The path to B2B CMO with Juliette Kopecky, CMO at LinkSquares

The path to CMO is not always a straight one, but to get there you’ll need ambition, confidence and a little bit of advice.

On this episode of the FINITE Podcast, hear from Juliette Kopecky, CMO at LinkSquares. Juliette started her career in sales at HubSpot, then bounded through the ranks to land on an executive leadership team.

Hear Juliette’s story to get inspired and gain key takeaways you can use in your own B2B marketing career.

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And check out more of the FINITE B2B marketing podcast here

Full Transcript

Alex (00:07):

Hello everyone and welcome back to another episode of the FINITE Podcast. On today’s episode, I’m joined by Juliette Kopecky who is CMO at LinkSquares, an AI powered contract lifecycle management platform. Juliette has had a particularly interesting career journey before becoming CMO at LinkSquares. So today we’ll be diving into her background, what she learned from her various roles and how a marketer can climb to the CMO level. I’m sure this will be an interesting one. I hope you enjoy.

FINITE (00:35):

The FINITE community and podcasts are kindly supported by 93x, the digital marketing agency working exclusively with ambitious fast-growth B2B technology companies. Visit to find out how they partner with marketing teams in B2B technology companies to drive growth.

Alex (00:55):

Hi Juliette, thanks for joining me today.

Juliette (00:57):

Hi there. Thank you so much for having me.

Alex (00:59):

I’m looking forward to talking. We’ve got a great episode lined up. As I mentioned before, this is a topic that I think is naturally very much on the radar of pretty much everyone in the community in terms of career progression and the journey to the CMO role. So I’m looking forward to talking. Before we do that, I’ll let you introduce yourself. Tell us a little bit about your background and experience and your kind of current role and team.

About Juliette’s current role and team

Juliette (01:18):

Absolutely. So my name is Juliette. I am the chief marketing officer at LinkSquares. LinkSquares is an end to end AI powered contract lifecycle management tool. So what we do is we help legal teams and we help businesses write better contracts, understand what’s in their existing contracts and collaborate better as a team. So we are based in Boston, we’re a startup, we’re about 65 to 70 employees and I run all of marketing there.

Alex (01:45):

Awesome. And tell us a little bit about your marketing team and its current shape at LinkSquares.

Juliette (01:50):

Sure. So I have six people on my marketing team across all the different functional areas of marketing. So I have product marketing, demand gen, content. One of the things that’s probably a little bit different about my team is one of my very first early hires when I came into LinkSquares about a year and a half ago is I hired a video producer. I really wanted to bring that function in-house and to produce a ton of video content. 

I think it’s just fundamentally the way people kind of consume content, that visual aspect as well. And so I wanted to include that really early on in the team.

Alex (02:26):

Awesome. And has it worked? I feel like there’s a whole nother episode we could record on this as a topic, but has it been effective?

Juliette (02:30):

Certainly, it’s been incredibly effective. I think one of the things that differentiates LinkSquares as a product is our amazing user experience that we deliver. And so one of the ways in which we can communicate that effectively from a marketing standpoint is through video to show people what that experience will be like when they become a LinkSquares customer, to help them get familiar with the product and understand it better and to understand the use cases.

Alex (02:56):

Awesome. Yeah, it’s an interesting role. I think some companies will probably have it on the radar, but not have not taken the plunge and invested in the full-time role. So interesting. We’re going to be talking about your journey into the CMO role, I guess. 

And this is actually a question that I ask a lot of guests, just because it’s interesting when they’re introducing themselves, in terms of how they got into marketing to begin with and particularly that education piece. Because I think, and people have probably heard me say this before, but the vast minority of guests we’ve had on the show have had a formal marketing education or marketing degree. 

I’ve had everything from like, I think I’ve had a nuclear physicist. I’ve had a huge number of different formal education backgrounds, and the number of people that have actually spent some time on the sales side, which I know we’re going to be talking about, but tell us about your journey from an education perspective.

