Manager Customer Success AI (Manager / Player-Coach)

The Manager of Customer Success- AI, acts as the subject matter expert and operational guide for Weave’s cutting-edge AI product suite, including our flagship AI Receptionist, and TrueLark legacy product. This individual manages and mentors a dedicated team of Weave across various designations- all firmly rooted in AI success- while maintaining strategic, hands-on ownership of a select portfolio of high-value, complex accounts. Your mission is to maximize product utilization, optimize conversational AI configurations to eliminate caller friction, and craft compelling data-driven ROI stories that secure long-term customer retention. Serving as a hybrid mentor and strategic consultant, you will bridge the gap between technical AI performance and executive-level business outcomes.

• Reports to: Director of Enterprise Customer Success

• This role is Hybrid

What You Will Own

• Team Leadership & Mentorship (Coach Scope):

  • Mentor, coach, and guide a team of Customer Success professionals, fostering a deep operational understanding of AI optimization methodologies and data translation.

  • Drive team-wide performance around core retention, feature adoption, and AI utilization metrics.

  • Conduct regular coaching, play review, and skill development sessions to build a team of highly consultative AI advocates.

• Strategic Portfolio Ownership (Player Scope):

  • Directly manage a high-impact, strategic book of business of Mid-Market and Enterprise accounts.

  • Partner with key client decision-makers to align Weave’s AI solutions with their complex operational workflows and growth objectives.

• AI Workflow Optimization:

  • Deeply analyze client operations, call coverage routing, scheduling patterns, and AI configuration to remove customer friction and maximize receptionist utilization.

  • Drive high-impact optimization playbooks to improve AI handle rates and operational efficiency for multi-location practices.

• Data-Driven ROI Storytelling & Retention:

  • Interpret complex usage dashboards, call handle metrics, and commercial value data to build robust ROI business cases for customers.

  • Craft compelling, executive-ready presentations and QBRs that demonstrate concrete cost-savings and revenue expansion driven by AI features.

  • Systematically identify customer health risks and operationalize repeatable playbooks to mitigate churn and drive net retention.

• Cross-Functional Collaboration:

  • Serve as the critical feedback loop between the front line and the Product, Engineering, Onboarding, and Sales teams to influence the AI product roadmap and refine the implementation process.

• Key Performance Indicators (KPIs):

  • AI Utilization & Handle Rates: Drive high feature adoption and call handle rates across both individual and team-managed portfolios.

  • Net Revenue Retention (NRR): Achieve target logo and net retention, minimizing preventable churn by proving the economic value of Weave's AI offering.

  • ROI Program Execution: Standardize the delivery of data-driven business reviews showing verifiable customer ROI across the team.

What You Will Need to Accomplish the Job

• SaaS CS & Leadership Experience:

  • 3+ years of experience in Customer Success, Account Management, or other consultative client-facing roles supporting Enterprise or Mid-Market customer segments.

  • 1+ years experience mentoring or coaching team members, leading projects, or demonstrating leadership in a SaaS environment.

• AI & Workflow Configuration Expertise: Strong technical and consultative aptitude with hands-on experience configuring telephony, call routing, conversational AI, or complex scheduling workflows.

• Data Literacy & ROI Storytelling: Exceptional analytical skills with the ability to interpret raw usage data, translate technical metrics (e.g., call answer rates, automated handle times) into financial ROI, and present them convincingly to senior executives.

• Strategic Stakeholder Management: Experience managing and advising complex multi-location accounts, establishing trust as a consultative business partner.

• Communication Excellence: Elite verbal and written communication skills and the ability to be effective in both internal and external communication.

What Will Make Us Love You

• You are deeply passionate about artificial intelligence, emerging SaaS trends, and finding creative ways to automate client operations.

• You possess a strong builder mindset—you enjoy creating playbooks, frameworks, and tools from scratch to help your team scale.

• You are an empathetic leader and culture-builder who inspires others and brings a supportive, positive energy to the workplace.

• You navigate growth-stage ambiguity with ease, adopting extreme ownership of obstacles and transforming them into strategic opportunities.

• You have experience in healthcare, dental, or beauty/wellness verticals.

Employment with Weave is contingent upon the successful completion of a background check, conducted in accordance with applicable laws.

At Weave, we use Artificial Intelligence (AI) tools to help us work more efficiently and create a smoother candidate experience. AI may assist with things like writing job descriptions, scheduling interviews, or reviewing applications against job-related criteria. For additional information, please review the External AI Policy Statement available on our Careers page.

Weave is an equal opportunity employer that is committed to fostering an inclusive workplace where all individuals are valued and supported. We welcome anyone who is hungry to learn, problem-solve and progress regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other applicable legally protected characteristics. If you have a disability or special need that requires accommodation, please let us know.

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