MSIG USA CHRO: 25 Years in HR Began With a Commercial Driver's License

A commercial driver's license earned at a beverage distributor started Darin Conselyea on a path that now leads to the chief human resources officer seat at specialty P&C insurer MSIG USA. His career in people leadership spans more than 25 years, multiple industries and two international assignments, in Japan and Ireland.

Before finishing his B.A. in Business Management from Pace University — which he completed at night while working — Conselyea joined United Parcel Service, where the license landed him in the safety department. It was there that senior HR leaders first encouraged him to explore more opportunities within the function. What drew him in, he said, was seeing how much influence HR could have when it understood both the business and its people. That insight shaped a core philosophy he still carries: understand the business first, then determine how people strategy can move it forward.

Along the way, Conselyea has held leadership roles at Guardian Life, Barclays, Prudential Financial and MetLife before arriving at MSIG USA. His advice for professionals is to take thoughtful risks and bet on themselves. The experiences that shaped him most came from stepping into unfamiliar roles, moving across the globe, or saying yes before feeling completely ready.

"Go in with your eyes open, but don't let uncertainty keep you from moving forward," he said.

Who shaped his approach to leadership?

Several leaders influenced Conselyea at different stages of his career. Early on, one manager told him not to "let the grass grow under me" — to keep seeking new experiences and stretch beyond what he knew. Others gave him opportunities to work with C-suite executives and take roles abroad.

He also worked for a CHRO who showed him that strong leadership and genuine empathy can coexist. The lessons he carried forward: stay curious, understand the business, create opportunities for others and never lose sight of the people behind the work.

His best professional mistake taught him the limits of speed. Early in his career, he sometimes mistook speed for progress. He has always had a strong bias for action, and when he could see where a business needed to go, his instinct was to move quickly and assume others would follow. He learned that having the right answer is not enough. People need to understand where you are going, why it matters and how they can be part of getting there. He still has that bias for action, but he now pairs it with communication and shared ownership.

What does he see as HR's real work?

His favorite part of the job is taking a business challenge and determining how people strategy can help solve it. Talent management is especially rewarding for him: identifying people with potential, helping them recognize strengths they may not see and watching what they accomplish.

His least favorite part is administrative work that consumes time without adding strategic value. Technology and AI, he argues, can simplify routine work and give HR more capacity to advise leaders, develop talent and address complex workforce challenges. The goal, in his words, is more time for human judgment and relationships.

On supporting people, Conselyea draws a distinction between support and comfort. Support does not always mean making people comfortable, he said, because some of the most meaningful growth happens when someone is given an opportunity that stretches them. As a leader, he tries to recognize potential — sometimes before someone sees it themselves — and create opportunities to test it. That might mean a stretch assignment, a new role or a challenge that requires applying skills in a different way. The key is giving people trust and ownership while making sure they can ask questions and acknowledge when they need help.

How can leaders make HR a value in the organization?

It starts with treating HR as part of the business strategy, not as a function that comes in after decisions are made, Conselyea said. When leaders bring HR into conversations about growth and transformation early, HR can help shape how the business gets there. But HR also has to earn that seat by understanding how the business operates and identifying the capabilities needed to move priorities forward.

The strongest partnership happens when business strategy and people strategy are developed together, he said. That is when HR becomes a driver of how an organization grows, changes and performs.

Looking ahead five years — a long horizon, in his view, given how quickly work is changing — Conselyea sees AI reshaping how work gets done and the skills organizations value. HR has to help employees build the skills to work differently today, which means meeting people where they are. The bigger opportunity is using technology to reduce administrative tasks and give people more capacity to apply judgment and solve complex problems.

What is he most proud of?

One experience from his time at UPS has stayed with him for more than 30 years. The company was struggling to recruit women into driver roles, and his manager believed the team could not sit in the office and wait for candidates to find them. He took the team into the community to look for talent differently.

One day at a diner, Conselyea watched the waitress work — on her feet for hours, lifting and carrying constantly — and realized she already demonstrated many of the qualities the job required. They recruited her, and she became a UPS driver.

That experience inspired him to create a program called Driving Women, which went to women's softball games and other venues to reach women the company was not finding through traditional recruiting channels. The program was recognized for its success, but Conselyea said the idea behind it matters most to him. It taught him that talent does not always arrive in the package you expect. Sometimes leadership means looking beyond the résumé and giving someone the chance to prove it.

What advice does he offer newcomers?

Learn the business, not just HR, Conselyea said. Understand how your company makes money, what its customers value and what drives performance. That knowledge makes you a more credible partner. And stay curious and empathetic: listen to people and understand how business decisions affect them.

For HR teams weighing how far AI should absorb routine work, his career offers a consistent test — whether every new capability returns time to judgment, relationships and the people behind the work.