How much does a formal marketing education help your career? 

Juliette (03:45):

Yeah, I think as I talked to more and more marketers, it’s evident that a lot of us have non-traditional marketing backgrounds. That’s something that’s really common and I’m certainly happy to tell you a little bit about my own background, which I definitely consider a non-traditional marketing background. 

So in undergrad I studied business. I minored in management information systems and finance. I’m definitely someone who is very quantitative, very analytical and sort of loves that side of the business. And after undergrad, I worked in accounting and finance roles and I’d always been really interested in marketing. 

I think actually my interest in marketing comes from a love of understanding people better and how they make decisions, how they process information, why they may be interested in one product over another and sort of that psychology behind it. And I worked in finance for about seven or eight years. 

And I think at that point in my career, I looked at what was next for me in a finance role, whether that would be a VP of finance or a CFO. And when I looked at those careers, that wasn’t really just where I saw myself. So I kind of took the opportunity to give myself the ability to think through things like, what is it that I want to do in the next five to 10 years. And I had always had this deep interest in marketing. 

And so I took the opportunity, I went to business school, I went to MIT school of management to pursue an MBA. And what I loved about the opportunity there, it was such a great chance to meet people across different careers, to really map out courses that I wanted to take and where I wanted to develop my skills and really where I wanted to pivot my career. And I had always been interested in technology and startups. And so that’s really what I focused on there. 

And so after I went to business school, I joined HubSpot, which was an incredible experience for me and the HubSpot, back in 2010 when I joined, was very different from the HubSpot of today. When I joined HubSpot, they were about, I wanna say maybe like 140 ish employees. And what I loved about the company is one, their focus on marketing. 

Obviously I’m sure your listeners are very familiar with HubSpot and what they do in terms of marketing software, but I love the product, I love the team. And when I was thinking about what I wanted to do next in my career, I wanted to join a company that gave its employees new opportunities and encouraged them to grow in different ways.

Moving from sales to product to marketing 

Juliette (06:16):

And so I actually joined the company in a sales role and it was an incredible experience for me. I learned so much by being a sales rep and getting on the phone every day and talking to hundreds of different marketers to learn more about their job, what are their challenges? What were they doing? Why were they taking a look at HubSpot and then skills like that I would consider life skills, that I still find myself pulling from today in my career in terms of how to message, how to position, how to sell, how to close the deal. 

So it was incredibly beneficial for my career as a marketer and as an executive. And at HubSpot, I’m probably one of the few people, if maybe not the only person there who worked on three completely separate functional teams there. So I started out in sales and as the company grew, there were always new opportunities that were being created. 

And from that sales role, I joined the product team in a customer research capacity and understood our user base even better in terms of how they use the software to help inform new features and functionality that we were developing. And when I think about that same sort of foundation in terms of understanding how people think, how they make decisions, how they use products, I love that role. 

Because I got to talk to a number of different people, understand their challenges, how they wanted to use the product, what were the different pieces of software that they were using to help inform the future of HubSpot and as a company, from that stage continue to grow. 

One of the teams that they were creating was product marketing. And I loved that opportunity because it was a way for me to combine those skills that I learned on the product side and the sales side to be that bridge between the two different teams and build out sales programs, sales tools, sales collateral, competitive intelligence, and things like that, for the company. And really from there is where I grew into marketing leadership. 

So the company I joined after, I took on a director of product marketing role, so really owning that functional area, to a VP of marketing to today being chief marketing officer. And so certainly, career growth is something that I thought a lot about personally for my own career in terms of what directions I wanted to take my career. And what does career growth mean to me? But it’s also, as a result of that, something that I think a lot about for my team that I manage. 

I think career growth can mean different things at different times to people. Certainly during my career at HubSpot, learning a new skill and a new functional area and going from sales to product to marketing was incredibly beneficial and foundational for my career in marketing. But that was career growth for me, even though maybe from the outside, it looked somewhat like a lateral move, but it really enabled me to take my career off and have that understanding of how different teams work together, how they should communicate, how they should collaborate and has really informed marketing programs and decisions that I make. 

