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A successful CMO has many roles, including leading an organization's marketing department, establishing marketing strategies, and tracking successes and failures. How can a CMO create a highly successful career? What tools, strategies, and approaches can a CMO use to be successful? As part of this series, we had the pleasure of interviewing Tara Robertson.

Tara Robertson

Tara Robertson

Tara has over 20 years of global experience leading award winning marketing teams. Before Bitly, Tara was the CMO at Teamwork, and held marketing leadership roles at Sprout Social, Hotjar, and TSL Marketing, an Inbound Marketing agency. With a passion for growth and results driven marketing, Tara builds full funnel marketing strategies and teams that drive both customer acquisition and retention. Outside of marketing, Tara is also passionate about her work as an ally for diversity, equity, and inclusion in the workplace and serves on the DEI council at Bitly.

Thank you so much for doing this with us! To begin, can you share your personal backstory and how you got started in your career? 

Thank you for the opportunity to do this! I’m originally from New Jersey, and I grew up in a family that came from little means. I remember how I watched my parents both work extremely hard to provide for myself and my sister. This motivated me in so many ways to develop a strong work ethic, but also be present as I embarked on my own journey and career.

I am now Chief Marketing Officer at Bitly, the world’s leading connections platform, where I am responsible for all facets of marketing, from acquisition and retention—which drives Bitly's more than 10 million monthly website visitors and millions of monthly active users—to content strategy, customer lifecycle marketing, brand and public relations, and product marketing.

Before joining Bitly, I was CMO at Teamwork and held other marketing leadership positions at Sprout Social, Hotjar and others. I now live in Vermont with my husband and our two kiddos!

What do you think was a pivotal moment that led you on your path to becoming a CMO?

I’ve always been interested in leadership roles, even before I entered the working world. My mom owned her own retail store, so I learned a lot about running a business at a very young age. In college, I started working as a general manager while I was getting my degree in marketing at a small tele-sales office. As I continued to lean in to my own career, marketing leadership was my primary focus both in work and in education. I was fascinated with connecting the dots between the psychographic behavior of what makes people buy with the analytical components of really creative campaigns.

This is silly, but back in 2000, I remember watching “What Women Want,” with Helen Hunt and Mel Gibson, and Hunt’s character was a badass creative director and I remember thinking: that job looks awesome! She’s a big advertising and marketing creative leader, a woman, and a serious boss lady. So that was where I started to pave my own path. I was lucky to achieve early success in my career and stepped into my first VP role in my 20s. There were parts that were super difficult in running a multimillion dollar agency and half the business while not really having any mentors and in a lot of ways, NO idea what I was doing. But I was always determined to figure it out!

As I continued to grow as a leader and marry that (literally) with starting a family, my ambitions became blended between wanting to lead, while also being the best parent and wife I could be. I had to learn to focus and find balance, understanding that I could not do it all and recognizing that “you don’t know what you don’t know,” which I refer to as my favorite quote below. So I took some time to really manage leadership growth with the ability to learn how to be the best leader I could. Finding results, balancing time, becoming great at prioritization, and communications were all critical skills that I had to become great at in order to have that “pivotal moment.”

Thinking back, I remember a conversation with my former CMO at Sprout Social about my 5-year growth plan and she mentioned the idea of me becoming a CEO or CMO someday and my immediate reaction was “HELL NO.” I was still learning to juggle and balance being able to manage my own career and growth trajectory and build a team: I hadn’t quite mastered the ability to say “no” just yet and was often burning myself out.

So at that point, it became less about chasing a title and more about chasing those things that drive my passion, aspiration and values. That journey was critical to where I am today as I needed to go through a substantial amount of  learning before stepping into the CMO role so that I could be in a position to be the best version of a leader, both at work and home. Having had the opportunity and experience to take several years to balance my early success with prioritizing what mattered most was what led me to that pivotal moment.

