Rebekah Iliff



Antioch University, Los Angeles – M.A., Organizational Management, Community Psychology

Loyola University of Chicago – B.A., Philosophy

A job in PR is all about connecting: making connections, keeping them and growing them. And any PR woman worth looking up to will tell you it’s the act of connection that leads to the biggest stories. Rebekah Iliff is one of those women — not only does she crave the act of connection with others, but also believes it’s vital for anyone in the space to be the best there is at connecting the dots within a story, too.

As chief strategy officer of AirPR, a PR analytics and insights measurement company serving Fortune 500 and technology companies, Rebekah was brought in to help build the right kind of measurement tool. She was the perfect fit too, being that she founded her own PR agency in 2007 specializing in technology launches.

“We look at how PR is really moving the wheel and what decisions we can make for future campaigns,” Rebekah says of her job. “In my job, I write and speak about how PR, technology and data are playing an ever more important role. I help people understand and define where PR is changing. You can’t build a technology and not be able to communicate to your audience, so that’s a large part of what I’m doing. We’re building a product around a relatively new way of thinking about measurement, so it’s my job to be able to articulate that and talk to our customer in a way so they understand why it’s really important.” But back to the connections: it isn’t just communicating her company’s message that feels like success for Rebekah. She says, “At the end of the day, it’s about the feeling I leave people with.”

If, by 30, you’re not being generative in your job and looking at other females or younger hires below you as the next succession, then you’re not doing your job.

What was your first job out of college?

I actually began my career as a professional ballet dancer. My college experience wasn’t traditional. While I was performing ballet, I would attend night school and summer school when I wasn’t traveling. So, you could say, my job as a ballerina was actually my first career.

At 23, I made the decision to leave ballet and work in marketing and PR, even though I had never studied it. I always liked to write and communications does have a performing aspect to it, so it made sense for me. I liked being around people and building relationships.

My first job in the industry was for an entertainment development company in Chicago. In that role, I produced fashion shows and events. It was a nice segue for me from performing in front of others to a role behind the scenes utilizing my people skills.

What would you say to others considering a career switch?

As long as you’re having fun, learning something and have a passion for what you’re doing — and then are able to express that passion in one shape or form — you’re in the right spot. When it doesn’t feel that way, it’s time to make a change. That timing is different for everybody.

I’m an artist at heart and am highly creative. There’s this artistic side to me that needs to be a little wild and crazy, and through this I’ve learned that careers don’t have to be super linear. I think they can go in variant directions that allow you to gain different experiences. During your 20s, it’s okay to jump around a bit in your career, but by the time you’re 27 or 28, you need to figure out where you’re headed. You also need to be staying put for three or four years, because otherwise it looks like you’re skipping around. And that’s not necessarily practical, because you don’t really learn anything if you keep jumping around.

With all the work you do for AirPR, as well as your freelancing, how do you organize your day?

All of my writing is related to AirPR and a large part of my job is creating that content. In a day, I’m writing articles, interviewing people and talking to people. It’s a good way for us to build relationships and get that constant marketing. I’m still an advisor for the agency I started as well, so I spend a couple of hours a week with them. I also advise a couple of other startups.

I’m able to get so much done because I’m hyper-organized with my time and prioritizing it. There are a lot of things I used to do and stress about, but I’ve since realized those things don’t actually add value to my work, so I’ve eliminated many of them. I’m very judicious about how I spend my time; I don’t take every meeting and I’ve learned to say ‘no’ in a nice way. I’m working 10-to-11-hour days as it is, so setting those personal boundaries is important. I also try now not to work on the weekends, unless I spend a couple of hours catching up on emails.

What responsibilities fall under you in your role?

Right now, it’s a combination of HR and culture as AirPR is growing quickly. I try to make sure that people who are coming on board feel integrated and welcome. The second part of my job is making sure that, essentially, the trains are running on time. Some of the chief operating officer responsibilities fall under my umbrella, like making sure the CEO has what he needs and gets where he needs to go. It’s my job to ensure we’re moving in the right direction, which is the strategic part of my job. I need to make sure that everything we’re doing is aligning with every other thing we’re doing and I need to ensure we’re not going in directions off course. This means I work to make sure each department is communicating with one another. I also, then, have the marketing and PR duties under me as well. It’s a lot.

My role changes depending on the day, which is another reason why it’s so important for me to be organized. Sometimes I block out times in my schedule to do calls and meetings. For example, my assistant knows I typically don’t take calls before 1 p.m., because I need the whole morning to really think and then to do those things that require thinking. Many mornings, I’ll work from home because I can plow through a bunch of work and my writing. Once 1 p.m. comes around and meetings and calls begin, forget it — the “doing” part of my day is done!

When building your team, what qualities do you look for in those you hire?