For me as a marketer, I want to make sure that the marketing campaigns, content, things like that that I create are meaningful and valuable to our end buyer. But also that they’re meaningful and valuable to our internal teams. I want to create sales collateral and sales content that our sales team uses and that they value and that helps them close deals faster. I’ve sat in that seat before, I know how difficult that job is and I want to make their job easier at the end of the day and help facilitate that process.

Alex (09:49):

It’s a common theme I think whenever I talk to anyone that’s got that sales background. Being able to relate to what your colleagues and on the sales side are going through and what they need. And just having, as you say, sat in that seat, I think makes such a difference overall. Do you think your non-traditional route into marketing has helped overall and made you a better marketer than say if you’d just majored in marketing at university and been a pure play marketer the whole time?

The benefits of a non-traditional route into marketing 

Juliette (10:16):

I think the real benefit that I’ve seen from having say like the specific non-traditional background that I have. The people that are in marketing leadership roles that come from a finance background are probably few and far between, let’s say in terms of as far as non-traditional backgrounds go. 

But I think for me where the benefit has really come has certainly been in an executive leadership role because I think the fact that I’ve worked in finance, I’ve worked in sales, I’ve worked in product, I’ve worked in marketing, makes me a better executive because I understand some of the challenges that my peers, other executives on the team face. 

The ways in which they’re making decisions, what their job is like. So that when I’m creating marketing, it’s not marketing in a vacuum and marketing that’s only for the sake of marketing, but it’s marketing that’s really going to help us as a business and help me work better with my peers. 

Because I do think the role of the executive, I break it out into three different areas almost, where there’s certainly my role as an executive as being the leader of the marketing team. How do I make marketing better at the company that I’m at? How do I help my individual employees and team with their own career growth? How do I get the things out of their way that they need to be able to do their job? 

Then there’s certainly, with being on the executive team, my team is also other people on the executive team, whether that’s our CTO or chief revenue officer or CFO. How do we as a team collaborate better, how do we work better together? How do we help the company meet our goals overall? And then there are things that I focus on in my executive role that I’ll call special projects that I’m involved in that benefit the entire company. 

And that helped us create a better environment for employees to work in, keep our employees engaged. So one thing that I’ll put in there is how we communicate as a company. And certainly that’s been really important during the current time that we’re in during a pandemic. We had to make a number of different decisions in terms of employees working from home, changing a number of different business processes. 

So how do we make sure that we’re communicating all of these changes with employees? How do we help them understand why we’re making these decisions and how do we create a great working environment for them? Another thing that I would bucket under that, that I’m really involved in at my team, and that I’m excited about is diversity, equity and inclusion. So how do we make LinkSquares more equitable and an inclusive workplace for people to work in and where they can do their best work.

Alex (12:53):

Awesome. I was going to ask you about whether you faced challenges in that journey from the sales side, but it sounds like HubSpot was just evolving in such a rocket ship at the time that as you say, opportunities arose and that there was a transition that was quite straightforward. Or would you say that were challenges in terms of going from the sales side into that product marketing role?

Making opportunities for yourself within an organisation 

Juliette (13:14):

I’d say yes and no. I would say that HubSpot certainly facilitated that in the sense that they were growing, that they encouraged employees. And I would say that they facilitated employees being able to move into different roles. I don’t think a lot of companies sort of afford their employees that ability to do that. 

I think a lot of companies prefer sometimes not to transfer employees into existing roles, but HubSpot I think was very progressive in that standpoint. But I would also say like, I don’t want to discount the things and the opportunities that I also created for myself. 

So for example, when I went from sales to product, I don’t think as they were building out the user experience team and the customer research role, that that was something that they said, let’s find someone from our sales team to do this role. I think I was a uniquely qualified candidate for that role because even as a sales rep, one of the things that I probably did differently from a sales rep is I love technology. I love software. 

