Driver Success Lead

About pickUP:  pickUP is more than a ride-hailing app; we're a homegrown startup with a big heart and a bold vision. We’re on a mission to revolutionize how people — visitors and locals alike — move across Barbados. With a vibrant community of over 500 registered taxi drivers, we're building a people-first movement grounded in safety, exceptional service, and local innovation. As we continue to grow, we're looking for a passionate and dedicated Driver Success Lead to be the champion for our driver network. This isn't your typical office job.

You'll be the trusted liaison, the go-to problem solver, and a key player in building a strong, inclusive, and successful driver community. What You'll Be Doing: Be the Heart of Our Driver Community: Serve as the primary point of contact for all driver questions, concerns, and feedback. Build Authentic Connections: Forge strong, trust-based relationships with our drivers through regular face-to-face meetings, phone check-ins, and clear, digital communication.  Listen and Innovate: Host brainstorming sessions and forums to gather ideas and suggestions directly from drivers, using their feedback to drive positive change. Improve the Driver Experience:

Identify trends in driver feedback and collaborate with our Operations team to propose and implement improvements. Welcome New Faces: Recruit new drivers and manage the onboarding and orientation process for new applicants. Spark Engagement: Plan and execute engaging driver events and initiatives that build a sense of community and appreciation. Wear Many Hats: As a startup team, we all pitch in. You'll occasionally assist with broader operational needs, especially during peak seasons. What We're Looking For: A True People Person: You genuinely enjoy listening to people, understanding their perspectives, and finding creative solutions.  An Exceptional Communicator:

You can chat comfortably and effectively with everyone, from seasoned taxi drivers to new recruits. A Proactive Self-Starter: You take initiative and are comfortable working independently without the need for micromanagement. We trust our team to get the job done. Experience that Counts: Previous experience in customer service, community relations, conflict resolution, or operations is a strong plus, but not a deal-breaker. Experience supervising teams is preferred.  Mobile: A valid driver's license and access to your own vehicle are highly preferred for this role.  A Few Things to Note: Startup Life:

We're a small, passionate team aggressively in a growth phase. That means every day is different, and we're all hands on deck. We value a "can-do" attitude and flexibility. Working Hours: Occasional weekend and public holiday work will be required, especially during peak seasons like Christmas and Crop Over. Vacation leave is generally not granted during these periods, except in exceptional circumstances. Rewarding Work: We believe in hard work and make sure to recognize and reward team members who go above and beyond. What We Offer: Shape the Future:

This is a unique opportunity to help build a fast-growing Bajan company from the ground up. A Great Team: Join a close-knit and collaborative team that values your voice and impact. Room to Grow: As we expand, so will your opportunities for increased responsibility and career growth. Flexibility: We offer flexible hours and a hybrid work setup. A Front-Row Seat: Be at the heart of the evolution of transportation in Barbados.

Ready to Ride with Us?Send your CV with 2 references and a brief note (500 words or less) telling us why you're the perfect fit for this role to hannah@pickupbarbados. comDeadline: August 22nd, 2025We can't wait to hear from you!