Pathstream

Role Description Pathstream is looking for a Senior Director of Strategic Partnership Management & Program Operations to own and grow our strategic relationship with a Fortune 50 client end-to-end. This is a high-visibility, cross-functional role at the intersection of strategy, analytics, relationship management, and execution. You'll work directly with the CEO to steward this partnership and our network of employer partners, and serve as the internal champion for our programs — aligning teams and ensuring we're hitting the outcomes our client and their learners depend on. On a day-to-day basis you'll work closely with our operations and marketing teams to drive execution, while also identifying longer-term opportunities for our engineering, product, and learning design teams to tackle. You won't need day-to-day direction — you'll bring it. This is a full-time position based out of our HQ in San Francisco, CA or remote, US and reports to Jo-Ann Tan, COO. Qualifications - 7+ years in program management, strategic partnerships, or a related role — ideally with experience managing a large enterprise or consumer-facing partner - Strong analytical skills: comfortable pulling and interpreting data and communicating findings clearly to non-technical audiences - Exceptional written communication — able to write a crisp executive summary, a thoughtful partner email, or substantive feedback on a marketing campaign - Proven track record of driving alignment across multiple internal teams without direct authority - Strategic thinker who can zoom out to set direction and zoom in to unblock execution - Strong intuition for consumer-facing marketing strategy — able to assess whether a campaign will drive the right learner behaviors and push back when it won't - Comfortable with ambiguity; energized by broad ownership, not intimidated by it - Experience working with or at large enterprise partners; prior strategy consulting experience a plus Requirements - Serve as the primary day-to-day point of contact for our Fortune 50 client stakeholders — building trusted relationships at multiple levels and translating their feedback and requirements into internal action - Identify, pursue, and grow relationships with relevant business partners to support the program - Represent Pathstream's interests confidently and diplomatically; navigate competing priorities with clarity and care - Draft and review internal and external communications related to the client relationship — from executive updates to partner-facing summaries - Directly guide our operations and marketing teams on an ongoing basis — diagnosing what's driving or inhibiting recruitment, program completion, user engagement, and job placement, and directing team focus accordingly - Track program performance closely: understand the data, identify insights, and ensure the team is intervening effectively when metrics need attention - Evaluate and give substantive feedback on learner-facing marketing — bringing strong instincts on what drives quality applications, program completion, sustained coaching engagement, and ultimately job placement - Identify longer-term opportunities and surface them to our engineering, product, and learning design teams - Continuously translate learnings about what's working — and what isn't — into more efficient, scalable operational processes and systems 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 - Tier 1 (SF Bay/NYC Metro): $177,000–$206,000 - Tier 2 Geo: $160,000–$185,000 - Tier 3 Geo: $142,000–$165,000 - Bonus eligible - Comprehensive benefits package - 100% employer-paid medical, dental, and vision insurance coverage for you and 50% for your partner/spouse and dependents - Health, commuter, and parking flexible spending accounts - 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 paid holidays - Generous paid parental leave - Short and long-term disability insurance - Annual professional development budget - Company-provided laptop - Remote-first culture - Life insurance (100% company paid) - 401(k)

• Own and lead full-cycle recruiting across a variety of roles and departments including Marketing, Customer Success, Operations, and Sales. • Partner closely with hiring managers to align hiring strategies with team goals and organizational needs. • Develop creative sourcing strategies using both passive and active recruiting techniques to identify high-quality talent. • Facilitate structured interview processes that create consistency, efficiency, and a strong candidate experience. • Build and maintain strong talent pipelines for current and future hiring needs. • Guide hiring teams through candidate evaluation, interview calibration, offer development, and closing processes. • Drive inclusive hiring practices by embedding DEI best practices throughout the recruitment lifecycle. • Represent Pathstream professionally and thoughtfully throughout all candidate interactions. • Assist in developing and improving recruiting processes, documentation, and hiring best practices across the organization.

