Scaling with Scrappiness: A Conversation with Keeper Security’s Anne Cutler

Q&A with Anne Cutler, Vice President of Global Communications at Keeper Security

At REQ, we’re fortunate to cross paths with leaders who understand the value of communications and embody the grit and creativity needed to make an impact in fast-moving industries. Anne Cutler, Vice President of Global Communications at Keeper Security, is one such leader.

Anne’s career has been defined by adaptability and ingenuity. Anne has moved from the scrappy world of local TV news to the frontlines of federal cybersecurity communications. Now, Anne leads communications at one of the industry's most innovative cybersecurity companies. At Keeper, she’s built systems from the ground up, scaled teams with intention, and helped shape the company’s evolution from a consumer password manager to a trusted enterprise-level cybersecurity platform.

In our conversation, Anne shares how scrappiness has been a constant throughout her journey and how that mindset shapes her approach to communications, leadership, and growth.

Q: Tell us a bit about yourself and your career path.

Anne Cutler:

I’ve been with Keeper for three years now. My career began as a TV news anchor, producer, and reporter in Casper, Wyoming. It was a scrappy start—I was definitely a jack-of-all-trades. Out of 210 television markets in the U.S., Casper is market 198. I came from UCLA and worked part-time at Saks Fifth Avenue in Beverly Hills. Going from there to small-town local news was quite a shift, but it was a great learning experience.

I moved through Reno, New Orleans, and eventually Washington, D.C., where I was a news anchor and reporter at Fox 5 DC. After 13 years climbing the TV ladder, I transitioned to communications. I joined the federal government, first at the DHS Science and Technology Directorate, and then at CISA, the nation’s cybersecurity agency. That’s where I really fell in love with cybersecurity and knew this was the field for me. Eventually, I moved into the private sector and landed at Keeper.

Q: What's an example of scrappiness in your current role?

Anne Cutler:

When I joined Keeper, it was a much smaller company. Our staff has since doubled. At the time, I had about half an employee who split their time with marketing. The process was reactive—media inquiries would come in, and we’d scramble to respond. There was no strategic planning or infrastructure.

So, I went ahead and built systems, processes, and databases from scratch. We developed a rapid response media process with templates, defined workflows, and a centralized repository of past responses, so we didn’t have to reinvent the wheel each time.

As our team expanded, I empowered team members to lead initiatives. I encourage independence and innovation. That’s helped us scale efficiently while maintaining the agility we had when we were smaller.

Q: With limited resources, what communications activities do you prioritize?

Anne Cutler:

Relationships with key media are huge for us. Those relationships are gold, and when a journalist needs input, we respond fast. We prioritize urgent requests that impact those relationships.

We also invest in high-quality content, especially research. We work with independent firms to survey the industry and use that research for media, social, and product development. It adds value beyond just promoting our product.

Social media is another priority. It’s constant—you can’t slow down there. So we’ve had to find efficiencies to maintain volume and quality without burning out.

Q: What do you look for when hiring for your team?

Anne Cutler:

Culture fit is the #1 thing I look for. Someone from a five-person startup has a very different mindset from someone who works for a huge company like Amazon. I look for candidates who’ve thrived in nimble environments and can pivot quickly.

I don’t require a background in cybersecurity, because that can be taught. One of our top communications managers came from meteorology and sports. She knew nothing about cybersecurity, and now she’s teaching me things. Passion, drive, and adaptability matter far more than specific industry experience.

Q: How do you keep your team motivated and energized?

Anne Cutler:

You have to love what you do. That doesn’t mean your job has to align exactly with your personal passions, but you should find your work fulfilling and exciting. At Keeper, strong work is recognized and rewarded, which helps a lot.

We’re also motivated by the real-world impact of what we do. When we publish research on emerging cyber threats, it helps protect businesses and individuals. That sense of purpose drives us.

Q: Has your approach changed as your team and company have scaled?

Anne Cutler:

Absolutely. Here’s one example: When I joined, we relied on scrappy tactics like jumping on holidays or viral trends to drive brand awareness. That worked great when we were primarily a consumer-facing product.

But as we’ve evolved into an enterprise-focused privileged access management platform, our messaging and targeting have had to mature. We’ve shifted from Easter Bunny jokes to engaging outlets like Forbes and the Wall Street Journal. 

We’re still creative, but our tone and audiences have evolved. We’re targeting that “mainstream middle ground”—not purely consumer, not purely B2B trade, but outlets with broad influence and credibility.

Q: Can you share a fun or unconventional campaign that worked?

Anne Cutler:

Sure! Last year for Cybersecurity Awareness Month, we flipped the script and called it "Cybersecurity Action Month." Awareness alone doesn’t solve problems, so we wanted to inspire actual change.

We created a campaign in which our team went to an adventure park. We filmed ourselves ziplining, rock climbing, and navigating obstacle courses—all to symbolize the actions people and organizations should take to improve their own cybersecurity. We also had custom T-shirts, drone footage, and week-by-week recommendations.

It was visually exciting, team-building, and made a real impact. We got great press and strong social engagement. It was wild—but it worked.

Do you have questions about how you can rework your communication strategy to keep up with fast-changing environments? Our team would love to chat!