[Hiring] Customer Success Operations Specialist @SimplePractice

Role Description

We’re looking for a friendly, AI-passionate, and impact-driven Customer Success Operations Specialist to join our team. You’ll help us scale and optimize our Customer Success organization by equipping our teams with the right tools, workflows, and data—with a special focus on AI innovation. This role is ideal for someone who loves operational excellence, thrives on cross-functional collaboration, and gets excited about the transformational power of AI and automation.

Responsibilities

• Be a Champion of AI for the CS Org
  • Serve as the owner and evangelist of all AI/automation initiatives across Customer Success
  • Train, evaluate, and maintain AI models (e.g., ChatGPT, Ultimate, custom workflows)
  • Partner with Enablement and Education to ensure AI tools are aligned with support philosophy and team readiness
  • Stay on the cutting edge of generative AI, surfacing use cases that drive efficiency, accuracy, and better CX
  • Advocate for AI-driven self-service improvements and help deploy them across channels
  • Track the impact of AI on metrics like resolution time, ticket deflection, and CSAT
  • Translate team feedback into iterative improvements and share key learnings with leadership
• Manage Customer Success Tools & Systems
  • Administer and enhance CS platforms, including:
    • Zendesk: Maintain all views, fields, triggers, automations, macros, forms, and reporting structures
    • Zoom, OnceHub: Support scheduling and call integrations
    • QA/WFM tools: Configure and manage systems like Assembled, Maestro
  • Maintain up-to-date internal documentation, SOPs, and workflow playbooks for tooling and process changes
  • Collaborate with Product, Engineering, and IT for system launches and improvements
• Enable Team and Business Success
  • Identify request trends through data and create additional workflows/initiatives to limit time spent by the CS team
  • Align tooling and workflows to support revenue-driving initiatives (e.g., trial conversion, feature adoption)
  • Identify and operationalize opportunities for upsell, retention, and self-service enablement
  • Deliver on cross-functional projects with Enablement, Marketing, and Product
• Secondary Responsibilities
  • Support product launches through documentation, training, and alignment
  • Jump in on live support (chat, phone, Zoom) during key events or as needed
  • Lead Q&A sessions or 1:1 walkthroughs to support customers

Qualifications

• 3+ years of experience in a CS Operations role
• Bachelor’s degree from an accredited college or university
• A sense of urgency to provide a world-class customer experience
• The ability to adapt to different situations and make adjustments as needed
• Experience leveraging customer success best practices
• Proven ability to develop strategies, translate them into initiatives, and track successful execution
• Demonstrated operational excellence in analytical thinking, process development and improvement, problem solving, communication, delegation, and planning that will drive organizational efficiencies and customer satisfaction
• The ability to collaborate effectively across the organization and with external stakeholders
• Proficiency with technology and web apps such as Slack, Asana, and Google Workspace

Requirements

• Preferred: 6+ months experience with Agile project management tools like Pivotal Tracker, collaborative interface design tools like Figma, HTML, CSS, JavaScript, Artificial Intelligence (AI)/Machine Learning (ML), API integrations, workforce management tools like Assembled, complex tech stacks, and specialized teams

Bonus Points

• 1+ years experience with tools like Pivotal Tracker, Figma, Assembled, Maestro, and Zendesk
• Familiarity with HTML/CSS/JavaScript, APIs, or SaaS integrations
• Experience maintaining or evaluating generative AI platforms
• Background in a high-growth, B2B SaaS environment
• Past work supporting complex tech stacks or product-led CS orgs

Benefits

• Medical, dental, vision, life & disability insurance
• 401(k) plan with company match
• Flexible Time Off (FTO), wellbeing days, paid holidays, and summer Fridays
• Mental health resources
• Paid parental leave & Backup Care
• Tuition reimbursement
• Employee Resource Groups (ERGs)