Cath Anderson on the Art of Managing Up as a Comms Leader

Mixing Board Studio Session

Mixing Board
16 min readAug 14, 2023

Cath Anderson is a corporate communications executive who has worked in-house at Apple, Google, and Meta (Facebook), while also building the communications function from the ground up at places like Amwell and, now, Cityblock Health. Her specialty is advising CEOs and founders on how to shape their company narratives, mitigate reputation risk and strategically position their brands to ensure relevancy for years to come.

Cath also advises early-stage digital health startups on their communications strategies and mentors PR folks at different stages in their careers. She’s passionate about empowering the next generation of communications professionals to ensure better representation and inclusion in storytelling.

In this Studio Session, Cath and Mixing Board Founder, Sean Garrett, talk about becoming a true business partner and influencing beyond comms; managing up and establishing the right information flow with your execs; doing comms within a highly regulated industry; and, the importance of hiring from the communities that you serve in.

SG: How did you get to Cityblock Health and tell us about your role?

CA: In my role as SVP of Communications at Cityblock Health, I am responsible for both the corporate communications function and brand reputation. I am primarily focused on evolving the brand narrative beyond being a high-growth health tech startup with strong fundraising and helping them mature in a way that showcases our impact.

When I started at Cityblock, I actually came back a month early from maternity leave. I said goodbye to my Facebook colleagues and jumped right in at the end of summer 2021. Before I got there, there was one person managing communications as their “side” job, with support from an agency, but that was it. There was no storytelling function, no one thinking more broadly about the company’s evolution. We have looked at everything from how to build structure around data governance, the proof points that we publish to show our model works, as well as building out and evolving the culture, as we grew very quickly during the pandemic. And then of course corporate communications around executive comms, investor relations, financials, and risk mitigation.

I had been in the startup world prior, spent two stints at Amwell, a leading telehealth company. I also spent time at Apple, Google, and Facebook. They say you have to ramp when you move to a global consumer brand, but I would argue the inverse is true as well. It’s very humbling to work at a startup. You don’t realize your ego is as big as it is until it rears its head. I believe in always having high standards, but sometimes you judge things by the sophistication of the program or the cross-functional team and how they operate. The truth is, that’s all well and good, but it may not actually be what the business needs. You have to meet the business where the business is, in the current moment. You can develop an extremely sophisticated comms strategy and program, hire the best of the best, but if you’re not meeting the business where the business is — not just mapping to the goals, but actually understanding how to best help them get there — you won’t really move the needle.

SG: There’s obviously a lot of comms people who have worked at Apple, Google, and Facebook, Meta. Many of them go on to do different things and many of those things are going to work at startups. Maybe they had previous startup experience, or maybe not. We all know about executives who lived in those places and then did a startup and their expectations of comms. But as a comms person, how do you reset your frame? Because you’re moving from a place that you are actively almost trying not to get attention to a place where very few people know who you are, on a relative basis. And you have to think about how to gain the right attention.

CA: It’s all about gaining the right attention. I remember cold calling until I was blue in the face, back in 2010, at Amwell. People not only didn’t know the company, but they didn’t even understand what telehealth was. People know who Cityblock is, especially in Silicon Valley, in New York, and on Wall Street, because of the investor’s eyes on the work we’re doing with the Medicaid space.

That being said, I joined right as there was starting to be some fatigue among journalists, who had this very positive emphasis on all of the good work happening in digital health with the pandemic. There was some fatigue around that and to be frank, a lot of the funding was running out. We saw some exposé stories hit fall 2021, spring 2022, and those were early signs that the rainbows and unicorns phase would not last — health tech companies, who had raised hundreds of millions of dollars, need to start proving their value.

That was a big piece of the strategy I laid out for leadership. We needed to take an “offense as defense” approach. We needed to look at what made us unique and maintain that, but also look at what needs to change. How can we be vulnerable in this moment to bring people along as we continue to evolve and grow?

SG: You mentioned displaying a form of vulnerability. How did you use that, in this moment where pressure was being put on? What about vulnerability helped you? And how did you define that as a comms strategy?

CA: As everyone who works in comms knows, trust is a huge piece of being able to pitch a strategy, to execute, and be successful. Building trust with your C-suite is a huge piece of that.

