Transitions done with intention and care
Boards that get leadership transitions right don't happen by accident. I partner with board leaders, incoming Executive Directors, and founders to navigate these pivotal moments with clarity, care, and real deliverables — not just conversation.
ABOUT
I am the founder and former Executive Director of Start Small Think Big, a national nonprofit that grew to serve 3,500+ entrepreneurs annually before I successfully transitioned out of the leadership role myself.
I now consult with boards, new Executive Directors, and founders on exactly that kind of work. My consulting tends to concentrate on the human and relational dimensions of transitions: supporting boards in managing the governance responsibilities that come with leadership change, coaching new EDs through their first 12–18 months, and helping founders clarify their evolving role and legacy.
My engagements go beyond conversation — I produce real deliverables alongside my clients: transition roadmaps, governance documents, stakeholder engagement plans, onboarding frameworks, and more. All work can be done remotely, serving organizations across the country.
Where I can help
Support for Boards & Board Chairs
Boards play a central role in successful leadership transitions. I help board leaders make high-stakes decisions with confidence and guide the organization through change with steadiness and respect.
→ Assess board readiness, composition, and culture
→ Define the board's role in succession and search
→ Design inclusive, transparent selection processes
→ Facilitate conversations about founder legacy and continuity
→ Coach board chairs as balanced partners to all leaders
Deliverables: Roles & responsibilities matrix · Succession and onboarding calendar · Governance effectiveness assessments
Support for Founders
Founder transitions are some of the most pivotal — and vulnerable — moments in an organization's life. I facilitate transparent, well-paced processes that build trust and continuity among founders, boards, and incoming leaders.
→ Clarify evolving vision, role, and boundaries
→ Strengthen staff, systems, and governance
→ Map institutional footprint for smooth handoffs
→ Design values-aligned succession plans
→ Confidential thought partnership and emotional support
Deliverables: Founder transition roadmap · Leadership role redefinition · Internal & external communications plan · Post-transition role description · Timeline for key handoffs · Founder legacy summary
Support for New Executive Directors
New EDs often step into roles rich with opportunity and pressure — passionate teams, complex histories, and high expectations. I offer real support: not just accountability, but a thought partner who understands the weight of the role from the inside.
→ Onboard authentically with staff, board, and funders
→ Set a focused 12–18 month leadership agenda
→ Navigate dynamics with founders and long-tenured staff
→ Ensure fundraising continuity and relationship handoffs
→ Clarify founder–ED agreements and role transitions
Deliverables: 30/60/90-day onboarding roadmap · First-year leadership agenda · Stakeholder engagement map · Founder–ED relationship agreement · Fundraising transition plan · Customized coaching plan
Board Effectiveness & Strategic Alignment
Beyond transition work, I strengthen board governance so that mission, strategy, and oversight are tightly aligned — and decision-making is clear and timely.
→ Sharpen board roles and accountability structures
→ Refresh committee structures and practices
→ Equip boards for growth, change, and strategic inflection points
Deliverables: Board self-assessment tools · Synthesized assessment findings with actionable recommendations · Annual board work plans · Updated charters for boards and committees · Refreshed board meeting templates
Engagements tailored to your moment
My work spans the full spectrum — from strategic advising and coaching to hands-on consulting where I produce documents, facilitate sessions, and drive deliverables alongside your team. Every engagement is scoped around what you actually need.
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 strategic initiative.
Short-Term Advisory
Focused strategic guidance during a key leadership inflection point — when you need clear, experienced thinking fast without a long-term commitment.
Retained Coaching
Ongoing thought partnership for founders, new EDs, or board chairs — 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. I'm particularly well-suited for organizations focused on economic mobility, entrepreneurship, community development, and access to justice — and for the boards and funders who support them.
Do you work with organizations outside your local area?
Yes — all engagements can be conducted remotely, and I work with organizations across the country. Leadership transitions don't require in-person work 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: a founder who has a clear, meaningful post-transition role and a documented plan for handing off relationships and knowledge; a new ED who has built early trust with their 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.
Is it too early to reach out? We're not in crisis yet.
The best time to engage is before a transition is urgent. Organizations that plan ahead make smoother handoffs, retain more institutional knowledge, and protect their culture. If a founder is quietly wondering whether it might be time to step down — that's exactly the right moment to start a conversation.
How is this different from traditional coaching or training?
Coaching focuses on the individual. My work focuses on the organization — the relationships, structures, and decisions that determine whether a transition succeeds. Where coaching is conversational, my consulting engagements produce tangible deliverables: documents, frameworks, plans, and agreements that outlast the engagement itself.
Do you work with funders?
Yes. I work with funders who recognize that leadership and organizational health are what make their program investments work — and want to act on that.
How do we know if our organization is ready for this kind of support?
Organizations don't need to have everything figured out before reaching out — in fact, the earlier in a transition process you engage, the more options you have. Uncertainty and complexity are exactly the conditions this work is designed for.
Can you work with just one part of the organization?
Yes. While transitions work best when all stakeholders are aligned, engagements can be scoped to support just the board, just the incoming ED, or just the outgoing founder. Some clients start with one relationship and expand from there; others need focused support for a single stakeholder. We'll work together to design what makes sense.
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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