Healthcare is among the most difficult and highly regulated industries in the world. In this demanding sector, RaeAnn Grossman, CEO of HLTHworks, has not only witnessed momentous change but holds the role of healthcare architect and builder – designing and repairing pieces of what is broken in healthcare. She has carved out a distinctive space as a leading expert in healthcare transformation and innovation.
Undeterred by obstacles or murmurs of doubt, she has earned her place through hard work and is emerging as a role model for a new generation of women leaders. According to RaeAnn, her career reflects a life spent “in the arena”: building, fixing, leading, and daring greatly. She personifies the spirit of Theodore Roosevelt’s famous quote: “It is not the critic who counts…but the man in the arena.”
For RaeAnn, her work in healthcare is both a sprint and a marathon. She points out that the healthcare industry is exhausting, fragmented, and slow to change, but patients cannot wait. So, every day, she wakes up with the same mission: “simplify care, restore dignity to the patient experience, and make healthcare work the way it should.”
Hard Work Creates Impact
RaeAnn believes that hard work always has consequences. Her success is the result of the effort she has put into every role she has undertaken. It has propelled her into the upper echelons of leadership, where her approach has been shaped by building teams, influencing with intention, and learning how alignment across government, health plan, physician, and patient drives impact and better outcomes.
As a woman in a leadership role, RaeAnn found herself on five separate occasions during company acquisitions – to venture capital, private equity, or strategic buyers – as the only woman at the table. That experience sharpened her resolve, preparation, and conviction. “It taught me to lead with credibility, composure, and results, regardless of the room,” RaeAnn says.
She continues to derive her motivation from doing good, helping others, and building better.
Challenge: Making the Broken Beautiful
Rarely does a leader traverse the business landscape without encountering challenges. RaeAnn has faced her fair share of challenges;some of them have been in the form of healthcare bureaucracy, care journey fragmentation, and lack of clarity and accountability.
For RaeAnn, the most defining challenge has been making broken systems more cohesive, brick by brick, step by step. “We are far from finished,” she says, “but progress comes from consistency, credibility, and relentless execution. One has to fight fiercely and have perservance to synthesis the complex into something simple, beautiful and elegant.”
Credibility is essential to influencing healthcare organizations. It can prove to be a challenge to gain that status. RaeAnn points out that credibility is earned by showing up prepared, delivering excellence, and protecting integrity. “You must do this every day,” she adds. “Prepare more, reflect more, envision more, and execute better.”
Achievement: Reflecting Long-term Vision – Do Good
RaeAnn is a highly accomplished leader. She has several achievements to her credit from selling companies such as Signify, Datavant, and building Medicare Advantage from the ground up with CMS and health plans. But at HLTHWorks, the achievement that best reflects her long-term vision is serving the people serve – redesigning community health systems and regional health plans care and quality programs to be more patient- and provider-centric. This has resulted in hundreds of millions of dollars in improved performance and reducing the cost of care, and then those dollars gained or saved can be reinvested into benefits, access, and care delivery. Redesign local and regional care even with national organizations – helps you change the course of the patient, physician, and community – improving lifes, increasing wellness, and slowing burnout.
“We are removing confusion, reducing administrative burden, and helping organizations deliver high-quality care, compliantly, consistently, and with empathy,” RaeAnn says.
A Brief Intro to HLTHWorks
HLTHWorks specializes in acquisition harmonization, due diligence, sustainable growth, care optimization, care journey simplification and strategic transformation. Since 2024, it has supported the growth, transformation, and revitalization of more than 50 healthcare organizations.
Through it’s thoughtful consulting pillar, HLTHWorks designs and implements – strategic vision, executes growth initiatives and drives operational clinical and administrative improvements. As a result, their clients achieve higher revenue, improved margins, scalability, and stronger team alignment with clear KPIs, delivering measurable and lasting impact. RaeAnn points out that every day, they partner with health plans, health systems, technology innovators, physicians, patients, plus CMS and HHS government stakeholders, as transformation only occurs when we are truly listening to each other and creating one roadmap.
Franklin D. Roosevelt once said, “The test of our progress is not whether we add more to the abundance of those who have much, but whether we provide enough for those who have too little.” According to RaeAnn, this principle defines HLTHWorks’ mission: “redesigning healthcare to serve patients first, not systems.”
