Brand Makeovers: Ashley Mason Of Helen + Gertrude On The 5 Things You Should Do To Upgrade and Re-Energize Your Brand and Image

Tap into Market White Space. Discover opportunities by diving deep into competitor analysis. Look for gaps in their visuals, personality, and product offerings. Warby Parker did just that in the eyewear market, finding a white space where stylish glasses were either too expensive or too bland. They seized this gap by offering fashionable, affordable eyewear with added convenience, revolutionizing how people shop for glasses.

As a part of our series about “Brand Makeovers” we had the pleasure to interview Ashley Mason.

As a Senior Communications Strategist, Ashley Mason is intrinsically curious and passionate about driving customer growth for her clients. By day, she develops digital content for healthcare, wine, and other premium brands. By night, she enjoys renovating her 1920s home and discovering new bottles of bubbly.

Thank you so much for doing this with us! Before we dig in, our readers would love to “get to know you” a bit more. Can you tell us a story about what brought you to this specific career path?

Ever since I was a kid, I’ve been that person who just can’t stop asking ‘why.’ My curiosity lead me to journalism — a career where asking strangers prying questions is not only accepted but expected. I found my groove writing for big lifestyle publications like Bon Appétit and New York Magazine, where I got to dive deep into topics, making the complex seem simple and the mundane fascinating. My favorite part was interviewing experts and translating unfamiliar topics into something simple and interesting to readers.

But after about a decade on the editorial side, I started craving something different — something a bit more stable and dynamic. So when my husband and I relocated to Upstate New York, I seized the opportunity to pivot. I connected with the brilliant minds at Helen + Gertrude and made the leap into digital marketing, first as a copywriter and now as a communications strategist. What I love most is the variety — one day I’m working on a campaign for a skincare brand, the next I’m diving into the intricacies of medical technology. I’m always learning something new, which keeps that “why” in me alive and well.

Can you share a story about the funniest marketing or branding mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I was first starting out, I thought creativity was the name of the game. We had a new client in Boston, and I was eager to impress. My team and I locked ourselves away for days, coming up with a bunch of clever names for their rebrand. We were so proud of our work that we practically waltzed into that meeting, expecting a round of applause. Instead, the room went dead silent. We’d completely missed the mark — our suggestions sounded like they belonged to a toothpaste upstart, not their industry at all. The funny thing is, they were kind enough to point us in the right direction, and we ended up learning a lot more about their brand than if we’d hit the nail on the head the first time.

Now, before the scope of the project is signed, we talk about meaningful research and what we can accomplish with their budget. I start my brand identity projects with a collaborative workshop where we go through the findings and discuss common threads with their existing brand. The process is still pretty quick, but I learned to bring the client along for the journey. Creativity is crucial, but alignment is everything — it ultimately needs to resonate with the client’s vision.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Is there a takeaway or lesson that others can learn from that?

I tend to define success as a happy client and results that speak for themselves. But if I had to pinpoint a real turning point in my career, it was when I started building more direct relationships with our clients. Don’t get me wrong, I have the utmost respect for our account managers — they’re the lifeblood of our projects — but there’s something invaluable about hearing what matters most straight from the client’s mouth. I noticed a shift once I started having those candid conversations and asking my sometimes probing questions. Projects became more tailored, the messaging hit a little better, and there was just more enthusiasm with the end result. For me, success wasn’t about working harder; it was about listening better and being willing to translate the client’s needs into a clear strategy.

Are you working on any exciting new projects now? How do you think that will help people?

While I usually focus on CPG projects, one of the most meaningful brand refreshes I’ve been involved with recently is for our regional child advocacy center. We relaunched their brand with a new name and a visual identity that feels more approachable and hopeful — something that emotionally resonates with the community. For this project, I worked closely with an advisory committee from their organization, diving deep into the many facets of child abuse. I interviewed board members, pediatricians, and law enforcement officers, which gave me a better understanding of the complex issues they face. This project was especially impactful because our rebranding efforts helped raise awareness about child abuse prevention. They recently celebrated their 20th anniversary, it’s exciting to see how a fresh identity can help them continue making a difference for another 20 years — and beyond.

What advice would you give to other marketers to thrive and avoid burnout?

