Jon Oberlander–or OB to his camp friends– is a lifelong Ramahnick. He was a member of Ramah Wisconsin’s first Halutzim, and Nivonim 1997. For the past five years he has worked at Ampush, a digital marketing company that uses a combination of technology and a high-performing team to run strategic marketing campaigns on Facebook, Instagram, Twitter, Pinterest and beyond. Though he has been incredibly successful in the digital marketing world, he did not follow a traditional path to get there, and credits Ramah for many of his achievements.
He studied journalism and history at the University of Wisconsin-Madison. After completing his undergraduate degree, he continued to New York University School of Law and afterward worked in Chicago at Kirkland and Ellis, a corporate law firm. In addition, Jon spent a period of his life playing poker professionally and jokes that camp could have been a possible origin of his passion. A counselor taught his bunk how to play Euchre, a card game which they played endlessly. “Euchre is probably a simpler game than poker, but there is some overlapping strategy,” he explains. At camp, he and his friends would stay up late and play Euchre, “and now we put babies to bed — and then stay up late and play Euchre,” he says.
After his stint as a poker player and his stretch as a practicing attorney, Jon pivoted to the startup world and landed his first position at Ampush. He joined the company in San Francisco when they were just five people. By the end of his first year, he relocated and opened the New York office. He soon came to lead the whole account management team, with 80 people reporting up to him across the organization. Ampush now has 150 employees nationally and manages over $200 million in ad spend on social media, and much of its growth can be traced back to Jon’s leadership. He is now transitioning into a new role as SVP of Performance Partnerships, launching a new division in a joint effort with Ampush’s strategic investment partners.
Years before Jon joined the start-up world, he was known as “the frisbee guy” at camp. As a camper, he spent most of his time on the sports courts. During inter-aidot softball games, you would find him playing Ultimate Frisbee on the adjacent field. Meals were less essential when compared to basketball and Ultimate; though when asked, he believes his favorite camp meal was grilled cheese. Jon was an energetic camper who loved to joke around with his friends and counselors. He was that kid who woke up his cabin every morning by blaring the same song: Beck’s “Devil’s Haircut.” The counselors would stumble “out of that little room and turn the volume down,” but as soon as they went back in Jon would return the volume to its rightful level. Beyond sports and music, Jon formed many relationships at camp that have only strengthened over the years. Many of his closest Ramah friends are his closest friends today–he was even connected to his wife Shira through a good Ramah friend. They had 11 former Ramah Wisconsin campers in their bridal party.
After his experience as a camper, Jon worked as a cabin counselor for four years, following the same campers through Nivonim. When Jon reflects on why he was originally hired at Ampush, he says poker playing may have developed his quantitative aptitude, but firmly states, “The best training I had was working as a counselor and learning how to lead a group.” He points to many similarities between the work he did as a counselor and what he does now at Ampush. As a counselor, he says, “you learn lessons about relationship building, about leadership, about communicating to a group, communicating directly one on one with people, about crisis management. It’s translated incredibly well to what I’ve done since I’ve been at Ampush.” He emphasizes how essential it is to build trust with both your campers and your employees. Once you have trust, he explains, “you can really push them, ask a lot from them, encourage them, and be direct with them if they need to be challenged on something in a way that doesn’t create friction.”
On top of learning as a counselor how to base relationships in trust, he also discovered the importance of empowering individuals in the group. He recalls an instance when a storm interrupted his cabin’s canoe trip. The campers were cold, wet, and complaining about how a few were able to return to camp first. One boy piped up amidst the whining and said he was “not leaving until OB leaves.” Jon recognized then that an “organic voice from the crowd” is often more powerful than a suggestion that comes from him. He has continually been able to draw from the “playbook” he gained working as a camp counselor and apply it to situations that arise on the job. He would not replace the years he spent at Ramah with anything and acknowledges the profound impact Ramah has had on both his professional path and his personal life.