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Associate Team Lead - Customer Support (T2)

Pennylane - Remote - Remote - posted 2026-10-19

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Pennylane is a financial and accounting management platform serving business leaders and accounting firms. We are seeking an Associate Team Lead for our Level 2 Support team to manage a team of 6-12 support agents handling complex customer inquiries requiring deep product and domain expertise. In this hands-on management role, you will be the operational relay for the Level 2 Support Team Lead, directly supporting your team's daily work to ensure efficient, high-quality, and empathetic customer responses. You will also contribute to operational oversight, continuous improvement initiatives, and cross-functional projects. Your daily responsibilities will include: - Running team meetings and monitoring daily workload and ticket volume - Coaching agents on tickets, priorities, and complex situations - Conducting call/conversation reviews and providing constructive feedback - Tracking performance and quality metrics (first response time, resolution time, customer satisfaction, ticket volume) - Participating in operational review rituals: workload tracking, request prioritization, alert identification, and coordination with other support teams - Escalating user pain points to Product, Tech, or Operations teams - Driving process, documentation, and internal tool improvements Key responsibilities: - Manage a team of 6-12 agents under the Level 2 Support Team Lead's supervision, supporting their daily activities, professional growth, and job satisfaction - Provide clear, regular, transparent feedback; conduct conversation reviews and analyses; track individual progress plans; propose coaching and identify training needs - Monitor team metrics and contribute to support quality (first response time, customer satisfaction, resolution time, volume handled, new ticket intake, ongoing ticket follow-up) - Participate in operational rituals and manage shared request queues, including on-call rotations; identify alerts and escalate reinforcement or arbitration needs - Propose optimizations for processes, tools, documentation, and support workflows - Collaborate with Level 1 support, technical support, operations, product, and tech teams; escalate user frustrations; contribute to cross-functional projects - Share best practices with peer Associate Team Leads and maintain fluid communication across Support - Occasionally handle urgent internal requests or complex situations requiring Level 2 expertise, knowing when to escalate Our support culture emphasizes transparency, positive team dynamics, mutual support, and resilience. We stay close to our users—business leaders and accounting professionals—to handle each request with domain expertise, product mastery, and empathy. We encourage two-way feedback, individual development, and initiative-taking, valuing autonomy, accountability, and trust. QUALIFICATIONS: - Bachelor's degree (Bac+2 or Bac+3 minimum) in accounting, management, or equivalent field - At least 1 year of experience in management or team leadership, ideally in support - Strong analytical skills; ability to make measured decisions and propose concrete solutions - Excellent communication and collaboration skills with assertiveness and diplomacy - Passion for feedback, teaching, and individual coaching - Comfort with software tools, particularly ticketing and documentation platforms (Intercom, Zendesk, Notion) - Ability to adapt to a rapidly evolving environment - Customer-service mindset and focus on user experience NICE-TO-HAVE: - Accounting knowledge - Prior experience as an individual contributor in a support team - SaaS or startup environment experience - Experience managing a primarily remote team - Collaboration experience with Product, Tech, or Operations teams - English B1 level minimum - AI proficiency for task optimization

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