[Remote] Senior Director, Customer Support

Note: The job is a remote job and is open to candidates in USA. Clio is the global leader in legal AI technology, empowering legal professionals and law firms of every size to work smarter, faster, and more securely. The Senior Director, Customer Support will lead a global team, enhancing customer support through AI integration while ensuring high-quality service and customer satisfaction. This role focuses on transforming the customer support experience and building a proactive support culture that leverages technology to meet customer needs.

Responsibilities

• Lead, develop, and inspire a 150+ person global team across five locations — fostering a culture of continuous improvement, psychological safety, and AI curiosity
• Recruit top-tier talent with a specific lens on AI-native and AI-fluent support professionals who are excited about redefining their roles alongside technology
• Serve as the escalation executive for critical customer and product incidents, representing the voice of the customer internally at the highest level
• Continue scaling support as a core growth engine for Clio — proactively surfacing customer needs, driving expansion, and proving that world-class support is a competitive differentiator, not a cost center
• Build proactive support partnerships with R&D and Post Sales (e.g., Onboarding, Professional Services, and CSM teams) to create a seamless customer experience
• Design and own the strategy to evolve support into an AI-first model — elevating our Clions to focus on complex, high-value customer interactions that require expertise, judgment, and relationship depth, while AI agents (e.g., Maven, Decagon, Sierra, or equivalent) handle routine inquiries at scale
• Build and deploy intelligent AI voice agents and chat agents that can handle complex, multi-product support workflows for legal professionals
• Develop AI-assisted agent tooling (agent assist, real-time suggestions, auto-summaries) to speed time to resolution for customers and increase first-contact resolution
• Partner with Product and Engineering to build a robust product feedback loop powered by support signal — turning customer pain points into roadmap inputs at velocity
• Drive PLG-integrated support motions that reduce friction at critical conversion and adoption moments within the product experience
• Own the end-to-end support lifecycle for both Clio's core practice management platform and Clio Work (Legal AI drafting, research, and intelligence)
• Build differentiated support models tuned to each product's complexity, customer segment, and AI-sensitivity — recognizing that Clio Work customers will have fundamentally different support needs than core platform users
• Develop specialized routing and escalation frameworks for complex customer questions
• Manage multi-channel environments (voice, live chat, email, AI chat, async messaging) with intelligent routing and consistent service levels across all
• Set and own critical support KPIs including AI-driven metrics
• Identify and convert CSQLs (Customer Success Qualified Leads) emerging from support interactions
• Lead Workforce Management (WFM) to forecast demand across traditional and AI channels, enabling intelligent staffing decisions and intraday optimization
• Manage budget with a clear ROI mindset
• Build and scale a Support Systems architecture across Salesforce Service Cloud, CCaaS platforms (e.g., Talkdesk), Knowledge Base, and AI support tooling

Skills

• 8+ years leading 100+ person customer support or CX organizations in high-growth B2B SaaS environments
• Demonstrated track record deploying AI support technologies at scale — you have actually done this, not just advised on it
• Direct experience with modern AI support platforms such as; Maven AI, Decagon, Sierra, Intercom Fin, or equivalent
• Deep understanding of AI agent architecture: how to design escalation logic, confidence thresholds, knowledge base curation, and human-in-the-loop workflows
• Strong command of support operations metrics with a bias toward outcome-driven, AI-augmented efficiency
• Experience supporting complex, multi-product SaaS environments with distinct customer personas and technical depth requirements
• Experience in legal tech, professional services SaaS, or other high-trust, regulated verticals where content accuracy and compliance carry real stakes
• Hands-on experience with PLG (Product-Led Growth) support models, including in-product nudges, proactive outreach triggers, and self-service optimization
• Familiarity with AI voice agent deployment (e.g., conversational IVR, voice AI for support)
• Track record building feedback loops between support signal and product roadmap — not just reporting bugs, but influencing roadmap priorities
• Experience in hypergrowth environments where the business doubles while headcount grows far more slowly

Benefits

• Competitive, equitable salary with top-tier health benefits, dental, and vision insurance
• Hybrid work environment, with expectation for local Clions (Vancouver, Calgary, Toronto, Dublin and Sydney) to be in office minimum twice per week.
• Flexible time off policy, with an encouraged 20 days off per year.
• EAP benefits for you and household members, including counseling and online resources
• 401k matching and Child Education Savings
• Clioversary recognition program with special acknowledgement at 3, 5, 7, and 10 years
• Variable pay that is based on company performance, with actual payout amounts calculated and paid on a quarterly basis.

Company Overview