Director of Service Experience

Location: Remote, Philippines-based

Schedule: EST Business Hours alignment

Compensation: Competitive Director-level rate, commensurate with experience

Lead the function that makes home care agency owners stay with OLIVIA for years, not months.

OLIVIA Professional Solutions trains and places highly qualified Filipino virtual assistants with U.S. home care agencies. We are hiring a Director of Service Experience to lead the post-onboarding client function as we continue to grow.

This is not a customer success role with a fancy title. This is a leadership seat where you will design the entire post-onboarding client journey, build the systems that catch churn before it happens, lead a team of Service Experience Coordinators across the client portfolio, and partner directly with the CEO and Director of Operations on retention strategy. The role exists because we believe that how a client feels six months in matters more than how they were sold in week one.

You will be successful here if you have run a service or success function before, you understand what compassionate accountability actually means in practice (not just as a phrase on a wall), and you can hold the line in hard conversations without losing the warmth that makes clients want to stay. Home care agency owners are mission-driven people running operationally complex businesses. They do not want a vendor. They want a partner who gets it.

You will report directly to the CEO. You will build the playbook. You will hire and develop your team. You will own the metric that matters most to this business: clients who stay.

About OLIVIA

OLIVIA Professional Solutions trains and places highly qualified Filipino virtual assistants with U.S. home care agencies. We support agency owners with trained virtual schedulers, caregiver recruiters, and administrative VAs who help them reclaim their time, scale their operations, and deliver exceptional care to their clients.

Our mission is twofold: help U.S. home care agency owners build sustainable, scalable businesses, and build meaningful, long-term careers for our VAs in the Philippines. We believe in compassionate accountability: high standards, delivered with empathy, consistency, and care.

What You Will Own

Retention Strategy

•       Design and own the post-onboarding client journey across the full client portfolio.

•       Set the retention target, build the program to hit it, and report against it to the CEO.

•       Lead the monthly retention review with cross-functional leadership.

•       Develop and refine the service recovery framework as the function evolves.

Team Leadership

•       Hire, onboard, develop, and manage the Service Experience Coordinators.

•       Set the culture, the standards, and the rhythm of the team.

•       Coach individual Coordinators through difficult client situations and stretch growth moments.

•       Build the career path that turns strong Coordinators into future Managers and Directors.

Client Relationships

•       Serve as the executive relationship owner for senior strategic accounts.

•       Step into escalations that exceed Coordinator-level authority.

•       Lead Quarterly Business Reviews and strategic client conversations.

•       Be the voice of the client inside OLIVIA's leadership team.

Cross-Functional Partnership

•       Partner with internal teams responsible for talent placement, training, and VA experience to ensure seamless handoffs and consistent quality.

•       Partner with operational leadership on remediation, performance, and quality consistency.

•       Partner with the leadership team on systems, process, and scaling.

Systems and Reporting

•       Build the systems that surface client health signals before they become churn risks.

•       Own the retention metrics dashboard reported to the CEO and senior leadership.

•       Drive CRM hygiene and documentation discipline across the function.

•       Recommend and implement tooling decisions that scale with the business.

Required Qualifications

•       Minimum 5 years of client-facing experience, with at least 3 years in a leadership role managing a team of 5 or more.

•       Proven track record in customer success, account management, client services, or service operations, ideally in healthcare, home care, BPO, SaaS, or staffing.

•       Direct experience managing retention as a primary metric, with documented results.

•       Excellent written and verbal English communication; able to engage U.S. home care agency owners and senior stakeholders with confidence, warmth, and credibility.

•       Demonstrated cross-cultural fluency, especially in bridging Filipino teams and U.S. clients.

•       Strong operational discipline: comfortable with CRM tools, structured reporting cadences, and established customer success methodologies.

•       Experience hiring, developing, and retaining high-performing client-facing talent.

•       Reliable home office setup with stable internet and a quiet, professional environment for video calls during U.S. business hours.

Preferred Qualifications

•       Prior experience serving or working with U.S. home care, hospice, or healthcare agencies.

•       Familiarity with WellSky, AxisCare, ClearCare, HHAeXchange, or similar home care software platforms.

•       Background in nursing, allied health, or healthcare operations leadership.

•       Experience building a customer success or service experience function from foundational stage to scaled execution.

•       Comfort presenting to executive audiences and partnering with founders or CEOs.

What You Bring as a Person

•       Calm under pressure. You de-escalate without absorbing the stress. When the room is loudest, you are clearest.

•       Compassionately accountable. You hold a high bar for yourself and your team, delivered with care. Standards and warmth are not in conflict for you.

•       Strategically operational. You can zoom out to design the program and zoom in to fix the broken handoff. You do not stay in either lane.

•       A coach, not just a manager. You make the people around you better. Your former direct reports are still grateful you hired them.

•       Genuinely curious about clients. You want to understand the agency owner's business, their goals, what keeps them up at night, why they started. Not to close a ticket, but because that is how relationships work.

•       A clear writer. Your reports, your client emails, your team feedback are all written in a way that is a pleasure to read and never leaves the reader confused about what comes next.

Why OLIVIA

•       Lead a mission-critical function in a high-growth company at exactly the inflection point where your work shapes the trajectory.

•       Direct partnership with the CEO. Your voice will shape strategy, not just execute it.

•       Real ownership: build the playbook, hire the team, own the metric.

•       Career-defining role for someone ready to step into Director-level scope in a U.S.-facing company.

•       Competitive Director-level compensation, performance bonuses, and meaningful professional development.

•       A leadership team that values your insight, acts on it, and tells you the truth in return.

How to Apply

Send us four things:

•       Your résumé with clear documentation of team size and retention results in previous roles.

•       A brief cover letter (no more than one page) that tells us why this role at this company, and what you would prioritize in your first 90 days based on what you know about OLIVIA from this posting.

•       A 5-minute video introduction responding to this prompt: Tell us about a time you turned a churn-risk client into a long-term advocate. What did you actually do, what did you change about how you worked afterward, and what did you learn about your own leadership in the process

•       Two references we can speak with at the final stage. Ideally one direct report you have managed and one peer or executive you have partnered with.

Applications are reviewed on a rolling basis. We will respond to every applicant. If you are uncertain whether your experience aligns with the role, send the application anyway and we will tell you honestly.

OLIVIA Professional Solutions is an equal opportunity organization. We welcome applications from candidates of all backgrounds.