Fran Pomerantz, founder of New York City-based retained search firm The Pomerantz Group, may never see a résumé as unique, serendipitous ― and utterly fearless ― as her own.

As a digital media pioneer and visionary, Pomerantz’s embrace of new ideas, innate business acumen and openness to personal reinvention have taken her from Los Angeles to Manhattan and from elementary school teaching to executive recruiting.

Oh, and did we mention her stint as a cocktail waitress?

Digital and Disruptive

A networker and conference speaker, Pomerantz focuses on identifying and recruiting top digital executives for early-stage venture capital, private equity and small public company opportunities. She has also served on the GlobalGiving New York Leadership Council, a non-profit that connects donors with grassroots initiatives in developing countries.

CMSWire sat down with Pomerantz recently to discuss her two decades in digital, her bicoastal career trajectory and what she sees on the horizon for 2016.

Sobel: You began your career as a fourth grade teacher. Yet at age 27, after earning your master's in Educational Counseling from Arizona State, you took a job as a cocktail waitress at the Hamburger Hamlet. You eventually worked your way up to Vice President, where you oversaw the chain’s national expansion. Can you share a bit of that journey?

Fran PomerantzPomerantz: I had taught for several years and although I loved teaching, I was game for a new experience. After finishing my MA, a friend and I went to Los Angeles on vacation where I ran out of money over the summer and applied for a job as a cocktail waitress.

The owner asked if I’d stay permanently and move into management and they relocated me from Phoenix to LA. I trained as a manager but wound up in Corporate, designing management training programs, supervising special projects and overseeing restaurant openings. Later, the company was sold to a private equity firm where our team of four doubled the chain from 17 to 35 restaurants.

Sobel: In 1995, you took an “Intro to the Internet” class at The Learning Annex, which led you to create a television commercial business based on the “900-number, pay-per-call” model. Can you tell us more?

Pomerantz: I had been “reorged” out of the restaurant company and had to decide what I was going to do next. Then, I had a business idea based on seeing a TV commercial. As I watched, I realized that I didn’t want the beauty product being advertised but I did want to buy the pants the actress in the commercial was wearing.

My idea was to place ads with 900 numbers in women’s magazines so that women could call and find out where they could buy the same clothing the actors were wearing. There were other moving parts but that was the general idea.

Sobel: When you attended the first Electronic Entertainment Expo (E3) in 1995, it hadn’t yet become the world's premier trade show for computer, video and mobile games. Was that the first time you consciously thought about bringing your human resources knowledge to bear on new technologies?

Pomerantz: At same the time I took the class on 900 numbers, there was also a class on virtual reality being taught down the hall. I was a big Star Trek fan so I took the class and that’s how I found out about that first E3 Conference. Having hired many people for different management positions at Hamburger Hamlet, I realized that the Internet would be a fantastic way to do recruiting differently.

I was so in love with the search industry and the possibility of expanding it online that I turned a blind eye to any of the hundreds of things that might have gone wrong. I shared office space with a talent agent, started attending networking breakfasts and voilà … a business was born.

Sobel: In 2005, you left Los Angeles to join global executive recruiter Korn/Ferry International in New York as a partner in their Media, Entertainment and Convergence sector. Can you tell us more about your work there and why you made the move?

Pomerantz: I had met Bill Simon, the head of Korn/Ferry’s media practice in Los Angeles and basically, he recruited me to expand his group on the East Coast. His vision for the role I could play in facilitating the convergence of digital media and traditional entertainment was very compelling and having the chance to move to New York City was also a huge plus.

Sobel: Last spring, as part of a panel of top-level talent executives and recruiters entitled “Digital Job Search 101,” you remarked, “98 percent of people in the digital sector [today] are in jobs that never existed before.” Can you share some of your thoughts about what digital employment trends we should look for in 2016?

Pomerantz: It seems that the Internet has always been with us but if we look at the tech changes that seemingly happen overnight, there’s a lot that is constantly changing. Let’s take marketing for example. Traditional marketing and advertising were done the same way for a long time but now they’re being dramatically influenced by different methods of distribution such as online and mobile.

That means we need people who know how to get a company’s messages out using these new channels. New technologies are disrupting business in every industry from transportation to banking. Just think how recently we said, “This is the year of mobile.” Now we’re looking forward to self-driving cars.