Location: Remote-friendly (must be available during US Mountain, Central, or East Coast Hours)

About Onfleet

Onfleet powers the future of commerce with modern logistics software that makes last-mile delivery fast, flexible, and delightful—for businesses and their customers. From intuitive apps for drivers to real-time tracking and APIs for developers, we’ve helped over 300 million deliveries reach doorsteps across the globe, supporting brands like Kroger, Sweetgreen, and Total Wine & More.

At Onfleet, we value collaboration, inclusivity, and ownership. Every team member contributes unique perspectives that shape our product, our culture, and our impact.

About the role

We’re seeking a Head of Customer Experience and Strategy to champion our Customer Success, Support, and Solutions teams. This is a strategic and people-centered leadership role reporting to the Chief Customer Officer, working closely with Product, Sales, and Marketing.

We welcome candidates who care deeply about delivering excellent customer experiences, fostering team growth, and bringing curiosity and creativity to complex challenges.

You Might Thrive Here if You:

• Find joy in collaborating across functions and aligning customer needs with product and strategy
• Ask thoughtful questions and seek to innovate with intention
• See feedback and experimentation as tools for growth
• Are motivated by helping others develop their potential
• Value inclusivity, balance, and impact over ego

What You'll Do:

• Lead and coach high-performing teams across Customer Success, Technical Support, and Solutions
• Create a culture of learning, inclusion, and shared goals across distributed teams
• Evolve support systems and digital-first service strategies that scale with our customers
• Serve as a strategic partner to our customers, understanding their goals and unlocking value
• Champion proactive service by implementing automations, workflows, and team enablement tools
• Analyze customer trends, engagement, and outcomes to inform product direction and team decisions
• Co-lead cross-functional projects that amplify value across the customer journey
• Establish and track clear metrics around customer satisfaction, retention, and team health

What You’ll Bring:

• 10+ years of experience in B2B SaaS customer-facing roles, including 5+ years of team leadership
• Experience supporting both SMB and enterprise segments across varied customer needs
• Familiarity with customer journey mapping, operational metrics, and service design
• Empathy-driven leadership style focused on coaching, clarity, and trust
• Strong communication and cross-functional collaboration skills
• Analytical mindset with experience using data to drive decision-making (e.g., Amplitude, Jira, Confluence)

Bonus (but not required):

• Experience in last-mile delivery, logistics, or fleet tech
• Prior work with implementation/onboarding or professional services teams
• Knowledge of AI- or automation-enhanced customer tools

About our Customer Team:

We take a holistic, team-oriented approach to customer experience, spanning onboarding, success, support, and growth. Our team thrives on curiosity, ownership, and collaboration. We believe success is shared, and everyone plays a part in delivering value.

What We Offer:

• Salary range: $150,000–$170,000 USD, depending on experience and location
• Equity in a values-driven company
• Comprehensive health, dental, and vision coverage
• Flexible PTO and supportive remote-first culture
• 401k program
• A people-first team that values learning and authenticity

Onfleet is an Equal Opportunity Employer:

We are committed to building a diverse, inclusive, and supportive workplace where everyone can thrive. We welcome people of all backgrounds, experiences, and identities to apply.

Employment decisions at Onfleet are made without regard to race, color, religion, creed, gender, sex, gender identity or expression, sexual orientation, national origin, citizenship, age, marital status, pregnancy, disability, veteran status, or any other characteristic protected by applicable law.

We strongly encourage individuals from underrepresented and nontraditional backgrounds to apply, including those with arrest or conviction records, in accordance with applicable laws.

If you’re excited about this role but don’t meet every requirement, we still encourage you to apply. Your unique experience and perspective are valuable to us.

Notice:

We may use automated tools or AI-assisted systems to support resume screening and candidate evaluation. These tools help us process a high volume of applications efficiently and fairly. All final hiring decisions are made by real humans. By applying, you acknowledge that such tools may be used in the early stages of the hiring process.