Vice President, Strategic Planning & Initiatives

Enterprise is a national nonprofit that exists to make a good home possible for the millions of families without one. We support community development organizations on the ground, aggregate and invest capital for impact, advance housing policy at every level of government, and build and manage communities ourselves. Since 1982, we have invested $92.0 billion and created 1.1 million homes across all 50 states, the District of Columbia, Puerto Rico and the U.S. Virgin Islands – all to make home and community places of pride, power and belonging.

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Working at Enterprise

At Enterprise, you’ll be part of a diverse, committed team making a difference every day. You will collaborate with some of the smartest minds and biggest hearts in our field. You’ll be empowered to drive systems change and take bold steps to advance racial equity. And you will find a career home where you’re valued and supported in your growth journey.

Enterprise offers career opportunities in our offices across the country with an exceptional benefits package.

Job Description Summary

The Vice President, Strategic Planning and Initiatives serves as the principal integrator and strategic right hand to the President, enabling the effective leadership and operation of the division. This role ensures that the President's priorities are translated into organized action, that the leadership team operates with coherence and accountability, and that the division's operating rhythm supports high performance.

This is a role of trust, discretion, and organizational influence. The VP, Strategic Planning and Initiatives operates at the executive level — managing enterprise-sensitive information, coordinating across organizational boundaries, and carrying peer-level credibility with senior leaders. The role does not direct the leadership team but works as a trusted coordinator who ensures alignment, reduces friction, and amplifies the President's impact.

Job Description

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.

Accountability and Outcomes

The following links the role's key responsibilities to their expected deliverables and measurable outcomes.

Responsibility

Executive advisory & decision support

Key Deliverables

Briefing materials; decision memos; tracking system for commitments

Measurable Outcomes

President reports high confidence in preparation; commitments tracked and met on time

Responsibility

Strategic planning

Key Deliverables
Annual strategic plan; planning calendar; leadership team inputs; progress reports

Measurable Outcomes
Plan produced on schedule; leadership team reports process is well-run and their input is reflected

Responsibility

Operating rhythm
Key Deliverables

Leadership meeting calendar; agendas; decision logs; follow-through reports
Measurable Outcomes

Meetings are purposeful; decisions documented; follow-through rate measurably improves

Responsibility
Strategic initiative oversight
Key Deliverables

Initiative charters; status reports; risk logs; escalation recommendations
Measurable Outcomes

Initiatives delivered on time and scope; President has accurate real-time visibility

Responsibility

Organizational health

Key Deliverables

Periodic health assessments; culture reports; recommended interventions

Measurable Outcomes

Early identification of risk; leadership team trust scores improve over time

Responsibility

Information architecture

Key Deliverables

Communication systems; President's communication calendar; key internal messages

Measurable Outcomes

Information bottlenecks reduced; staff report clarity on division priorities

Responsibility

External engagement

Key Deliverables

Briefing packages; stakeholder maps; follow-through on external commitments

Measurable Outcomes

President rates external preparation highly; external relationships are maintained with consistency

Responsibility

Change management

Key Deliverables

Change management plans; stakeholder engagement strategies; progress reports

Measurable Outcomes

Change initiatives achieve intended outcomes; staff report feeling informed and involved

Decision-Making Authority

The VP, Strategic Planning and Initiatives operates with significant delegated authority in defined domains. The following framework describes the expected degree of autonomy:

Decides Independently

• Operating and process decisions within the President's office

• Day-to-day management of the operating calendar and meeting rhythm

• Routine external coordination and scheduling on the President's behalf

Decides with President Consultation

• Strategic initiative scope and resource decisions

• Communications from the President's office on sensitive matters

• Significant changes to planning process or operating calendar

President Decides

• Strategic priorities and direction

• Personnel decisions affecting the leadership team

• External commitments with material organizational consequence

Core Competency Framework

The following competencies define what high performance looks like in this role, based on Enterprise’s Leadership Competencies. Behavioral anchors are provided at two levels to support evaluation and development.

Executive judgment and discretion/Customer and client focus

• Meets expectations: Handles sensitive information appropriately; knows when to escalate; provides sound, balanced advice in familiar situations.

• Exceeds expectations: Navigates ambiguous, high-stakes situations with composure and precision; advises the President on complex political or organizational dynamics with insight that consistently adds value; trusted with the most sensitive matters without close oversight.

Cultivates innovation through strategic thinking and planning

• Meets expectations: Understands the division's strategic priorities and can translate them into organized work plans; tracks progress and flags misalignments.

• Exceeds expectations: Proactively identifies strategic opportunities and risks; synthesizes complex inputs into clear strategic recommendations; over time, leads the design and execution of the strategic planning process with minimal direction.

Drives results

• Meets expectations: Builds productive working relationships across the leadership team; coordinates effectively and follows through on commitments; earns credibility through competence and reliability.

• Exceeds expectations: Operates as a genuine peer to senior leaders; shapes decisions and behavior through trust and persuasion rather than authority; resolves cross-functional tensions with skill and without escalation.

Collaborates and communicates effectively

• Meets expectations: Communicates clearly and concisely in written and verbal form; manages information flow within the President's office effectively.

• Exceeds expectations: Designs and maintains systems that ensure the right information reaches the right people at the right time; drafts communications that consistently reflect the President's voice and intent; proactively addresses information gaps before they cause problems.

Manages ambiguity and situational adaptability

• Meets expectations: Supports change initiatives by keeping stakeholders informed and coordinating logistics; manages own work effectively during periods of change.

• Exceeds expectations: Leads the change management workstream on complex initiatives; anticipates and addresses resistance; builds coalitions and sustains momentum across organizational boundaries.

Values differences and supports culture-building

• Meets expectations: Monitors team dynamics and reports concerns to the President; supports culture-building activities.

• Exceeds expectations: Functions as a reliable early-warning system for organizational risk; designs and leads culture interventions; builds trust across the division through consistent, visible investment in organizational health.

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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