NONPROFIT STRATEGY AND LEADERSHIP SUPPORT, done with intention and care
I help nonprofits invest in the people and relationships that carry the mission — its leaders, its board, and the partnership between them — so they're strong now and steady through whatever comes, including moments of leadership change.
My work is grounded in a full-ecosystem view of the nonprofit sector — shaped by founding and leading a national nonprofit organization and advising the funders who help support this field.
ABOUT
I'm an executive coach and nonprofit strategist, and my work rests on a simple conviction: an organization is only as strong as the people who carry it and the relationships that hold it together — and the time to invest in them is in the quieter stretches, well before any moment of change. I focus especially on the partnership an organization quietly runs on — the one between a board and its executive — supporting both as a single relationship. Governance strengthening, leadership development, and my particular specialty in leadership transitions all grow from that same root. I bring a full-ecosystem vantage point to the work, shaped by founding and leading a national nonprofit and advising the funders who help shape the sector.
As founder and Executive Director of Start Small Think Big for over 13 years, I grew the organization from a single-founder idea into a national nonprofit serving 3,500+ marginalized small business owners a year, with a $6M budget and 40+ staff — and then did the thing that tests everything you've built: I handed it to new leadership, where it continues to operate and grow today. Along the way I built the management infrastructure, performance systems, and culture of accountability that let a distributed team scale without depending on any one person — the same durable, people-centered structure I now help other leaders build.
That full-organization experience grounds a practice built around board and executive leadership: strengthening governance and the board's partnership with its executive, developing the depth that keeps a mission from resting on one person, and guiding leaders and organizations through change — including the transitions that are my specialty, where I support outgoing founders through the practical and emotional work of letting go, help new EDs through their critical first 12–18 months, and prepare boards to govern change well.
My commitment to equity and access to justice runs as a throughline across my career — from early legal work on the national Election Protection campaign to board leadership with The Access Project, focused on record-clearing for formerly incarcerated community college students, and Compass Family Services, supporting unhoused families in San Francisco. And my engagements always produce real, tangible deliverables — transition roadmaps, governance documents, stakeholder engagement plans, onboarding frameworks, and more — work you keep long after we're done, available remotely to organizations across the country.
Where I can help
Every engagement below is one way of doing the same underlying work — strengthening the people and relationships an organization runs on. Each is scoped to what you actually need, and many start with a single question and deepen from there.
Much of my work centers on the relationship between a board and its executive, held as a whole — because that partnership, more than any plan, is what carries an organization through.
Organizational Assessment & Readiness
This might be you if: things feel mostly steady, but you sense how much rests on one person's shoulders — or a board not quite sure of its role — and you'd rather understand it now, while there's time and room to act.
Together, we take an honest, careful read of where the organization is strong and where it leans too heavily on any one person or relationship, including how the board and executive are really working together. Low-pressure, and it shows us where to start.
Deliverables: Organizational health assessment · Key-person risk map · Board–executive working-relationship review · Synthesized findings with prioritized recommendations
Typical shape: a short, contained engagement — often the first step, and one that can stand on its own or open into deeper work.
Board Development & Governance
This might be you if: the lines between board and staff have blurred, a new board chair is finding their footing, or you've felt that the board and executive aren't quite partners in the way they could be.
Together, we build the trust, role clarity, and mutual support that let a board and executive lead as genuine partners — the relationship an organization quietly runs on, every day, long before any change.
Deliverables: Governance effectiveness assessment · Roles & responsibilities matrix · Annual board work plan · Refreshed charters & committee structures · Board-chair partnership plan
Typical shape: ranges from a one-time assessment or board retreat to an ongoing advisory relationship as the board builds new habits.
Leadership Pipeline & Bench Strength
This might be you if: so much lives in one person — the relationships, the history, the fundraising — that you've caught yourself saying, "we couldn't do this without them."
Together, we spread that weight: developing the people one layer down, and helping the knowledge and relationships held by one person become the organization's, not just theirs. Depth is what lets a mission last.
Deliverables: Leadership development plan for senior/second-tier staff · Knowledge & relationship transfer plan · Fundraising continuity & diversification plan · Key-person risk mitigation plan
Typical shape: a sustained, project-based engagement, since building depth happens over time rather than in a single sitting.
Executive Coaching & Leadership Sustainability
This might be you if: a leader is carrying a great deal, often quietly — stretched, isolated, or running low; a new ED wants a real thought partner; or you simply want to hold on to the good people you have.
Together, we tend to the people at the heart of the work — confidential coaching and honest thought partnership for the person in the role, not just the role. Caring for them well is how missions endure.
Deliverables: Customized coaching plan · 30/60/90-day onboarding roadmap (new EDs) · First-year leadership agenda · Stakeholder engagement map · Confidential ongoing thought partnership
Typical shape: an ongoing, retained relationship — a steady sounding board through the arc of the work, at a cadence that fits the leader.
Organizational Design & Restructuring
This might be you if: you've grown faster than your structure, roles and reporting lines have tangled, or the way you're organized no longer fits the work you do now.
Together, we redesign how the organization is built — roles, teams, reporting, and the management infrastructure underneath — so the structure fits the mission, and people aren't left stretched across the gaps a mismatched structure creates.
Deliverables: Organizational structure & design review · Role & reporting redesign · Restructuring plan · Management infrastructure recommendations
Typical shape: a focused, project-based engagement with a clear beginning and end, scoped to the redesign at hand.
