Interview
The Gist
- Team development. Understanding individual motivations and strengths is key to enhancing team performance.
- Remote management. Initiating personal connections and regular meetings is crucial for leading remote teams effectively.
- Marketing focus. Aligning marketing strategies with actual market demands can significantly improve demand generation and brand awareness.
Gurdeep Dhillon, chief marketing officer at Contentstack, discusses the nuances of stepping into a new leadership role and how to align team dynamics with strategic goals.
In this episode of CMSWire's The CMO Circle, Dhillon explores his approach to understanding and leveraging team strengths within the first 90 days of his tenure. He delves into the challenges and opportunities of managing a fully remote team, the strategic shifts necessary for enhancing market alignment and demand generation and insights on fostering a culture of innovation and adaptability.
Table of Contents
- Team up-Leveling vs. Focusing on Strategy (0:27)
- Getting to Know a Remote Team (3:04)
- Challenges of Transforming a Go-to-Market Strategy (4:46)
- Making Team Members Part of the Solution (6:45)
- Balancing Marketing Creativity With Pipeline Demands (8:52)
- Tactics to Rise About the Marketing Noise (10:35)
- How to Approach AI With the Team (13:16)
- A Look at the Next 90 Days (15:36)
- The Biggest Unexpected Lesson (17:31)
Episode Transcript
Michelle Hawley: Hi everyone, and welcome to another episode of the CMO Circle. I'm your host, Michelle Hawley, and today with us is Gurdeep Dhillon, chief marketing officer at Contentstack.
Hi, Gurdeep. Thank you for joining us today.
Gurdeep Dhillon: Hey Michelle, thanks for having me.
Michelle: So I know in your role at Contentstack, you recently completed your first 90 days as CMO, and I'd really love to dig into that and maybe see what you learned in those first three months.
Gurdeep: Yeah, three months went by really fast, but definitely a lot of learning and what I love best is a lot of fun.
Team up-Leveling vs. Focusing on Strategy
Michelle: You had mentioned the importance of quickly trying to figure out if you need to up-level your team or help them better understand the strategy. Can you talk a little bit about where you applied that insight in your role?
Gurdeep: Yeah, definitely. It's funny because there's sometimes an assumption that when someone enters into a new role, especially at an executive level and especially as an external hire, that the team needs an overhaul, or I think I used the words up-level. It's funny because what I've found is actually that's not often the case.
Most people, I think, start with the assumption that most people want to do really great work. They're motivated to do great work. And then as a leader, I think it's your job to get to know them on a personal level. So what I did was really dive in with my leadership and with their teams to understand what motivates them, what scares them, what they are truly great at. Because then I think it's the job of the CMO to match their passion, their skillset, and their motivations with the right roles. And specifically tying into the strategy, because I think what you tend to see is that, yes, there might be some cases where the talent isn't the right fit, but most often it's a lack of understanding of the overall strategy and why we're asking folks to do what they're doing.
Once that roadblock is cleared and there's key understanding there, it kind of unlocks them to just run free. And I've seen it time and time again. In a case where if someone hadn't put in the effort to learn, they wouldn't have been able to put that person in a position to run free and succeed and they would have spent their time instead looking for that person's replacement, which I think is a huge mistake probably 95% of the time.
Michelle: Is your team fully remote, or are you guys a mix?
Gurdeep: We are fully remote since COVID. So we've got people all over the US as well as international. We have hubs of people that are co-located, but we don't have offices. So we try to get together when we can, but definitely remote first.
Getting to Know a Remote Team
Michelle: That's really similar to us. We have a lot of hubs and have a lot of meetups. So when it comes to getting to know your team then when you first came in, and that's a lot harder when you're remote, what did that look like for you?
Gurdeep: Yeah. Immediate engagement virtually, as quick as possible, just to engage and say hi. For people that were local here in the Bay Area, it was face-to-face. Again, within the first week, and in some cases, like my direct reports, I met with them before I even started. We went out to lunch or dinner in a one-on-one format, which was great.
The fast follow on that was getting approval to do a team offsite, starting with my leadership team, so just my direct reports, and then what I call my extended leadership team. So anyone who's basically a manager in the marketing org, we all got together within my first month and did some brainstorming, some planning and alignment around where we wanted to go as a team. And this really helps with getting buy-in and helping people feel like they're part of the solution.
And then one thing that I like to do is quarterly skip levels, which is basically a one-on-one with everybody in my organization once a quarter, regardless of if they are one level down, two levels down, three levels down, four levels down, doesn't matter. Everybody gets 30 minutes to meet with me. They drive the agenda. Any questions they have, any ideas they have.
It helps me keep my finger on the pulse of what's going on, but it also helps them get to know me a little bit better.
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Challenges of Transforming a Go-to-Market Strategy
Michelle: You had mentioned — and for people listening, I'm referencing this great post on LinkedIn where you talk about your first 90 days — but you had mentioned significant transformation in how Contentstack goes to market and aligns internally. Can you walk us through like one of the major changes that you had spearheaded?
