Director of Learning

Swooped; United States; On-site; USD 130,000 - 145,000; Full time

Job summary

Swooped in the United States is seeking a Director, Learning to lead the organization's Learning function, overseeing strategy, content creation, client certification, and learning operations while partnering with Product and Marketing.

Reporting directly to the Chief Operating Officer, this role will shape onboarding, client certification processes, and release planning, with responsibilities spanning budget management and performance reporting to improve client outcomes.

Qualifications

• 5+ years in learning, enablement, or technical training
• 3+ years directly leading and managing a team
• Experience managing documentation and LMS estates at scale
• Experience partnering with Product or Engineering teams
• Hands-on technical capability to inspect product behavior

Responsibilities

• Define and execute comprehensive learning strategies from onboarding to client certification
• Lead, mentor, and manage the Learning team, including consultants and learning operations specialists
• Participate in release planning with Product and Marketing to coordinate content updates
• Oversee the lifecycle of client-specific learning environments and the proprietary online learning portal
• Manage the Learning department budget
• Develop and maintain reporting and scorecards linking learning engagement to client outcomes
• Collaborate cross-functionally to evaluate training impact and address operational challenges

Skills

Leadership experience

LMS management

Cross-functional collaboration

Content development

Product/Engineering partnering

Job description

The Director, Learning will lead the organization's

Learning function, serving both external clients and

internal teams across product lines. Reporting directly to

the Chief Operating Officer, this role oversees learning

strategy, content creation, client certification, and

learning operations while collaborating directly with

Product and Marketing peers in release planning.

Key Responsibilities

• Define and execute comprehensive learning strategies, from internal team onboarding through client certification.
• Lead, mentor, and manage the Learning team, including a consultants, and learning operations specialists.
• Participate in release planning alongside Product and Marketing leadership to coordinate content updates across the knowledge base, client portals, and vignette library.
• Oversee the lifecycle of client-specific learning environments and the proprietary online learning portal from build through retirement.
• Manage the Learning department budget.
• Develop and maintain reporting and scorecards that connect learning engagement metrics directly to client.
• Collaborate cross-functionally with Product, Engineering, Client Success, and Client Support to evaluate training impact and address operational challenges proactively.

Required Qualifications

• 5+ years of experience in learning, enablement, or technical training.
• 3+ years of experience directly leading and managing a team.
• Demonstrated experience managing documentation and learning management system (LMS) estates at scale.
• Experience partnering with Product or Engineering teams
• Hands-on technical capability to independently inspect product behavior, such as reviewing environments and permission sets prior to developing content.

Preferred Qualifications

• Experience in B2B SaaS, especially within fast-paced release cycles.
• Familiarity with the Salesforce ecosystem and terminology.
• Experience in financial services or wealthtech, or a demonstrated aptitude for rapidly learning specialist industry terminology.
• Experience utilizing AI-assisted tools in content development.

Role Details, Compensation, and Benefits

• Base Salary: $130,000 to $145,000
• Travel: Attendance at semi-annual company summits
• Benefits: Paid time off, including sick and volunteer leave, and a professional development stipend

Notices

The organization is an equal opportunity employer and all

qualified applicants will receive consideration for

employment without regard to race, color, religion, sex,

sexual orientation, gender identity or expression,

pregnancy, age, national origin, disability status,

genetic information, protected veteran status, or any

other characteristic protected by law.

Portions of the recruitment process may involve the use of

AI-assisted tools to help review applications and match

candidates to job requirements. All final hiring decisions

are made by human recruitment personnel, ensuring fair and

thoughtful consideration for every applicant.