Succession & Continuity Planning
This might be you if: there's no real plan if a key person were suddenly out, and you'd like the quiet confidence of knowing the organization could meet the unexpected with care.
Together, we put the groundwork in place — a continuity plan, interim provisions, and a thoughtful way to carry change to staff, funders, and community — so that whatever comes, it's met with steadiness and respect.
Deliverables: Emergency succession plan · Planned succession & continuity plan · Interim leadership plan · Transition communications plan
Typical shape: a contained, deliverable-driven engagement — the emergency version is quicker; a full planned succession runs longer.
The Full Arc → Ready Together
This might be you if: a founder or long-tenured executive is beginning to think about stepping back — and you want the whole organization carried through it together, with care: the board, the departing leader, and the one who comes next.
This is my signature engagement, and the heart of my practice. A leadership transition touches everyone at once — the board, the departing leader, and the one who comes next — and the relationships among them are what determine whether it goes well. That web of relationships is what I hold. I'm not your search firm; I'm the person making sure the organization is ready, aligned, and steady around whatever search you run — and that everyone comes through it intact. We move through the arc together: readiness, preparing the board to govern the change, distributing what one person has carried, supporting the outgoing leader through the practical and emotional work of letting go, defining what the next leader truly needs to be, and planning the handoff and onboarding so the new leader inherits clarity, not a vacuum.
Deliverables: Transition roadmap & timeline · Board readiness & governance plan · Founder legacy & knowledge-transfer plan · Future leadership profile · Post-transition role description · Internal & external communications plan · Successor 30/60/90 onboarding & founder–ED agreement
Typical shape: a phased engagement that unfolds over the life of the transition, scoped to your timeline and moving with you rather than on a fixed clock — and designed to complement a search firm, not replace one.
Engagements tailored to your moment
My work spans the full spectrum — from focused advising and coaching to hands-on consulting alongside your team. Each engagement is shaped to the moment you're in: how much support you need, and for how long.
Hands-On Project Consulting
I take an active role: drafting documents, facilitating sessions, building frameworks, and driving deliverables alongside your team. Scoped around a specific transition, governance project, or organizational redesign.
Short-Term Advisory
Focused, experienced guidance at key inflection points — when you need clear thinking fast, without a long-term commitment.
Retained Coaching
Ongoing thought partnership for boards, new EDs, or founders — a trusted sounding board and advisor through a sustained period of change.
Is this right for your organization?
Who do you typically work with?
I work primarily with small to medium-sized nonprofits with annual budgets under $15–20M, operating nationally or at regional scale, particularly those focused on economic mobility, entrepreneurship, community development, and access to justice.
Do you work with organizations outside your local area?
Yes — all engagements can be conducted remotely, and I work with organizations across the country. This work doesn't require in-person time to be done well.
We already have an executive search firm. Is this different?
Yes. Search firms focus on finding the right candidate. My work focuses on everything around that: preparing the organization for transition, aligning the board, supporting the incoming leader once they arrive, and helping the outgoing founder navigate their exit. The two can complement each other well.
What does an engagement look like, and how long does it take?
Every engagement is scoped to your organization's specific needs. Some are short-term advisory relationships during a key inflection point; others are longer project-based engagements with clear deliverables and timelines. I take on a small number of clients at a time to ensure focused attention. Reach out to discuss what makes sense for your situation.
What does success look like at the end of an engagement?
It depends on the engagement, but common outcomes include: an organization that no longer rests on any one person, with a board and executive working as genuine partners; a founder with a clear, meaningful next chapter and a documented plan for handing off relationships and knowledge; a new ED who has built early trust with board and staff and has a focused first-year agenda; and a board that understands its governance responsibilities and has the tools to carry them out.
Do you only work on leadership transitions, or other governance and strategy work too?
Not at all. Most of my work is helping organizations invest in their people and relationships well before a transition is ever on the table — governance and board development, leadership sustainability, and building depth so no single person carries too much. Leadership transitions are my specialty within that. If you're not sure whether your situation fits, reach out and we'll figure it out together.
Is it too early to reach out? We're not sure we need this yet.
The best time to engage is before something feels urgent — whether that's a transition, a governance gap, or a strategy question. Organizations don't need to have everything figured out first; in fact, the earlier you engage, the more options you have. Uncertainty and complexity are exactly the conditions this work is designed for. If a founder is quietly wondering whether it might be time to step down, or a board senses something isn't quite working but can't yet name it — that's exactly the right moment to start a conversation.
How is this different from traditional coaching or training?
I do coach — one-on-one support for a leader is part of my work. What sets these engagements apart is that they also work at the level of the organization: the relationships, structures, and decisions around a leader, not only the leader alone. And where pure coaching stays in conversation, my engagements produce tangible deliverables — documents, frameworks, plans, and agreements that outlast the engagement itself.
Can you work with just one part of the organization?
Yes. My work is strongest when the board and executive are in it together — that partnership is usually where the real change happens — but engagements can be scoped to a single stakeholder: just the board, just a new ED, or just an outgoing founder. Some clients start with one relationship and grow from there; others need focused support for one person.
Ready to begin ?
If any of this resonates — whether you're a board navigating a leadership change, a funder thinking about investing in leaders, a new ED who wants real support, or a founder privately asking yourself whether it's time to step down — I'd love to hear from you.
PHONE
347-989-5139
jennycdasilva@gmail.com
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