• Lead end-to-end technical recruiting efforts for high-impact roles • Serve as a strategic advisor to technical teams • Build and manage a strong, diverse technical talent pipeline • Partner with engineering and product leadership to ensure hiring processes are calibrated • Own and optimize our use of ATS tools, integrating performance metrics and reporting insights • Champion inclusive hiring by embedding DEI best practices • Stay ahead of industry trends, compensation shifts, and talent market dynamics • Assist in developing and enhancing best practices in the overall recruitment process

Role Description The Learning Experience Designer (LXD) is a full-time, exempt role reporting to the Learning Experience Design Manager. This position is primarily a hands-on learning design role—crafting high-quality, learner-centered curriculum for online delivery through the Pathstream platform. Design & Development - Course Design and Scoping: Transform program goals into clear course structures by defining learning objectives, outlining instructional approaches, and creating actionable execution plans. - Interactive Curriculum Development: Design and author high-quality, learner-centered asynchronous curriculum—including lessons, activities, and assessments—that build real-world skills for learners working in industry contexts. Quality & Execution - Content Quality: Iterate on course materials, incorporating feedback from stakeholders and subject matter experts, and ensuring alignment with learning objectives, LXD best practices, and Pathstream’s internal standards. - End-to-End Course Ownership: Manage the entire course creation lifecycle from concept to delivery, ensuring timely execution, instructional quality, and alignment with program goals. Innovation & Strategic Alignment - Learning Design Innovation: Leverage learning science and research to shape instructional approaches and enhance the effectiveness of learning experiences. - Business and Learner Impact Alignment: Leverage program data, learner feedback, and performance metrics to refine instructional strategies and ensure learning experiences drive measurable outcomes. - AI in Learning Design: Thoughtfully leverage established AI tools in your day-to-day work, while actively exploring new ways to use them more effectively in service of better learning experiences. Qualifications - You have meaningful experience designing and developing online learning experiences, and a background that includes direct contact with learners — whether through teaching, coaching, facilitation, or something else entirely. - You enjoy diving into industries that are new to you and building a deep understanding of learner contexts and pain points. - You’re comfortable working across complex or technical subject areas (currently including topics like fraud, claims, mortgages, and financial literacy) and translating them into engaging learning experiences. - You’re a hands-on builder who enjoys the day-to-day work of designing and developing learning experiences, not just setting direction. - You're passionate about creating learning experiences that genuinely change outcomes for people who are working hard to advance their careers. - You’re collaborative by nature, energized by cross-functional work, but also happy to spend a large portion of your day heads down. - You think about the full learner journey, not just individual lessons. - You possess strong technical skills and a creative drive to explore and use new technologies. - You are an excellent communicator, especially in writing, and have the ability to express and break down complex topics clearly and easily. - You’re highly detail-oriented and have excellent organizational skills. - You’re interested in working in a fast-growing, fast-paced environment with changing responsibilities. - You understand that a job goes beyond a job description and are willing to lend a helping hand wherever it’s needed. - You stay informed about new tools and approaches in LXD, and apply them selectively to improve learning experiences and workflows. 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. - Salary and total compensation offerings are contingent upon the candidate's level of expertise and geographic location, ensuring equitable remuneration. - Comprehensive benefits package. - 100% employer-paid medical, dental, and vision insurance coverage for you and 50% for your partner/spouse and dependents. - Health, commuter, and parking flexible spending accounts. - 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 paid holidays. - Generous paid parental leave. - Short and long-term disability insurance. - Annual professional development budget. - Company-provided laptop. - Remote-first culture. - Life insurance (100% company paid). - 401(k). Company Description Pathstream was founded on the premise that substantial unrealized economic & 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.

