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US Canada Unlimited PTO

  • Architect GitLab's AI-native learning ecosystem, including adaptive learning paths, coaching agents, and automated content workflows.
  • Lead the company-wide AI fluency and enablement strategy in partnership with the Enterprise AI team.
  • Own the multi-year learning platform strategy and roadmap, driving operational excellence across the Talent Management & Development team.

AI Enablement Program Management Instructional Design Vendor Management

20 jobs similar to Lead, Learning Architecture & AI Enablement

Jobs ranked by similarity.

US

  • Shape Degreed's learning experiences, from self-paced pathways to structured, cohort-based programs.
  • Own the full data model behind Degreed's skills product: how skills are defined, organized, and kept accurate.
  • Design the full learner journey: how someone finds a skill gap, engages with content, and demonstrates they have closed it.

We are the leading enterprise learning system for workforce transformation, bringing together everything people need to learn and advance. Named to Fast Company's World's Most Innovative Companies of 2026, we foster a culture of learning, collaboration, and growth.

US Unlimited PTO

  • Design and implement leadership development programs to cultivate talent across the organization.
  • Collaborate with cross-functional teams to identify skill gaps and create tailored learning experiences.
  • Measure program effectiveness through data analysis and feedback to ensure continuous improvement.

GitLab provides an intelligent orchestration platform for DevSecOps, enabling organizations to increase developer productivity, improve operational efficiency, and reduce security and compliance risk. Trusted by over 50 million users and more than 50% of the Fortune 100, GitLab fosters a high-performance culture driven by AI integration and continuous knowledge exchange.

US

  • Lead, coach, and grow a team of Learning Experience Designers and Content Developers, setting clear goals and development plans.
  • Develop end-to-end execution plans for learning experiences, ensuring programs are engaging, scalable, and tied to measurable outcomes.
  • Partner with sales leadership and subject matter experts to translate skill gaps into structured curricula and establish standards for instructional design.

Samsara (NYSE: IOT) is the pioneer of the Connected Operations Cloud, enabling organizations that depend on physical operations to harness IoT data for actionable insights. The company helps improve safety, efficiency, and sustainability across industries like agriculture, construction, and transportation, and is a publicly traded company with a culture encouraging rapid career development and hyper-growth.

US 4w PTO

  • End-to-end ownership of product milestones, revenue targets, and customer impact for the individual learning pod.
  • Translate company vision into product roadmap, define problems with design thinking, and drive AI-native operating model.
  • Lead voice of customer programs, own commercial outcomes, and communicate clear narratives to senior leadership.

Continued is an EdTech leader empowering professionals through online learning. The company is medium-sized with a 100% virtual team, and its culture is driven by curiosity, love of learning, and solving complex problems.

$126,100–$210,100/yr
US

  • Design scalable learning experiences using adult learning principles and instructional design best practices for internal GTM teams.
  • Translate complex technical concepts into clear enablement content integrating AI, automation, and workflow optimization.
  • Collaborate cross-functionally to identify skill gaps and improve learning effectiveness through data and feedback.

Our partner is a technology company focused on AI-driven workflow innovation and learning solutions for Go-To-Market teams. They foster an inclusive culture centered on learning, innovation, and career growth in a remote-first environment.

Canada

  • Serve as primary technical and delivery leader, transforming enterprise requirements into production-grade agentic AI solutions.
  • Lead customer discovery and solution design, owning the complete deployment lifecycle from kickoff to production launch.
  • Partner with cross-functional teams and stakeholders to ensure scalable, high-quality deployments with measurable business outcomes.

Netomi is a leading agentic AI platform for enterprise customer experience, working with global brands like Delta Airlines, MetLife, and United. Backed by WndrCo, Y Combinator, and Index Ventures, the company helps enterprises drive efficiency and higher quality customer experiences.

Global

  • Own an AI-native product end-to-end, from customer discovery to shipping weekly iterations.
  • Drive growth, activation, conversion, and monetization metrics while building alongside your team.
  • Prototype with AI tools and fix your own interface instead of filing tickets.

airSlate is a global SaaS technology company that develops no-code workflow automation, electronic signature, and document management solutions. With hundreds of millions of users and over one million customers worldwide, the company has teammates in more than 20 countries across three continents and fosters a culture of growth and innovation.

Canada

  • Own end-to-end AI system layer across product and platform.
  • Drive shift from AI-powered features to AI-powered business operations.
  • Lead ~30 engineers across 4-6 teams to build intelligent workflows.

Jobber helps small home service businesses like plumbers and landscapers manage their operations through technology. With over 250,000 businesses on the platform, Jobber fosters a supportive, diverse culture focused on impact.

Europe Unlimited PTO

  • Lead AI enablement for business teams end-to-end: assess, conduct workshops, and track adoption KPIs.
  • Work with champions and stakeholders to drive change management and ensure sustained AI usage.
  • Deliver workshops personally and facilitate sessions with external trainers to produce concrete outcomes.

Neurons Lab is an AI consultancy that runs enterprise AI adoption programs for major clients. It is a fast-growing consultancy with a focus on enabling business teams to use AI effectively.

$199,100–$348,400/yr
North America Canada Unlimited PTO

  • Drive large-scale, cross-functional new product development programs for APEX Strategic Initiatives, translating business objectives into execution strategy.
  • Develop trusted relationships with stakeholders and functional leaders to ensure program delivery and accountability.
  • Operate as an AI-native program manager, using AI tools to synthesize intelligence, surface risks, and provide actionable insights.

ServiceNow is the AI control tower for business reinvention, enabling 85% of the Fortune 500 to work smarter, faster, and better. The company fosters an AI-native culture where technology and talent work together, and is building a large, collaborative team focused on innovation.

