Manager, Customer Enablement & Learning

Hi Marley • Boston, MA

16h • $84,000 - $157,000 • Hybrid

About The Position

At Hi Marley, we’re not just a technology company—we’re on a mission to revolutionize the insurance industry with our conversational platform that makes communication simple, efficient, and delightful. Built for carriers, powered by SMS, and designed by insurance experts, Hi Marley connects people through seamless, friendly conversations that save time, money, and hassle. Our platform helps insurance carriers strengthen customer relationships while streamlining operations. With a focus on collaboration, coaching, and powerful analytics, we deliver the insights insurance teams need when they need them—creating a smooth, frictionless experience for customers along the way.
As the Manager of Customer Enablement & Learning, you will own and evolve the system that helps customers and internal teams adopt our products with clarity and confidence. You’ll operate at the intersection of execution and strategy by setting direction, building scalable programs, and ensuring every product release, workflow shift, and innovation lands smoothly and drives measurable impact. This is a run-the-engine and build-the-engine role with real opportunity to reinvent it over time. If you're looking for a purely strategic seat, this isn't it yet.
This role is ideal for a high-performing SaaS learning leader who loves getting things done by working with and through other people. Someone who thrives in pace and complexity. Someone who enjoys designing systems and then rolling up their sleeves to make them work. Someone who sees enablement not as content creation, but as a strategic lever for growth. You’ll have real ownership here. This is a role with trajectory and designed for someone who is a high performer today and has the capacity and ambition to grow into broader strategic leadership over the next 2 - 3 years.
If you’re energized by building, motivated by impact, and excited to shape the future of learning and enablement in a company that’s scaling quickly and thoughtfully, we’d love to meet you. Teamwork and shared enthusiasm is a core part of our culture, which is why this role involves joining us in the Boston office for two days each week.

Requirements

• 3 - 5 years experience leading a learning, change management, or education team in a SaaS or product-led environment
• Demonstrated ability to operate in ambiguity and make prioritization decisions with incomplete information
• Fluidity in adapting communication styles to various levels of stakeholders and audiences
• Comfort being deeply hands-on while also setting direction for others
• Strong cross-functional collaboration skills, particularly with Product and Customer-facing teams
• Bias toward action and iteration over perfection
• Familiarity with release-driven enablement or ongoing product change
• Experience building or maturing a learning or enablement function in a growing company
• Openness, practice, and a willingness to embrace the efficiency and effectiveness that AI creates to accelerate value and speed

Responsibilities

• Own the Learning & Enablement Operating Model
• Serve as the single point of accountability for learning prioritization and sequencing decisions
• Make clear prioritization decisions and tradeoffs in partnership with Product, Product Marketing, Customer Deployment & Delivery, and Customer Success
• Establish a sustainable operating rhythm that balances speed, quality, and impact
• Drive Hands-On Execution
• Lead the design and delivery of learning and enablement assets across formats (live, virtual, and self-serve)
• Step in directly to deliver training or unblock work when needed
• Ensure learning and enablement strategies and tactics consistently keeps pace with product updates and customer needs
• Consult with customers and/or CSMs on learning and enablement approaches to successfully build confidence and competence with Hi Marley products and solutions and sustain adoption and engagement over time
• Partner Cross-Functionally
• Collaborate closely with Product, Product Marketing, Customer Success, and Onboarding to align learning to product evolution and customer outcomes
• Serve as the clear decision-maker for enablement-related priorities
• Build Toward Scale
• Identify and implement improvements that increase leverage over time (e.g. clearer learning paths, e-learning, improved documentation structure)
• Balance immediate execution needs with incremental improvements to scalability
• Reduce reliance on reactive, one-off efforts and build towards repeatable and scalable design and development tools
• Shape the Future of Enablement at Hi Marley
• Define and evolve Hi Marley’s multi-year enablement vision as our product portfolio expands
• Reimagine how learning and change management supports adoption of AI-driven and agentic solutions
• Design an enablement model that balances live delivery, scalable content, embedded product guidance, and AI-enabled support
• Serve as a strategic thought partner to senior leadership on how enablement drives adoption, retention, and growth
• Build a roadmap that connects today’s operational execution to tomorrow’s learning and enablement vision
• Lead and Develop the Team
• Provide direction, prioritization, and coaching to members of the Learning & Enablement team
• Create clarity around roles, responsibilities, and expectations
• Define the future needs of the team so that it evolves with the right capabilities and capacity
• Foster a culture of action, growth mindset, and continuous improvement

Benefits

• Equity grants for all employees
• A 4% matching 401(k) program
• Medical, dental, vision, disability, and life insurance coverage for employees working 30+ hours per week
• Monthly wellness stipend
• Paid parental leave
• A flexible vacation policy - we all work hard and take time when we need it

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed