Bob MacDonald

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Bob MacDonald

Bob serves as Chairman and Chief Strategic Advisor for All Things Annuity.

A Trailblazing Innovator in the Insurance Industry

Bob MacDonald has built an illustrious career in the insurance industry, marked by his unique ability to challenge the status quo and drive transformative change. As a visionary leader, he has held various key positions in top insurance companies, founded and sold a successful insurance company, and played a pivotal role in shaping the life insurance landscape.

Bob’s journey in the insurance world began in 1965 as a door-to-door insurance agent for New England Mutual Life, which was later absorbed by Metropolitan Life. His early career saw him build a sales agency in Southern California for Jefferson-Pilot (now Lincoln Financial Group), serve as the director of marketing support for State Mutual of America (which later became Allmerica Life), and hold the positions of chief marketing officer, chief operating officer, and eventually president and CEO of Minneapolis-based ITT Life, owned by The Hartford.

During his tenure as president and CEO of ITT Life Insurance Corp., Bob emerged as a prominent and influential figure in the life insurance industry. His unapologetic approach to challenging industry norms made him a force to be reckoned with. As reported by The New York Times, he was an “innovator and unrepentant bad boy” in a largely conservative industry.

In the early 1980s, Bob launched a public campaign against whole life policies, which were the industry’s most popular family of policies at the time. His bold stance that whole life insurance was no longer a good buy, coupled with his criticism of the industry as “ossified, petrified, myopic and inbred,” earned him both admiration and vilification. Despite the backlash, his “Your Whole Life is a Mistake” campaign proved to be a significant success.

After leaving ITT Life Insurance, Bob founded a new life insurance company, Life USA, in the late 1980s. The Minneapolis-St. Paul-based company offered independent agents an ownership stake in the company and encouraged them to become “capitalists rather than captives.” Under Bob’s leadership as founder, chairman, and CEO, Life USA became a profitable, publicly traded company with over $1 billion in sales, more than $6 billion in assets, and over 80,000 contracted agents.

In 1999, Bob sold Life USA to Munich-based financial services giant Allianz in a deal valued at $540 million. The company was subsequently merged with Allianz Life of North America. In an unusual move, Bob was asked to continue as CEO of the merged companies, where he helped make Allianz Life a star performer in the Allianz worldwide group.

Throughout his remarkable career, Bob MacDonald has been a relentless innovator and a catalyst for change in the life insurance industry. His fearless pursuit of improvement and his unwavering commitment to challenging the status quo have left an indelible mark on the industry and set an inspiring example for future generations of insurance professionals.