Remote Director Flight Operations Jobs (NOW HIRING)

CareTracker, a division of Harris; is seeking a Director of Support who will be responsible for leading and evolving the Client Support organization to deliver exceptional customer experience while driving operational performance, scalability, and continuous improvement.

You will oversee the people, processes, technology, and performance of the Support function, ensuring alignment with business objectives and service level expectations.

Reporting directly to the VP of Operations, you will partner closely with Product, Engineering, Customer Success, Professional Services, and Executive Leadership to advocate for customers, improve product quality, and strengthen end-to-end service delivery. This role requires deep healthcare technology experience, strong operational and analytical discipline, and a proven track record of successfully leading enterprise software support organizations.

The ideal candidate is an experienced support leader with executive presence and demonstrated success building and scaling organizations, driving transformational improvement, and developing future leaders. This role is well suited for someone seeking continued career growth and the opportunity to take on broader organizational leadership responsibilities over time.

This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed, approximately 20%. Candidates must hold a current, valid passport and be legally eligible to travel internationally. This includes either passport based visa exemption or possession of any required travel visas for entry into Canada, the United States, and the Caribbean. Preference will be given to candidates who can work in EST timezone.

Salary:

100K - 120K

AI & Innovation Mindset

We are committed to leveraging emerging technologies to improve how we work, serve our customers, and drive business outcomes. The successful candidate will demonstrate curiosity and a willingness to actively adopt and leverage AI tools to improve workflows, solve problems, and increase efficiency. Candidates should be comfortable using AI enabled technologies, including copilots, chat based AI assistants, and automation tools, as part of their everyday work while maintaining appropriate judgment, security, and compliance standards.

What your impact will be:

Strategic Leadership

• Develop and execute the long-term vision, strategy, and operating model for the Client Support organization.
• Lead organizational transformation initiatives that improve scalability, customer satisfaction, and operational efficiency.
• Establish objectives and key results for service excellence and monitor performance against departmental and corporate goals.
• Drive adoption of automation, AI, knowledge management, and process improvements to increase efficiency and enhance the customer experience.
• Oversee the strategy and optimization of support technologies, knowledge management platforms, and automation tools to improve team efficiency and customer outcomes.

Operational Excellence

• Lead a high-performing Support organization responsible for delivering timely, effective, and consistent customer service.
• Own departmental KPIs, including customer satisfaction, SLA attainment, response and resolution times, backlog health, escalations, quality, and productivity.
• Contribute to Maintenance (MA) revenue forecasting and operational planning through insights into customer health, retention trends, and support performance.
• Partner with Customer Success and executive leadership to drive customer retention, reduce attrition, and support long-term recurring revenue growth through exceptional support delivery.
• Develop resource plans, staffing models, budgets, and forecasts that support business growth and customer demand.
• Analyze operational trends and performance metrics to proactively identify risks and opportunities for improvement.
• Ensure support processes are standardized, documented, scalable, and aligned with industry best practices.
• Maintain compliance with healthcare regulations, security standards, and organizational policies.

Customer & Cross-Functional Leadership

• Serve as the escalation point for strategic customer issues and critical incidents.
• Build trusted relationships with customer executives through business reviews and service discussions.
• Partner closely with Product and R&D to translate customer feedback and support trends into product enhancements, reduce recurring issues, and improve overall product quality.
• Collaborate with Customer Success and Professional Services to deliver a seamless end-to-end customer experience.
• Represent the voice of the customer in leadership planning and organizational decision-making.

People Leadership

• Mentor, coach, and develop managers and future leaders within the Support organization.
• Create a culture of accountability, ownership, continuous learning, and customer advocacy.
• Lead succession planning efforts and establish career development pathways for employees.
• Foster an environment where performance expectations are clear, measurable, and consistently reinforced.

Travel Requirements

• Limited travel expected (typically not to exceed 20%), primarily for strategic customer engagements, leadership meetings, conferences, or business planning sessions.

What we are looking for:

• 8+ years of progressive leadership experience in Client Support or Technical Support, including multiple years leading managers or large teams.
• Demonstrated success leading a healthcare technology Support organization, with accountability for operational performance, customer satisfaction, service delivery metrics, and strategic transformation initiatives.
• Deep understanding of healthcare software, Practice Management and EMR/EHR platforms, ambulatory workflows, HIPAA requirements, and healthcare operations.
• Proven experience building and scaling support organizations through process improvement, automation, and organizational change.
• Strong financial acumen with experience managing departmental budgets, forecasting, workforce planning, and operational metrics.
• Exceptional executive communication skills with the ability to influence customers and internal stakeholders at all levels.
• Track record of developing leaders and building succession pipelines within an organization.
• Ability to evaluate complex operational challenges, synthesize data from multiple sources, and make strategic decisions that improve business outcomes.
• Comfort or proven track record with transforming support organizations through AI, automation, and digital initiatives.

What would make you stand out:

• Experience leading Support within a SaaS or healthcare technology organization serving ambulatory or provider markets.
• Strong financial acumen, with experience managing recurring revenue forecasts and profitability.
• Demonstrated success building high-performing leadership teams and developing successors within a growing organization.
• Demonstrated ability to partner effectively with Product and Engineering to improve customer outcomes.
• Experience managing executive-level customer relationships and high-profile escalations.
• Evidence of progression into increasingly strategic leadership roles with readiness for Senior Director or Vice President responsibilities.
• Experience with Microsoft Dynamics 365 CRM.

What we can offer:

• 3 weeks' vacation and 5 personal days
• Comprehensive Medical, Dental, and Vision benefits starting from your first day of employment
• Employee stock ownership and RRSP/401k matching programs
• Lifestyle rewards
• Remote work and more!

About CareTracker:

Harris CareTracker is a leading provider of cloud-based Electronic Health Records (EHR) and Practice Management solutions, serving thousands of healthcare providers for over 20 years. Our integrated platform streamlines operations, enhances patient care, and ensures compliance with healthcare regulations. With a focus on user-friendly design and continuous innovation, we empower medical practices to achieve operational excellence and improve patient outcomes. Learn more at: harriscaretracker.com

About Harris:

Harris is a leading provider of mission critical software to the public sector in North America. As a wholly owned subsidiary of Constellation Software Inc. ("CSI", symbol CSU on the TSX), Harris has become the cornerstone for CSI's investment in utility, local government, school districts, public safety, and healthcare software verticals. Our success has been realized through investments in our proprietary software and market expertise. This focus, combined with acquiring businesses that build upon or complement our offerings, has helped drive our success. Harris will continue to growth through reinvestment - both in the people and products that we offer and making investments in acquiring new businesses.

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