Over the past year, we have increasingly focused on enterprise partnerships, working with national health plans, large provider organizations, and multi-market health systems.
Enterprise healthcare partnerships require a fundamentally different go-to-market model. The buying cycles are longer. The stakeholder groups are larger. The operational complexity is far greater.
But the shift is not just about scale. It reflects something deeper about the intersection of technology and healthcare.
Healthcare organizations are not simply adopting software. They are integrating technology into the delivery of care itself. That requires partners who understand both the power of technology and the realities of healthcare delivery.
As our President Dennis Hillen often says, succeeding at this intersection requires a different go-to-market model built on three things:
- Next-generation healthcare talent
Teams must be tech-savvy, empathetic, and grounded in the realities of healthcare delivery at the local level.
- Strategies that balance platform and market thinking
Organizations need value propositions that scale nationally while remaining relevant to the local healthcare ecosystems where care is actually delivered.
- A team model built for trust and accountability
Enterprise healthcare partnerships succeed when expectations are clear and teams stay engaged through implementation and long-term outcomes.
To support this shift, we have rebuilt our client-facing organization around a market leadership structure led by President Dennis Hillen and four locally-based Market Presidents across the country.
These leaders bring experience from across the healthcare ecosystem, including large market-driven organizations such as Humana, Oscar Health, CVS Health, Lumeris, Oak Street Health, and Agilon.
Their focus is simple: build durable enterprise partnerships that help organizations succeed in value-based care.
Along the way, we’ve learned a few lessons about what enterprise healthcare sales actually requires.
Healthcare is still deeply local
Even when working with national organizations, healthcare decisions are largely shaped by local market dynamics - provider networks, payer relationships, regional care delivery models, and the nuances of the communities they serve.
That reality is why Pearl’s market leadership team is organized regionally. Each Market President focuses on a specific geography and brings deep familiarity with the communities and healthcare organizations operating there.
“In healthcare, you aren’t just selling a product or service — you’re navigating complex change management in an environment where decisions directly affect patient care,” said Matt Castelli, Pearl’s Northeast Market President.
Credibility matters more than speed
Enterprise healthcare organizations are making decisions that affect thousands of clinicians and millions of patients.
They are not looking for vendors, they are looking for partners they can trust.
“Enterprise relationships in healthcare are defined by a deep sense of stewardship and a shared responsibility to the patients we serve,” said Joe Green, Pearl’s Midwest Market President.
And increasingly, organizations are looking for partners who strengthen their capabilities rather than replace them.
“Health systems aren’t looking to hand off value-based care to an outsourced vendor,” said Marshall Sunshine, Pearl’s South Market President. “They want an enablement partner that keeps them in the driver’s seat and delivers real, demonstrable results.”
In this environment, credibility and operating experience matter far more than traditional sales velocity.
The best enterprise leaders understand how healthcare works
Healthcare organizations quickly see through generic enterprise sales motions that don’t appreciate the intricacies of what it takes to improve the value equation.
The most effective leaders understand the operational realities of value-based care, from payer contracts to physician and patient engagement to care delivery.
“Organizations are looking for more efficient ways to scale value-based programs while reducing the administrative burden on providers,” said Jamie Benedict, Pearl’s Central Market President.
Pearl’s Market Presidents have spent their careers inside value-based care organizations, health plans, and provider groups, bringing firsthand experience to the partnerships they build.
Meet Pearl’s Market Leadership Team
Pearl’s market leadership team includes:
This team plays a central role in helping more primary care organizations succeed in value-based care. We’re looking for a rockstar West leader — if you’re interested, reach out.
Pearl Health is powering the future of healthcare
We’re a team of physicians, technologists, and risk-bearing experts with a passion for enabling our partners to deliver better care and reduce health system costs. Want to learn more?