When I was recruited for my first CMO role I was thrilled and ready to take on the challenge (which ironically was less than 5 years from that conversation listed above!) because I thankfully invested my time and energy into the soft skills along with the hard ones and surrounded myself with a network of people that I knew I could lean on. My mindset on my own growth changed because of the time I invested in leveling up myself as a leader. 

Can you share the most interesting story that happened to you since you began leading your company?

My onboarding experience at Bitly was nothing short of traditional! When I joined (only 5 short months ago) we were deep into launching a top-of-the-funnel brand campaign and I needed to lean in quickly while also getting acclimated to my new role!

We were launching a new OOH brand advertising campaign, and kicked it all off through sponsoring an event at Advertising Week NYC. At the event, Bitly’s  CEO, Toby Gabriner, was speaking on stage with the VP of Marketing at Marvel Studios about the impact QR codes had on their recent video series, Moon Knight. It was an incredible story and we knew there was an opportunity to turn it into a brand moment at Advertising Week, in addition to the advertising we were already planning.

In less than one week, the team went from ideation to production and quickly created an activation in which we partnered with a top food vendor in the city and we gave away cookie dough to attendees. For every cookie dough dessert given away, Bitly made a donation to the World Resource Institute, a globally recognized non profit organization we partner with through our Bitly Cares program. We had a “dough-nation” wall that attendees could sign and take pictures in front of, and that tracked the number of donations we were making.

This initiative had a great impact and was an incredible way to get our brand initiatives off the ground. Seeing this all come together, from concept to launch, in less than 3 weeks' time was a really thrilling way to get started and also my favorite story because it shows how quickly this team can achieve success all while having fun. This isn’t something you see or experience often and I am truly grateful and honored to serve this team. 

None of us are able to achieve success without some help along the way. Is there a particular person you're grateful for?

There are so many people who I’ve learned from over the course of my career.  One of my first memories of my career in software as a service (SaaS) is through an interaction with a now close friend Kyle Lacy, CMO of Jellyfish.

I first met Kyle at an event where we were both speaking when I was VP of Marketing at Hotjar. I remember being incredibly impressed by Kyle’s depth of experience and knowledge as a marketing leader within the SaaS industry. Being new to leading marketing at a SaaS company, I nervously asked Kyle if he’d be open to being my mentor. I'll never forget when he responded, “No, I'm not going to mentor you because I don't really bring on mentees, but you know what we'll do? We'll network. We're going to share things with each other and we're going to spend some time getting to know each other.”

To this day,  so many years later, Kyle and I still talk on a regular basis! It really just started an incredible friendship that taught me not to be afraid to approach people who you admire and ask them for guidance. But also that networking isn’t just about a mentor/mentee relationship, and instead there is so much more to surrounding yourself with people you can continue to learn from and grow with together. 

I also am super grateful for my Shine crew, which is a collection of incredible women, and leaders across the SaaS industry in various places. We have a small but mighty community where we all can jump in and ask questions, share best practices, and most importantly connect with one another as we build our careers and businesses. These women are leaders I admire in so many ways, and outside of learning from them (literally every day) they have also become some of my closest friends across the world.

Finally, Jamie Gilpin, my previous CMO at Sprout Social, is another person who I’m extremely grateful for. She’s always made time to hop on a call with me if needed and has helped me on my own CMO journey in countless ways! 

As I continue to grow, I always hope to also pay it forward and share what I’ve learned with anyone who reaches out to me (as best as I can). There are a lot of people who have worked through the same challenges, and even if you think you know, there’s still other ways that things can be done. So it's great to have people in your network who you can continue to connect with—and as Kyle taught me, it doesn’t have to be within a formal mentorship model.  

Can you please share your favorite "Life Lesson Quote"? How is it relevant to you in your life? 

