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.
What You’ll Do:
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
What We’re Looking For:
- 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
Compensation, Benefits & Perks:
At Hi Marley, we are committed to fair and transparent pay practices. The annual base salary for this role is expected to fall within the range of $84,000-$157,000, depending on experience, skills, qualifications, and location. Offers are determined based on these factors as well as internal peer equity. It’s most common for new hires to start near the midpoint of the range, allowing room for growth as employees develop in their role. In addition to base pay, this role includes a variable compensation component. Total earnings will vary based on individual and/or team performance.
- 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
At Hi Marley, our culture is built on three core values that every employee embodies:
- Max Courage – We encourage our team, our customers, and their customers to dream big, try new ideas, and maximize impact by measuring risk.
- Be Humble – We lead with appreciation and promote a culture of humility, compassion, and openness to learn from anyone, anywhere.
- Ubuntu (“I am because we are”) – We believe true success is much bigger than any single individual or company. By aligning our individual aims behind a shared purpose, we can achieve our fullest potential — together.
- A fun, lively startup culture that embraces creativity and innovation
- Core values-based leadership that guides our decision-making and daily interactions
- A culture of engagement, diversity, inclusion, and belonging — everyone’s voice matters
- Flexible, hybrid work environment that values balance and trust
- Ample opportunities to learn, take on new challenges, and make an impact in a fast-growing organization
- Meaningful work that directly supports our mission to help people and organizations communicate with empathy and clarity
Hi Marley is proud to be an equal employment opportunity employer. We celebrate diversity and do not discriminate based on gender, sexual orientation, gender identity, religion, race, veteran status, disability status, or any other characteristic protected by applicable law. We are committed to building an inclusive work environment representing a variety of backgrounds, perspectives, and skills, where all employees are encouraged to be their authentic selves.
Hi Marley participates in E-Verify and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S. For more information, please review the documents under "E-Verify Poster" here: https://e-verify.uscis.gov/web/OnlineResources.aspx
Hi Marley Boston, Massachusetts, USA Office
10 Post Office Square, Boston, MA, United States, 02109
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