Senior Learner Support & Outreach Specialist

Role overview A senior learner-success role on a remote Customer Support team, guiding new learners through onboarding and ongoing engagement in certificate programs. Rather than reactive ticket work, the role emphasizes proactive outreach and "white-glove" support, adapting tone and approach to each learner's background. The position also helps refine AI-powered support tools and channels learner feedback back into the product and marketing organizations.

Responsibilities - Ramp quickly on new partner programs and stay current as they evolve, tracking nuances across a growing portfolio. - Guide new learners through onboarding as a trusted resource for information, encouragement, and support. - Design and execute intervention and follow-up strategies across email, SMS, and phone to improve retention and completion. - Track outcomes of outreach efforts, share learnings with the team, and refine approaches over time. - Support the development and tuning of AI-powered support tools so learners get faster, more accurate responses. - Channel learner feedback to Marketing, Product, and other internal teams, helping close the loop on unclear messaging or product issues. - Collaborate cross-functionally with Support, Program, Product, and Marketing on learner-reported issues.

Requirements - 3-5 years of experience in a high-touch, relationship-driven support role (customer support, customer success, coaching, or student/learner services), with at least 1-2 years in a senior, lead, or mentorship capacity. - Natural ability to build trust and rapport quickly with people from a wide range of backgrounds. - Empathy and patience, especially with frustrated or struggling learners. - Strong written and verbal communication skills with the ability to adjust tone across email, SMS, and phone. - Exceptional organizational skills and attention to detail when juggling many learners and moving pieces. - Ability to absorb context across multiple client programs and translate it into clear, learner-appropriate communication. - Analytical mindset that spots patterns in engagement data and feedback. - Proactive, self-directed approach to identifying and fixing problems. - Flexibility to work early East Coast hours to support outreach to European learners.

Nice to have - Experience training or tuning AI or chatbot tools, refining prompts, or improving automated response quality and tone.

Benefits and work setup - Remote-first role based in the United States. - Salary range of $85,000-$110,000, commensurate with experience and location. - 100% employer-paid medical, dental, and vision coverage for employees, with 50% coverage for partner/spouse and dependents. - Health flexible spending account, Employee Assistance Program, and free access to wellbeing apps. - Flexible paid time off plus 13 paid holidays, and generous paid parental leave. - 100% company-paid short- and long-term disability and life insurance, with optional supplemental life coverage. - 401(k), annual professional development budget, company-provided laptop, and discounted pet insurance.