I love the quote “You don’t know what you don’t know” by Socrates. I’ve come to realize that it is okay not to know everything, but I learned this the hard way. I think many of us early in our careers struggled with the imposter syndrome. We felt that we didn’t earn a seat at the table and that we might be ‘found out.’ I remember feeling like I always had to have the answers. I put pressure on myself to answer all questions and might have given the wrong response, and then have to backpedal later, instead of saying, “That’s a great question, let me get back to you.” This just made me more and more nervous.

When I was new to SaaS, I worked with a CEO who was really experienced in growth and would ask me a bunch of questions when I was still learning but not giving me the space to learn... It was really challenging. I found myself waking up at 3:00 a.m. and going to bed at 11 p.m., constantly checking Slack. I couldn't shut down because I was trying to do everything.

In retrospect, instead of feeling like I had to have all the answers and do all things, I should have said, “I don't know" or "Hey, let's consider bringing in more people to lesson these gaps.” I mentioned this above but I am prone to burning myself out and learning that it’s OK to not have the answers was one of the most important lessons I’ve learned in my own ability to lead effectively.

Fortunately, these experiences have made me a stronger marketer and leader.  Now, when I look at organizational design, I make sure I don't look for lookalikes. Instead, I look for people who are smarter than me in certain areas or who are really strong in areas that I know that we're going to need to invest in. What makes a marketing team extremely strong is the way we bring our individual strengths to the table. If we all agree that ‘You don’t know what you don’t know,” then together we can figure it out by looking to each other for the answers that we don’t know together. 

Can you share with us three strengths, skills, or characteristics that helped you to reach this place in your career? 

  1. Empathy -  One of the most important things I think you have to bring to your marketing team is empathy. I'm a huge believer in servant leadership first. We aren't here to tell people what to do. We're here to serve the teams that we're working with. And, you've got to let people fail. But in order to let them fail, you have to create a safe and a brave space to try. You have to have empathy with the people you're working with and the people you work for. This is especially true with remote work and having to build relationships over a screen. It’s so important to take the time to understand what people are bringing with them day to day, how they work, how they like to work, how you work together. Setting this foundation and connection will make work a lot easier as you dig in.
  1. Networking -  I can’t stress enough the importance of networking. I’ve learned so much from my professional colleagues and continue to do so every day. I’m fortunate enough to be part of a women’s networking group called Shine Crew (as listed above), which consists of highly successful women from around the world; many have started businesses, written books, and currently serve or have served in leadership roles at top brands. We also try to get together annually in person, where we talk about work, experiences, life, and all the things that matter to us. These amazing women in so many ways have become some of my best friends and most trusted advisors.  
  1. Results, but also balance - Early in my career, I struggled with wanting to do it all because I thought that was how you get all of the opportunities. What I’ve since learned is that it’s important to hone in on the most important outcomes and to devote the majority of your energy to delivering those results. And while results matter, they need to go hand in hand with balance, otherwise you will burn out. Or even more importantly, burn out your team. Staying focused and saying ‘no’ are game changing, but they’re skills I had to learn over time. 

How can others actively build these areas within themselves? 

One critical bit of advice that I touched on earlier is you should never be afraid to ask for help. It’s also important to have the ability to listen with intent. We can all walk into roles with preconceived notions or ideas about what we think is going to work. The reality is we have no idea because every business is different and every team is different. I’d recommend reading a great book for those starting in a new role called “The First 90 Days,” which provides a framework for how to enter into a position with the idea of listening first. 

When I started at Bitly six months ago, I had a very intentional listening plan and called it the listening roadshow. I took the time to ask my colleagues all the same questions, parsed through the feedback and honed in on the ideas and goals that came up across the entire business. I did the work to really understand what the businesses needed and developed an intentional plan to drive priority projects forward. This, in combination with the quantitative and qualitative marketing results, has set an intentional roadmap for us to scale.  

Which skills are you still trying to grow now?

