Differentiate or Die: Interview with Chris Keene, CEO Gigster

In this first interview edition of our podcast, Chris Keene, CEO of Gigster is interviewed by Firebrick founder, Bob Wright and Positioning Strategist, Bob Macdonald. Listen to real-world insights into the role positioning plays in disrupting a category and competing against larger, well established competitors. Chris also shares his perspective on the right timing to embark on positioning, who to include and the powerful impact positioning brings to operationalizing a new business strategy. (duration 11 min)

Bob Macdonald: On this edition, Firebrick founder, Bob Wright, and I are going to be talking about positioning with Chris Keene, the CEO of Gigster. Firebrick worked with Chris and the Gigster team earlier this year, in August 2019.  Prior to Gigster, Chris’s career has included driving the product and market vision at VMWare for the $400M spinout of Pivitol Labs. And, most notably, Chris founded Persistance Software and led the company to a successful $600M IPO. Bob, why don’t you get things kicked off?

Bob Wright: Chris, you were brought in as a change-agent CEO  to Gigster. How important was positioning to your efforts when you took on this new challenge, your current work at Gigster?

Chris Keene: Well, I think anytime you are doing a company transformation, really you are shifting the narrative from a story that may not have been producing the business results that you wanted to a new story. So to me, the word for that story is positioning. I really saw creating a new positioning as a core element of our business transformation.

Bob M: What do you think, Chris, were the shortcomings of what you inherited in terms of the positioning that existed when you took over at Gigster:

Chris: Well, we had a little bit of a unique situation. Gigster really started as a marketplace for freelancers and a way for enterprise companies to get access to teams of freelancers. So, really kind of a services and marketplace play. I came in to lead the company to more of a product vision, a platform vision. It was really important for us to reimagine ourselves, reposition ourselves, as not just being a way to get talent and on-demand teams, but really be a platform for staffing and managing distributed teams.

Bob W: As you took this company through it’s transition to a platform, what were the key elements for a successful positioning story in your mind?

Chris: Well, I think we really needed to reimagine the problem we were solving, specifically, the market problem that we could solve, not just with a services offering, but with a platform offering. And then, having defined that problem, articulate what we were delivering, both in terms of the service capability that we’ve had as well as growing into the product vision. This is really where we came up with the idea of focusing on how to staff and manage distributed teams.

Bob M: As part of this process, you were integrating a team of Gigster veterans with a team of new executives that you had brought in. What impact did this recent positioning process have on your effort to bring people together?

Chris: I think that’s one of the biggest challenges for me in doing a business transformation. It’s to lay out a story that connects the dots for the veterans, from where they’ve been to where they, and the new team, are going. So, to me, positioning is not just for the external market —how we go to market— it’s also about how we align and focus internally.

Bob W: In addition to the alignment and focus of your team, what other values have you seen taking Gigster through the Firebrick process?

Chris: I think the process that we went through as a team —which, as you know, is quite intensive— really gave us an opportunity to think hard about, not just what we want to say as a company, but think hard about the strategy. What are the key value drivers here? So I feel that we not only got a new positioning, we really transformed the strategy itself as we went through the process.

Bob M: That’s interesting! We talk a lot about that with clients. The fact that doing this is not just a market facing thing, but it becomes a framework for guiding what’s going to be happening at the company and within the company moving forward. So, you’ve seen that same kind of impact from this process?

Chris: Absolutely! I think if you can’t say it, you can’t live it. So, as we figured out what we wanted to say, almost by definition, that started to really  change our strategy and our conception of who we wanted to become as a company.

Bob W: Chris, right when we got involved with you, you had hired a seasoned CMO. Why use a third party for positioning? What are the benefits of using a 3rd party versus trying to do this in-house?

Chris: That’s a great question. One of the very first conversations I had with our new CMO. We brought in Jen Dimas, who is just phenomenal. She had a very troubled look on her face, and she said, “I know you guys have worked very hard on a strategy, and I know you’ve worked really hard on a positioning. But, frankly, it’s been evolving quite a lot since you did it… and you never really did it at a foundational level. I’m really going to recommend that we go back to a foundational positioning study.” Then she sort of waited with baited breath to see what I was going to say. And, I was really all on board for it. I think what happens when you do a turn around is, you’re really trying to change the engine on the plane while flying the plane at the same time. A lot of things get done by gosh and by golly. You do something that’s good enough to keep the plane flying for a bit more, but didn’t necessarily get full buy in and didn’t necessarily go through a really formal process. So, bringing Jen in at about the 3 or 4 month mark of our transformation, and then having her bring in Firebrick. And, having Firebrick lead now the new team, through a positioning exercise was a great way to really align and focus, not just the old executives, but also the new executives.

Bob M: One of the things, Chris, that we feel strongly about. And, I think it was reflected in the makeup of who participated in the positioning process at Gigster, was that we like to see all functions represented in the room. Especially field sales who are very close to what is happening with the customers. Had you done that in the past, where you had such a wide variety of functions together working on positioning?

Chris: I think there were a number of really critical values of going through this critical exercise. One was really blocking off the time for the executive team to spent two full offsites and weekly meetings, to really talk about what we wanted to be. That’s something I don’t think we would have done on our own. And then making sure that it wasn’t just the little echo chamber of new executives coming up with this, but that we really were reflecting the viewpoints of the company and incorporating the knowledge and experience of our veterans. That was another really important value of the way Firebrick ran this process where some meetings we had a very broad group and were really able to get a lot of inputs, other meetings we worked with a smaller group and really tried to hone the messages. That is again something I don’t think we would have been able to do on our own.

Bob W: You’ve been a very successful executive. How did the Firebrick process compare to other positioning initiatives you’ve done or experienced during your career?

Chris: I really have to say, I’ve never been through anything quite like this. I’ve done a number of positioning exercises. One of the things that we found when we looked at some other companies to help us with that effort was that just doing kind of an academic positioning exercise was not what we needed. We also needed to be able to drive that into a customer facing deck which would also require some design work and design elements. And, we also wanted that to inform our new website. So again, having some idea about how the positioning works not just in the abstract as an elevator pitch, but also what it looks like when you present it to a customer and really how you present your whole look and feel along with the positioning. Those were things that I’ve always really wanted to do together but, frankly, I’ve never had anyone tell me they could be done together. Having done that now, with Firebrick, I can’t imagine doing it any other way.

Bob M: If you were talking with someone who was about to start the whole process with us, the whole positioning process, what would your advice be to a fellow CEO who’s kicking off a project with us?

Chris: I think my advice would be to look at this process as really being the entire foundation of your strategy going forward. Don’t look at this as just crafting an elevator pitch in isolation. Look at this as a foundational exercise to align your broader team and align your vision and also create a visual representation of that vision —a tangible, customer-facing deck. I think taking the time to do that right and incorporating the breadth of resources that are required to get alignment is critical.