Entitlements Manager Jobs in Spring Hill, FL (NOW HIRING)

The Land Trainer plays a critical role in building the capabilities, readiness, and performance of Stanley Martin’s Land teams by delivering practical, field-connected learning experiences across Land Acquisition, Entitlement, and Development.

This role is ideal for a high-performing land professional who brings deep expertise in at least one land discipline and is passionate about helping others grow.  Working closely with Land leaders, subject matter experts (SMEs), and Learning & Development instructional designers, the Land Trainer translates real-world experiences into impactful learning, coaching, and development solutions that accelerate onboarding, strengthen technical expertise, and promote consistent execution of the Stanley Martin Way.

The role requires the ability to travel up to 25% to support division, field, and project-based learning initiatives.

Responsibilities and Duties

Subject Matter Knowledge & Business Partnership

• Serve as a primary subject matter contributor in at least one land discipline (Acquisition, Entitlement, or Development) while developing a working knowledge of related disciplines to support cross-functional learning and collaboration
• Partner with Land leaders, division teams, and Team & Culture to identify capability needs, training priorities, and opportunities to improve onboarding, development, and performance
• Build and maintain strong relationships with SME’s across the organization to ensure learning content reflects current business practices, market realities, and operational excellence 

Curriculum Development & Learning Administration

• Partner with Learning & Development instructional designers to translate complex operational and technical land concepts into engaging, practical learning solutions
• Contribute field expertise and real-world examples to the creation of learning materials, including instructor-led programs, case studies, simulations, virtual learning solutions, job aids, and performance support resources
• Lead onboarding programs that accelerate readiness and effectiveness for new Land team members
• Contribute to the development of role-based learning paths that build capability over time for new, emerging, and experienced Land professionals
• Maintain training content that reflects evolving processes, market conditions, and company standards while reinforcing consistent application of the Stanley Martin Way and recognizing appropriate local market nuances
• Coordinate and manage training operations, including classroom and virtual session logistics, learner communications, enrollment tracking, learning system administration, training material production, and participation support to ensure a high-quality and engaging learning experience from registration through completion

Facilitation & Field Coaching

• Deliver engaging learning experiences through classroom, virtual, and field-based instruction, leveraging real projects, case studies, guided discussions, and problem-solving activities that promote knowledge retention and practical application
• Provide ongoing coaching, mentoring, and field support to help team members successfully apply learning on the job and build proficiency in core land processes, including prospecting, feasibility analysis, budgeting, scheduling, due diligence, contracting and negotiations, Land Investment Committee presentations, and project coordination
• Facilitate ongoing development opportunities that strengthen technical expertise, professional effectiveness, and the core competencies required for success within Land roles
• Reinforce learning through observation, feedback, and in-the-field coaching to support consistent execution and continuous improvement across the Land organization

Continuous Improvement & Learning Effectiveness

• Leverage learner feedback, stakeholder input, training metrics, and relevant business performance data to evaluate learning effectiveness and continuously improve L&Ds programs across the Land organization
• Identify trends, skill gaps, and development opportunities through data analysis and field observations, and collaborate with Land leaders and Team & Culture to implement targeted learning solutions

• Working knowledge of land acquisition, entitlement, and/or development operations
• Track record of building credibility and trust with Land teams, division leadership, Team & Culture, and cross-functional partners
• Capacity to manage multiple priorities, training initiatives, and stakeholder needs with strong attention to detail
• Collaborative approach to partnering across functions to support learning and business outcomes
• Skills in translating complex land, financial, and operational concepts into clear, practical learning for a variety of audiences
• Experience contributing to the design and continuous improvement of training programs, materials, and learning experiences
• Expertise in facilitation, presentation, and coaching across classroom, virtual, and field-based environments
• Self-motivated work style with strong accountability and the ability to work independently while maintaining proactive communication
• Proficient with Microsoft Office, Teams, Excel, Copilot, and common project or training tools
• Familiarity with land and project management systems (e.g., Smartsheet, PlanSwift, LandVision)
• Willingness to travel up to 25% to support training, coaching, and field engagement

• 5+ years of Land Acquisition, Land Entitlement, Land Development, or related real estate, homebuilding, project management, or related subject matter experience
• Strong professionalism, sound judgment, and ability to represent Stanley Martin Homes in alignment with company values and standards
• Ability and willingness to travel to divisional offices, active communities, and project sites as needed to support training and field engagement
• Demonstrated knowledge of the land lifecycle, including elements such as site evaluation, prospecting, due diligence, feasibility analysis, budgeting, contracts, project scheduling, field execution, and/or closeout activities (preferred)
• Exposure to or experience across multiple stages of land process (preferred)
• Experience coaching, mentoring, or supporting the development of others in a professional or field-based environment (preferred)
• Working knowledge of financial and project-related tools and concepts, such as pro formas, acquisition tracking, budgets, schedules, contractor documentation, or land-related systems (preferred)
• Familiarity with field coordination and development execution, including integration with plans, municipal requirements, inspections, and project closeout processes (preferred)