Championing diversity, equity and inclusion is an area I am always investing in. I first want to give shout outs to the leaders in this space who have helped me along this journey: Jackie Cureton, our Vice President of Diversity, Equity and Inclusion at Bitly, and Michelle Bess, who was the Director of Diversity, Equity and Inclusion at Sprout Social when I was there. These women are two leaders who in so many ways have changed my perspective as a leader and also as a person and I’m so thankful to leaders who dedicate their careers to this space. DEI cannot and should not ever be an “in addition to”—it is embedded into everything we do as leaders and as a business. 

As a privileged white woman, I need to always open my eyes, learn, and listen deeply. I took my privilege for granted in the first part of my career because I hadn't done the work of learning about the importance of DEI in the workplace but also the world. We need to understand bias better, and while I’ll never understand the experiences that other people or communities may face, I can be a better ally, always. Along with this, not only do we need to show up and create a more equitable workplace and future, we also have a commitment to show up as a brand so that we are creating a more inclusive and equitable  brand experience for ourselves and our customers. 

Having reached this space, what do you believe are the five things you need to be a highly successful CMO?

1 . People first - I think it was Zig Ziglar who originally said, “You don’t build a business. You build people and then people build the business.” This quote is one that has stuck with me through my entire career. In our industry you really are nothing without your people. And we are all always learning and growing in various ways.

In order to be a highly successful CMO, I believe you need to always lead with a people first mentality. This includes getting really great at active listening, being empathetic, and making sure you understand and can commit to learning as much as you possibly can around diversity, equity, and inclusion in the workplace. In a previous role I worked for a leader where the majority of the team I was working alongside did not believe in the vision of our leader. This created major friction, turnover, and a lack of psychological safety; it’s no surprise that results and creativity then struggled.

When people feel empowered and believe in your “why” everything becomes that much more exciting (and fun)! Today, my favorite days are when someone in the marketing department launches a new initiative or takes a risk and tells me about it afterwards. People should never be afraid to fail forward and creating a safe space to learn and grow is what drives collective success.

Finally, it’s also important to remember this mentality is as much external as it is internal. As a CMO you are responsible for not only building your team but also building a brand that showcases people. Regardless of if you’re B2B or B2C, you are marketing to people. And people connect with brands that are authentic, meaningful, and align to their values. Never underestimate that! 

2 . Just because you can doesn’t mean you should - Through many stages of my career I have had scenarios where I wanted to roll up my sleeves and simply “do the work’ but priority and focus becomes harder to manage as you continue to grow. Depending on stage, CMOs need to learn to become great at recognizing where the business needs them most, and be sure to empower people and trust around them to execute.

I've had to learn to be able to be OK with not giving feedback on everything or inserting myself into the projects that are distractions from where the business needs me most. Get ruthless on what the most important initiatives are and spend your energy and time on those things, and then empower your team to run with the things that are needed to keep the business running. Learning to let go where necessary, lean in where critical, and getting really great at prioritization is a critical skill for every CMO. 

3 . Be data curious - You have to be data curious to understand the impact of what you are driving. As a creative, it’s critical to connect your empathetic side with your data driven side to really understand the outcome. You need to look at what people are clicking on and why. When you tie your creative side with a data driven mindset, you will drive toward the most success.

4 . Communicate often and in every direction - Communicating effectively is one of the most important things you can do outside of setting a North Star and the strategy for your team. You can have the best strategy in the world, but if you haven't communicated it and generated buy-in from your peers across the business and CEO, then it really doesn't matter.

At Bitly for example, after my “listening roadshow,” I would then communicate my observations both to the marketing team as well as the leadership team, and suggest where we should prioritize and invest to reach our objectives. Communicating up, down and sideways on a daily basis to ensure company alignment is one element of success.

It’s also important to understand who you are communicating with. In the same scenario, you might be sending your CEO a high level tl/dr, clear and concise results for your board, and then much deeper context and not just the what but also the why for your team. Make sure you know who you are communicating with and then tailor your comms accordingly. 