Don’t let your work be the only thing that defines you. It’s easy to get caught up in the deadlines and client dynamics, but when I start bringing agida with me outside of working hours — I know it’s time to hit pause. For me, that means grabbing my paddleboard and getting out on the water, or catching up with friends who remind me there’s more to my vlaue than the latest round of feedback. When you rely solely on your job to bring you happiness, you’re setting yourself up for burnout. Your job is never going to love you back. By nurturing your passions outside of work, you’ll come back refreshed, with more energy and patience for whatever you need to tackle. Whether it’s paddleboarding, crafting, or just binge-watching your favorite show, find what recharges you and make it a priority.

Ok, let’s now jump to the core part of our interview. In a nutshell, how would you define the difference between brand marketing (branding) and product marketing (advertising)? Can you explain?

Starting with the big questions, I see! I view brand marketing as shaping the overall perception of a company. When I work on these projects, I’m trying to build a long-term emotional connection with a desired audience. This can get into evaluating positioning, brand values, and core messages that communicate who we are as a company and why you exist.

I equate product marketing to driving action, whether it’s increasing awareness, purchase, or signing up for something. It’s much more tactical, but it still relies on having a strong brand foundation to build trust and credibility.

Can you explain to our readers why it is important to invest resources and energy into building a brand, in addition to the general marketing and advertising efforts?

I like to think of the whole marketing machine as building a house. Branding is your foundation — without it, everything else risks crumbling. A solid brand sets the stage for how far you can go, whether you’re aiming for a cozy beach cottage or a towering skyscraper. Pouring your resources into research, insights, and collaboration gives you a strong, stable base that is scalable for the future. It’s important to know who you are and what you stand for. Otherwise, you risk chasing the next trend as the market evolves, which can feel disjointed from your company’s DNA. Consumers see right through that stuff.

Many people think branding is just colors and a logo, but it’s so much more than that. A well-built brand should clearly articulate how you’re different from the competition and why people should care. It helps you connect emotionally with your audience, which can directly be related to sales and increased reputation, whatever your advertising goals are.

Let’s now talk about rebranding. What are a few reasons why a company would consider rebranding?

A common reason we see with rebranding, especially with established brands, is when the market has evolved significantly. It’s like owning an old house that was built to code decades ago, but now, those standards have completely changed. The foundation might be solid, but the wiring and plumbing need a serious upgrade to meet the new demands. Rebranding in this context is about more than just a fresh coat of paint — it’s a complete renovation that ensures the brand stays relevant, competitive, and aligned with the current market dynamics.

Another reason we often see is that the business has evolved, whether by expanding into a new category or aiming to attract a different audience. It’s like adding an extension to a house — there’s some foundational work to ensure stability, but the main goal is to make the new addition feel seamless and cohesive with the original structure, not like a tacked-on afterthought. Those tend to be the main reasons clients come to us.

Are there downsides of rebranding? Are there companies that you would advise against doing a “Brand Makeover”? Why?

There’s an old saying: ‘You can have it good, fast, or cheap — pick two.’ Rebranding is no exception. Done right, it’s a significant investment in both time and money, and not every company is prepared to make those commitments. If you’re in a rush — like needing it done in less than two months — it’s worth asking why you’re doing it in the first place. Do you truly need a complete makeover, or would refining your current brand serve you better?

It’s not necessarily a deal breaker, but internal alignment is crucial before diving into a rebrand. When there are too many cooks in the kitchen, or if the vision of success is unclear, you risk wasting valuable resources as you figure things out on the fly. Clear goals and a solid understanding of what you want to achieve can also justify investments in creative testing or audience research, ensuring the final result ticks all the boxes.

Some companies, like Starbucks, Coca-Cola, and Target, have built incredible brand equity over the years. For these brands, it’s crucial to back any major changes with extensive research. This allows them to preserve the elements that loyal customers love while still evolving the brand. Skipping this step can be risky — it could lead to a brand that’s unrecognizable or alienate customers who made it successful. The key is to strike a balance between innovation and continuity, ensuring that the brand evolves without losing its core identity.

Can you share 5 strategies that a company can do to upgrade and re-energize their brand and image? Please tell us a story or an example for each.

Let’s do it!