I wanted to understand the HubSpot product inside and out. And that was kind of my avenue for being an effective sales rep, that when I had a prospect that I was talking to that really wanted to deeply understand, how am I going to use the product day in and day out? What is it like from that experience? I loved taking people through a really deep dive of our product and showing them and putting them in that driver’s seat to envision themselves and how they would do it day in and day out. 

Also at that point in time, we offered a free trial of the HubSpot software. And I loved when I got free trial leads because it gave me the opportunity to showcase our product. And to me, that was someone that was saying, I want to understand what it’s like being a user of your product before I purchase it. 

And so that was a really effective tool for me as a sales rep. I would not say that was the case for all sales reps across the board, in terms of wanting to deeply understand the technical features and functionality of the tool. I think that some sales reps are much more, let’s say, charismatic than me on the sales side. And are the types of people that could sell anything really at the end of the day. 

But the ways in which I was effective as a sales rep was understanding the product. And so I actually engaged with our product team and our product managers and our engineers to understand our product, even when I was in sales. And so in many ways, for me taking on that role on our product side, because I had already established those relationships, I knew the product inside and out. 

I really wanted to understand our customers and understand them better. I think that was an opportunity that was afforded to me. So I think it was the combination of those two. HubSpot was growing, encouraging employees to look at other opportunities within the company, especially for people that were high performers. And then for me, I had that interest and I created that opportunity also for myself.

Alex (16:01):

Yeah. It sounds like the perfect storm and yeah great environment. And then in the three years or so that you were at HubSpot, what was the growth and head count change overall?

Juliette (16:09):

So I want to say, let’s say the company was about 140 employees when I joined in 2010. I want to say in that three-year period, maybe we were about 800 or 900 employees when I left. Which is also crazy to think about the size that they are today and how much they’ve grown even since then.

Alex (16:27):

Definitely. We did an episode on this recently around scrappiness, cause I think 140 people, even that’s not a small business. It’s not by no means a startup that’s definitely in the scale up phase. But that doesn’t necessarily mean that things are calm and steady, particularly when you’re growing that quickly. Was there a kind of a scrappiness and busy-ness that you think had that typical startup-y culture that prepared you for everything else that’s come since? 

Marketing lessons learned from a startup culture 

Juliette (16:57):

Definitely. So I think when I look at HubSpot, even when I joined at 140 employees, I certainly talk about that being like a startup when I joined. But one of the things that I probably learned over the course of my career in like the past 10 years from working at a number of different startups are certainly different flavours of startups. 

And whether that’s in terms of employee size overall, in terms of the funding that they have, and certainly whether the company has achieved product market fit or not. And so the company I joined after HubSpot was a 70 person startup. The company I joined after that was more like a 20 person startup and then LinkSquares being that 70 person startup as well. 

And I think for me, what I’ve learned is certainly that determines a lot in terms of what the marketing needs are, what the roles are on the team, alignment on different goals and how that influences that and finding that sweet spot for me personally. I love the stage that LinkSquares is at. 

I think we have that sort of scrappiness that everybody gets pulled into in different ways. People have cross-functional roles and are handling a number of different things. And it’s just the pace that we’re working at. For us as a company over the past two years, even in the midst of a pandemic, we grew 800%. So I love that sort of rocket ship feeling. But one of the things that I’ll say about HubSpot, even though now with some of that experience behind me, I look at it and I’m like, well I don’t know if 140 people is a startup, right? 

I think one of the things that HubSpot did really well was maintain that startup culture and that feel, so even though maybe employee count wise, maybe funding-wise, they kind of are a little bit bigger than what I consider a startup, that feeling of being fast paced, the focus on experimentation, but also focus on like let’s not just do what everybody else is doing. Let’s clearly differentiate how we’re doing it and why we’re doing it. 

And also be really like numbers and analytical focused. That’s something that I have definitely taken from my experience at HubSpot to my current career at LinkSquares. So HubSpot in terms of the marketing that they were doing, even in 2010 with the focus on video is something that I think I really brought to LinkSquares and it informed and inspired my decision to make video a big part of our marketing from the very start. That it wasn’t something that I wanted to outsource or use an agency for. 

