BreakingBounds Senior Director of Strategy & Delivery

Positively Partners•Attleboro, MA

3d•$135,000 - $150,000•Remote

About The Position

BreakingBounds® is a consulting firm that delivers high-impact business solutions for organizations driven by social good. They partner with nonprofits to operate with the rigor, strategy, and financial clarity of high-performing businesses. Through core services in strategic planning, leadership development, and executive coaching — and through its signature Accelerator Program, a business education built specifically for nonprofit leaders — BreakingBounds equips organizations to move from good intentions to measurable outcomes. As BreakingBounds® grows, Founder & CEO Patty Williams-Downs is seeking a senior leader to own the client experience: a Senior Director of Strategy & Delivery. This leader will own delivery quality across a defined scope of 30–50 client organizations, lead assigned Accelerator cohorts, and ensure every engagement results in clarity, alignment, and measurable progress. This is a high-ownership role designed for someone who leads from the front, operates with strong strategic judgment and financial and business acumen, and is energized by translating business frameworks into real outcomes for leaders and organizations. The ideal candidate brings a rare combination: consulting experience, direct experience as a nonprofit operator, strong financial and business acumen, and the credibility to sit across from a CEO and immediately earn their trust.

Requirements

Strong financial and business acumen, including the ability to analyze financial statements, assess revenue diversification, evaluate business model viability, and coach leaders on financial strategy.
Proven ability to translate for-profit business frameworks into accessible, practical strategy for social sector leaders.
Direct experience as a nonprofit operator at a senior level (VP, CEO, Executive Director, or equivalent), combined with deep familiarity with business models, financial structures, and the operational realities of mission-driven organizations — and the ability to distinguish strong financial management from surface-level familiarity.
Executive-level consulting and facilitation skills; ability to design and deliver high-quality strategic planning and leadership development engagements.
Demonstrated capacity to manage a complex portfolio of clients and deliverables simultaneously, maintaining depth and quality under volume.
7+ years of progressive professional experience with a demonstrated track record in consulting, strategy, or senior leadership.
High emotional intelligence and personal ownership — a track record of operating with independence, taking accountability, and solving problems without waiting for direction.
Excellent communication and executive presence; ability to build trust quickly with CEOs and senior leaders and to challenge thinking while preserving relationships.
Comfort operating in ambiguity and making sound decisions with incomplete information.
Commitment to BreakingBounds' core belief that no money means no mission — and that the most impactful organizations operate with both strategic clarity and financial discipline.

Responsibilities

Own strategy, design, and delivery for a portfolio of 30–50 client organizations across core services and the Accelerator Program, serving as the primary senior consultant and senior facilitator for assigned cohorts.
Lead financial design work with clients, including analysis of financial models, revenue diversification strategies, and business model viability assessments.
Proactively identify risks and issues across the portfolio; develop data-informed, strategic alternative plans.
Operate with a high level of independence, building trusted relationships with nonprofit CEOs and senior leaders while enabling the CEO to focus on organizational growth and business development.
Design and deliver BreakingBounds' Accelerator Pathways and consulting sessions with consistency, rigor, and excellence.
Translate for-profit business frameworks into accessible, actionable learning for nonprofit leaders, applying financial and business acumen to make complex concepts practical for social sector leaders.
Facilitate complex, high-stakes conversations with skill, adapting in real time while maintaining quality and structure.
Ensure clients leave each session with tangible outputs aligned to session, Accelerator Program outcomes and organizational standards.
Design content that aligns with BreakingBounds' values, facilitation norms, and commitment to reducing barriers to entry for social sector leaders.
Identify patterns across the portfolio and cohorts and translate insights into actionable recommendations for the CEO.
Make incremental improvements to session flow, tools, facilitation pacing, and client materials.
Prevent quality drift as delivery volume grows by maintaining high standards across all engagements, meeting experience outcomes.
Engage in regular reflective practice; give and receive direct feedback with clarity and care.
Act as a trusted partner to the Founder & CEO, owning execution within scope and communicating transparently on priorities, risks, and progress.
Maintain a strong communication cadence with the CEO; demonstrate ownership without overreach.
Model BreakingBounds's values — people, partnership and progress— both internally and externally.
Contribute insights that inform program innovation, organizational learning, and the evolution of service offerings.
Support delivery capacity by managing 1–2 team members, which may include internal staff and external contractors.
Collaborate with the CEO on the use of external consultants and facilitators supporting assigned cohorts.
Provide clear feedback and coaching tied to delivery quality; set and maintain high expectations.
Escalate capacity or performance risks appropriately, proactively with clear strategic recommendations.