About Us:

Checkbook is a leading FinTech company modernizing how businesses send and receive payments. Our platform supports both digital and paper check payments, allowing businesses to issue, receive, and manage payments securely and efficiently, whether delivered online or mailed as a physical check. By eliminating manual processes and reducing operational friction, we provide simple, reliable, and cost-effective payment solutions for our clients. 

The Role:

We’re looking for a Customer Support Manager to lead and scale our customer support function as the company grows. This role is responsible for building a high-performing support team, defining best-in-class support processes, and ensuring our customers receive timely, empathetic, and effective support across all touchpoints.

You’ll sit at the intersection of customer experience, operations, and product, acting as both a people leader and a strategic partner to the business. This is a hands-on role that requires comfort jumping into tickets when needed, while also building systems and processes that scale.

Responsibilities:

Team Leadership & Development

• Lead, coach, and develop a team of Customer Support Representatives.
• Set clear expectations around performance, quality, and customer experience.
• Support onboarding, training, and ongoing development of support team members.
• Foster a customer-first, collaborative, and accountable team culture.

Support Operations & Process Ownership

• Own day-to-day customer support operations, including ticket management, escalations, and response SLAs.
• Design, document, and continuously improve support workflows, policies, and playbooks.
• Ensure consistent, high-quality support across all channels (email, chat, etc.).

Customer Experience & Escalations

• Serve as an escalation point for complex or sensitive customer issues.
• Ensure issues are resolved efficiently and with a strong focus on empathy and clarity.
• Identify recurring customer pain points and proactively drive solutions.

Cross-Functional Collaboration

• Partner closely with Product, Engineering, Payments, Risk/Fraud, and Operations teams to resolve customer issues and improve product experience.
• Advocate for the customer internally by surfacing insights, trends, and feedback.
• Support launches of new features or workflows by preparing the support team and updating documentation.

Reporting & Insights

• Track and report on key support metrics (e.g., ticket volume, response times, resolution times, CSAT).
• Analyze trends to identify gaps, training needs, or opportunities for process improvement.
• Use data to inform staffing, tooling, and operational decisions.

Tools & Systems

• Own and optimize customer support tools and platforms (e.g., Zendesk).
• Help implement automation, macros, and self-service resources to improve efficiency and customer experience.
• Maintain internal and external knowledge bases and FAQs.

About You:

• 4+ years of experience in customer support or customer experience, including at least 1–2 years in a people management role.
• Proven experience leading and scaling customer support teams in a fast-paced environment.
• Strong operational mindset with the ability to build processes that scale.
• Excellent communication skills, with a calm, empathetic, and customer-first approach.
• Comfortable handling escalations and navigating ambiguity.
• Data-driven, with experience using metrics to drive improvements.
• Ability to work cross-functionally and influence without authority.
• Experience in fintech, payments, SaaS, or a regulated environment is a plus.
• Familiarity with support platforms such as Zendesk is preferred.

Benefits & Perks:

• Medical, Dental, Vision, LTD, and additional insurance programs
• 401(k)
• Equity

Compensation: Competitive base salary + bonus + equity (based on experience)

Equal Opportunity Employment

It is our policy to provide equal opportunities for all employees in relation to recruitment, training, and promotion. Decisions will be made solely based on job-related requirements and without regard to age, disability, gender reassignment, marriage or civil partnership, pregnancy or maternity, race, religion or belief, sex, or sexual orientation.

If you need accommodations during the application process, please contact us directly