Senior Program Manager - Content Ops and Learning Technology

Senior Program Manager, Content Operations & Learning Technology Location: Remote ABOUT TOGETHERWORK Togetherwork is the emerging leader in software and payments for groups and organizations of all kinds — 650+ employees, 33+ products across 9 vertical product groups, primarily remote across the United States. Our mission is to provide communities, groups, and organizations with essential and reliable technology solutions to help them thrive, by combining technical and operational excellence with deep, specific market expertise. We function as one company, not a collection of acquisitions. Our roots are in entrepreneurial companies with deep vertical expertise and loyal customers. Together we expand functionality, improve and scale operations, drive profitability, and help employees realize their full potential. ABOUT THE ROLE Togetherwork is building a Customer Education function from the ground up — and this role is the operational engine that makes it work at scale. As Senior Program Manager, Content Operations & Learning Technology, you will own the systems, platforms, and workflows that sit between content strategy and customer impact. You will manage Togetherwork’s learning management platform (Skilljar), own the content operations infrastructure across 9 product verticals and 33+ products, and build the processes that ensure customer-facing education content is accurate, discoverable, and continuously improving. This is not a content creation role — it is the role that makes content creation scalable, measurable, and connected to business outcomes. You will work closely with the Director of Customer Education, Support leadership, AI Enablement, Kantata and Zendesk platform owners to design and operate the ticket-to-article workflow, govern the help center content ecosystem, and ensure that learning technology is configured to deliver maximum deflection and customer value. WHAT YOU WILL OWN Learning Management Platform (Skilljar) Own day-to-day administration, configuration, and optimization of Skilljar across all product verticals Lead the reconfiguration of Skilljar’s current multi-domain structure into a scalable single-instance architecture Manage the Skilljar vendor relationship, contract, and roadmap in partnership with the Director of Customer Education Design and maintain learner paths, course structures, and content taxonomies within the platform Integrate Skilljar with Zendesk and other support tooling to create a connected help and learning ecosystem Track learner engagement, completion rates, and content utilization — and use that data to drive prioritization decisions AI & Tooling Integration Partner with the AI Enablement & Operations Lead to integrate AI tooling into content creation and content review workflows Own the configuration and utilization of Stylo Scribe — Togetherwork’s AI-assisted article drafting and content gap detection tool — which is currently underutilized within an existing contract Ensure help center content is structured so it can be effectively ingested and surfaced by AI agents and automated response tools Monitor and evaluate emerging content operations tooling and make recommendations for adoption Analytics & Performance Build and maintain dashboards that track content performance, ticket deflection rates, and learner outcomes Establish baseline metrics in the first 90 days and report progress against them on a regular cadence to the Director of Customer Education and Support leadership Identify content gaps using ticket trend data from Zendesk and translate them into prioritized content briefs for the broader team Content Operations & Governance Manage content project tracking and prioritization across 9 verticals and 33+ products, maintaining clear visibility into what’s in progress, what’s blocked, and what’s next — and communicating that status to the Director of Customer Education on a regular cadence Build and operate the ticket-to-article workflow — the process by which high-volume support contacts become self-service knowledge content Own the content governance model: who creates, who reviews, who approves, and how content stays current across 33+ products Establish and maintain content taxonomy and tagging standards across all Zendesk help centers to improve search and AI discoverability Coordinate with product teams to ensure help center content is updated when releases happen — building a proactive release-to-content process Conduct regular content audits to identify outdated, missing, or underperforming articles and route them for update or retirement Partner with Zendesk platform owners to align help center architecture with the broader Zendesk re-implementation effort WHAT YOU BRING Required 7–10+ years of experience in content operations, knowledge management, learning technology administration, or a closely related function Hands-on experience administering an LMS or learning experience platform — Skilljar experience strongly preferred; Thought Industries, Docebo, or similar platforms also relevant Demonstrated ability to manage multiple concurrent workstreams across a complex, multi-product environment — you can hold context across several products and verticals simultaneously without losing track of priorities, dependencies, or stakeholders Demonstrated experience building or managing a ticket-to-knowledge-article workflow or similar content triage process Strong understanding of content taxonomy, metadata, and search optimization within help center or knowledge base environments Experience working within or alongside Zendesk — familiarity with help center structure, article management, and AI integration (Stylo or similar) Comfort working with data: you can pull and interpret content performance and ticket trend data without needing a dedicated analyst Ability to operate independently in an ambiguous, build-from-scratch environment — this function is new and the infrastructure largely doesn’t exist yet Strongly Preferred Experience in a multi-product or multi-vertical SaaS environment Familiarity with AI-assisted content creation tools and workflows Experience working with or alongside support operations teams — you understand how ticket data works and how to use it Background in instructional design, curriculum development, or customer education — even if operations has been your primary focus THE TECHNOLOGY ECOSYSTEM YOU’LL WORK IN Platform How It Fits Skilljar Primary LMS — you own it Zendesk Help center infrastructure across all verticals — your primary audit and publishing surface Stylo (Assist, Solve, Scribe) AI layer on top of Zendesk — Scribe specifically is your content drafting and gap detection tool Claude / ChatGPT Enterprise Approved AI tools for content creation workflows Confluence Internal knowledge base — source material for content migration and article drafting Jira Product release tracking — input for content update triggers Microsoft Teams + Copilot Daily collaboration and meeting AI BENEFITS Medical, dental, and vision insurance options 100% Employer paid short/long term disability 100% employer-paid Basic Life and AD&D insurance 401(k) retirement plan with a 100% company match up to 4% Flexible paid personal/vacation time built on mutual trust and accountability 10 sick days annually 10 company paid holidays 12 weeks paid parental leave INCLUSION & DIVERSITY Togetherwork is an Equal Employment Opportunity Employer. We value diverse backgrounds, experiences, and perspectives. Employment decisions are made without regard to race, color, religion, gender, gender identity, sexual orientation, disability, veteran status, age, national origin, or any other protected category under applicable law. WHY TOGETHERWORK Togetherwork serves tens of thousands of organizations across the country — associations, camps, pet businesses, youth programs, faith communities, and more — with software and payments that help them run better. We are growing through acquisition and organic expansion, and our customer base is maturing alongside our product portfolio. This role sits at the center of the customer experience. You will have real ownership, real cross-functional visibility, and the infrastructure to do the work well. The Director of Customer Education has a mandate to build a best-in-class education and knowledge organization — and this role is foundational to that vision. If you believe that great content infrastructure is a competitive advantage and want to build something that actually helps customers succeed — this is the role. Interview Process & Expectations Our interviews are designed to be interactive and conversational. Candidates are expected to respond based on their own experience and thinking during live interviews. To ensure a fair and consistent interview experience, the use of real-time AI tools or other external assistance to generate or guide interview responses is not permitted. Interviews are intended to reflect an individual's judgment, problem-solving approach, and communication. CCPA Disclosure Notice: Click Here