Saas Learning Development Jobs in Massachusetts (NOW HIRING)

M.S. Walker has built our foundation and future on our people – our employees are truly our greatest asset. Our company boasts a diverse pool of exceptionally special team members who each bring their unique skills and experience to the organization. We are always looking for talented individuals to join us and we encourage you to explore our current job postings.

Position:Director of Learning & Development

Location: Norwood, MA

Job Id:235

# of Openings:1

Director of Learning & Development
Location: Norwood, MA (Hybrid)
Department: Human Resources
Reports to: Chief Human Resources Officer (CHRO)
Employment Type: Full-Time | Exempt

Role Overview
The Director of Learning & Development builds and leads M.S. Walker’s L&D function. The core mandate is organizational capability: identifying where the business needs to grow its people, building role-based development and career paths that make employees promotable, strengthening the internal talent pipeline, and equipping the workforce with modern skills — including AI fluency and the adoption of new enterprise systems.
This is a true build role — the strategy, the programs, and the technology are yours to design, with the opportunity to grow a team behind them. The Director establishes the foundation in Year 1 and scales toward an integrated talent system — development, career pathing, leadership growth, and digital enablement — connected directly to business performance. The role reports to the Chief Human Resources Officer and partners closely with function leaders across the business, the broader HR leadership team, and Operations on mandated safety and regulatory training. A flagship Year-1 deliverable is enabling adoption and proficieny of the company’s enterprise systems, including its SaaS ERP.

Key Responsibilities
Build and Lead the L&D Function

• Define and execute an L&D strategy aligned to business priorities, workforce needs, and the company’s multi-year HR roadmap.
• Establish the operating model: program portfolio, intake and prioritization, governance, vendor management, and budget ownership.
• Select and own the learning technology stack, including the decision to leverage the existing Paycor learning module or stand up a dedicated LMS/LXP.
• Build needs-assessment and evaluation discipline that measures development against business outcomes — promotion readiness, retention, and capability — not activity.

Organizational Capability & Needs Identification

• Partner with leaders across corporate functions, sales, and operations to identify capability gaps and translate business strategy into concrete development priorities.
• Design role-based development paths and curricula tied to the skills each function needs now and as the business evolves.
• Establish a repeatable way to surface emerging capability needs and convert them into programs

Career Pathing, Promotability & Internal Talent Development

• Build career frameworks and development paths that make employees promotable and create clear lines of progression across the organization.
• Strengthen the internal talent pipeline and bench for critical roles, in partnership with HR leadership and the business, supporting succession and fill-from-within.
• Partner with HR leadership on the competency model and job architecture underpinning the company’s performance management and compensation work, so that development, career paths, and progression operate as one connected system.

Leadership & Management Development

• Build development programs spanning frontline supervisors through senior leadership, with emphasis on the manager capabilities that drive engagement, performance, and retention.
• Coach and equip leaders to develop their own teams and reinforce learning in the flow of work.

AI & Digital Enablement

• Define how M.S. Walker develops its people for the AI era — building AI literacy and role-based AI enablement across the organization, helping teams adopt new tools to work more effectively, with the change management to make adoption stick.
• Lead enablement for enterprise-system adoption; as a flagship Year-1 project, deliver role-based, process-driven training for the company’s SaaS ERP implementation, partnering with the ERP program team, IT, and affected functions.
• Translate complex systems and tools into practical job aids and learning paths, and sustain enablement through enhancements and new functionality.
• Own New Hire Orientation and role-based onboarding, ensuring a consistent, engaging experience that gets new employees productive and connected quickly.

Safety, Regulatory & Compliance Learning

• Oversee mandated safety and regulatory training for the operational workforce (e.g., OSHA, powered-industrial-truck, DOT/FMCSA, and alcohol-beverage handling), ensuring programs are current, delivered, and auditable.
• Coordinate delivery and recordkeeping with Operations and Safety to meet regulatory, insurance, and workers’ compensation requirements.

