Senior Learner Support & Outreach Specialist

Pathstream; United States; Remote; USD 85,000 - 110,000; Full time

Benefits offered by this job

Medical, dental, vision insurance

Flexible spending account (health)

Employee Assistance Program

Wellbeing apps (Ginger, Headspace)

Paid time off

Paid holidays

Parental leave

Disability insurance

Laptop provided

Remote-friendly culture

401(k)

Pet insurance

Job summary

Pathstream is expanding its Customer Support team and seeks a Senior Learner Support & Outreach Specialist to guide new learners through onboarding and provide proactive, white-glove support for certificate programs.

You’ll monitor engagement, design intervention strategies, and help develop AI-powered tools while surfacing opportunities to improve marketing, product, and learner experiences.

Qualifications

• 3–5 years in a high-touch, relationship-driven support role with at least 1–2 years in a senior/mentorship capacity
• Strong written and verbal communication with the ability to tailor tone for different learners
• Empathy and patience when supporting learners who are struggling or frustrated
• Demonstrated ability to quickly absorb and synthesize context across multiple clients/partners
• Comfort working with metrics and data to inform decisions
• Experience training or tuning AI/chatbot tools is a plus

Responsibilities

• Ramp up quickly on new client/partner programs and keep guidance accurate as programs evolve
• Guide new learners through onboarding and provide information, encouragement, and support
• Design and execute intervention strategies via email, SMS, and phone to improve retention and completion
• Track results of interventions and refine approaches based on what works
• Support AI-powered support tools to deliver faster, more accurate responses
• Surface learner feedback to Marketing, Product, and other teams to drive improvements
• Collaborate with Support, Program, Product, and Marketing to close the loop on issues

Skills

Relationship-driven support

Communication skills

Empathy

Analytics

AI tools feedback

Tools

AI-powered tools

Job description

Senior Learner Support & Outreach Specialist

Remote

Senior Learner Support & Outreach Specialist

Location: Remote (US) Type: Full-time

What we do:

Pathstream was founded on the premise that substantial unrealized economic and human potential exists within each organization’s frontline workforce. We are reshaping the way employees and managers on the frontlines excel in their careers. In this age of rapid tech evolution, our enterprise partnerships transform frontline teams from transactional to relational, from back office to middle office, and from task-oriented to strategic.

Pathstream impacts companies’ bottom lines through improved productivity, increased retention, and enhanced customer experience. Employees experience greater success in their current roles and unlock future professional growth.

About the Role

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 - 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

What We're Looking For

• 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

WHAT WE OFFER

• 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
• 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)
• 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.