US Canada

  • Own the roadmap and execution for customer workflow products, driving AI-native development and cross-functional collaboration.
  • Define product requirements and success metrics while conducting continuous customer research to validate decisions.
  • Partner with engineering and analytics teams on technical decisions, scalability, and integration strategies.

Jobgether is an AI-powered job matching platform that connects candidates with hiring companies through objective skill-based reviews. It is a growing technology company focused on transforming employment access, with a culture emphasizing curiosity, ownership, and collaboration.

$300,000–$450,000/yr
Global

  • Own technical delivery across 1-2 enterprise accounts, setting direction and managing risk.
  • Build reusable Tribe IP from client work, including architecture patterns and deployment playbooks.
  • Act as senior technical partner for C-suite stakeholders, translating business problems into architectural decisions.

Tribe embeds senior AI engineers and technical leaders directly into enterprise clients to drive AI transformation that actually ships. We're a team of operators who build alongside clients, own outcomes, and leave behind systems that endure, growing rapidly as the fastest-growing role in tech.

$140,000–$170,000/yr
Canada US

  • Own product strategy, roadmap, and delivery for the talent portal, AI Coach, Career Passport, and job matching surfaces.
  • Work AI-natively using agents and LLM tooling to compress the cycle from customer problem to working prototype.
  • Partner cross-functionally with engineering, data, customer success, and GTM to ensure the job seeker perspective drives every decision.

FutureFit AI uses an AI-powered platform to help job seekers, especially those facing barriers, get to better jobs faster and cheaper. The company has 30-50 employees across the US and Canada, with hubs in NYC and Toronto, and a culture of high velocity, high trust, and meaningful impact.

Canada US Unlimited PTO

  • Define the multi-horizon roadmap for GitLab's data analytics and insights platform, balancing immediate customer needs with long-term platform investment and setting clear success measures.
  • Partner with engineering leaders to shape core platform capabilities, including data pipelines, storage, and APIs, that support analytics experiences across GitLab.
  • Design a tiered analytics experience that meets customers where they are: conversational AI discovery, out-of-the-box dashboards, and custom dashboard creation.

GitLab is the intelligent orchestration platform for DevSecOps, enabling organizations to increase developer productivity and improve operational efficiency. With over 50 million registered users and more than 50% of the Fortune 100 trusting GitLab, the company fosters a high-performance culture driven by values and continuous knowledge exchange, embracing AI as a core productivity multiplier.

Pakistan

  • Lead a cross-functional engineering team to drive technical direction and deliver a cloud-based learning and compliance platform.
  • Evaluate and implement AI-powered capabilities including LLM features and intelligent automation.
  • Design scalable, secure, and observable cloud-native solutions while mentoring engineers and promoting engineering excellence.

Smart Working connects skilled professionals with global teams for full-time, long-term remote roles. It is a highly-rated workplace on Glassdoor that values community, growth, and well-being in a fully remote-first environment.

US

  • Lead AI strategy, standards, and governance for responsible enterprise adoption.
  • Partner with business leaders to identify and deliver high-value AI automation solutions.
  • Establish reusable patterns and best practices for scalable AI deployment.

FormFactor provides essential test and measurement technologies for the semiconductor product life cycle. The company serves customers globally and fosters an environment where diverse perspectives are celebrated and contributions matter.

$150,000–$180,000/yr
US Unlimited PTO

  • Build and operationalize the company's first formal sales enablement program, including scalable onboarding, certification frameworks, and AI-supported training systems.
  • Develop curricula that turn generalist AEs into construction experts through persona guides, discovery questions, objection libraries, and AI role-play.
  • Partner with sales leadership, product marketing, and cross-functional teams to embed enterprise methodology and maintain playbooks across the customer lifecycle.

Doxel brings computer vision and AI to construction, giving teams real-time visibility into progress, risk, and execution. Backed by Insight Partners and Andreessen Horowitz, the company has a rapidly growing team of engineers, scientists, construction veterans, and Enterprise go-to-market professionals.

US Unlimited PTO 12w maternity 12w paternity

  • Own the product end-to-end, setting the vision and roadmap, and driving the human-to-AI progression across a multi-stage workflow.
  • Coordinate a broad cross-functional surface across engineering, design, data, and platform partners to keep a small, high-velocity core team unblocked.
  • Own go-to-market for early cohorts alongside sales and customer engagement, sharpening the value proposition and protecting the business model.

Upwork Inc. connects businesses with global, AI-enabled talent across every contingent work type, including freelance, fractional, and payrolled. The company has facilitated over $30 billion in total transactions and fosters a culture of trust, risk-taking, customer focus, and excellence.

US

  • Serve as primary technical advisor to customers, leading discovery sessions and translating business priorities into AI-enabled solutions.
  • Lead cross-functional engineering teams to design and deploy secure, scalable, and high-performing AI software systems.
  • Mentor engineers, establish engineering standards, and drive delivery of enterprise-scale AI solutions.

LTS delivers AI-powered software solutions for complex business and mission challenges. The company values innovation, growth, collaboration, and quality, and offers a culture that rewards ambition and performance.

US

  • Lead the strategy and execution of AI-enabled SDLC automation across large-scale engineering teams.
  • Build AI-assisted workflows including agents, copilots, and automation integrated into CI/CD pipelines.
  • Establish governance frameworks for responsible AI use and drive cross-organizational adoption.

US Security & IT is a technology-focused organization dedicated to secure and efficient IT operations. They foster an inclusive, collaborative engineering culture with a focus on innovation and continuous improvement.