The work is hard enough. Your strategy shouldn't make it harder.
Strategic counsel to help progressive leaders hit their goals on campaigns, advocacy, and sustainable fundraising.
Our work
Fieldwork is for senior leaders in NGOs and advocacy organisations facing the decisions that matter most, and that are too complex, or too politically loaded, to work through alone.
That might mean a fundraising program that isn't growing the way it needs to. A campaign that's stalled, or too important to get wrong. A strategic question the team keeps circling without resolving.
Organisational strategy
Your strategy should be flexible enough to account for funding shifts, structural change, and political headwinds. Worth pressure-testing with someone outside the organisation before committing to a direction.
Fundraising
Grassroots digital, monthly donors, mid-level giving. Whether the goal is growing a program or building one from scratch, the question is usually the same: is the approach actually working?
Campaign strategy
Campaigns need to survive contact with the opposition, the coalition, and the politics inside the organisation. The leaders I work with want someone who's been through this before.
Hard calls & wicked problems
A restructure, a coalition decision, a campaign pivot. Work through it with someone who's been there before you dive in.
Three ways to work together
Book a Strategy Session
The right starting point when there's a specific challenge that deserves proper thinking.
A focused day together, working through a pressing challenge. Before we meet, I'll send a short brief so we both arrive prepared. After the session, a one-page summary of key takeaways and a follow-up call seven days later to see what's landed and how your progress is tracking.
In person where possible. Online where not.
Priced at $2,500.
Get dedicated support with an Advisory Partnership
For leaders who want ongoing counsel rather than a one-off conversation.
We start with a half day onboarding session to establish goals and how we'll measure progress. Then fortnightly 90-minute sessions, online or in person, with email and text access between sessions when something comes up. Every quarter we review where things stand against what we set out to do.
The agenda comes from what's actually pressing. I bring the experience and the outside view.
Price upon enquiry - everyone has different needs.
Engage your team in a Strategy Retreat
Take your team away from operations, and engage in a facilitated retreat focusing on strategy, alignment, and team cohesion.
Most leadership teams don't lack capability. They lack the time and space to use it properly. Hard conversations get pushed off. Big decisions get made in a rush, or not at all.
A retreat can fix that, but only if it's designed to. We proivide pre-retreat work so the real conversation starts on day one. Facilitation that gets into the hard stuff. Follow-up so decisions actually stick.
For teams heading into a big year, coming through a difficult period, or planning a major campaign or structural change. Get in touch to discuss.
Pricing depends on your situation. Get in touch and we'll figure out what makes sense.
What I learned in two decades
After twenty years inside change-making organizations, I learned that leaders are usually grappling with the same challenges:
They solve for tactics when the real problem is strategy. Hiring for campaigns when the organisation should be building infrastructure. Running harder in the wrong direction.
They carry too much alone. The people around them are either too inside the organisation to see it clearly, or too outside the sector to understand it. A peer can offer solidarity. Outside counsel offers perspective.
They confuse activity with progress. Meetings, reports, planning days. They feel productive while the real problems go unaddressed. The to-do list gets longer. The approach doesn't change, and neither do results.
They mistake a plan for a strategy. A clear direction, the discipline to say no, and the follow-through to act on it. Most organisations have the first. Fewer have all three.
About me
My name is Jack Milroy. I've been convening and advising progressive leaders for two decades.
For five years, I produced Activate Conference—bringing together senior leaders from the White House, Biden for President, Australian Labor Party, NDP, and major unions for strategic conversations on Cortes Island, BC.
I've also spent two decades inside the work: running campaigns, navigating government relations, building coalitions, designing organizational strategy for unions and advocacy groups across Australia, Canada, and the United States.
I've been the Director prepping the Mayor for council. The Regional Organizer managing multiple campaigns. The senior staffer securing $1.3 billion in federal funding for unions. I’ve been the fundraising director tasked with raising millions from an email list. I know what it's like to carry responsibility and make calls when the stakes are real.
That experience - across jurisdictions, sectors, and kinds of organisations - is what I bring to the work.
Background
Almost 20 years of experience across Australia, Canada, and the United States.
Experience includes:
Founder & Producer, Activate Conference (2018-2023)
Manager of Strategic Engagement, City of Hobart
Director of Engagement, Vision Vancouver
Vancouver Regional Organizer, BC NDP
National Political Coordinator, United Workers Union
Managing Director, Defiance
Education:
Master of Arts, Political Science — Simon Fraser University
Bachelor of Laws (First Class Honours) — University of Newcastle
Bachelor of Arts, History and Politics — University of Newcastle
Frequently Asked Questions
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We meet fortnightly for 90 minutes, via Zoom or in person depending on location. The agenda is set by what's urgent or difficult.
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Email and text access for when something comes up. I'll review any relevant materials before we meet - board papers, campaign plans, fundraising strategy, whatever's useful.
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A focused day together from 10am to 3pm, on one pressing question. Includes a pre-session brief, a one-page summary of key takeaways, and a follow-up call seven days later.
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No. Most advisory work happens via Zoom and works across time zones. In-person sessions are available in Australia and Canada. I travel frequently to North America.
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Not exactly. To me coaching implies a rigid program of personal development that goes deep into personal motivation, behavours and biases. This is advisory counsel. I'll be in the room with the strategic and operational challenges, drawing on sector experience to help work through them.
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Two nights, away from operations, in an environment worth being in. Pre-retreat work so the real conversation starts on day one. Facilitation focused on strategy, alignment, and team cohesion. Follow-up to make sure decisions stick.
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Designed around the organisation and its situation. Get in touch to discuss options.
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The Working Session is $2,500. Advisory Partnership and Team Retreat pricing depends on scope and situation - get in touch to discuss.
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Yes. Conversations are strictly confidential.
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Fill out the contact form or reach out via LinkedIn. We'll have a conversation about what's going on and whether working together makes sense.
Get in Touch
If any of this sounds like what's needed, the best next step is a conversation.