Engineering Director Pathstream | Engineering | Remote, U.S. ROLE / DEPARTMENT OVERVIEW Pathstream is seeking an experienced Engineering Director to lead one or more engineering teams and drive the next chapter of our technical growth. This is a senior member of the engineering leadership team reporting to the SVP of Engineering. We are looking for someone who has already built a strong foundation in engineering management and technical delivery, and who now brings the maturity, range, and ambition to operate across teams while influencing strategy, engineering culture, and developer productivity. A core expectation of this role is the ability to advance Pathstream’s AI-native engineering practices. AI adoption is already deeply embedded in how we build software at Pathstream. We are looking for a leader who not only embraces this approach but actively pushes the organization forward in adopting AI-enabled development tools and agentic engineering workflows. 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, and from task-oriented to strategic. We impact companies' bottom lines with improved productivity, increased retention, and differentiated quality of customer experience — while employees experience greater success in their current roles and unlock future professional growth. We're a tight-knit, hardworking, mission-driven team of ~60 employees eager to scale our solution and transform careers across the United States. Want to learn more? THE ROLE LEADERSHIP & TEAM MANAGEMENT - Lead, grow, and develop one or more engineering teams — with an active role in shaping engineering team health and capability beyond your direct reports — accountable for all aspects of people management including coaching, performance reviews, compensation, promotions, and when necessary, performance management - Independently plan and execute changes to team structure and staffing: identify capability gaps, define new roles, manage team size, and partner with recruiting to attract and close top engineering talent. - Build and sustain a culture of collaboration, ownership, psychological safety, and continuous learning, where engineers feel empowered to experiment with new approaches, including AI-enabled development practices.. - Resolve interpersonal and technical conflicts within and across teams; develop engineers at all levels through mentorship, direct feedback, and thoughtful career development. - Operate as a leader through others: elevate the skills and capabilities of those around you and position your team — not yourself — as the driver of execution and momentum. - Serve as a credible voice at the engineering org level — influencing how Pathstream's engineering teams collaborate, prioritize shared work, and build collective capability beyond your direct team STRATEGY & EXECUTION - Own the technical vision and roadmap for your team's domain, ensuring alignment with broader company priorities and the needs of cross-functional partners in product and design. - Drive alignment on cross-team goals and initiatives, independently resolving conflicting priorities across teams without escalation; lead effectively in environments of uncertainty and ambiguity, bringing clarity and structure to complex spaces. - Define what success looks like by setting clear goals, establish measurable outcomes, and track progress so the impact of your team's work on customers and the business is always clear. - Clarify ownership and decision-making across initiatives. Delegate tactical decisions appropriately while maintaining accountability for overall outcomes. - Work across team and service boundaries to lead multi-team initiatives and keep dependent work unblocked, operating independently; proactively adjust team pace to maintain urgency while protecting against burnout and sustaining long-term productivity - Contribute to the broader engineering organization by actively shaping strategic direction, leading roadmap conversations that span team boundaries, and independently identifying and driving resolution of org-level risks or opportunities — not just escalating them AI & AGENTIC ENGINEERING LEADERSHIP - Lead by example in an engineering culture where AI is already central to how we build software. You are hands-on with modern AI-enabled development tools (Claude Code, Cursor, GitHub Copilot, and similar AI-assisted development environments) — regularly explore how they can improve engineering workflows. - Drive the adoption of agentic engineering workflows across your team(s) where AI systems assist with or automate multi-step engineering tasks. This may include building internal frameworks, playbooks, or reusable patterns that allow engineers to leverage AI safely and effectively. - Coach engineers on how to collaborate effectively with AI systems - Partner with engineering leadership to shape Pathstream's evolving AI engineering strategy, including evaluating