A lot of people shy away from vulnerability because they’re fearful. They feel like we need to show strength, never talk about something until it’s fully buttoned up, and only poke holes in things behind closed doors. All of those things are absolutely true, but oftentimes the fear that is sometimes embedded in that process prevents us from being authentic and genuine.

For example, sharing your learnings along the way is really a version of lifting the veil on product development. It often allows you to give yourself more air cover or show people why you did something, and therefore they have a lot more grace for you as you evolve, learn, and grow. If you make a mistake or you decide to pivot, they’re not going to read into that as quickly as they might if you were a brand that was really always shiny and sexy and put together.

It’s not right for every moment, but in the last couple of years, coming out of a global pandemic and even more recently with the war in Ukraine, there have been so many things that we’ve all had to navigate — not just as communications professionals, but as humans. There’s a real appreciation for vulnerability and giving grace. I’ve always looked to see how that vulnerability can be a strength as a leader.

We need to redefine the word vulnerability. It has a negative connotation in many circles. Personally, as a parent, I’ve come to see it as a huge strength. I’m leaning into using my vulnerabilities to continue to grow and advance the priorities in my life that matter.

SG: Is there a tangible example of how you’ve brought this to the fore, either on your team or with your CEO?

CA: Some of the examples I’ll point to are a little bit earlier in my career, but even inherent to the beta program that Apple puts out around their new software releases every fall, vulnerability is definitely not a word you would use, unless you’re talking about security vulnerabilities in the literal sense. But in truth, a beta or a test period is simply inviting people to try something and to find the issues to help you further the product.

A lot of the storytelling I did during my time at Facebook, in the wake of Cambridge Analytica, was around the things that we just didn’t anticipate when it came to privacy. Not just as a company, but really as an entire industry. The internet evolved so rapidly and there was so much focus on speed; there were a lot of things we didn’t think about when it came to data sharing. I just typically lean towards saying the thing, owning it, and then looking at how to make something better, versus trying to bandaid something or hide.

SG: To a new leader who’s maybe being told by their investors and their lawyers to not talk about this or that, to just keep their head down, how do you manage that? Especially as a new leader, how do you approach that relationship and think about managing up? To me, this is very underrated. And it’s one of the harder things about a role. It’s very easy I think for comms leaders to be like, “Well, they don’t get it, so I’m just going to do my job. If I do my job well, I will end up getting credit for it and people will know that I’m good at my job,” which is unfortunately not true.

CA: Absolutely not true, biggest lie there is.

Sean: So explain that, because I’ve lived that lie.

CA: The most important thing as a communications leader is to see yourself as a true business partner, especially as you come alongside a new executive and they step into the CEO role. Establishing yourself as a business partner, beyond just the comms piece, from the very beginning enables you to have influence beyond however they might define comms. That will help give you a seat at the table.

The moments where you want to lean into vulnerability are not always apparent. It’s not the type of thing I would bring to the table day one with a new executive. First and foremost, I would come with a curiosity and a dialogue around the business, the direction the business is going and what is most important to this leader in their new role. What is the legacy that they would like to leave on the company, on the industry?

From there, you ensure that that is feeding into the business goals from a corporate standpoint (in terms of what the board’s expectations are, et cetera). Then you develop your strategy and your content — you land on the top three messages for the executive’s profile, you begin to build their stump speech, as it pertains to the industry and their SME.

And as we know, a strategy and a content calendar are never set in stone. They’re evolving, living things that we’re developing as we go. We are pressure testing daily to ensure that they resonate, that they are relevant to the top news of the day, and that we’re pivoting and making ourselves as helpful as possible in the areas that we can provide a unique perspective. In those moments, you ask yourself those questions and you say, “Is this a moment for us to weigh in on thought leadership? Is this a moment for us to announce this new thing or this partnership?” And then you find the opportunities to lead with vulnerability.

Right now I also advise some startups in the women’s health and wellness space. With some recent layoffs, one of the concerns I’ve heard from a lot of different leaders, is, if they do look to make cuts, they’re very concerned they’ll get lumped into this broader trend around companies that are at the end — they have six months left, in terms of money in the bank. Their concern is, if we make cuts much earlier from a place of financial stability, will we just get added to the layoff roundup that’s issued every Friday? I think the answer is no, but it all depends on how you tell the story.

