
Join us as we share stories of sales leaders who make a difference, their challenges, their wins, and the human connections that drive results, one solution at a time.
Jarod Greene (00:00):
Hey everybody. Welcome. Welcome to V5, where we spend exactly five minutes getting on our soapbox with some of the hottest takes on all the topics in B2B SaaS, B2B sales, B2B AI, whatever the heck we're doing these days. James, I am super excited. This one long overdue. This has been in the hopper for a while. This is the man, the myth, the legend. This the James Kaikis, CRXO at TestBox. How you doing James?
James Kaikis (00:25):
I'm great man. It's so good to see you and thanks for having me. I'm very honored to be here.
Jarod Greene (00:30):
Man. I'm glad to have you. So you know the rules, you know how to play Spicy Take is Loaded. What you got?
James Kaikis (00:36):
That companies actually give a shit about their customers. I've been thinking about this a lot over the last couple of years, and if you think about SaaS and what's actually happened, we say we care about our customers, but our actions don't always support that. We've built orgs, we've built silos, we've built gates, we've built so much friction in the process for us internally. And we say who matters is the customer, but if you actually put yourself in the customer's shoes, it's not the truth. And then I don't know if you have bought software recently, but it sucks.
(01:08):
It absolutely sucks and the process sucks. And unfortunately, sometimes you work with sales teams or sales organizations that are adding no value. And so you wonder why people don't trust salespeople. They want a rep free experience. And we've been sitting here for the last decade being like, deal signed. Everything's all good. But that's just the start of the journey. The sales process is a great checkbox because it's all about the implementation and the onboarding and the ongoing value. And I just think we've lost sight of that, man. We've just lost sight of it because as a buyer and as someone who has bought software and is trying to get value out of software, yeah, the value prop's not delivering, man.
Jarod Greene (01:49):
Yeah, I told you James going to bring the heat on this one and you're not wrong on any of it. I've purchased software. I know what it's like to not get exactly what you need when you need it. I know what it's like to want more resources on the post-sales side. How do we fix this thing? I don't think most folks disagree with you. I think they absolutely like yes, but from your point of view in your seat, man, what's the remedy?
James Kaikis (02:10):
And the big thing that we've looked to do and I've been trying to lead, is look at the jobs to be done within the buying process and the implementation, the onboarding experience, and start building jobs and job roles around that. It's so easy for us to go work at Salesforce, which I did, and then take the playbook and go somewhere else and run the playbook. Every business is very similar, but they're all very different at the same time. And I think the big thing for us is a bit of role consolidation. And I think this is something that's near and dear to our hearts is like what is the role of the salesperson? What is the role of the solutions engineer? And I think the two biggest things that I'd say is solutions engineers, and I'm biased from my experience with PreSales Collective. We are this wealth of knowledge within a business.
(02:55):
Why should it not be deployed throughout the entire customer? We're only brought in safe situations. You can deploy that solutions engineer in implementation, in onboarding, in ongoing expansion, renewal, right? Because the SC and the AE took me out to lunch, they took me out to dinner, they took me to concerts. I spent time away from them with my family and then all of a sudden, man, they disappeared. So think about that. And then one more take is the account executive. What is the account executive's role and how do they bring value? Because every statistic you see out there says people don't trust salespeople. So how do they actually get on the buyer side of the table? How can we teach them to have a point of view, to understand the value of the product, to understand use case and proof points so that the buyer's like, oh wow, James is on my side right now trying to make me make an informed decision. Those are just two things that are near and dear to my heart that I think that anybody can go and attack right now.
Jarod Greene (03:53):
Right now. No, I love it. We've talked about this a lot. The role consolidation between that SE is super value. I think. I don't go with V5 without the Gartner stat from years ago. The person buyer trusts the most through that process is the SC. Without a doubt. My technical expert, the person that's going to show me what's what, the person I trusted to buy this thing, and I don't know if they come with the meal, I'm going to buy the meal. I don't know if they come with it because I want them to show me that use case they showed me in the presales process. I want to buy the thing that they showed me here. I want to understand this feature that they said was in the roadmap that's finally deployed. Now I want to figure out how to work it and I'm not allowed to talk to that person? That's kinda crazy.
James Kaikis (04:33):
That's crazy, right? But this is what we've been doing in SaaS for the last decade, and I think it's because it's been the growth at all costs, right? All kinds of software companies have spun up. There's been so much technology. You look at the roadmap and landscape, it's just been like sell, sell, sell, sell, sell. Without really caring about what happens. Now you have all these companies who've got all this funding who have no path to an exit. They can't go get another round of funding and they're churning customers like crazy. It's like we got to get back to who matters. And that's building value and delivering value for the customer.
Jarod Greene (05:07):
Amen. See? James is going to bring the heat, told you guys, it's like long overdue to get him on, but I knew he'd bring the heat. James, where can people find you? Connect with you? You're out there in the streets, but how do people talk to you directly if they want to?
James Kaikis (05:22):
I appreciate that. Love good engagement on LinkedIn. So you can find me at LinkedIn, James Kaikis. I also have my own interview series called The New Go-to-Market Playbook and a newsletter on testbox.com/gtm. And I actually have my own consulting company, which I haven't been doing as much on GTM Shift. So I've been doing that for a couple of years as we think about the changes in go-to-market. So that's where you can find me. Love these conversations, love to engage. I love to learn. I want to hear what people are doing, what's working, what's not working.
Jarod Greene (05:51):
Alright, you heard of James. Thank you so much. Spending five minutes with us, man. Really appreciate you.
James Kaikis (05:55):
Thanks for having me. Great to see you.
Jarod Greene (05:56):
Alright, you got it.
James Kaikis (05:57):
Take care.