Resolution Support Lead

The Customer Resolution Support Lead is the central owner of Owl Practice Suite’s most complex and high-impact customer issues. This role operates at the intersection of Customer Success, Product, Engineering, and Compliance to ensure critical issues are resolved quickly, communicated clearly, and prevented from recurring.

This is a hands-on, high-ownership role responsible for driving incident resolution, maintaining customer trust, and improving the reliability of the platform at scale.

What You’ll Do

Own Critical Customer Incidents

• Act as the single-threaded owner for high-severity customer issues impacting satisfaction, SLAs, compliance, or revenue
• Manage end-to-end resolution from intake through root-cause identification and final closure
• Assess risk level and prioritize incidents based on customer impact, regulatory implications, and business urgency

Drive Cross-Functional Resolution

• Rapidly mobilize and coordinate teams across Customer Success, Product, Engineering, and Compliance
• Define clear resolution plans with accountable owners, timelines, and milestones
• Facilitate incident stand-ups, remove blockers, and ensure momentum through to resolution

Communicate with Customers & Leadership

• Provide proactive, clear, and empathetic updates to impacted customers
• Deliver concise, executive-ready summaries to internal leadership
• Translate complex technical issues into clear, actionable communication for non-technical stakeholders

Lead Root Cause & Continuous Improvement

• Conduct post-incident reviews and document root causes with precision
• Ensure follow-up actions are owned, tracked, and prioritized across teams
• Identify recurring failure points and drive systemic improvements to product, processes, and operations

Build & Scale the Escalation Program

• Establish and refine escalation workflows, intake criteria, SLAs, and communication protocols
• Develop playbooks for incident management and high-risk customer scenarios
• Partner with Customer Success teams to improve escalation quality and consistency

Data, Reporting & Insights

• Track and report on key metrics including Time-to-Resolution, escalation volume, root cause trends, and customer risk
• Produce weekly and monthly insights to inform leadership decisions
• Use data to identify opportunities to reduce escalations and improve customer experience

Enable the Team

• Serve as the escalation point and coach for Customer Success and Support teams
• Mentor team members on structured troubleshooting, stakeholder management, and escalation best practices
• Contribute to internal documentation and knowledge base improvements

What Success Looks Like

• Critical customer issues are resolved quickly, with high confidence and minimal disruption
• Customers remain informed, supported, and confident during high-stakes issues
• Cross-functional teams operate with clarity, accountability, and urgency during incidents
• Root causes are consistently identified and resolved at the system level, not just patched
• Escalation volume decreases over time due to systemic improvements
• Leadership has clear visibility into risk, performance, and trends
• Customer satisfaction, retention, and product reliability measurably improve, * This role serves as a key escalation point for critical customer issues and may occasionally require support outside of normal business hours, including evenings and weekends. Are you comfortable with this expectation?
• How many years of experience do you have managing customer escalations, incident response, or high-priority customer issues within a SaaS environment?
• Describe a time when you led a cross-functional team (e.g., Support, Product, Engineering, Operations) to resolve a complex customer issue. What was your role and what was the outcome?
• This role requires communicating complex technical issues to both customers and executive leadership. Please describe your experience providing updates during high-impact customer incidents.

Do you have experience in Zendesk?, * 5+ years of experience in Customer Success, Technical Support, or Program Management within SaaS or healthcare

• 2+ years leading escalation management, incident response, or cross-functional resolution workflows
• Strong technical fluency, including APIs, integrations, authentication (SSO/OAuth), and debugging approaches
• Experience working with tools such as Zendesk, Jira, and customer success platforms
• Familiarity with incident management frameworks, postmortems, and SLAs

Core Strengths

• Exceptional problem-solving and ability to navigate complex, ambiguous situations
• Strong analytical skills with the ability to turn data into insights and action
• Executive-level communication skills with ability to summarize complex issues clearly and concisely
• High emotional intelligence and ability to manage sensitive customer situations with empathy and professionalism
• Confident in influencing senior stakeholders and driving decisions across teams

Nice to Have

• Experience in mental health or healthcare SaaS environments
• Familiarity with privacy and compliance frameworks such as PHIPA, HIPAA, and PIPEDA
• Experience building or scaling incident management or escalation programs

Work Environment

• Full-time, remote (Canada or US)
• Primarily aligned to Eastern Time working hours
• Occasional travel for team offsites or planning sessions
• A strong, reliable internet connection is required for this role.

On-Call & Escalation Coverage

This role serves as a key escalation point for critical customer issues and platform incidents. While the position is primarily aligned to Eastern Time working hours, there will be occasions where urgent customer situations require attention outside of normal business hours, including early mornings, evenings, and weekends. The successful candidate must be comfortable responding to high-priority escalations and coordinating cross-functional teams when time-sensitive issues arise.

1.51.5 out of 5 stars Remote $75,000 - $85,000 a year - Full-time