---
title: 'Senior Learner Support & Outreach Specialist at Pathstream'
canonical: 'https://feeny.ai/job/senior-learner-support-outreach-specialist-pathstream-remote-e50affxsb0kc'
type: 'job'
last_seen: '2026-10-19'
---

# Senior Learner Support & Outreach Specialist at Pathstream

- **Company:** Pathstream
- **Location:** Remote
- **Work type:** remote
- **Posted:** 2026-09-28
- **Last confirmed live:** 2026-10-19
- **Apply:** https://job-boards.greenhouse.io/pathstream/jobs/8006948003

## Job description

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—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

## 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
- 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.

#LI-Remote

## About Pathstream

## Company Overview
- **One-liner**: Pathstream provides professional development programs for frontline teams, delivered outside work hours as a benefit, to improve retention, productivity, and customer satisfaction.
- **Entity Type**: Private (Series A & later venture rounds; last round $38.8M in 2023)
- **Headquarters**: San Francisco, California, United States
- **Founded**: 2018
- **Founders**: Eleanor Cooper (Co-Founder, CEO)

## Core Business
- **Primary industry/industries**: Professional Training and Coaching; Workforce Development; Frontline Talent Enablement
- **Target customers**: B2B – Fortune 500 companies with large frontline workforces in financial services, healthcare, insurance, retail & distribution, and telecommunications.
- **Mission or purpose statement**: “To unlock the unrealized human potential of the frontline workforce” and drive shared success for businesses, society, and each frontline team member.

## Products & Services
- **Pathstream Program Suite**: A scalable, off-the-clock professional development solution delivered as an employee benefit. Includes 1:1 coaching, AI simulations, and career guidance tailored to company-specific performance metrics (e.g., AHT, SLA, NPS). Focuses on foundational capabilities like critical thinking, problem-solving, adaptability, and emotional intelligence. Supports key business priorities: peak performance, essential capabilities, and continuous growth.

## Market Standing
- **Valuation/Market Cap**: Not publicly available (private company)
- **Key Metric**: Total Funding $51.8M across three rounds (Seed 2018, Series A $12M led by TDM Partners in 2019, and a $38.8M venture round in 2023); Annual Revenue ~$7.3M (LinkedIn estimate)
- **Notable Investors/Partners**: TDM Partners (lead investor in Series A); partnership with 100+ companies including Fortune 500 names (e.g., in insurance, retail, telecom).
- **Growth Signals**: 3.1x increase in retention, 20% increase in customer satisfaction, 34% increase in engagement, 70%+ adoption rate, NPS of 65 (top 1% of software companies). However, LinkedIn reports a 16.9% year-over-year headcount decline (81 employees, down 20 people). Recognized as a Great Place to Work and America’s Best Startup Employers 2025.

## Competitive Advantages
- **Differentiator**: Programs are delivered entirely off-the-clock as a benefit (no impact on operations or compensable hours), leading to high opt-in and adoption. No PII sharing required for setup. Minimal contracting (NDA + purchase order). Launch in <1 month with results within 2 weeks. Purpose-built for frontline teams – not generic upskilling.

## Strategic Focus
- **Current priorities**: Scaling among Fortune 500 business leaders, deepening industry-specific solutions (financial services, healthcare, insurance, retail, telecom), and equipping frontline leaders to manage technology adoption and change. Focus on driving in-role performance improvement tied to measurable business outcomes.

## Why Work Here
- **Culture highlights**: Mission-driven workplace dedicated to frontline workforce development; recognized as a Great Place to Work (top 75 Best Small Workplaces 2022-2023) and America’s Best Startup Employers 2025. Emphasis on team member development and career advancement.
- **Remote/hybrid/office policy**: Remote-friendly – current open role (Senior Director, Strategic Partnership Management & Program Operations) is listed as United States, Remote. Headquarters in San Francisco.
- **Notable perks or engineering culture**: Small team (~80 employees) with opportunities for ownership across functions. Engineering and product teams are present (SVP Engineering, Director of Engineering, VP Design & Product Innovation). Alumni go on to Amazon, Walmart, LinkedIn, among others.

## Sources
1. [Pathstream About](https://pathstream.com/about)
2. [Pathstream Home](https://pathstream.com/)
3. [Pathstream Careers](https://pathstream.com/careers)
4. [Pathstream Greenhouse Jobs](https://job-boards.greenhouse.io/pathstream)
5. [Pathstream LinkedIn](https://www.linkedin.com/company/pathstream)

## Other roles at Pathstream

- [Operations Lead, Coaching](https://feeny.ai/job/operations-lead-coaching-pathstream-san-francisco-4dbz01mepvgt) — San Francisco, CA
- [Mechatronics Curriculum Consultant / SME](https://feeny.ai/job/mechatronics-curriculum-consultant-sme-pathstream-united-kingdom-5nyrgextqc13) — United Kingdom
- [Product Researcher](https://feeny.ai/job/product-researcher-pathstream-united-states-fc6t8x8kxmc0) — United States
- [Client Partner](https://feeny.ai/job/client-partner-pathstream-new-york-8z1qkk9z4gt5) — New York, NY
- [Learning Experience Designer](https://feeny.ai/job/learning-experience-designer-pathstream-united-states-d0q1y9ra463d) — United States
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