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Veteran human resources professional Ann Jackson has been in the industry long enough to recognize a rare opportunity when she sees one, and she immediately saw something special at the Oak View Group. In 2021, the sports and entertainment venue company was in growth mode, and its leadership team courted Jackson to drive an important people strategy. They didn’t want her to simply enhance or improve an existing HR function—they wanted her to build it from the ground up.
For Jackson, it was a dream come true. “HR leaders often come in to apply their expertise to a well-defined program, but most of us never get the chance to truly make our mark on an organization from the very beginning,” she explains. “This was a great opportunity for me to apply everything I’ve been able to learn and accomplish in my long career.”
That career started at NBC, where Jackson managed daily operations for its renowned Page Program that puts entry-level candidates through a rotation on high-level media assignments. Participants work on shows like Saturday Night Live and the Tonight Show, where they get immersive exposure on marketing, business development, production, and public relations teams.
“HR leaders often come in to apply their expertise to a well-defined program, but most of us never get the chance to truly make our mark on an organization from the very beginning.”
Ann Jackson
Jackson built relationships with numerous colleges and universities to diversify the program as well as handled employee relations matters for its sixty-five employees, which helped her grow as a professional. “The NBC Page Program taught me to really understand people’s individual goals and then put them on the right path.” she explains. Jackson later launched special seminars, summits, and career development programs to provide additional opportunities.
After six years at NBC, Jackson had found a niche in entertainment, but left the organization to join the Madison Square Garden Company (MSG) to lead HR for the Rockettes. She stayed with MSG for more than sixteen years, ultimately serving as vice president of human resources. In that role, she partnered with business leaders to drive strategy for nine thousand employees at venues including MSG Arena, Radio City Music Hall, the Beacon Theatre, the Chicago Theatre, and the Forum.
In 2021, after stints with Charter Communications, Jackson came to Oak View Group to build the right teams to facilitate an aggressive growth plan. CEO Tim Leiweke and his partners started the organization in 2015 to disrupt the venue management and operation space. Since then, they’ve expanded through acquisition and organic growth to become the world’s largest sports and entertainment venue developer.
When Jackson arrived as chief people and culture officer, the company was emerging from its start-up phase. Members of its small core team were accustomed to filling many roles and pitching in where needed to help launch the organization. Jackson wanted to maintain a fun and entrepreneurial culture while building more formality to the HR function which was then managed by legal.
“At some point in the life of every business, leaders have to transition from exciting start-up to mature disruptor, and we were at that inflection point,” Jackson recalls. “As an HR leader, I wanted to formalize the function and create an experience for employees so Oak View Group would be a place where they want to stay and grow and thrive.”
And that’s just what she’s done. After building a strategy, Jackson got to work. She hired systems, compliance, and talent management leaders; introduced employee resource groups; got new policies and procedures in place; and conducted an employee survey.
As this was taking place, Oak View Group was acquiring companies, growing its employee base, and working with municipalities to build and renovate arenas. When Jackson started, Oak View Group had just a few hundred employees on its team. Today, the company has more than two hundred venues—including five owned and operated—with more than three thousand full-time and twenty thousand part-time employees.
“I’m always asking questions of people who start here because helping people reach their dreams is good for the people and the organization as a whole as you create culture.”
Ann Jackson
As she moves the function forward, Jackson is drawing from the lessons she learned at NBC and MSG and still strives to match employees with the opportunities they most desire. “I’m always asking questions of people who start here because helping people reach their dreams is good for the people and the organization as a whole as you create culture,” she says.
Now that Oak View Group’s HR foundation is in place, Jackson will focus on strengthening what she’s built so far. She’s implementing new technologies to drive efficiencies, rebranding culture to “One OVG,” unifying all facilities to one centralized system, improving development programs, and taking more steps to emphasize diversity, equity, and inclusion.
In recent years, Oak View Group has finished key projects in major cities like New York and Seattle. In March 2022, it announced plans to build a $3 billion hotel and casino complex near the Las Vegas Strip. The Sin City deal is the biggest gamble in Oak View Group’s history, and Ann Jackson has the right people in place to help them hit the jackpot.
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