Fast Facts
Join Coursedog as the first AI Enablement Lead to define and scale artificial intelligence adoption across the company, driving measurable business impact and operational excellence in a fully remote position.
Responsibilities: Define the AI strategy and operating model, oversee execution and scaling of AI applications, build AI fluency across the organization, and track AI adoption and ROI.
Skills: Experience in AI adoption, technical fluency in LLM-based systems, data platforms, and strong communication skills are essential.
Qualifications: 4-6 years in a tech or SaaS environment, with 2+ years leading AI initiatives and a proven track record in cross-functional team enablement.
Location: Remote, open to candidates located anywhere in the continental US
Compensation: $130000 - $160000 / Annually
AI Enablement Lead
Department: Finance, Legal, & People
Employment Type: Full Time
Location: Remote
Compensation: $130,000 - $160,000 / year
Description
The Opportunity
As 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 (OTE) to $140,000–$160,000 when goals are met.
What You'll Do:
AI Strategy & Operating Model
- Define and own Coursedog’s enterprise AI strategy, aligned to company priorities and business outcomes
- Build and maintain a multi-year roadmap for AI adoption, innovation, and governance
- Partner with senior leadership to translate business needs into prioritized AI initiatives and secure alignment and buy-in
- Track industry trends and emerging technologies to inform strategic direction and investment decisions
Execution, Orchestration & Delivery
- Build and own Coursedog’s AI Central Operating System, connecting agents, data, and workflows to enable cross-functional automation and decision-making
- Oversee the design, deployment, and scaling of AI applications, agents, and integrations across the organization
- Establish standards for AI integration, data usage, security, and safe use across tools and vendors
- Lead vendor selection, tool rationalization, experimentation, and scaling of high-impact AI solutions
Enablement, Adoption & Capability Building
- Own the AI enablement operating rhythm, including roadmap execution, learning content, internal documentation, and feedback loops
- Build AI fluency across the organization through onboarding, workshops, playbooks, and function-specific best practices
- Lead a cross-functional AI Scrum Team to develop reusable assets, guidance, and support for teams
- Partner with functional leaders to embed AI into workflows, KPIs, and operating playbooks
Measurement, Change & Communication
- Define and track AI adoption, ROI, productivity gains, and business outcomes
- Translate complex technical concepts into clear, actionable insights for executives and stakeholders
- Champion AI adoption through storytelling, executive briefings, and visible wins
- Maintain reporting and feedback loops to continuously refine AI priorities and maximize impact
What You’ll Bring
- 4-6+ years of experience in a fast-paced tech or SaaS environment, including hands-on ownership of cross-functional initiatives.
- 2+ years leading AI or advanced technology adoption from experimentation through scaled, production use.
- Strong technical fluency in LLM-based systems (prompts, agents, retrieval patterns, embeddings, vector databases).
- Experience designing and integrating AI workflows across tools, data platforms, and APIs.
- Experience 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 use.
- Proven track record enabling and training non-technical teams and driving adoption at scale.
- Entrepreneurial, process-oriented mindset with strong communication, judgment, and comfort operating in ambiguity.
Not 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 Coursedog
Healthcare, Dental & Vision
We 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 premiums
- Employee plus dependents: 45% to 75% of monthly premiums
We 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).
To 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.
We 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.
We 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.
As 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.
We 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.
