Senior Director, Customer Support

Senior Director, Customer Support Location: Remote - 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. We are transforming the legal experience for all by bettering the lives of legal professionals while increasing access to justice. Summary: The Opportunity This is a rare opportunity to lead world-class support at one of the fastest-growing legal SaaS platforms in the world. You'll own the full customer support experience across Clio's core practice management platform and Clio Work, our intelligent Legal AI assistant — with a mandate to build a team where every Clion is focused on the complex, high-value interactions that require real expertise, judgment, and relationship depth — while AI agents handle the rest. You won't just be managing queues and SLAs. You'll be deploying AI support agents, building AI voice channels, and scaling your team's ability to identify and convert Customer Success Qualified Leads at every touchpoint — continuing to scale support as a core growth engine for Clio, where world-class service is a competitive differentiator. You'll make customers feel like they have a brilliant, always-on legal tech partner, and you'll be the leader who made that possible — not by replacing great people, but by accelerating them and enabling them to be extraordinary. Team & Culture 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. AI-First Support Architecture & Outcomes 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. Multi-Product Support Excellence 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. Operational Excellence & Scale 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. Strong Differentiators 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. What You Bring: 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. You Are: An operator who thinks in systems — you see the whole board, not just the next move. Energized by ambiguity and building new things, not just optimizing existing ones. Genuinely excited about AI — you follow the space, have opinions on it, and want to be on the frontier. A communicator who can translate complex AI and operational concepts for executive audiences and frontline teams alike. A culture carrier who creates environments where high performers thrive and everyone has a clear path to growth. Technology You'll be expected to evaluate, select, and drive adoption of tools in these categories: AI Support Agents: Maven AI, Decagon, Sierra, Intercom Fin, etc. AI Enterprise Platform: Claude CRM, CCaaS: Salesforce Service Cloud; Talkdesk Analytics & WFM: Looker, Playvox Knowledge Management: Zendesk, etc. What you will find here: Compensation is one of the main components of Clio’s Total Rewards Program. We have developed a series of programs and processes to ensure we are creating fair and competitive pay practices that form the foundation of our human and high-performing culture. Some highlights of our Total Rewards program include: 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 ​ The expected salary range* for this role is $184,000 to $230,000 to $276,000 USD. There are a separate set of salary bands for other regions based on local currency. In addition, this role is eligible for variable pay that is based on company performance, with actual payout amounts calculated and paid on a quarterly basis. *Our salary bands are designed to reflect the range of skills and experience needed for the position and to allow room for growth at Clio. For experienced individuals, we typically hire at or around the midpoint of the band. The top portion of the salary band is reserved for employees who demonstrate sustained high performance and impact at Clio. Those who are new to the role may join below the midpoint and develop their skills over time. The final offer amount for this role will be dependent on geographical region, applicable experience, and skillset of the candidate. Diversity, Inclusion, Belonging and Equity (DIBE) & Accessibility Our team shows up as their authentic selves, and are united by our mission. We are dedicated to diversity, equity and inclusion. We pride ourselves in building and fostering an environment where our teams feel included, valued, and enabled to do the best work of their careers, wherever they choose to log in from. We believe that different perspectives, skills, backgrounds, and experiences result in higher-performing teams and better innovation. We are committed to equal employment and we encourage candidates from all backgrounds to apply. Clio provides accessibility accommodations during the recruitment process. Should you require any accommodation, please let us know and we will work with you to meet your needs. Learn more about our culture at clio.com/careers We're a Human and High Performing AI company, meaning we use artificial intelligence to improve all of our operations. In recruitment, AI helps us streamline the process for greater efficiency. However, we've built our systems to ensure that a human always reviews AI-generated output, and we never make automated hiring decisions. Disclaimer: We only communicate with candidates through official @clio.com email addresses. Additional Locations: Vancouver, Remote - Canada, Toronto, Calgary