I really felt like it was important to bring that function in-house and then obviously have the focus on content marketing. I think even for a very small marketing team at LinkSquares, we produce a ton of content. Whether that’s video content, whether it’s blog content, whether it’s longer form like written content like eBooks. 

I think we punch above our weight there and that sort of feel of always experimenting and always trying new things and being more creative than what other people are doing on the market. Those are some of the different things that I’ve learned over that course of my career that I’ve brought to LinkSquares.

Alex (20:08):

And tell us a bit about those steps forwards in terms of product marketing at HubSpot. I think then you were a director of product marketing elsewhere, VP of marketing, now CMO, what were key moments in terms of those steps up the ladder?

Journey from product to CMO 

Juliette (20:21):

Yeah, obviously with the way in which I got into marketing, being product marketing itself, I think a big obvious component is my love for technology, love for really understanding the product. But it’s always been really important for me in those roles to believe in the product that I’m marketing and to understand the value that we’re delivering to users and customers. 

And certainly LinkSquares has been no different in that regard. Even though the product we sell to in-house legal teams, we sell to a general counsel, chief legal officer, occasionally it’s a CFO. I’m not the end buyer of the product, but I can see the ways in which we help that user move their business forward to close deals faster, to write better contracts, to understand what’s inside of them. And that was really important for me at LinkSquares. 

And over the course of my career, especially with that technical side, understanding the value that we’re delivering to customers at the end of the day, especially in the roles that I’ve joined. And I think that’s so important in terms of, I would say my own personal satisfaction in the job and the role that I have and believing in the company and also believing in the team.

It’s so important to me in terms of, these are people that I spend so much time in my week with, I want to genuinely enjoy working with them and also feel like there’s something that I can offer for them and help them grow their own career, but also things that I can learn from them in terms of how to be a better leader, how to be a better manager, even different marketing skills and areas that are continuing to emerge. How do I become a better marketer at the end of the day?

Alex (22:09):

Yeah. And that was something I was going to ask you: lessons learned from building teams and things that you consider. I guess an interesting question is, and I think this obviously differs from company to company, but if you were building a marketing team from scratch, is there a first role that you think you would have to fill to get your marketing team up and running?

What’s the first role you should hire in a marketing team? 

Juliette (22:30):

That’s a hard question because I think the answer is, it depends. And I think one of the things that I did, for example, when I joined LinkSquares, so I joined about a year and a half ago and I joined as CMO. But it was also to come in, build out the marketing function and to hire a team. 

And so define what is marketing at LinkSquares and the way in which I approach that. So I wouldn’t say, I’ve had this question before where it’s like, who was the first person that you hire? And I think it depends on the company. I don’t think there’s any one person that you always need to hire first. 

So what I did when I joined is I met with the different team leads across the organisation, understood how they viewed marketing, where they thought marketing could have the biggest impact. And then I also met with a number of our customers and other people who fit our ideal customer profile that were in my network to better understand, how does this audience like to be marketed to and what are the channels and things that are going to reach them most effectively? And then also understood our product in terms of how we sell our product? What does that process look like? And what are the areas in which we can layer on marketing to facilitate the process? 

And so I knew that I wanted to hire a video person, but part of what informed that was just by the nature of our product, because we’re a contract management tool to help people understand within their contracts. I know I mentioned early in the call that on the HubSpot side, I loved it when I got a free trial lead that this was someone who wanted to take a look at our product that signed up and was kind of poking around already. 

At LinkSquares we really don’t have a free trial on our website that somebody can just jump in and start and get dropped into our software. And the reason behind that, it’s just a fundamentally different sales process that no chief legal officer or general counsel is going to come in to an unvetted piece of software and put 10 of their contracts that have their important company information or information on partnerships or NDAs or anything like that into something that they haven’t vetted already. 

