Sales Engineering discussion with James Kaikis

Published on: April 19th, 2021

Guest Speaker


James Kaikis

Co-founder, PreSales Collective

James Kaikis is the Solutions Engineering Leader and Co-Founder of “The PreSales Collective”, the most popular platform for Solutions Engineers. He has worked in SE leadership roles at Salesforce and Showpad.

About the Podcast

James Kaikis, Co-founder of PreSales Collective joins as a guest in this episode of Proof is in the Pudding podcast. Vik and James discuss proof of concepts, SE leadership, the inception of PreSales Collective, and many exciting topics.


Vik: [00:00:31] Hi, welcome. I’m your host, Vik Arya. With me today, I have wonderful guest, James Kaikis. He is a co-founder of Pre-sales collective, which you may already know.

It’s making a lot of buzz nowadays in the pre-sales world. Uh, how are you, James?

James Kaikis: [00:00:47] Vik, hey, I’m great. Thanks for having me. How are you?

Vik: [00:00:50] I’m doing very well. Thank you. James, can we start with your introduction, with how, where you started and how you got into presales?

James Kaikis: [00:00:59] Yeah, well, I’ve got a pretty wild journey, right?

I think my journey has been a very twisty and turny, but it is really interesting because I started my career in op in operations and athletic operations and went to hospitality operations um, and at one point I decided, Hey, I don’t really want to be in hospitality operations anymore because I was working, you know, 10, 15 days in a row.

And, you know, 12 hour a day. And I said, Hey, like, how do I take these transferable skills and do something that I want to be doing? And so, I joined a software company called Revinate and Revinate did hospitality technology. And so, guess what, Vik, I got to be the subject matter expert. That was the individual who came from the hospitality world.

And I actually did implementation and post-sale at that organization, but at the time we didn’t have a pre-sales team. And because I knew the industry because I knew how hospitality professionals and I knew our product inside now, the sales team would, would bring me

[00:02:00] on calls and say, Hey James, like, we want you to talk to this company about, about why our products working.

And so, they kept bringing me on to these calls. And Vik, I’m not going to lie. I was like, wow, this is a lot more fun. And so, I was enjoying a lot of the sales process and a couple of times I did some really large POCs because I knew the competition inside and out. And so, um, my company at the time was like, Hey, this sounds like a really good opportunity.

For you to make a full-time move to the sales team and the pres and start our pre-sales org. And I was flattered. It was amazing. So, I started to make that move and then I jumped to a company called Showpad and, um, worked there for, for over four years. And I’m not going to lie Vik. I found my footing.

So, for me, you know, I like to say that people stumbling the presales and that was my, my, I, excuse me. I stumbled into pre-sales as well. And that was my journey. Um, throughout and here we are a couple of years later and now we have the Pre-sales collective.

Vik: [00:02:57] That’s awesome.

So, the next topic, what I want to ask you is, so how did you get into starting pre-sales collective? Uh, what motivated you to create a platform for presales people or pre-sales, uh, you know, the people who are involved in to sales engineering, solution engineering, what motivated you to get started?

James Kaikis: [00:03:19] Yeah, Vik, you know, it’s, it’s so interesting because when I was at revenue and then I went to Showpad, I was the first sales engineer at both of those companies.

And at the time at Showpad, because really that’s where a lot of my, my presales, um, career exists is that I always reported to a sales leader. I always reported to a VP of sales, even a co-founder or president, whatever it was. But it was always me just trying to figure out what we needed for the organization.

And so, I lived in San Francisco at the time. I spent five years in the Bay area and there was this awesome San Francisco sales engineering meetup. And so, I

[00:04:00] went one day and I’ll never forget, I can still visualize the room. It was 150 people there. And I was like, oh my gosh, this is unbelievable. And so, I started going to these events every once in a while, and meeting people and networking because I always reported to somebody in sales.

And so, I was like, Hey, how do I do this? How do I do this? And I want to pick people’s brains understand how they ran their pre-sales teams and pre-sales organizations. And then a time that we don’t know, Yuji Higashi, my other Pre-sales collective co-founder and I were connected because I was building Showpad. He was building Outreach.

And we would call each other about different things that we were seeing problems that we were trying to solve. And then I moved to Chicago and when I moved to Chicago for Showpad, it was supposed to be a temporary move. And I realized, Hey, there’s no sales engineering meetup. I should go ahead and start one.

And so, I started that group and then Yuji started a group in Seattle.

[00:05:00] And we were talking about this time last year, it was, uh, early January 2020, little did we know what the world was going to bring us? Right. But we said, Hey, if you’re not in like one of these four or five cities that has a group, how do you connect with pre-sales professionals?

And the answer was you did it unless you worked at a big company that, that had a good network, or you kept in touch with some individuals. So, we decided to say, hey, let’s, let’s throw a conference for pre-sales people. And we were like, eh, let’s maybe not do a conference. Hindsight’s always 2020. Let’s build a community around that because people need to connect and they need to learn from each other.

