Vice President, Strategic Planning & Initiatives

The VP, Strategic Planning and Initiatives occupies a unique position in the division's leadership structure. The role sits within the President's office and operates with delegated authority in defined domains. It is not a line of leadership role — it does not hold formal supervisory authority over the President's direct reports — but it is expected to function as a peer to that group in terms of organizational weight, credibility, and access. 

The role handles matter of significant sensitivity, including confidential personnel and organizational issues, cross-divisional political dynamics, and matters with board or enterprise-level exposure. Absolute discretion, sound judgment, and the ability to navigate complexity with composure are non-negotiable requirements. 

The VP, Strategic Planning and Initiatives will have two direct reports: the Senior Executive Administrator, responsible for the President’s calendar management, travel, expenses, task management, meeting prep, and other administrative responsibilities; and Program and Resource Fellow, responsible for providing project support.  

Key Responsibilities 

1. Executive Advisory and Decision Support 

• Serve as a trusted thought partner and sounding board to the President on strategic, organizational, and operational matters. 

• Prepare the President for key meetings, decisions, and engagements — synthesizing information, anticipating questions, and surfacing relevant considerations. 

• Track decisions, commitments, and follow-through across the leadership team; flag risks or gaps before they become problems. 

• Manage the flow of information to and from the President's office, ensuring timely, accurate, and actionable communication. 

2. Strategic Planning — Facilitation to Ownership  

This responsibility could evolve over time as the VP, Strategic Planning and Initiatives builds organizational relationships and demonstrates effectiveness. 

• Year 1 — Facilitate and support: Coordinates and manages the strategic planning process under the President's close direction; ensures the process runs effectively, structures inputs from the leadership team, and produces clear documentation of priorities, goals, and accountabilities. 

• Year 2 — Lead with oversight: Takes ownership of the planning process design and facilitation; drives timelines and deliverables; brings recommendations to the President for review and approval; manages leadership team engagement throughout. 

• Year 3 and beyond — Own: Holds full accountability for the strategic planning process; translates the President's vision into a structured, actionable, multi-year plan; leads execution tracking and mid-cycle adjustments. 

3. Operating Rhythm and Leadership Team Effectiveness 

• Design and manage the division's operating calendar, including leadership team meetings, planning cycles, performance reviews, and key governance touchpoints. 

• Ensure leadership team meetings are well-structured, purposeful, and outcome-oriented — preparing agendas, managing pre-reads, facilitating follow-through decisions. 

• Monitor the effectiveness of cross-functional collaboration; identify and address breakdowns in coordination, communication, or accountability. 

• Serve as a trusted coordinator among the President's direct reports — managing alignment and operating rhythm without directing or superseding their authority. 

4. Strategic Initiative Oversight 

• Lead or co-lead cross-functional initiatives on behalf of the President, carrying full accountability for scope, timeline, and outcomes — not merely visibility and monitoring. 

• Coordinate the work of multiple leaders and teams on high-priority projects; remove obstacles, resolve ambiguity, and escalate risks appropriately. 

• Ensure the President has accurate, timely visibility into the status of strategic initiatives and that leaders are meeting their commitments. 

• Building off the Division’s annual planning and the implementation of Enterprise’s Strategic Framework, and in coordination with the VP of Business Operations, develop a process for elevating initiatives and opportunities for investment by the Resource Allocation Framework.  

5. Organizational Health and Culture 

• Serve as an early-warning system for organizational risk — monitoring team dynamics, morale, and cultural health across the division. 

• Identify emerging tensions, trust deficits, or dysfunction within the leadership team or broader division and surface them to the President with recommended responses. 

• Support the design and execution of culture-building initiatives; ensure organizational values are reflected in internal practices and operating norms. 

• Oversee implementation of Division’s action plan based on bi-annual employee survey results and future of work initiative.  

6. Information Architecture and Communications 

• Design and maintain systems that ensure information flows efficiently across the division — reducing bottlenecks, duplication, and gaps. 

• Oversee the development of key internal communications from the President's office, ensuring clarity, consistency, and alignment with organizational priorities. 

• Manage the President's communication calendar and ensure that key messages reach the right audiences at the right times. 

7. External Engagement Coordination 

• Coordinate and prepare the President for external engagements — including partner meetings, stakeholder interactions, and governance appearances — ensuring thorough briefing and follow-through. 

• Represent the President in select external settings where delegated; manage relationships with key external contacts on the President's behalf as appropriate. 

• Coordinate inter-divisional and cross-organizational relationships to advance the division's priorities. 

• Manage the Enterprise Community Leadership Council 

8. Change Management 

• Support the planning and execution of organizational change initiatives — including restructuring, process redesign, and major strategic pivots. 

• Build stakeholder buy-in for change; manage communications and engagement strategies that reduce resistance and sustain momentum. 

• Monitor organizational response to change and advise the President on adjustments needed to maintain effectiveness and trust. 

Required Qualifications 

• Bachelor’s degree in a relevant field plus a minimum 15 years of related experience, with at least 3 years of operating at or near the executive level; or a graduate degree with 8-12 years of experience with at least three operating at or near the executive level.  

• Demonstrated experience managing organizational performance metrics, dashboards, and reporting, including aggregating key KPIs for internal and external audiences, to support accountability and storytelling. 

• Demonstrated experience managing organizational performance metrics, dashboards, and reporting, including aggregating key KPIs for internal and external audiences, to support accountability and storytelling.  

• Demonstrated experience supporting or serving as a chief of staff, executive director, or senior strategic advisor in a complex organization. 

• Proven ability to manage enterprise-sensitive information with absolute discretion. 

• Strong track record of facilitating cross-functional collaboration and delivering results through influence rather than authority. 

• Exceptional written and verbal communication skills, including executive-level presentation and briefing capabilities.  

• Strong change management and problem-solving capabilities. 

Preferred Qualifications

• Demonstrated experience leading or co-leading a strategic planning process. 

• Experience in organizational development, change management, or executive operations. 

• Experience managing external stakeholder relationships at the senior level. 

Working Conditions and Expectations 

• This role operates in a fast-paced executive environment and requires flexibility in hours and availability. 

• Frequent interaction with senior organizational leaders, board members, and external partners. 

• Some travel may be required in support of the President's external engagements. 

• The role requires high tolerance for ambiguity and the ability to manage multiple competing priorities without loss of quality or composure. 

Salary Transparency 

You will be joining a team of talented professionals motivated by serving the community and addressing the need for affordable housing. 

Enterprise offers a comprehensive total rewards package for you and your family. The pay range for this position is $195,000 - $225,000. The salary range represents the low and high end of what may be paid for this position. It is not typical for an individual to be hired at or near the top of the pay range, and compensation decisions may be influenced by a variety of factors, including skills, qualifications, experience, and location. 
 

Total Rewards at Enterprise 

This range is just one component of our total rewards package, which also includes annual performance bonuses and generous paid leave programs. 

Our benefits form a major part of the total rewards package. These include dental, health, and vision care plans, as well as family-building benefits such as adoption and surrogacy support. Enterprise supports flexible work arrangements to promote work-life balance and offers health advocacy, an Employee Assistance Program (EAP), and mental health benefits. We round out our package with financial education, wellness programs, and auto-enrollment in the company’s 401(k) plan with employer matching contributions. 

Finally, you will have access to learning and development opportunities, including tuition reimbursement for job-related courses and certifications. Thank you for your interest in joining the Enterprise team and contributing to our mission to serve others. 

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