A lot of that is based on a more complex strategy around landing several messages in the same moment. Which simply cannot be accomplished effectively if you are just going through the motions daily, if you’re just a “yes man” or if you are not considered a true business partner to your executives. You’ve got to look at things from multiple angles and you’ve got to be all in. Honestly, you’ve got to be one of those comms people that is always working with one ear to the ground. Some of my best syntheses, analyses, and brainstorms happen in off-hours. That’s just something that most comms leaders develop over time and you learn to balance, ideally with autonomy over your schedule.

SG: When you’re thinking about managing up and going through these acute moments, how often are you connecting with the CEO? How much do they need to know about what you’re doing? How much do they not need to know? What’s the right back and forth to divide and conquer?

CA: A lot of that depends on how long you’ve been working together and the CEO or executive’s preferences and their work style. Because for some people, if you give them too much information, they’re just going to get so bogged down in the weeds or they’re not even going to read it. My MO, over the course of many years, has been to share less and less information. I just give high level analysis and make sure every single thing I share is actionable.

But one of the things I’ve found, going back into the startup world, that’s a bit counterintuitive, is if you have an executive who hasn’t done a lot of comms in their career, it actually is helpful to share more detail. I haven’t cracked the code — at times I’ve probably gone too far in one direction. But as with any relationship, I feel like you begin working with someone, there’s a pendulum, and eventually you find the right space.

Over the years I’ve had executives that I’ve had to go track down on campus because they’ve very blatantly said, “I don’t read email,” or they wouldn’t always show up in meetings. I’ve had other executives I just text with all the time and then I’ll put much more formal decisions that are more cross-functional into email.

More recently, as I’ve gotten more senior, I do a lot more texting and quick phone calls to pre-wire and do the managing up piece to set expectations. Then I have my senior leaders, who own particular bodies of work, share. I’ll only really weigh-in if there’s a clarification that’s needed.

SG: You work in this highly regulated industry. Your actual comms are regulated, literally. Yet you want to be interesting, you want to convey something different. You’re a startup after all. The value of what you bring is that you’re not the old thing. How do you balance that in an industry that is not used to that?

CA: We’re doing something new — introducing a radically new model of care, but we’re operating within the existing system. When it comes to healthcare, I’ve seen a lot of startups be very unsuccessful by trying to operate in a vacuum or a silo on the side and avoid the regulatory environment completely. This will never work. The hybrid approach is the only approach.

Cityblock is flipping the healthcare delivery model on its head for a very specific subset of the US population, primarily Medicaid and dually-eligible beneficiaries. People who are dealing with chronic conditions, often multiple chronic conditions, they’re living at below the poverty line, and they’re primarily Black and Brown communities because of the history of our country and the racism that is inherent in the system. The country has been trying to make healthcare work for these people, but it just hasn’t been successful; we have not seen a long standing impact. But the exciting thing is that it is a huge opportunity. We spend the majority of our government dollars on this population and a lot of our customers and partners in the payer space are really excited to finally have a new way to look at things.

One of the things you always want to do when you’re working within an established industry is to use the existing language that people can relate to. You don’t want to reinvent the wheel and come in and throw a bunch of new things. You want to bring as much familiarity as possible, keep the message simple, and get to the differentiation as quickly as possible. So what are we doing differently? We are showing up and knocking on people’s doors and helping them navigate their healthcare.

In comparison, somebody might go see their doctor twice a year, get a prescription and then never fill it because they don’t have the transportation, the childcare, they’re dealing with a mental health condition on top of diabetes or hypertension or whatever. We are saying, “Okay, you’ve had your doctor visit, you’ve now qualified for a wheelchair. You have three prescriptions waiting for you at the Walgreens down the street, but you have young grandkids that you’re watching during the day so your kids can go work. We’re going to help you, connect to those social services to ensure that you can actually go get the care you’ve been prescribed.” Only then can we actually determine if you’re going to then have an improved health outcome.

What resonates for me, individually, is cutting through some of the bureaucracy. The irony is, we’re working within the government system. But we’re also rebuilding trust with a population that has frequently been left behind. It’s infuriating when you think about the number of people who end up with really reduced quality of life because of the conditions they’re living with. They’re not getting the care they deserve.