I look for people who are really adept at one specific thing; someone who is the “best of” at something. I also look for a person who is team-oriented and willing to collaborate, but who is also self-directed and fine to manage themselves. I look for people who are light-hearted and upbeat. We’re a happy culture that’s fun and we laugh a lot. We try to keep things light here, so people who take themselves too seriously or who think they’re hot shit, for lack of a better term, are people who are not conducive to a small company. They can be extremely toxic, distracting, and frankly, annoying.

We talk a lot on the site about work/life balance, but lately we’ve been focusing more on work/life integration. Do you feel like your life is more of a blend of the two?

Yes. As an entrepreneur you’re always thinking about your passion, so ‘work’ is a very difficult term for me, because I don’t feel like I’m working when I’m creating, producing and doing really cool things.

That said, I do know that when I’m not doing my yoga, meditation, eating healthy, spending time with the people I love or riding horses, then I start to feel out of it. Randi Zuckerberg and I had this conversation one time. She said, “You know, it’s not every day that you’re going to feel balanced.” It’s like overtime. When you take everything overtime, there are days when you’re working 15 hours, and then there are days when you’re not working at all. It was an interesting shift for me to realize that some days I can be incredibly chaotic and on other days totally disconnect.

I also am adamant about disconnecting, so if I’m dating somebody and we go to dinner, my phone is not out and I’m fully present. It’s the same at work when I’m in meetings. I’m present, and this allows me to feel balance and prevents me from shifting into distraction mode.

I would say that 75 percent of the time, I try and take an inventory at the end of the day. I’ll ask myself: Did I do one thing that mattered? Did I do something good for the business? Did I personally gain something today? In a startup especially, you can get caught up in tasks, then lose sight of what you’re actually doing and how it’s having an impact. I make sure I reflect on the same questions from a personal perspective too, asking questions like: Did I do something that can help somebody? Did I help somebody connect who asked to be connected?

What is an accomplishment on your resume that you're the most proud of?

It’s funny you ask me this question, because right now I’m working on a blog post about bragging and how atrocious it is. It’s a satire piece, so it’s funny you should ask.

I really think that when I look at my list of accomplishments from an outside view, like attaining a certain level of education, starting a company, etc., I realize all of these things are great and people tap into these things. But at the end of the day, it’s about the feeling I leave people with. Someone who walks away from a meeting and they think, “This person was cool, insightful and inspiring. I want to get to know her better. I want to do business with her.”

Over time, it’s these things that build your legacy. It’s like that saying that it’s not about what you say or do, but about how you make people feel. That’s why I get up in the morning. I’m not always good at it, and I don’t always do it, because it’s hard and sometimes I’m not in a good mood. But the accomplishment for me is the ability to recognize that feeling. That’s why people do business with you. It’s not because you have the best technology or because you have some stupid award or because you’ve been published here or spoken there. Nobody cares about that, but they care how kind and caring you are and if you’d be a pleasure to do business or hang with. This is how I built my business and my reputation. There are certain people who don’t like me. I’m not saying I haven’t said or done my fair share of things I shouldn’t have just out of frustration, but you never know when on relationship is going to come back and benefit you or your work. It’s a practice in karma, really.

What do you feel is a secret to success in the PR industry?

Right now especially, it’s about being able to move and adapt really quickly and to be able to connect the dots. It’s PR, so people are essentially dot connectors, because they’re communicators. I think if you can communicate well and if you can connect the dots for people, then you can turn that into something meaningful. It’s also important to be flexible, a good communicator and to be able to understand the bigger picture. The best PR people I’ve seen just get it. They see all these different parts moving at a rapid speed and they can decipher what’s important and what’s not, then communicate that accordingly.

What’s a piece of career advice that you think everyone should know and understand?

On a high level, don’t waste your time doing things you don’t like to do. If you’re really unhappy, find something else to do because life is way too short. Find something you like to do, get really serious about it, then be the best at it. Find that job that is a full expression of your gifts.

Another piece of advice is to realize your work and personal lives blend. For example, you know how a politician will get caught in a scandal and then say, “That’s my personal life.” I don’t buy that. What you’re doing in your personal life is connected to your career. Therefore, your career is a channel for how you operate in the world and people should look at it as such.

What’s your take on mentorship?

I think that as women, we’re obligated to find at least two people to mentor or sponsor by the time we reach 30. I’ve been mentoring since I was 25, but if, by 30, you’re not being generative in your job and looking at other females or younger hires below you as the next succession, then you’re not doing your job. These people are not competition and if you look at them like they are, or if you just don’t have time for mentoring, then your career will be extremely limited in how far you go.

As women, we have to make an effort to foster and mentor other women, to be intentional about it and to make it a priority. By the time you’re in your 30s and into your career, you should be giving back to some degree. We live in an extremely self-absorbed culture, so as an executive, it’s really easy to get caught up and forget that there’s a whole army of people holding you up. Be grateful for that, and in some way, shape or form, give back. It’s the minimum you can do.