And we started that. And then in March, the pandemic happened. And we had a Chicago meet, uh, Chicago pre-sales community group event. And I called Yuji I said, Hey, I’m going to announce Pre-sales Collective. And we were originally planning for May or June. And then we pulled the timeline up to April and here we are, you know, 9, 10 months later, 9,000 people signed up across the globe.

It has been an unbelievable journey across, but that’s really the Genesis of, of how the collective started.

Vik: [00:06:10] Wild man. Great story. You know, uh, I saw pre-sales collective growing in front of my eyes. I still remember your group in Chicago and you know, the one, uh, in, on the, on the Seattle and then how it all came together.

The community has been growing and, and I think it is one of the very active community as well. I mean, not only large people, but also very active, a lot of people get involved and, uh, that’s great. So, what do you think, what changed? I think. A lot of people who started let’s say working in sales engineering maybe more than 10 years ago, uh, almost everybody can feel that sales engineering was not an independent function.

It was, it was kind of a supporting role for, for salespeople to close their deals. Uh, the main focus was on the salespeople to bring the customer, sales

[00:07:00] engineers were more in a supporting role as like, okay, whatever you need technically to close this, we’ll be there. But things have changed in last 10 years.

I think this role, as we’ve all told to a whole new level, there are many new titles are you know, showing up now at the director, VP, global VP. And you know, I think the whole landscape has changed. What do you, what do you think happened? I mean, what has caused this to change?

James Kaikis: [00:07:23] Yeah. I mean, Vik, you’re, you’re spot on there’s, there’s a couple of things that I think that have changed.

And let me maybe talk, talk about them a little bit separately, but the introduction of technology into our day and day, day to day has really accelerated the need of sales engineers, and solutions consultants in a sales cycle, because at one time, you know, well, I guess let me, let me rephrase is that.

Every company is turning into a technology company, whether it’s a happening overnight or it’s a slow move, technology’s becoming part of our

[00:08:00] DNA and everything that we do. And so, sales is changing and really the crux. And one of my favorite things to talk about is buying is changing because if you think about what Amazon and what Netflix are doing to us and our B 2 C consumer behaviors that is changing in the B2B world as wide.

Right. And what happens is that sales is becoming more complex. There are more decision-makers garnered force are putting out a lot of research. And so, the sales engineering role has gone from sales support to true copilot. I mean, in some of these organizations, you know, it’s, it’s crazy, but the sales engineer and the frontline sales leader are the point of continuity and accounts because, you know, rep transition is really high. It’s like 12 to 18 months right now. And so, the SE role has become so vital and so important that as technology expands, as buying changes, this role is the centerpiece of both internal and external

[00:09:00] collaboration. And so. it also it’s a sales role, but it exudes trust because our job is to solve problems and do what’s best for the customer. And that is just the crux of the concept of, of buying changing. Right? And so that’s why I think that this role has gone through this evolution is becoming more important than ever.

Vik: [00:09:21] Well, I, I agree. And in fact, uh, I think one more thing that I, I can see changing in the technology landscape is that almost every technology vertical is very crowded today, whether you take a cyber security, industrial IOT or whatever technology you take, now, there are so many companies providing the solution.

So, from the buyer perspective, it becomes more and more important to validate what they’re buying to compare with other products. And that’s where exactly the sales engineering comes in, solution engineering comes in to play their role in showing their product and making sure the customer’s happy with it.

James Kaikis: [00:09:55] You’re exactly right.

Vik: [00:09:57] Yeah. Um, can you share some of the experiences from your journey as a sales engineer, to a sales engineering leader, how you saw the whole process changing and some of the learnings that you can share.

James Kaikis: [00:10:11] Yeah. I think what was interesting was, and, sorry, let me clarify with you Vik. The change of, of sales engineering from like an IC to a leader or the, the change of what’s happened in the industry generally?

Vik: [00:10:27] No, I would say more from the process perspective, let’s say when you started, how you saw things happening and maybe share some of the learnings that you saw, maybe some of the best practices as a sales engineer that you saw working well for you, uh, maybe specific to certain segments to certain companies.

What have you seen personally that has worked well for you in your role of a sales engineer or at the, as the role of a director and a leadership level role?

James Kaikis: [00:10:55] Yeah, I think when it came, when it comes to being in an, on the ground, hands in the product solutions engineer, where I was able to see that this role was changing and be able to provide the most value is when I realized that my role was shifting from just being able to give demos, to be a real value added in the sales cycle, because if I came in and just kind of showcase the product and then, you know, kind of in and out.

I wasn’t bringing enough value to that sales cycle because I was instilling trust with the customer at that point. But once I started to be able to say, these are the use cases, these are the customer stories that I have. Let’s do a hands-on workshop and be able to expand the sales cycle from like disco demo, uh, to disco demo hands-on workshop, you know, POC at times.

I was able to one as myself, build more credibility with my internal team, but I started building credibility with the external team. And then I started being able to align with some of those champions in the sales process, because a lot of

[00:12:00] times organizations will be like, all right, the AE’s aligned, the sales leaders aligned, the executive sales leaders aligned, and they’re talking to different points at the customer.

