Director of Client Success — Healthcare and Entire Family

Director of Client Success — $0 Healthcare for You and Your Entire Family

Healthcare shouldn’t be something you worry about when it comes to taking care of your family.

That’s why when you join our team,
your healthcare costs $0 out of your paycheck —and the same is true for your spouse and children.

No monthly premiums.
No deductibles.
No surprise medical bills.

Most team members avoid tens of thousands of dollars in healthcare costs compared to traditional health plans.

This isn’t a perk.
It’s part of our mission.

Redirect Health exists to make healthcare affordable for small businesses and people who can’t afford traditional employer insurance . We help real people navigate a system that is often confusing, expensive, and frustrating—and we do it with empathy, accountability, and simplicity. If you want your work to matter to families every single day, you’ll find purpose here.

At Redirect Health, our values guide how we show up for each other, our clients, and our members.

We do our best work when we:

Obsess Over People
We are always helpful, friendly, and human.

Own It to Completion
If we take something on, we see it through.

Always Improve & Adapt
We learn quickly and adjust without ego.

Always Start with “Yes, We Can Help You”
We lead with solutions and figure out the rest.

Succeed as a Team
We win together through trust and collaboration.

Detest Waste & Unnecessary Complexity
We remove friction so we can focus on what truly helps people.

If these values resonate with you, you’ll feel at home here.

Director of Client Success exists to lead the Client Success function and ensure our clients consistently see value, clarity, and results from their partnership with Redirect Health.

In this role, you will:

Serve clients, brokers, and internal Customer Success and care teams
Be responsible for client retention, renewal performance, enrollment growth, and overall client satisfaction
Directly impact the long-term growth and stability of Redirect Health by building strong client relationships and scalable Client Success practices

This is a role for someone who:

Enjoys strategic thinking, relationship-building, and hands-on leadership
Takes ownership and follows through
Wants their work to have real-world impact

In this role, you will:

Own: Client management strategy, including client segmentation, value proposition, coverage model, and renewal approach

Support: Clients and members by ensuring they understand and can fully use their healthcare benefits, with guidance from a strong Client Success team

Collaborate with: Healthcare Consultants, AR Specialists, Brokers, Care Logistics, Claims, and Member Success teams to deliver a consistent “WOW” client experience

Improve: Renewal performance, upsell outcomes, and client retention by using data, trends, and proactive communication to prevent surprise terminations

Advocate for: Clients and brokers by representing their needs, feedback, and results across Redirect Health teams and leadership

A strong performer in this role is known for:

• Building and leading a high-performing Client Success Advocate team
• Using data and insight to drive smarter client strategy and renewal outcomes
• Consistently delivering strong retention, growth, and client trust

Success in this role is measured by:

• Net renewal growth, upsells, and invoice expansion across the client portfolio
• Client retention and enrollment growth across assigned client segments
• Client satisfaction among owners, HR leaders, benefits teams, and brokers
• Effective leadership, development, and performance of the Client Success Advocate team

We’re looking for someone who:

• Brings 5+ years of experience managing Customer Success teams
• Has 10+ years of experience in customer-facing roles (support, service, or account management)
• Communicates exceptionally well, both verbally and in writing
• Demonstrates strong analytical thinking and experience leading data-driven client management work
• Brings a proven commercial mindset and strong business judgment
• Is a friendly, self‑motivated team player who thrives on supporting others
• Has a genuine passion for…