Tess Conrad, CFRE first appeared on this podcast as a fully-booked generalist fractional fundraiser. Since then, she's niched her business into planned giving - a deliberate, gradual shift sped up by an endorsement from a well-known planned giving expert who saw her as a successor.

She also lived through the scenario a lot of fractionals fear but rarely plan for: an unplanned two-month medical leave that stretched to four, followed by a long-term client relationship ending unexpectedly right after she returned. Half her income disappeared at once. An emergency fund, a subcontractor network, and a return to basic business development brought her back to fully booked within months.

Key Takeaways

• Niching into a long-sales-cycle specialty like planned giving takes patience - Tess expects to be fully booked in her niche by mid-2027, years after she started positioning for it.
• An emergency fund isn't optional once you're running a fractional business - it's what let Tess take medical leave without panicking about income.
• Line up subcontractors before you need them. Tess's network covered her client relationships during her leave and kept continuity with the organizations she serves.
• Content built around a specific niche compounds - weekly LinkedIn posts and a weekly newsletter kept Tess visible in planned giving even while she wasn't taking new clients.
• Time management systems will keep changing as your business does. Tess moved from Asana to Motion to pen and paper, adjusting each time her client mix shifted.

Guest Bio

Tess Conrad, CFRE, is the principal consultant at Full Potential Fundraising, specializing in fractional and done-for-you planned giving for nonprofits. She previously built a fully-booked generalist fractional fundraising practice before niching into legacy and planned giving work.

Resources + Links

Full Potential Fundraising

Connect with Tess

Website | LinkedIn

Fracture is for nonprofit professionals who refuse to choose between doing good work and having a good life. Hosted by Cindy Wagman, founder of the Nonprofit Fractionals Network, it's real talk on building a fractional consulting business that actually pays - and still matters.

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An unpaid invoice hits differently than a late bill. Grace Tabib, founder of DUPAY, knows that firsthand - she left a law firm offer to return to nonprofit work, then went three months unpaid on a role she still loved. That experience became a business built on recovering unpaid invoices for freelancers, fractionals, and founders.

In this conversation, Grace and Cindy break down why late nonprofit payments are almost always admin delays rather than malice, what a solid fractional contract needs to spell out from day one, and how to send a payment reminder that stays professional without feeling cold. They also get into the harder cases: when a client goes quiet, when the money genuinely isn't there, and when it's time to stop chasing an invoice yourself.

Key Takeaways

• Most late nonprofit payments come from admin delays, not bad faith - missing approvals, absent signers, or invoices routed to the wrong inbox.
• A contract should spell out payment terms, approval steps, and timelines before work starts, even with a client you already know well.
• Reminders work best sent early and often - the first one the day payment is due, not weeks later.
• Keep reminders professional, not personal - lead with the invoice number and due date, not the relationship.
• If a client goes unresponsive after repeated professional outreach, it's reasonable to hand the collection to a third party rather than keep spending your own time and energy on it.

Guest Bio

Grace Tabib is the founder and head of advocacy at DUPAY, a platform that protects income and recovers unpaid invoices for freelancers, fractionals, and small businesses. She is a lawyer with her own history of unpaid nonprofit work, which shaped DUPAY's mission to help people get paid for work they've already done.

Resources + Links

DUPAY

Connect with Grace

Website | LinkedIn

Fracture is for nonprofit professionals who refuse to choose between doing good work and having a good life. Hosted by Cindy Wagman, founder of the Nonprofit Fractionals Network, it's real talk on building a fractional consulting business that actually pays - and still matters.

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Before Jocelyn Helland was a fractional consultant, she was Cindy's client. In 2018, as an executive director in Toronto, she brought Cindy's team in to shore up a fundraising department in crisis - and watched, up close, what "done for you" fundraising could look like.

Years later, Jocelyn left the ED chair and built her own fractional practice. She refuses to niche into one function, running fundraising and interim leadership engagements at once, and she's learned to tell the difference between a genuine red flag and a client who simply doesn't understand fractional support yet. She also talks candidly about walking away from a relationship that had good bones but the wrong fit - and why protecting that decision protected her reputation.

Key Takeaways

• Fractional doesn't require a niche - Jocelyn runs fundraising and interim ED engagements side by side because the range keeps her sharp.
• Fit matters more than budget. Anxiety before every meeting is a clearer red flag than a mismatched invoice.
• A red flag and an uninformed client aren't the same thing - coachable organizations just need the model explained.
• Trust is the deliverable. The best fractional clients let go of oversight and let the expertise work.
• Reputation outlasts any single contract. Ending a mismatched engagement well protects future referrals.

Guest Bio

Jocelyn Helland is the founder of Jocelyn Helland Consulting, offering fractional fundraising and interim executive leadership to small and mid-sized nonprofits. She spent over two decades in-house, including as an executive director, before building a fractional practice on her own terms.

Resources + Links

Jocelyn Helland Consulting

Connect with Jocelyn

Website | LinkedIn

Fracture is for nonprofit professionals who refuse to choose between doing good work and having a good life. Hosted by Cindy Wagman, founder of the Nonprofit Fractionals Network, it's real talk on building a fractional consulting business that actually pays - and still matters.

Subscribe to Fracture | Join the OS