Fracture

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 TakeawaysMost 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 BioGrace 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 + LinksDUPAYConnect with GraceWebsite | LinkedInFracture 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

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 TakeawaysFractional 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 BioJocelyn 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 + LinksJocelyn Helland ConsultingConnect with JocelynWebsite | LinkedInFracture 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

In early 2025, one of Holly Rustick's students lost $100,000 in contracts in a single week. Holly has been writing grants for more than 20 years and has run Grant Writing & Funding through five US administrations, the 2008 recession, COVID, and 2025.In this conversation with Cindy, Holly breaks down what her students' experience shows about how the sector is buying right now, how to reposition your services when the market tightens, and why the consultants who are thriving got serious about the business side.Key TakeawaysGrant funding dropped in Holly's programs in 2025, but her students' business revenue went up. Nonprofits are still buying - the form has changed, not the demand.Repositioning from "grant writer" to "grant strategist" changes what you offer, how you price it, and what results you can promise.The Minimum Valuable Product framework: what is the minimum scope of work that gets the client the result they actually need? Cut the extras.Credit-based retainer systems give clients flexibility without costing you recurring revenue.Before every sales call, write down every objection you think might come up - then write how you'd respond.Guest BioHolly Rustick is a grant writing strategist with more than 20 years of experience and founder of Grant Writing & Funding. Her students have collectively won over $225 million in grants and generated $4+ million in business revenue. She hosts the #1 ranked grant writing podcast in the world.Resources + LinksGrant Writing & FundingGrant Writing & Funding PodcastNFN OS ProgramConnect with HollyWebsite | 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

Episode SummaryYour clients are starting to ask about AI - and some have policies banning contractor use. Valerie Ehrlich, PhD has spent her career at the intersection of learning, evaluation, and organisational strategy, and now focuses on what responsible AI adoption actually looks like in the social sector.In this conversation, she and Cindy get into the questions nonprofit consultants are actually facing: what to say when a client asks whether you use AI, how to think about data privacy, and why the most effective AI users are critical thinkers - not early adopters.Key TakeawaysConsultants need to decide whether they'll be proactive or reactive about AI disclosure. Getting caught off guard when a client asks is not an option.Separate client-facing AI use from backend use. Both are acceptable - but they require different levels of disclosure.Pay for AI tools rather than using free versions. Free tools often monetise your data. Read the terms of service.Never record a client conversation without consent. Even if it's technically legal, it's a trust issue.A consultant's deep sector knowledge produces better AI output than someone without it. That's an argument for your value, not against it.Guest BioValerie Ehrlich, PhD is the founder of Mission Bloom, supporting mission-driven organisations in learning, evaluation, and AI adoption. She also writes The Bloom Shift, a Substack newsletter on responsible AI in the nonprofit sector.Resources + LinksMission BloomThe Bloom Shift on SubstackNFN OS ProgramConnect with ValerieWebsite | 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

Kelsi Kriitmaa spent 25 years across the UN, global NGOs, and private sector consulting before building what she calls a portfolio career - multiple revenue streams, multiple professional identities.In this conversation, Kelsi and Cindy map out how the portfolio model actually works: relationship-first business development, why generalists are undervalued, and why seasons of life matter more than long-term plans.Key TakeawaysA portfolio career means multiple revenue streams and professional identities - not just one consulting client.Business development in the social impact sector is relationship-first. Mass marketing tactics won't get you clients here.Generalists are undervalued and essential. Niching too early means missing the market.Build for now, not forever. What you need from your business in year one is different from year three.No in-house role is as safe as it used to be. Portfolio careers give you more options, not fewer.Guest BioKelsi Kriitmaa, PhD is a social impact coach and consultant with 25 years of experience across the UN, global NGOs, and private sector consulting. She founded Kriitmaa Coaching & Consulting, holds an ICF accreditation, and has a PhD in Epidemiology.Resources + LinksKriitmaa Coaching & ConsultingPortfolio Career Playbook on Maven - search "Kriitmaa Portfolio Career Playbook"BridgeSpan Group article on generalists: [URL to confirm with guest]NFN OS ProgramConnect with KelsiWebsite | 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