Well, how about James as a solutions engineer being aligned to the CTO or the CIO or whoever that might be. And I think that was the change that I went through. And then as a leader, in sales engineering and solution engineering is trying to make sure what made me successful could be turned into a bit of a framework that would allow my team to excel.

And so, again, going from, you know, that, that term of like demo jockey, so to say to true copilot, you know, it does depend on the product. It depends on your organization, but that is how you maximize the value of this team. And that’s, what’s worked for me.

Vik: [00:12:45] Right. That makes sense. So, you know um, recently I, uh, started this poll on LinkedIn, where I asked people that how they got into sales engineering, and interestingly, almost 65% people said.

[00:13:00] That they were there right in the right place at the right time. And they got pulled into sales engineering. Uh, I want to ask you two things here. Um, you know, if you can share something, how your transition from, uh, into sales engineering was, and what would you say, especially to new people who are moving into sales engineering?

I think because now this role is getting more into mainstream and more people are even starting as sales engineer, or they are moving from another team to a sales engineering role. So, what would you say to them, especially now that, we have resources like Pre-sales collective there where they can go in and read a lot, learn a lot, learn about processes, learn about how things work, but how has been your journey and what would you say to the people who are starting, um, you know, how they should be starting?

James Kaikis: [00:13:43] Yeah. Well, Vik, I’m looking forward to seeing you run that poll again in like two or three years, and then people actually joining pre-sales as a career path. Right. That’s what we’re all getting to. Some of the advice that I give people all the time is utilize your subject

[00:14:00] matter expertise. I mean, you heard that in my story, generally, there are things that people have a lot of working experience in.

Things that people are really good at, and that can translate to a sales engineering role. And I think, you know, when people say, Hey, I want to get in this role. I don’t know where to start. Well, like, look at my example, I worked in hospitality and in operations. And so, what I did is I went and founded hospitality technology company where I can come in and provide immediate value.

And that was something that the organization needed at the time. And so, you know, even if you’re in customer success, like I love hiring customer success managers as sales engineers, and solutions engineers, because they know what it’s like to work with customers. And so, like utilizing those and finding those opportunities, although they might be few and far between at times, understanding like how you can make the best transition.

And so, like, that is my advice for people who want to get into this role is figure out where your SME experiences and figure out how you can bring it to that role.

Vik: [00:15:06] Right. Well, that’s great. That’s great, James. So now at the end, I’ll probably ask you a couple of more questions about maybe some resources, um, while you are running Presales Collective, and you have been working, you know, as a leader of sales engineering organization.

What are some of the resources that you found? Very useful, maybe some of the books that you read or any specific resources that you found very useful. Can you? 

James Kaikis: [00:15:34] Yeah. Well, Vik, I will say maybe to, to finish answering the last question because I realized it didn’t there. This is why Pre-sales collective exists.

Because if you try to go out there to how to build a pre-sales team or you know how to do this with that, those resources haven’t existed. And Joel Duffield, who got hired at a Pre-sales collective hiring event said that he utilized the Pre-sales collective and the blogs and the podcasts and the webinars to get experience without

[00:16:00] experience. Right. And so, he knew the terms, he knew the lingo, and again, that’s really why we started this, this community. And so, we are trying to highlight the amazing work of amazing pre-sales professionals all over the globe. Right? It’s not like, it’s James and Yuji creating content. We’re highlighting content and things that people are doing.

And so obviously, you know, we’re hoping that the Pre-sales collective can continue to be a good resource. Um, one of my favorite books is, Selling is hard, buying is harder by Garin Hess. I really liked that book because I thought it aligned with a lot of the ideals that I have around customer experience, a big fan of Bob Rhinestone and to win.

Right. I think that his book does really demonstrate. You know how to, you know, take your demo and make it a little more digestible for your customers. There are a lot of good resources out there and a lot of good items. I would say that with the Pre-sales collective, we’ve also created an educational page. So presalescollective.com/education, and we’re

[00:17:00] highlighting the individuals that are building companies and have resources for those individuals, right. Again, we’re trying to make sure that we’re bringing exposure to everything that exists. So those are, those are my perspectives on those items.

Vik: [00:17:14] That’s great, James.

I think it’s a great point to wrap up this podcast, but it’s a, it’s a pleasure speaking with you, James. And I’m excited to see where Pre-sales Collective goes. It’s already making waves and I can’t wait to see what other things you guys are doing. So, thank you so much for joining today.

James Kaikis: [00:17:31] Vik, thanks for having me.

Thanks for your support and thanks for everything that you’re doing for the pre-sales professional as well.

Share this:

Other Podcasts You Might Like


Sales Engineering discussion with Greg Holmes

In this week's episode of Proof is in the Pudding podcast, Vik is joined by Greg Holmes, Regional Vice President of Presales at Apptio. Greg shares his views on the evolution of presales, best practices for POC, product evaluation process, his contribution to the PreSales Collective, and more exciting topics.

June 3rd, 2021

POC Success and Win rate discussion with Jeff Blake

In this episode, Jeff and Vik discuss fundamental sales engineering activities, defining winning success criteria, POC success rate, key insights for SE's, and many other sales engineering topics.

May 24th, 2021