Advertising, AI & Understanding your Audience: A Q&A with Ashley O'Connor

Ashley O'Connor is an advertising and marketing expert with robust experience both at top tier agencies and leading marketing in-house.

I met her during a stint at creative agency SS+K where we were both on the account management side. We worked together only briefly but I loved any chance to work with Ashley, who is such a hard worker who brings joy, curiosity, and realism to her work. Ashley is also super kind and hilarious - an absolute gem of a colleague and human who everyone wants to be around.

I love this Q&A with Ashley, especially for anyone considering going into advertising. She summarizes the advantages of the industry, from how it can ingrain a detail-oriented mindset to the social aspect of the culture. She also talks about the experience of pivoting her career trajectory and the way that she melded the impact of activism and organizing that she found intriguing about her PoliSci major with the fast-paced and creative drive of advertising agencies.

How did you get into communications and marketing? Tell us your story.

I majored in Political Science in college. One of the things that draws me to politics is the impact of activism and organizing—I like organizing people, from being on event committees to alumni group activities.?

As I looked ahead to graduation, I reached out to several professionals, including alumni from my college. I was lucky enough to connect with the CEO of Deutsch NY, Val DiFebo, who piqued my interest in advertising. I interned at Deutsch for two years. That experience provided the foundation for my project management skills, while also allowing me to develop strong client relationship skills through effective communication. I loved how it was fast-paced and unlocked my creativity, and I found myself wanting more. This led me to pursue internships in PR and public affairs, effectively combining my political science background with my passion for marketing and communications.?

My career has spanned creative advertising to tech and production, as well in house marketing and communications work.?

Marketing is a bit of an art and a science. We need audience insights to guide strategy and data to make good decisions. But as marketers we also need to trust our gut. What is your approach to using data but keeping it human at the same time??

Exactly, a major focus has to be who the audience is and a deep understanding of what they need. That comes out in the data and in conversations and direct feedback from audiences.?

At Work & Co, a digital product agency, one of our marketing objectives was to attract and retain talent – we held events for women and people of color, as well as those from non-traditional backgrounds who were seeking to break into tech. We worked to position the company as a leader, not only because of the quality of our product, but also our values around building an inclusive community. Our marketing strategy fostered human connections, positioning our brand as a trusted source of inspiration, design expertise, and education. This approach cultivated a loyal audience that actively sought us out.

As a platform leader in venture capital, the audience is founders. I strategically built a firm’s reputation and positioned the company in new spaces, using marketing channels as both a sales tool and also a source of education and learning. I always test and measure what is resonating with founders. Cybersecurity or AI content might spark engagement, while defense might not. We track not just clicks, but who reaches out – our content is designed to ignite conversations.

This role is unique in part because I’m building from scratch. As the first staff member that is not an investment expert there was a lot of room to test and experiment. I leveraged my agency experience and tried completely new things. At any agency, it’s easy to get caught up in perfection, which can stand in the way of learning. One of the most thrilling aspects of my role is the ability to move quickly and constantly iterate.?

What is a challenge or trend that you're excited about in the communications and marketing field?

AI is definitely the first thing that comes to mind. I see it as a powerful ally, especially for solo practitioners. Without a team to brainstorm or review work, AI writing tools become game-changers. For instance, I can draft an article and then leverage an AI tool to generate targeted social media posts based on the content. It provides a springboard for creative social media pieces. Similarly, SEO AI tools offer invaluable assistance in uncovering optimization opportunities I might miss.? These tools are typically affordable, and they help me do more with less.?

How do you think about pivoting when it comes to career trajectory??

The great thing about our line of work—which is also a bit of a challenge—is that there are so many directions to explore. Every brand needs communications and thought leadership, so learning how to represent your skill set to show transferability is needed.?

The agency world gave me a lot of transferable skills. When I’d be put on a new account, I had to become an expert really quickly. I stepped into a role where investors have different thesis areas, and I might not be well versed in the technical aspects of each one, but I know how to get up to speed and become an expert fast so I can shape content to appeal to audiences. Advertising offers exposure to the full process–how to take something from an idea to a campaign. I have seen this up close and it’s taught me how to tap the right people to ensure good execution and strategy storytelling.?

You’ve worked at all kinds of agencies - from Weber Shandick and creative shops like SS+K, to a recent stint at Work & Co, a digital product agency. What is your advice for someone interested in a career at an agency?

Agencies are a great place to start a career. Marketing is so broad, and there are many directions to explore. Specialization is great, but a generalist background can help shape someone’s path. I’ve worked with cross-disciplinary teams, and I’ve met and worked with amazing producers, strategists, designers, and developers. I absorbed more about disciplines and functions than I could have if I specialized too soon.?

I think agencies also cultivate a need to be detail-oriented. My time at agencies gave me a strong foundation of design and visual strategy that has helped me throughout my career. Also, it is fun to be in those work environments! At agencies, people typically want to be social. You build strong connections over late nights, reviewing a ridiculous deck. This helps with connections, as does the agency model of meeting and working with a wide variety of clients.