Personal Values Influencing Business Decisions: Accountability
Personal values often form the core principles that guide decision-making. RaeAnn has often tapped into them – such take ownership and accountability – no matter what level you hold. For instance, in 2019, when she was leading Medicare Advantage at Bright Health Plan, she decided to directly engage with frustrated members.
She recalls that at the time, patients in Denver were struggling to get prescriptions filled. It was turning out to be a frustrating experience for the members. RaeAnn understood their problem. Instead of directing someone else to handle the issue, she gave members her personal cell number so that she could help them personally.
Then, she also took steps to ensure members would not have to face the same frustration again. RaeAnn says that during the following bid season, the team redesigned the pharmacy formulary and simplified copays, and educated both physicians and pharmacists how to support the new policies. This led to a significant decrease in complaints, reduced ER utilization, and a marked improvement in adherence.
“That experience reinforced a core belief: when you make care easier for patients, outcomes improve,” she points out. “And so does performance.”
Creativity, Collaboration, and Accountability
RaeAnn believes that creativity thrives when expectations are clear and accountability is shared. As noted earlier, transformation does not happen in silos. She explains that it is made possible through alignment, shared accountability, and courageous leadership willing to redesign what no longer serves the patient or the physician.
As CEO, RaeAnn creates a culture of creativity, collaboration, and accountability through war rooms, focused offsites, whiteboarding, and an atmosphere of intensity and energy. “We bring the right minds together, align on the vision, and attack the problem,” she points out.
Daily Habits: Discipline and Resilience
RaeAnn adheres to a set of daily habits. “Discipline is non-negotiable. Mind, body, and holistic health are critical to success” she says. At 5 a.m. every day, she starts her day with strength training and a run. First thing she does everyday, she handwrites her to-do list and reads healthcare headlines and The Wall Street Journal. On weekends, she refreshes with trail runs in the Arizona desert. Every day, she makes sure to stay anchored to her sense of purpose as well.
“And every day, I recommit to fixing what is broken in healthcare,” RaeAnn says.
Work-Life Balance
RaeAnn has struggled with maintaining a work-life balance. “Honestly, I didn’t always get this right,” she says. When her children were in middle and high school, they missed out on simple routines, including family dinners, everyday moments, and a sense of consistency. “That still weighs on me,” RaeAnn shares.
“Today, they are remarkable adults,” RaeAnn says, “and I am proud of the people they have become.”
Inspiring Next-Gen and Mentorship
Inspirational leaders like RaeAnn believe in influencing the next generation and passing the baton forward. So, she is not just focused on ego and the present. She is rooted in servant leadership and bettering tomorrow. She is paving the way for the next generation by building platforms, not empires. She is opening doors, sharing networks, and modeling what principled leadership looks like in action, not theory.
And, according to her, she is teaching emerging leaders how to think systemically, ethically, and courageously.
Leaders who inspire are great mentors as well. For RaeAnn, “mentorship is everything.” She points out that leadership without service is hollow. Through mentorship, board participation, and community involvement, she is giving back and investing in the next generation of leaders and innovators.
Advice for Aspiring Women Leaders
For many young women professionals, RaeAnn may be a role model, but does not think of herself as such. She has created path and inroads for others to follow in her footsteps and make a meaningful impact. Drawing on her experiences, she offers them and other aspiring women leaders a few pieces of advice to serve as their guiding light. First, she advises them to learn the corporate language.
As someone who continues to believe in the power of hard work, RaeAnn’s second piece of advice is “be the hardest working person in the room.” She also underscores the importance of dressing for where they are going and not where they are today.
“And never apologize for being passionate and focused in purpose,” RaeAnn tells aspiring women leaders.
Legacy: Simpler, Equitable, Accountable Healthcare Ecosystem
RaeAnn strives to make healthcare better and the healthcare journey simpler. She hopes to leave behind a legacy of a healthcare ecosystem that is simpler, more equitable, and more accountable. She wants her name counted among a generation of influential leaders who believe execution excellence and compassion are not mutually exclusive in healthcare.
As CEO of HLTHWorks, RaeAnn wants her legacy to be “ how people did we serve, how many lives are better because we created a simpler, better care pathway for them.”
Final Word: Unconventional, Purpose-driven Leader
RaeAnn embodies Coco Chanel’s belief that “in order to be irreplaceable, one must always be different.” She lives this through her unconventional, purpose-driven leadership. “I refuse to accept complexity, inequity, and bureaucracy as the cost of doing business,” she says.
