Learning Specialist - Property Management

Location: Foster City

Learning Specialist – Property Management

Reporting to the Director of Talent Development, with a strong matrixed partnership to functional leadership, this Learning Specialist is embedded within a specific business function to build its capability from the ground up. For this role, that function is Property Management. The Specialist owns this function’s Academy end-to-end, maintains close, current knowledge of their operations, policies, and procedures, and delivers training on-site and in the field as needed. While the primary focus is uplifting capability within Property Management, this role also flexes to support other L&D programs as capacity allows.

Responsibilities:

Academy Ownership:

• Own and continuously evolve the Property Management Academy, including its multi-level curriculum, learning pathways, and progression structure from new hire through experienced practitioner.
• Design, update, and deliver Academy content using adult learning principles, ensuring alignment with property management roles, career pathways, and certification requirements.
• Establish and manage an annual Academy calendar and cadence in partnership with functional leadership and the Director of Talent Development; track participation, completion, and outcomes, and report on business performance impact.

Functional Needs Assessment & Stakeholder Partnership:

• Maintain current knowledge of Property Management's operations, priorities, organizational structure, and performance metrics to proactively identify capability gaps.
• Serve as the primary L&D point of contact, building trusted relationships across the function and conducting targeted needs assessments through site visits, interviews, performance data, and incident/complaint trends.
• Translate business priorities and identified training needs into a prioritized, business-aligned learning roadmap in partnership with the Director of Talent Development.

Training Delivery & Facilitation:

• Facilitate regular instructor-led and virtual training sessions, up to five days per week, covering onboarding, professional skills, leadership, technical, and compliance topics.
• Deliver consistent, engaging learning experiences using adult learning principles and active learning techniques across in-person and virtual platforms (Zoom, Microsoft Teams), adapting delivery style, pacing, and examples to a diverse, distributed workforce.
• Manage classroom and virtual session logistics in partnership with the Learning Administrator, including materials, technology setup, and participant engagement.

Policy, Procedure & Compliance Training:

• Design and deliver training on Property Management policies, procedures, and regulatory requirements, including fair housing, affordable housing compliance, and safety standards, in collaboration with functional partners (e.g., Compliance, Property Management leadership).
• Keep training content current as policies, procedures, and regulations change, and proactively flag needed updates.
• Ensure Property Management training initiatives meet applicable regulatory and organizational requirements.

In-Field Training & Coaching:

• Travel regularly to MidPen properties to deliver in-field, hands-on training and coaching for property management and site teams.
• Observe on-site interactions and workflows, providing actionable, in-the-moment feedback to reinforce best practices and consistent execution; support site teams through onboarding, transitions, and performance challenges with tailored coaching.
• Build and coach a network of on-site subject matter experts and peer trainers to promote consistent practices across locations.

Enterprise Program Support & Collaboration:

• Deliver or co-facilitate enterprise-wide L&D programs as needed (e.g., New Employee Orientation, leadership development, and professional skills), balancing capacity with Property Management priorities.
• Collaborate with the Senior Learning Specialist, Learning Specialist, and Learning Administrator to share content, tools, and delivery support across the L&D team while representing Property Management's learning needs in enterprise talent development strategy and roadmap discussions.

Evaluation, Reporting & Continuous Improvement:

• Design, conduct, and evaluate post-instruction outcomes using methods beyond Kirkpatrick’s Level 1, connecting learning outcomes to business performance metrics.
• Synthesize and communicate insights, progress, and Academy outcomes to functional leadership and the Director of Talent Development, recommending evidence-based adjustments.
• Maintain accurate Learning Management System records and tracking tools in partnership with the Learning Administrator; stay current on industry trends and translate best practices into pragmatic MidPen solutions.
• Perform other duties as assigned.

Qualifications:

To perform this job successfully, an individual must be able to perform each essential function satisfactorily. The requirements listed below are representative of the education, knowledge, skill, and/or ability required. 

Education and Experience

• Bachelor's degree in Education, Human Resources, Communication, Organizational Development, or a related field, with a minimum of 2 years of experience in training facilitation or delivery, or an equivalent combination of education and relevant work experience.
• Experience in property management, affordable housing, or a related operational field is strongly preferred.

Knowledge, Skills, and Abilities

• Strong facilitation and presentation skills, with the ability to lead groups of varying sizes in person and virtually with consistency, energy, and professionalism.
• Strong understanding of instructional design methodology and adult learning principles, with the ability to develop structured, multi-level curricula.
• Demonstrated ability to quickly build deep working knowledge of business operations, policies, and procedures.
• Ability to analyze performance and training data to identify capability gaps and measure program impact.
• Strong consulting, relationship-building, and interpersonal skills, with the ability to partner with operational leaders at all levels and engage diverse audiences and learning styles.
• Proficiency with virtual meeting and training technologies, including Zoom, Microsoft Teams, polling, and breakout tools.
• Familiarity with Learning Management Systems and instructional design principles.
• Highly organized and reliable, with the ability to manage multiple training schedules, sessions, and locations.
• Ability to receive and apply feedback quickly to continuously improve training delivery and quality.
• Excellent written and verbal English communication skills.
• Valid California driver's license, reliable transportation, and proof of current auto insurance, required for regular property travel.

Physical Requirements 

• Constantly perform desk-based computer tasks 
• Frequently sitting 
• Frequently stand/walk
• Occasionally reach/work above shoulders, grasp lightly/fine manipulation, grasp forcefully, use a telephone, sort/file paperwork or parts, lift/carry/push/pull objects that weigh up to 15 pounds 
• Rarely twist/bend/stoop/squat, kneel/crawl 
• This description reflects management’s assignment of essential functions, it does not proscribe or restrict the tasks that may be assigned.

Pay Range

$77,600.00 - $87,300.00 - Annual Salary - Pay based on applicable experience and qualifications

Bilingual in English and Spanish preferred