And so to me that said video could be a really effective channel for helping the sales process move faster because it’ll give someone sort of that feeling of a free trial and understanding what the product is like when you become a user without having to do a free trial with your own company’s data. And I also knew that the speed at which we were launching new features and functionality from talking with our product team and our engineering team, we move so fast.

 And my experience with working with outside agencies, because you’re one of many clients they’re working with, is that sometimes by the time you get to a finished product, it’s already in some ways obsolete because you’ve made updates in terms of features or functionality, you’ve changed the UI. 

And I wanted to be able to make video production really fast within the organisation. Which is why I would say it’s non-traditional for one of their first hires to be a video person, but it made sense for LinkSquares in terms of our sales process, product and the way in which our buyers purchase. 

And so I encourage people when they’re trying to make that decision about who their first hire is and how they build out their team to really look at those things, because I don’t think it’s a one size fits all. I don’t think that everybody needs to hire a video person or a content person as their first hire, but I think it’s what made sense for our business and for the customers and for our sales process.

Alex (26:11):

Makes sense. I guess to wrap up I’m interested in understanding now that you’re in the role that you’re in, a bit about that relationship with others in the C-suite as such. So you mentioned the chief revenue officer and I’ve assumed CFO and other kinds of functions. And I assume the MBA that you did was maybe helpful in some respects in this area. But I think a common thing I hear from marketers is kind of struggling to have that C-suite conversation to speak the language of finance, to speak the language of whoever else they’re working with. How did you find that and how do you find that now?

Should marketers get an MBA? 

Juliette (26:44):

So I don’t know. That’s a really big question and I can only answer it from my own perspective. I think in particular, I get this question a lot in terms of, should I go back to school for an MBA? Do I need that to get to the next stage of my career? And I think it depends. 

I think for me doing an MBA was huge for my career and my ability to sort of pivot really quickly from finance to startups to a marketing role. But I think that everybody needs to kind of evaluate, what are they hoping to get out of an MBA and make that decision that way? 

I think for me, I was at a point in my career where I wanted to do some self reflection and evaluation and really figure out what I wanted to do next and also explore and experiment and take courses in a number of different areas and figure that out for myself. But I don’t think it’s necessarily like a prerequisite for getting to the C-suite. 

And I think for me then a lot of the learning that I did in terms of how those different functional areas operate and how to work effectively with other people on the executive team was through that experience like I had at HubSpot and sitting in those roles on different teams. I don’t think it’s something that everybody needs to do, but it’s the thing that worked for me in terms of how I was able to grow my career. 

I also think for my own personal interests and abilities and what has grown me to different areas of career, I love startups, and it’s always this mix of being hands-on and rolling up your sleeves and doing the work. And also a combination of being strategic. And that’s a great fit for me and what I love about startups, but that’s not how everybody needs to get to the C-suite. 

And so what I encourage people to do is really like reflect on where it is that you are now? Where is it that you want to go? And what do you want that journey to look like? And to be somewhat prescriptive about what those different steps are and map that out. 

Sometimes I think the mistake that I see people make is let’s say you’re in a marketing manager role and you want to be a CMO, that’s not going to happen overnight. So what are the opportunities that you create for yourself along the way? And maybe sometimes it’s taking something that feels like a lateral move, but is that going to get you closer to where you want to be at the end of the day? 

And then how is it that you want to grow your career and how do you want to create that opportunity for yourself and to develop those skills? And if I think about my career at HubSpot, it was very much that way, that sometimes it felt like lateral moves. But I was understanding different sides of the business and shaping the ways that I could think about like our buyer and our user and about the functional area of marketing and then growing my career, through product marketing and sometimes involved making company jumps for different opportunities and creating that opportunity for myself.

Alex (29:49):

Some great tips that I think anyone that’s on the career progression pathway will get lots of value from. So I really appreciate you sharing all your insights and telling the story. Because it’s a great one. So thanks again Juliette.

FINITE (30:05):

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