[Hiring] Senior Learner Support & Outreach Specialist @Pathstream

Role Description

Pathstream is growing its Customer Support team, and we're looking for a Senior Learner Support & Outreach Specialist to guide new learners through onboarding and serve as a key resource for information, guidance, and encouragement as they work toward completing their certificate programs.

This is not a reactive, ticket-queue or call-center role. We do proactive outreach and provide learners with "white glove" support—which means adjusting your tone, approach, and outreach style to meet each learner where they are, given the wide range of backgrounds and industries they come from.

You'll monitor learner engagement metrics and outcomes, and help design and execute intervention strategies—such as outreach via email, SMS, and phone—to improve retention and engagement. You'll also support the development of AI-powered support tools that help learners get faster answers. Through your direct contact with learners, you'll surface opportunities to clarify our marketing and flag product bugs that need attention.

What You'll Do

• Quickly ramp up on new client/partner programs and stay current as they evolve, keeping track of nuances across a growing portfolio so learners always get accurate, up-to-date guidance regardless of which program they're in.
• Guide new learners through onboarding, serving as a go-to resource for information, encouragement, and support throughout their certificate program.
• Design and execute intervention and follow-up strategies—including outreach via email, SMS, and phone—to improve learner retention and completion rates.
• Track and evaluate the results of your intervention strategies, helping the team understand which approaches are most effective for retention and engagement, and refine the approach over time.
• Support the refinement and development of AI-powered support tools to help learners get faster, more accurate responses.
• Productively surface learner feedback to the relevant internal teams—whether that's flagging unclear messaging to Marketing, product issues to Product, or other concerns to the appropriate team—so learners get the support and fixes they need.
• Collaborate cross-functionally with Support, Program, Product, and Marketing teams to close the loop on learner-reported issues.

Qualifications

• 3–5 years of experience in a high-touch, relationship-driven support role (e.g., customer support, customer success, coaching, or student/learner services), with at least 1–2 years in a senior, lead, or mentorship capacity.
• A natural ability to connect with people—you build trust and rapport quickly, and learners feel genuinely supported when they talk to you.
• Empathy and patience, especially when supporting learners who may be struggling or frustrated.
• Strong written and verbal communication skills, with the ability to adjust your tone for different learners and channels (email, SMS, phone).
• Exceptional organizational skills and attention to detail—you keep track of many learners and moving pieces without letting anything slip through the cracks.
• Demonstrated ability to quickly absorb and synthesize context across multiple clients/partners, then translate it into clear, succinct communication tailored to each learner's situation.
• A thoughtful, analytical mindset—you can look at engagement data and learner feedback and spot patterns or trends others might miss.
• Comfort working with metrics and data to inform decisions, not just anecdotes.
• A proactive, self-directed approach—you notice when something isn't working and take initiative to flag it or fix it.
• Experience training or tuning AI/chatbot tools is a plus—if you've given feedback on AI outputs, helped refine prompts or responses, or worked to improve an AI tool's accuracy and tone, that's a strong signal for this role.
• Flexibility to work early East Coast hours as needed to support outreach to learners based in Europe.

Benefits

• Transparent and social culture, challenging work, fast learning cycles, practical training, and meaningful feedback.
• Strong sense of ownership and strategic work that impacts our product, users, colleagues, business, and world.
• Competitive salary commensurate with experience and geographic location: $85,000-$110,000.
• Comprehensive benefits package.
• 100% employer-paid medical, dental, and vision insurance coverage for you and 50% for your partner/spouse and dependents.
• Flexible spending account (health).
• Employee Assistance Program (mental health, financial health, legal support, and more).
• Free access to wellbeing apps like Ginger and Headspace.
• Flexible paid time off and 13 paid holidays.
• Generous paid parental leave.
• Short and long-term disability insurance (100% company paid).
• Annual professional development budget.
• Company-provided laptop.
• Remote-first culture.
• Life insurance (100% company paid).
• Optional supplemental life insurance.
• 401(k).
• Discounted pet insurance.

Commitment to Diversity and Inclusion

Our company values diversity and believes diverse teams make innovation possible. We work on complex, difficult problems with no linear or clear solutions. We need a diverse team that can bring different perspectives and approaches, and whose experiences reflect the full set of stakeholders we seek to serve. As such, Pathstream is an equal opportunity employer. We encourage all qualified applicants from any race, color, religion, sex, gender identity, sexual orientation, national origin, disability status, protected veteran status, or other characteristics to apply.

San Francisco Fair Chance Ordinance

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.