5 . Deliver value not just demand - We have to remember that we're not just marketing to businesses if we're B2B or consumers if we're B2C—we're marketing to humans. We all are fundamentally looking for value in the things that we purchase. Marketing is not only about driving demand, it's about driving value.

If you’re just focused on the number that you need to drive from demand, you may be missing the point but also the outcomes that will matter. If you focus on value first and take all that upfront work and customer research to understand your buyers (why they buy, what connects with them), then you're actually going to get incredible demand. I'm not suggesting not to think about demand, but if you start with value, you will then in turn drive demand. 

Are there any underrated skills or qualities that you encourage others not to overlook?

In general, I think a strong understanding and prioritized focus on competitive research and customer intelligence is a significantly underrated skill for CMOs. I was very lucky to work under some really amazing growth leaders earlier in my career and learned a ton about customer surveys, parsing qualitative feedback, and finding patterns in customer research and data. This has helped me extraordinarily when it comes to building campaigns and strategies that you know will convert and empower your team to do the same.

Not enough people talk about or prioritize qualitative feedback along with quantitative, or even make the space in their strategy to make sure this is a priority. But in all cases this has also been the 10x difference in marketing strategies that drive substantial impact and demand creation.  

What are some of the main issues that other CMOs commonly struggle with? What can be done to address those challenges?  

One of the biggest challenges CMOs face is defining and focusing on priorities, as I mentioned earlier. To address this, CMOs need to identify what's important to the business and what's important to leadership. What are they looking at day to day, and what numbers are they presenting to the Board? How do these things line up with their team needs in order to be successful, and what does the business need in order to grow? This is where they really start to put together a roadmap that goes deeper into how to achieve objectives and determines where to invest to fill gaps and roadblocks.

This coming year will even be more challenging as we’re being asked to do more with less given an uncertain market. This is where having a clear path on what the big bets are, and making sure you are ruthless is focus is going to be critical. Your team will only have so much capacity, but results are even more important for scale. Chart a path, and stick to it! 

What do you believe is the most effective way to stand out and make an impact as a CMO?

As mentioned above, outside of focusing on great results, I believe you also need to communicate your story, give back to the communities, and lean into networking. Early in my career I invested a lot in public speaking, networking with peers, and learning as much as I possibly could. Today, I am still an active part of several communities and continue to speak at conferences where I can share results, stories, and stand out strategies that have helped me continue to grow in my career and with the teams I am a part of.

This has brought me countless opportunities and also scaled my network beyond acquaintances to close friendships and allies across the world. This is externally. For internal effectiveness, focus on communicating often and bring people in to understand your strategy, results, and vision. 

Lastly, if you could inspire a movement that would bring a great amount of good to many people, what would it be? 

Over the years I have invested a lot of work and time into learning how to be a better ally and lean in to educating myself around the importance of DEI, both in the workplace and in my everyday life. I’m also the proud parent of an LGBTQ child and would love to find ways to inspire a movement on how we can create a more inclusive and equal opportunity future for our children.

The more I learn, the more I struggle with current demographics of our Industry and while I am proud to work for a company that prioritizes this as a focus, there are still so many companies that don’t. I’d love to see a world where we have equal representation with not only LGBTQ, but also BIPOC, neuro-diversity, gender, and all underrepresented communities.

I’d love to connect with people (perhaps more marketers) who are equally passionate not just about what we do but how we can leverage our skills to create a better future workplace. 

Stephanie Hood
By Stephanie Hood

Stephanie Hood is an experienced marketing professional and Editor of The CMO. With nearly a decade spent as Marketing Manager at Discover Holidays and Executive Editor at VIVA Lifestyle & Travel, she built her career leading editorial and marketing teams and strategies that turn six-figure budgets into seven-figure profits. She now enjoys connecting with the world's top executives to learn their secrets to business success, and shares those insights right here with her community of like-minded professionals. Curious what she’s uncovered? Be sure to sign up for The CMO newsletter.