Cityblock is still at the phase where we’re scaling, but the more we can tell the story in its most simple form, the better. We just rebranded last year, and a lot of our rebrand was built around some very in-depth interviews that we did with our members, with the population that we serve. That helped us determine what it is that makes you answer the phone or open the door when we call? One of our biggest messages is that we really want people to feel seen and heard. We don’t think that they can truly achieve health in a new way without that — but the onus is on the healthcare system. That’s actually a big piece of the new focus in health overall these days, not just at Cityblock, which is really exciting to see.

SG: ​​Given your audience, how do you integrate DE&I at Cityblock? How is that woven into your approach?

CA: I can’t take any credit for this, this is how the entire business was built at its conception (kudos to our co-founders!), but we hire from the communities that we serve. Similar to the way in which a lot of cities are rethinking civil servants, whether it’s police officers, firefighters, or teachers — there’s been a huge dialogue around teachers actually teaching in the communities where they live. We hire community health providers (CHPs) from the communities we serve. One of our focus areas is economic empowerment and one of the best ways to do that is to hire intentionally. There’s a really interesting story there as we expand across the country.

By default, we also have a very high bar when it comes to DE&I and inclusion. To be honest, we actually don’t talk about it nearly as much as I have at past companies because it is so integrated into everything that we do. It shows in the numbers. A lot of companies are still working to achieve 25%, but we have pretty strong numbers. The last time I checked, we had approximately two-thirds people of color across our workforce and this carried over to our board and executive leadership team. It’s a really diverse group of people.

That’s one of the reasons I took the job. I felt like coming out of the pandemic, having managed a team through the social movement that came after the murder of George Floyd, I needed to put myself, as a white female leader, squarely in a camp where I could no longer afford to be passive. I wanted to be learning and challenged in my storytelling every day. I started to recognize how much subconscious bias is just inherent. It’s true for each and every one of us, but as storytellers, in order to move anything forward, we have to make statements and draw conclusions.

Within several months of my time at Cityblock, I found myself in a meeting talking about what is the typical scene, who is the typical Medicaid patient sitting in the ER. We were talking about unnecessary emergency room visits and we started to define and talk about the physical traits of this elderly female Black woman sitting in an emergency room in Brooklyn, or wherever. I had someone on my team challenge that and say, “Well, wait a minute, why are they Black?” We had a whole conversation around that.

We talk about this every day, and again, it’s okay to be vulnerable around the fact that I didn’t have a lot of these conversations prior to this role. And that’s a problem as a communicator and as a storyteller. I’ll always be learning in this space, and in every space really. But I have a very different view on hiring now as well. I refuse to accept that the pipeline just isn’t diverse. If I’m not getting the candidates that I need to feel comfortable with my commitment to interviewing 50% BIPOC, then I go out and find them. It’s also sparked some side projects around building out mentorship to ensure that in 10, 15 years there’s a more diverse group of candidates for others to choose from.

SG: You mentioned you come up with some great ideas outside of the typical workday. But outside your typical workday you’re also wrangling kids. How does this flow for you? In this post-COVID world where all this stuff is mixed together, at least we’ve all agreed upon the fact that this is more of the reality versus the 2019 scenario where theoretically things were split apart. But how does that work for you? Comms is an always-on, 24/7 thing, but so is parenting. How do you figure that out?

CA: For me, it’s three things. It’s recognizing that it’s just complete chaos and resetting expectations. Within that, it’s applying my comms skillset around pulling the value out of the noise and getting really crisp and clear on the priorities for that day or that week. It can be chaos, but as long as you know you’re moving something forward.

Second, you know the dialogue around — can women have it all? I’m definitely in the camp of you cannot have it all in every moment, but you can have it all in aggregate. I’ll have days where I feel like I’m just so behind on work or I’m less available to my team than I wish I could be, but I’m available to my kids, I’m showing up when they need me. Other days I will say no to my own kids multiple times and I will just stay hyper focused because I know that’s what I need that day. It’s a constant balancing act, it’s tuning the dial a little up or down, pulling back, depending on what’s needed.

Lastly, it’s extremely refreshing that we have seen this mix of work and personal lives blending. Maybe it’s the nature of my career path and the industry I work in, but I would just much rather be on all the time with everything and then also not feel like I have to be shy or hide the fact that I’m a working parent. That, to me, was the most exhausting thing there was. And I feel more confident about being unapologetic about it.

Authenticity and vulnerability are really good things. There’s a lot in the world today that’s frustrating and disappointing, but there’s actually been some silver linings.

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