Labor Relations Partnership

• Partner with Labor Relations and counsel so training programs are designed consistent with collective bargaining agreements, recognizing where training intersects with compensable time and contract provisions.
• Use apprenticeship and skills-progression programs as development pathways that help represented employees grow and advance.

What Success Looks Like (First 12–24 Months)

• A functioning L&D operating model, technology platform, and governance in place.
• Role-based development and career frameworks live for key corporate, sales, and management populations — with a measurable increase in internal promotion and fill-from-within.
• Identified bench strength and succession readiness for critical roles.
• AI literacy and role-based AI enablement rolled out, with measurable adoption.
• ERP training delivered to support an on-time, high-adoption go-live, measured against the system’s business case.
• Safety and regulatory training current, complete, and auditable as a compliance baseline.
• Improved retention of high-potential talent.

Qualifications
Required

• 7+ years of progressive L&D experience, including building or substantially rebuilding an L&D function.
• Demonstrated experience building role-based development, career-pathing, and leadership/management development programs that move people into broader and more senior roles.
• Experience identifying organizational capability needs and translating business strategy into development plans across multiple functions.
• Experience building or integrating competency models / job architecture that support performance management and talent decisions.
• Experience leading enablement and change management for technology adoption — ideally including AI tools and/or an enterprise-system (ERP or comparable) implementation.
• Strong command of adult learning, instructional design, change management, and evaluation methodology.
• Excellent facilitation, communication, and stakeholder-management skills.

Preferred

• Bachelor’s degree in Human Resources, Organizational Development, or a related field; Master’s preferred.
• Experience in an operations-intensive environment — distribution, wholesale, logistics, or CPG.
• Familiarity overseeing regulated-industry safety and compliance training obligations (e.g., OSHA, DOT).
• Experience operating in a unionized environment.
• Experience standing up or migrating an LMS/LXP.
• Relevant certification (e.g., ATD CPTD/APTD or equivalent).

Location & Travel

• Based at company headquarters in Norwood, MA, with a hybrid work approach
• Occasional travel to regional locations in Rhode Island, New York, and New Hampshire to support cross-functional learning initiatives and gain operational understanding

About M.S. Walker
M.S. Walker is a fifth-generation, family-owned importer, distributor, and bottler of wine and spirits, operating across multiple states with a workforce spanning corporate, sales, and operations teams. As we invest in the continued growth of our people and our business, we are creating a dedicated Learning & Development function — and hiring a Director to build and lead it. This is a rare opportunity to shape an enterprise-wide capability from the ground up, with executive sponsorship and the mandate to do it right.

Benefits:
We offer a Comprehensive Benefits Plan that includes the following:

• Medical & Dental Insurance
• Vision Coverage
• Paid-Time-Off Program
• Fidelity Investments 401k
• Disability, Life, Accident & Illness Insurance Packages
• Discounted Fitness Memberships
• Free & Discounted Work/Life Resources

Mission Statement:
Since 1933, our mission has been firmly rooted in our core values of family, integrity, respect, honesty, and hard work. We are deeply committed to upholding these principles for our team members, customers and suppliers alike. We seek to build and maintain long-lasting relationships based on trust and reliability. By honoring our heritage and embracing innovation, we aim to continuously improve and adapt to meet the evolving needs of our industry, while responsibly contributing to the communities we serve. Together, we strive to elevate the spirit of hospitality and foster a vibrant and respectful culture in all facets of the organization and beyond.

Pay Range: $140,000 - $160,000 annually

M.S. Walker is proud to offer best-in-class benefits to its employees. We offer a variety of flexible plans intended to fit each individual’s circumstances and needs.

• Medical
• Vision
• 401(k) Plan Offered Through Fidelity Investments

• Life Insurance
• Short-term Disability Insurance
• Long-term Disability Insurance
• Critical Illness Insurance

• Weekly On-Site Yoga Classes
• Annual Biometric Health Screenings
• Annual Flu Shot Clinics
• Ongoing Company-Wide Walking & Fitness Challenges

617-776-6700
975 UNIVERSITY AVE.
NORWOOD, MA 02062