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Posted 4 months ago
Requirements and responsibilities
The OpportunityAs Coursedog's first AI Enablement Lead, you’ll define, operationalize, and scale how artificial intelligence is adopted across the company to drive measurable business impact. Sitting within our newly formed Centralized Operations & Systems team, this role owns end-to-end AI enablement — from enterprise strategy and operating model design to hands-on execution, governance, and adoption. You’ll partner closely with senior leaders, technical teams, and external vendors to translate business needs into scalable AI-powered workflows, tools, and systems.This role is well-suited for a strategic, hands-on professional who thrives at the intersection of technology, systems, and outcomes. You’ll move fluidly between long-term vision and day-to-day execution, building foundational capabilities from scratch while driving real adoption across functions. If you’re energized by being a first-of-its-kind hire, enjoy turning experimentation into durable operating systems, and are motivated by improving how teams work through responsible AI, this is an opportunity to shape a critical capability at company scale.This fully remote role reports to the SVP Of Operations and is open to candidates located anywhere in the continental US.This role offers a competitive base salary ranging from $130,000–$145,000, depending on experience. The position includes a performance-based variable compensation plan, bringing the total on-target earnings to $140,000–$160,000 when goals are met.What You'll DoAI Strategy & Operating ModelDefine and own Coursedog’s enterprise AI strategy, aligned to company priorities and business outcomesBuild and maintain a multi-year roadmap for AI adoption, innovation, and governancePartner with senior leadership to translate business needs into prioritized AI initiatives and secure alignment and buy-inTrack industry trends and emerging technologies to inform strategic direction and investment decisionsExecution, Orchestration & DeliveryBuild and own Coursedog’s AI Central Operating System, connecting agents, data, and workflows to enable cross-functional automation and decision-makingOversee the design, deployment, and scaling of AI applications, agents, and integrations across the organizationEstablish standards for AI integration, data usage, security, and safe use across tools and vendorsLead vendor selection, tool rationalization, experimentation, and scaling of high-impact AI solutionsEnablement, Adoption & Capability BuildingOwn the AI enablement operating rhythm, including roadmap execution, learning content, internal documentation, and feedback loopsBuild AI fluency across the organization through onboarding, workshops, playbooks, and function-specific best practicesLead a cross-functional AI Scrum Team to develop reusable assets, guidance, and support for teamsPartner with functional leaders to embed AI into workflows, KPIs, and operating playbooksMeasurement, Change & CommunicationDefine and track AI adoption, ROI, productivity gains, and business outcomesTranslate complex technical concepts into clear, actionable insights for executives and stakeholdersChampion AI adoption through storytelling, executive briefings, and visible winsMaintain reporting and feedback loops to continuously refine AI priorities and maximize impactWhat You’ll Bring4-6+ years of experience in a fast-paced tech or SaaS environment, including hands-on ownership of cross-functional initiatives2+ years leading AI or advanced technology adoption from experimentation through scaled, production useStrong technical fluency in LLM-based systems (prompts, agents, retrieval patterns, embeddings, vector databases)Experience designing and integrating AI workflows across tools, data platforms, and APIsExperience owning or evolving enterprise AI search solutions (e.g., Glean, Moveworks, Slackbot, Onyx, or similar)Hands-on experience with modern data platforms (e.g., Snowflake, Databricks)Ability to establish AI governance, safe-use policies, and risk controls in partnership with Security and IT, including day-to-day best practices for company-wide AI useProven track record enabling and training non-technical teams and driving adoption at scaleEntrepreneurial, process-oriented mindset with strong communication, judgment, and comfort operating in ambiguityNot sure if you should apply? Research shows that women and people from underrepresented backgrounds are less likely to apply unless they meet every qualification listed. At Coursedog, we’re focused on finding the best person for the role, and that person may come from a non-traditional background. We encourage you to apply even if you don’t meet every requirement — our evaluation focuses on your ability to thrive in this role and make an impact.Working at CoursedogHealthcare, Dental & VisionWe follow a fixed contribution model to promote equity and transparency. Every employee receives the same annual dollar amount to apply toward medical, dental, and vision coverage. This approach gives you the flexibility to choose the plan that best fits your needs, whether that is a base-level option or more comprehensive coverage.Depending on the selected coverage level, the company covers:Employee-only coverage: 65% to 99% of monthly premiumsEmployee plus dependents: 45% to 75% of monthly premiumsWe partner with Aetna and Guardian, and offer access to best-in-class wellness and support programs, including:Spring Health (mental health support)XP Health (vision benefits)Carrot Fertility (family planning support)One Medical (primary care)We also support pre-tax savings through Health Savings Accounts HSA and Flexible Spending Accounts FSA.Retirement PlanningTo support long-term financial health, we offer a Safe Harbor 401(k) plan from day one of employment. Coursedog provides a 4% employer match on your total compensation (subject to federal limits) each pay period for employees contributing to a tax-advantaged retirement account.Paid Time OffWe trust our employees to manage their time responsibly. That’s why we offer an unlimited Paid Time Off policy — because flexibility and balance are critical for sustained excellence and personal well-being.Remote-First Since InceptionWe were built for distributed work. Our culture emphasizes flexibility over rigidity, outcomes over hours, and transparency over gatekeeping. We are committed to being a remote-first organization indefinitely, empowering you to work where and how you thrive best.EquityAs a valued contributor to our collective success, you’ll participate in the upside. All employees are granted equity in the company aligned to your role and tenure. Equity grants are reviewed and adjusted with promotions to reflect your evolving impact.Paid Parental LeaveWe proudly support working parents with industry-leading benefits. Employees are eligible for up to 12 weeks of fully paid leave. This benefit is available to all eligible employees, regardless of gender or family structure.About CoursedogOur mission is to break down barriers to opportunity for students. Coursedog provides higher ed with modern technology solutions – empowering institutions, students, and communities across the globe. Coursedog's founding story is rooted in the desire to help students achieve their highest goals. In 2018, Coursedog's co-founders and then college students, Justin Wenig and Nick Diao, were frustrated by how difficult it was to get into the classes they needed to graduate on time. After speaking with higher education provosts and registrars to better understand how academic scheduling works, they came away with a vision that permeates the company today. Coursedog has raised $113M total capital as a remote-first, hyper-growth startup currently backed by JMI Equity, and with past investments from YC and First Round Capital. We were recently ranked in Forbes top 500 US startup employers and our employee engagement scores rank in the top 5% of tech companies.
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