Health Care & Benefits Power Breakfast

Amber Chittenden helps employers regain control of benefit costs while building sustainable, long-term strategies that protect both people and financial performance. With more than 25 years of experience in the employee benefits industry, she is widely recognized for translating complex benefit structures into clear, actionable decisions that drive measurable value.

After a 19-year career with Cigna, Amber joined Apex Benefits in January 2013, bringing deep expertise in group benefits strategy, plan execution, and trusted client partnership. Serving employers nationwide, she offers both national insight and local perspective, with a focus on cost containment, long-term trend management, and sustainable benefits design. Her work centers on helping employers understand not just how their benefit plans function, but the strategic implications behind every decision they make.

Amber’s leadership philosophy is grounded in ownership and advocacy. She believes the role of a benefits partner is to proactively manage risk as if it were their own—anticipating exposures, addressing long-term cost drivers, and safeguarding the financial integrity of benefit plans over time. This approach has been central to advancing Apex’s legacy of service excellence and building a consultative, strategy-driven client experience that differentiates the firm in the marketplace.

As President, Amber leads Apex with a focus on challenging conventional approaches to benefits, strengthening operational discipline, and guiding clients away from short-term fixes toward sustainable, long-term strategies. She oversees the full client lifecycle—from strategic planning and implementation through ongoing account management and long-term stewardship—ensuring alignment, accountability, and results at every stage. Her leadership is defined by clarity, consistency, and a commitment to creating outcomes that matter for employers and their employees.

A native of Indianapolis, Amber and her husband, Jason, are small business owners who are deeply committed to giving back to the community they call home. Outside of work, she enjoys spending time with their three children, traveling, and participating in equestrian activities—interests that reflect the same discipline, stewardship, and long-term perspective that guide her professional leadership.

As Senior Vice President and Chief Strategy Officer at Hendricks Regional Health (HRH) since 2013, Gary is responsible for formalizing HRH’s strategic-planning processes and establishing new mutually beneficial business relationships, market development and expansion, is involved in state/federal legislative initiatives, and has positioned HRH as the leader in Indiana regarding direct-to-employer arrangements with over 630 employers under contract with HRH.  Gary is also responsible for establishing greater transparency and accountability for those people carrying out the company’s vision and strategy. 

Prior to joining Hendricks Regional Health, Gary spent 15 years at Ascension St. Vincent, based out of Indianapolis, with responsibility for marketing, business development and strategy. He was most recently the System Executive over Business Development for Indiana.

For the past several years, Gary served on the Plan Commission for the Town of Plainfield and as Town Councilman in his first term.

Gary received his B.S. degree at Greenville University and his MBA at the University of Indianapolis. He is also a frequent speaker and panelist at industry events on the topic of direct contracting and how to achieve strong results through collaborating with brokers and employers.

Gary and his wife, Jackie, have been married since 1992 and reside in Plainfield, Indiana.  He’s also a proud grandpa of two.