Gurdeep: Sure, yeah. Obviously, we play in the CMS space and marketing's job is to own and drive the pipeline. And so when I came in, it was a really interesting situation where we weren't focused on our demand generation efforts. And what I mean by that is we weren't tuned to what the market's actually looking for. We're a disruptor. And so because of that, we were trying to own some of the keywords that are more related to category disruption and creation versus the market reality of what our buyers are actually looking for today.
And so the tangible example of that is, you know, we were tuning our demand engine to things like a composable DXP, which if we're being honest, it's not really a thing. The thing that we actually sell and the thing people are looking for is a headless CMS.
And so we just immediately shifted our demand strategy to let's go, let's be where the market is and what they're looking for. And we saw immediate returns in terms of the pipeline turning around. And then I think, you know, the challenge of course, with that is the balance between where are we going and where are we today?
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And so that's just the fine line that we have to balance. But for me, it’s all capturing all existing demand. Have to be in every deal and we're not going to do that unless we're showing up in places and around themes and topics that our customers or our ideal customers actually care about. And that's what we fixed immediately. And it's been great.
Making Team Members Part of the Solution
Michelle: We kind of touched on how you got to know your team members and the regular meetings that you set up and that cadence. And it seems like team involvement is critical to your strategy. How do you go about making sure that every team member feels like they're part of the solution?
Gurdeep: Yeah, I think it's really important that everybody in the organization feels like they had a hand in architecting the solution. And the solution could be macro or micro, but I think where it really comes to life is, you know, we talked about off-sites and brainstorming sessions and that's all really good, but I think where it really comes to life is, there's always strategic initiatives that come out of these things and delegating those to the team.
What that allows for is it allows team members to flesh out the initial idea, kind of make it their own, poke holes in it and come back with a fully baked proposal for what we should actually do. And so I think the key is there's always going to be ideation at a leadership level, but you leave freedom and space for the team to take that idea and run with it versus saying, hey, we thought this all the way through. This is what we're going to do. Just go get it done.
Like that's kind of demoralizing for the team. So what I prefer is this: a 30, 40% baked idea. We're asking you plus a couple of peers to go take it to the finish line. And you might discover a bunch of stuff we didn't think about along the way. We want that, you know, come back in two weeks and let us know. That's kind of the approach that we take. And it's not a long list. It's probably three or four major initiatives.
Because again, you're asking people to do stuff in many cases outside of their day job. But, I found that that works really well because then they absolutely feel tied to the outcome, feel like they were a part of it versus just being handed something.
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Balancing Marketing Creativity With Pipeline Demands
Michelle: You had mentioned too in that LinkedIn post that marketing owns the pipeline. So how do you balance the creative aspects of marketing with the more analytical demands of pipeline management?
Gurdeep: That's the job. The job is the balance. You know, you often hear the art and science of marketing. I love that it is an art and a science. I think marketing and a go-to-market function is not going to achieve its goals without both. Why? So the truth is today we are in a, what we call a brand relevancy crisis.
There's so much noise. It's so hard to get your message across to your audience. And it's only getting worse with things like AI. The cost to create kind of mediocre content is basically zero today. So our audience is just completely saturated with content and messages. And our job as marketers is to rise above that. And you're not gonna rise above it with data-driven messaging decisions. You're going to rise above it with real human creativity and connection and engagement.
And so I think that's what AI unlocks, is room to do that creative thinking and ideation. But then of course, to your point, you have to stay vigilant on conversion to pipeline and ultimately revenue, because that's the key to closing the loop and then learning what works and what doesn't. But for me, one doesn't come without the other.
Tactics to Rise About the Marketing Noise
Michelle: You had mentioned rising above the noise. So I know that you've achieved a lot of growth in organic traffic, in new target account visits. What specific marketing tactics then do you attribute to that success?
Gurdeep: Yeah, this might be a little controversial, but it was really launching our first ever brand awareness campaign. Contentstack has never focused on really amplifying and elevating our brand within our target audience. And so we said we need to fix that. And what we did is we launched our Reimagine Possible campaign. And this was an effort to showcase two things.
Number one, how the best brands in the world run their digital experiences on Contentstack. So really telling our story through the eyes and words of our customers.
And then two, highlighting the amazing differentiation of what it means to work with a product like ours versus legacy. And so we decided we were going to tell this story in two ways. And we were going to launch this campaign through multiple channels, including out of home, which is probably the controversial part.
People are hesitant to do that. But out of home, digital, ABM, we did our first ever sports partnership with the new women's soccer team here in the Bay Area called Bay FC. A new website refresh, we've done a lot to really invest in our brand and in gaining awareness. And what's really cool is, you know, we've been live for about six weeks. And we've had already 20% of our target account universe globally has visited our website for the first time ever. And that's like, man, I'm over the moon excited about that.
Now, of course, we’ve got to convert them down funnel eventually, and then we want them all to be Contentstack customers. But these are now accounts that are more aware of us than they ever have been. And so we've definitely seen an uptick in web traffic. We've seen meetings booked increase. We believe we're getting into more deals that already exist.
I call it demand capture. We're part of more deals than we were before simply because people are more aware of us as a company. So that's really the tactic that I think is working the best right now is just making sure that we don't miss out on deals that exist and planting the seed with accounts that are not quite ready yet. They're kind of out market, but eventually when they're ready to modernize their CMS, they'll come to us.