emerging tools, determining where AI creates the most leverage, and ensuring responsible adoption aligned with internal AI guardrails. - Stay informed about advancements in AI-assisted and agentic development; bringing practical insights back to the team and continuously raising the bar for how engineering teams use AI to improve speed, quality, and impact. CROSS-FUNCTIONAL PARTNERSHIP - Build strong relationships with stakeholders including product managers, designers, customers, and cross-functional partners. Represent your team's goals, metrics, and progress clearly to senior leadership. - Collaborate closely with engineering teams to ensure seamless integration across systems and enable rapid delivery of impactful features. - Maintain a deep understanding of Pathstream’s business goals and ensure your teams are structured and prioritized to deliver the greatest value. - Promote strong knowledge-sharing practices across teams so that no individual — including yourself — is a single point of failure. ABOUT YOU EXPERIENCE - You bring 7–10 years of professional software engineering experience, with at least 4 years of hands-on technical work and 3–5 years in engineering leadership, with 3+ years directly managing engineers - You have a proven track record of successfully leading people, teams, or projects across multiple contexts.. - You have experience managing or influencing across multiple teams, or have led a single team through growth and complexity at a scope where you were regularly driving alignment, unblocking cross-team dependencies, and influencing decisions beyond your immediate org - You are comfortable independently owning the full scope of people management responsibilities, including performance management, compensation discussions, career development planning, promotions, and difficult conversations when needed. - You bring familiarity with modern web application stacks similar to ours, including technologies such as: Ruby on Rails, React, JavaScript, Docker, PostgreSQL, and AWS. AI & TECHNICAL LEADERSHIP - You are genuinely hands-on with modern AI-enabled development tools and agentic engineering approaches. This is not “a nice-to-have” skill—we are looking for someone who has already integrated AI into their engineering workflow and can speak from practical experience. - You understand how AI can be incorporated across the software development lifecycle, and you have experimented with or implemented agentic workflows where AI systems assist with or automate multi-step development tasks. - You are able to represent and be accountable for the technical output of your team, either through your own technical depth or through strong collaboration with senior engineers. You know when to go deep into technical problems and when to empower your team to lead. - You have a strong understanding of scalability and system design, with experience building or guiding systems that support significant growth. - You stay curious about the rapidly evolving AI tooling landscape and can translate new developments into practical improvements for a lean, high-velocity engineering organization. LEADERSHIP & COLLABORATION - You are a highly collaborative leader with curiosity, humanity, and generosity. You invest deeply in the professional development of those around you and communicate complex technical ideas in ways that are accessible to a wide range of stakeholders. - You have well-developed stakeholder management skills, with the ability to build trust, influence decisions, and drive positive outcomes across product, design, and business teams. - You are comfortable operating in environments with ambiguity and shifting priorities, and you bring a proactive, data-informed approach to decision-making even when perfect information is unavailable.. - You are energized — not intimidated — by working alongside senior individual contributors who may be more technically specialized than you. You see your role as amplifying the impact of great engineers, creating conditions where they can do their best work and where teams succeed collectively. 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 (plus equity) commensurate with experience and location - Tier 1 Geo (SF/NYC): $180k - $210k - Tier 2 Geo: $160k - $190k Tier 3 Geo: $143k - $170k - Comprehensive benefits package - 100% employer-paid medical, dental, and vision insurance coverage for you and 50% for your partner/spouse and dependents - Health, commuter, and parking flexible spending accounts - 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 paid holidays - Generous paid parental leave - Short and long-term disability insurance - Annual professional development budget - Company-provided laptop - Remote-first culture - Life insurance (100% company paid) - 401(k) 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. WORK AUTHORIZATION Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.