• Do the Opposite of Your Competitors. Embrace what strategist Marty Neumeier calls “the art of the zag.” This means if everyone in your category is playing it safe, take a bold leap in the opposite direction. Look at how your competitors present themselves and choose a different path. Take Preparation H, for instance. In a sea of clinical, blue-packaged First Aid products like Band-Aid and Tuck’s, they went with a vibrant, provocative personality and bright yellow packaging. Knowing the unique application of their product (butts!), they turned the mundane into memorable, standing out in a crowded field.
• Draw Inspiration from Different Industries. Break free from industry norms by viewing your brand through a fresh lens. Former Disney exec Duncan Wardle showed how this can work wonders by transforming a car wash into an auto spa. What was once a routine service became a luxury experience with just a shift in perspective. Similarly, look beyond your immediate competitors for inspiration. If both shipping and athletic shoes emphasize speed, why not borrow from their dynamic approaches to create visuals and messaging that feel innovative and unique?
• Adopt an Unconventional Brand Archetype. Think outside the box by choosing a brand archetype that shakes things up. While many medical technology brands play it safe with the Caregiver archetype, consider the Explorer instead. Imagine your brand embodying adventure and discovery, a refreshing change from the usual. By mapping these traits onto your brand, you can infuse it with fresh energy and stand out in a field that often sticks to tradition.
• Tap into Market White Space. Discover opportunities by diving deep into competitor analysis. Look for gaps in their visuals, personality, and product offerings. Warby Parker did just that in the eyewear market, finding a white space where stylish glasses were either too expensive or too bland. They seized this gap by offering fashionable, affordable eyewear with added convenience, revolutionizing how people shop for glasses.
• Celebrate Your Legacy Brand’s Strengths. For established brands, your history is a powerful asset. New, disruptive brands might grab headlines, but your decades (or even centuries) of expertise and credibility are invaluable. Take General Mills and Dove — both have built strong reputations over time by staying true to their core strengths. Use your rich narrative of craftsmanship and innovation to reinforce your position and demonstrate why you’re still at the top of your game.

In your opinion, what is an example of a company that has done a fantastic job doing a “Brand Makeover”. What specifically impresses you? What can one do to replicate that?

I loved Dunkin’s decision to drop ‘Donuts’ from their name a few years back. This move was a brilliant example of how to modernize a brand without losing the essence of what makes it special. Dunkin’ didn’t just toss a new name into the mix and call it a day; they tuned into how people actually talk about them — embracing the fact that they’re more than just donuts. With a menu bursting with sandwiches, coffee drinks, and other breakfast goodies, they realized they were so much more than their old-school moniker suggested.

What really impressed me about this rebrand was Dunkin’s restraint. They didn’t go wild with changing their colors or typeface, which could have felt like ripping the comfort blanket off of a beloved morning ritual. Instead, they kept things simple, honing in on their strengths while keeping the familiar elements that customers love. If you’re looking to replicate this kind of success, take a page from Dunkin’s playbook: know your audience, listen to how they engage with your brand, and make smart, thoughtful tweaks that build on what’s already working. It’s all about evolving with your customers while staying true to your brand’s core identity.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Well, since you asked, I kind of hate what cars do to our communities. So, if I could spark a movement, it would be all about creating more walkable, bike-friendly urban environments that champion green spaces and native plants. Imagine pedestrian paradises not just in big cities but in every town and city.

Beyond the obvious environmental perks, this shift would promote physical activity and cut down on car dependency — potentially lowering obesity rates and related health issues. Plus, it levels the playing field, giving everyone, regardless of their socioeconomic background, better access to their communities. Imagine not needing a car to get around. Think grocery stores, pharmacies, and doctor’s offices — everything you need within a few-mile radius.

Smart urban planning, lush community gardens, and efficient public transportation would be at the heart of this movement. It might sound a bit out there, but these are the kinds of things I geek out about when I’m not in marketing land.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Whenever I had to choose between sitting through a lecture or chasing a student newspaper assignment, my high school English teacher would always ask, “What will matter more in five years?” It’s a question that’s followed me into my career, especially when juggling work and life.

In the whirlwind of deadlines and meetings, this question is my north star. It nudges me to make choices that fuel my growth and happiness, rather than just reacting to the daily grind. For instance, when I’m deciding between taking on a new project or spending time with my family, I think about which choice will bring me more joy and fulfillment in the long run. Sometimes, it’s worth losing out on sleep so I can do both.

How can our readers follow you online?

I’m on Instagram at @amason_916, and I occasionally post unsolicited marketing advice on LinkedIn.

Thank you so much for these excellent insights! We wish you continued success in your work.