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How to Approach AI With the Team
Michelle: Kind of backtracking a little bit, because you had mentioned using AI and it allowing you to be a little more creative. How do you approach that with your team and kind of this fear or anxiety around AI replacing jobs?
Gurdeep: Yeah, we treat it as a corporate imperative. Obviously, it's native to everything we're doing from a product perspective. But if we put that to the side, it's an imperative at an organizational and individual level to being into the wave of AI and generative AI. And I think a couple of reasons that we're doubling down on it.
Number one, from a company efficiency and productivity perspective and being able to scale what we do. There are so many use cases for AI across all functions, but it requires exploration and experimentation and that doesn't happen unless the company creates space for that.
But then number two, at an individual level, kind of future-proofing your career by really leaning into the learning that AI, the rapid pace of AI, development and adoption is driving. It's not that AI is going to take anybody's job. It's that somebody who's amazing with AI tools will take your job. Right. And that's the shift in mindset we have to drive with our employees. And I have to do it myself, because it's true. Like you'll get left behind if you don't lean into the wave.
And so what we're trying to do is create that motivation and that intrinsic desire to lean in and adopt AI. And even if it fails, it's fine. You tried something, move on to the next thing, because it helps you and your career development. And it also helps the company in our pursuit of scale and productivity. I think the challenge is people don't know where to start. And so they don't start. And so you got to create that space to just try.
Michelle: Yeah, that's definitely true. I think a lot of people are just kind of, they don't know where to start and they feel like maybe they have to put AI into everything when they can just start, you know, pick and choose where they want to put it in at first.
Gurdeep: Yeah, exactly.
A Look at the Next 90 Days
Michelle: So you've gotten past your first 90 days, blown through it. What are your goals for the next 90 days?
Gurdeep: Yeah, I'm already in the middle of it. It's crazy. The reward for good work is always more work. For us, I think it's building on momentum. We've created a lot of momentum. We've reshaped the strategic importance of marketing internally. We've started to change the way the world sees our company and the place we occupy in this market.
But really capitalizing on the new products we've brought to market around personalization and AI and what that brings in terms of scale. And this is technology that has never been possible before and now it is. And that's really exciting and talking to customers.
You know, some of the biggest retailers and wholesalers in the world specifically are looking to do real digital personalization at scale. And they haven't even tried before because the technology wasn't there. It is now.
We want to capitalize on that momentum and really drive that through. Other than that, you know, we're planning for the fall. We've got a big event coming up in Europe in September, ContentCon and MIA, which we're really excited about.
And then, you know, we have a vision as a company, which is the world's best digital experiences run on Contentstack and starting to flesh that out and really drive the right level of engagement with all members of our ecosystem. So our partners, our customers, our prospects, our employees, our prospective employees, really rallying our community around this vision and how we eventually get there. And that includes our product roadmap and where we go as a company.
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The Biggest Unexpected Lesson
Michelle: During your time at Contentstack, what's been the most unexpected lesson that you've learned?
Gurdeep: I think it's the AI piece, the incredibly almost insanely rapid adoption, AI in marketing and the implications on our internal productivity. But also our messaging and our product innovation and how we speak to our prospects. Because it really does tie back to the people don't know where to start.
I think the biggest lesson for me has been that our job is almost to paint the art of the possible with AI internally and externally. And I didn't expect it to happen so fast. I knew it was coming quickly, but like literally within four weeks, I had already talked to enough customers to the point where we knew we needed to create a product offering, which is basically services that handhold somebody from zero to a fully implemented AI use case within 45 days, we call it our AI accelerator. This didn't exist, but basically customers were demanding it because they don't know where to start. And so we productized it and we're actually handholding people through how can you use AI to make your team, company more productive, more efficient and scale. And that's something I just didn't expect right now. I expected it maybe in the next year or so.
And as a CMO, I feel compelled, especially given who we sell to, to be at the leading edge of that. So that's definitely been a, I knew it was a priority. I didn't realize it was such an urgent priority until I started, because I had been out of the Martech space for a little while, jumping right back in, it became very real, very fast.
Michelle: Yeah, even just watching, I mean, over the past couple of years when ChatGPT came onto the market and then just how crazy the growth has been since then, it's really mind-blowing.
Gurdeep: Mm-hmm. It is.
Michelle: Well, that's all the time we have for today. Where can people find you online and follow what you're doing?
Gurdeep: Yeah, well, you found me on LinkedIn. So that's a great place to find me personally. I spend a lot of time on LinkedIn. You can engage with me. You can engage with the company Contentstack. But that's where you'll find me.
Michelle: Well, thank you, Gurdeep. It was great having you here today.
Gurdeep: Michelle, thank you so much. It was great to be here, and I appreciate you taking an interest in the topic.
Michelle: Yeah, definitely.
Gurdeep: Thanks.
Michelle: Thank you so much for joining us for this episode of the CMO Circle. Don't forget to join us next month for an all-new episode. And in the meantime, don't forget to check out our other CMSWire TV shows, Beyond the Call and The Digital Experience.
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