Job Title: Director, End User Content Strategy Reports to: COO / Head of Lifecycle Marketing Location: Remote Employment Type: Contract-to-Hire Company Description: Pathstream was founded on the premise that substantial unrealized economic & 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. We impact companies' bottom lines with improved productivity, increased retention, and differentiated quality of customer experience; employees experience the benefits of greater success in their current roles while unlocking future professional growth. The Role As Director of End User Content Strategy, you'll own the voice and content experience for the employees Pathstream serves. This is a senior individual contributor role with real scope: you'll define the content strategy, shape the creative direction, produce and manage campaigns across channels, and coordinate with contractors to bring it all to life. You'll be working at the intersection of acquisition and engagement — first helping prospective learners understand why Pathstream is worth their time, then keeping enrolled learners motivated and active throughout their programs. The audience is primarily frontline employees; the challenge is reaching them where they are and speaking to what actually matters to them. This role begins as a 6-month contract engagement with the intention to convert to full-time employment based on mutual fit. It reports to the Head of Lifecycle Marketing and works closely with the Lifecycle Marketing team, as well as Customer Success, Operations, and Coaching. In your first 30 days, you'll audit existing end-user content, establish a clear point of view on voice and strategy, and ship your first winning piece of content or media that drives measurable engagement or activation. Within six months, you've built a functioning content operation, demonstrated measurable impact on enrollment and engagement, and become the go-to person for how Pathstream talks to the learners we serve — and both sides have a clear basis for evaluating the full-time opportunity. What You'll Do - Own end user content strategy across the full funnel — from initial awareness and recruitment through program enrollment, engagement, and completion - Produce and art-direct high-quality content yourself across formats — from writing a punchy SMS to scripting and directing a 60-second video - Mine learner success stories from survey data and coaching call notes, and transform them into content that makes a real frontline employee stop scrolling — finding the human moment in an imperfect source and shaping it into something their peers can genuinely see themselves in — building and maintaining a library that scales across multiple industries, employers, and employee groups. - Develop a repeatable, scalable process for gathering, tagging, and refreshing success stories — one that can flex from employer-specific content (always the goal) down to industry-level content where needed - Direct and manage freelance contractors and creative vendors to scale production without sacrificing quality or voice - Build and maintain a content calendar that aligns with program cohort cycles, employer partner timelines, and key learner moments - Develop and maintain consistent brand voice for end user communications that is warm, motivating, and credible — distinct from B2B messaging - Test, measure, and iterate: use data to understand what drives opens, clicks, sign-ups, and sustained engagement, and apply those learnings continuously - Collaborate with employer partnership and program teams to understand learner context, employer expectations, and program-specific messaging needs - Over time, help build the playbooks and systems that make end-user marketing scalable as Pathstream grows What We're Looking For Required: - 7+ years of content strategy or content marketing experience, with demonstrated success in B2C or consumer-facing contexts - Exceptional writer with the range to work across channels and formats — email, SMS, social, video scripts, and more - Ability to extract powerful narratives from raw, unpolished source material — survey responses, coaching call notes, interview transcripts — and shape them into persona-specific content at scale - Experience writing for and directing video production — including scripting, briefing producers, and providing creative direction through the edit - Strong creative direction instincts — you can give specific, actionable feedback to designers and video producers, not just approve or reject their work - Systems thinking: you can design and manage content libraries and production workflows across a complex matrix of audiences, not just produce one-off pieces - Strong strategic instincts: you can connect content decisions to business outcomes and explain your reasoning clearly - Experience managing contractors or external creative partners, with the organizational skills to keep production on track - Comfort with data: you use performance metrics to guide decisions without needing someone else to translate the numbers for you - Ability to work cross-functionally and synthesize input from multiple stakeholders into clear, effective creative - High ownership orientation — you run toward ambiguity, set your own priorities, and follow through Nice to have: - Experience marketing to working adults, non-traditional learners, or frontline / hourly employees - Experience with audio or motion graphics production - Hands-on experience with mixed media production (video, audio, motion graphics) - Familiarity with SMS marketing platforms, email automation tools (e.g., Customer.io), and social scheduling tools Compensation & Details This role begins as a 6-month contract engagement, with the intention to convert to full-time employment based on mutual fit. Compensation during the contract period is competitive and commensurate with experience; we'll share specifics early in the process. Full-time compensation and benefits will be discussed as part of the conversion conversation. 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. WORK AUTHORIZATION Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.