We were lucky to catch up with Bill Oberlander recently and have shared our conversation below.
Hi Bill, thanks for joining us today. Let’s kick things off with your mission – what is it and what’s the story behind why it’s your mission?
I started my purpose-led marketing/advertising agency OBERLAND for two reasons:
A. I wanted to use my creative talents to not only sell goods and services to an audience through meaningful story telling, but also to serve the community by raising awareness of and producing positive change for today’s most pressing social issues;
B. After much analysis, I knew beyond the classic determining factors of price, taste and convenience for purchase decisions, GenZ and GenAlpha were putting a premium on the behavior of corporations behind the brands they have in their lives as consumers. Brands like Patagonia, NIke, IKEA, Lego, Whole Foods, Unilever, Toyota, Master Card, GE, REI, Dove Soap, Ben&Jerry’s Ice Cream, Pepsi, Benetton, Target, Chipotle, Apple, to name a few, were all advertising to ring the cash register AND at the same time have a positive impact on communities.
You could say I wanted to do the classic “do well by doing good”.
Ten years later, our mission is more important than ever with the Trump Administration rolling back legislation for DEI, sustainability and other progressive initiatives.

Bill, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
As a kid, I was always drawing, writing and telling stories. When I left university as a Design Major and Business Minor in 1981, I immediately landed a job as a junior art director on Madison Avenue, working on brands like ABC Television, Air Canada, American Express, Coca-Cola and Shearson-Lehman Investing.
For the next 30 years, I went from Junior Art Director, to Art Director, to Senior Art Director, to Associate Creative Director, to Creative Director, to Executive Creative Director, to Chief Creative Officer, to Creative Chair, all in New York City.
For four three decades, I was thrilled to work in an industry that valued good ideas, gave high-profile media exposure to my work, paid well, traveled often and every day at the office was fun.
In late 2000s, I joined the Ad Council Creative Review Committee, working on social issues like teenage pregnancy, financial illiteracy, gun violence, forest fires, educational inadequacies, digital privacy, drug addiction, cigarette smoking, allergy epidemics, to name a few. This was kind of creative work I truly cared about and got brain firing on all cylinders.
With this new energy and focus to my career, I transitioned out of the ad world to the philanthropic powers of the Robin Hood Foundation as the Managing Director of Marketing. It was there that I thrived for two years, raising $400M/year to fund 300+ struggling grantees in the five boroughs of NYC. When Hurricane Sandy devastated the NYC metro area, I co-produced the 12.12.12 Concert at Madison Sqaure Garden, raising $53M in one night to aid all those deeply effected by the horrors of the superstorm.
From there at age 54, I launched OBERLAND, with the Robin Hood Foundation as our first client. With smart strategies and breakthrough creative ideas, the agency grew dramatically with more purpose-driven clients like The Nature Conservancy, The Blue Man Group, ACLU, Strong Roots Vegan, Thinx, and ELF Beauty, To date, the agency is thriving with 35 team members in Soho, New York City, just returning from the Cannes Lions Festival where OBERLAND was honored with a Silver Lion for our ELF Beauty “So Many Dicks” campaign, driving for more women and people of color to join corporate boards in America.

How’d you meet your business partner?
My business partner/CEO Drew Train was an Account DIrector at J. Walter Thompson when I was an Executive Creative Director there at JWT. We never crossed paths in the hallways of the agency, but when I left for the Robin Hood Foundation things aligned. My first assignment was to create a program and an awareness campaign to help military vets coming back to NYC to assimilate into society, all the while struggling with substance abuse, joblessness, homelessness and mental illness, To say the least, it was a daunting brief.
I reach out to my former employer’s CEO at JWT, Bob Jeffrey, to see if he could send over a socially-motivated strategically minded executive from his ranks. He sent over Drew Train.
For eight months, I sat in meetings reviewing very complicated approaches and programs to address these issues with Vets coming home from Iraq and Afghanistan. Through it all, Drew was genuine, focused, thorough, patient, strategic and committed to the cause. I knew then he would be a great partner.
We met at an East Village Ukrainian Eatery, shook hands with 50/50 ownership and respected and trusted each other over the last ten years.
Fun note: One week after we partnered and launched OBERLAND, Drew called to tell me he and his wife conceived their their third child. An urgent call : we must hustle and muscle to get established and successful ASAP!

Let’s talk about resilience next – do you have a story you can share with us?
I started OBERLAND in the most perfect storm:
Exited the cash cow of Madison Avenue to launch my agency without a client nor investor; asked my wife of 20 years for a divorce (aka 50% gone); moved back to expensive New York City from the Westchester suburbs; funded two high school boys into private universities and fell in love with fine artist who generated zero revenue to our new dwelling in the West Village.
Although I knew I was doing the right thing, I did not have a strategy. I knew to put faith over fear. But nonetheless, there were many many sleepless nights.
Contact Info:
- Website: https://thisisoberland.com
- Instagram: Bill Oberlander
- Facebook: Bill Oberlander
- Linkedin: Bill Oberlander
- Twitter: nycmenyc
- Other: Facebook:
Bill Oberlander






Image Credits
Craig Cutler, photographer.

