Head of Customer Experience

Remote (United States)

About the Role

This opportunity is for an experienced customer experience leader to guide and scale a high-performing support organization serving self-employed professionals across the United States. The role focuses on customer strategy, team leadership, operational performance, product feedback, escalation management, and cross-functional collaboration.

The broader mission is to support the growing self-employed workforce by helping customers manage business finances, taxes, accounting, bookkeeping, banking, and expense tracking with greater confidence and less friction.

Employment Type: Full Time

Location Type: Remote

Compensation: $150,000 - $170,000 per year

What You’ll Do

• Partner with cross-functional stakeholders to influence the product roadmap and broader company strategy.
• Synthesize customer trends, gather product feedback, and identify points of friction in the customer experience.
• Coach managers and help ensure their teams meet goals, perform effectively, and grow in their day-to-day work and long-term development.
• Monitor, define, and improve KPIs, OKRs, and operational workflows that keep the Customer Experience organization moving efficiently.
• Set and refine the overall strategy for the Customer Experience organization.
• Collaborate on internal processes, policies, documentation, and training materials that support the broader team.
• Support customers by handling high-visibility internal and external escalations with professionalism, empathy, and strong problem-solving judgment.

Qualifications

• 7+ years of experience managing a customer support team in a start-up or technical environment.
• Direct experience with hiring, training, performance management, and team development.
• Demonstrated ability to lead independently and adjust management style as organizational needs and platform priorities change.
• Experience using common customer support platforms and analytics tools.
• Interest in or experience with AI as it relates to customer support and customer experience operations.
• Ability to communicate effectively with both technical and non-technical partners.
• Experience partnering closely with Engineering, Product, Design, and Risk teams.
• Experience setting roadmaps for a Customer Experience organization.
• Strong problem-solving ability in a fast-paced, high-growth environment.
• Self-starter approach to learning, improving processes, and solving ambiguous challenges.
• Excellent written and verbal communication skills, with a strong focus on empathy, clarity, and customer-centered problem solving.
• Experience communicating effectively with customers, employees, managers, and cross-functional stakeholders.
• Experience managing a distributed team.

Nice to Have

• Experience or interest in financial services, accounting, taxes, and/or self-employment.
• Experience working in a fast-moving, high-growth start-up environment.
• Proficiency in data analysis and using insights to improve customer experience operations.

Perks and Benefits

• 401(k), FSA, and commuter benefits: Employees have access to tax-efficient benefit options along with competitive base compensation.
• Paid parental leave: New parents are eligible for 16 weeks of flexible parental leave.
• Health benefits: Comprehensive medical, dental, and vision coverage is provided, with employee coverage paid at 100% and dependent coverage paid at 90%.
• Remote work support: Team members outside office locations are supported in working fully remote within the United States.
• Office options: Office locations are available in San Francisco and New York.
• Meaningful equity: Employees receive competitive equity so they can share in long-term ownership and impact.
• Generous vacation policy: Employees are encouraged to take time for vacations, appointments, mental health, and personal needs.