Summary

Generosity X is hiring a Head of Marketing Strategy & Insights to lead marketing strategy for our charity clients, helping them grow donor acquisition, strengthen retention and improve the donor experience. This role focuses on our clients’ fundraising programs rather than Generosity X’s own marketing.

This is a role for someone who can zoom all the way out to see the strategy and all the way in to understand what is actually happening in the data, the campaign or the donor experience. You'll own reporting and analytics across the client portfolio, lead Generosity Experience Roadmaps (GXR), become a trusted strategic resource for the team and clients and help build the next evolution of Generosity X's strategy function.

If you're a strong technical marketer who loves the craft, asks why the numbers moved rather than simply reporting that they did and wants the opportunity to build something, this may be your next step.

At a glance

- Organization: Generosity X
- Location: Remote; anywhere in Canada
- Reports to: Matthew Hussey, Founder
- Compensation: $105,000 to $130,000 CAD, depending on experience
- Application deadline: Open until a qualified candidate is hired
- Position status: New

About Generosity X Generosity X is a fundraising growth partner built on one belief: generosity is designed, not demanded. We partner with charities to grow annual giving through a combination of data, experimentation, strategy and thoughtful donor experience. We want to understand not only what caused someone to give, but why it worked and how we can build on that insight to make generosity happen again.

Our work brings together two things that are too often treated as opposites: the rigour of data and experimentation and the art of understanding real human behaviour. We work with charities that want to grow, which makes donor acquisition the cornerstone of all that we do.

Learn more: https://generosityx.com The Opportunity

Generosity X has grown to the point where we need another senior strategic mind who can bring technical depth and keep raising the bar.

This isn't a role where you'll sit above the details.

One day you may be looking across an entire donor program, spotting patterns and advising a client on where their strategy needs to go. The next, you may be deep in retention cohorts, reviewing an A/B test or improving how we use AI to generate reporting.

You need to be comfortable doing both.

You'll lead our Donor Experience function, own reporting and analytics across our client portfolio and be a senior strategic resource for our Client Experience Managers and clients.

You'll also be building something. There's no established strategy team waiting for you. At first, you'll be hands-on in the work while shaping the function, improving our systems and eventually building the team.

For the right person, that's part of the opportunity.

Key Responsibilities

Own the Generosity Experience Roadmap (GXR)

- Own the data analysis, financial forecasting and senior strategic lens for each GXR, working closely with the project lead and Client Experience Manager
- Look across the full donor experience while still being willing to get into the details
- Continuously improve the GXR and turn what we learn into a stronger, repeatable product for every client

Own reporting and analytics across the client portfolio
- Set the cadence, standard and substance of what a Generosity X report says about a client's year, quarter or campaign
- Personally work with the data rather than simply overseeing the process




- Own key measures across acquisition and retention, including cost per lead, lead-to-donor conversion, cost to acquire a donor by channel, retention by cohort, second-gift and monthly conversion, reactivation, revenue per thousand, mid-level giving and lifetime value by channel.
- Build forecasting and projections
- Prepare and present standard donor and retention reports to clients every two months, with additional quarterly, annual or board-level reporting as required for certain clients.

Be a strategic resource for the team
- Serve as a senior subject matter expert that Client Experience Managers can turn to when they're thinking through strategy, testing an idea or trying to solve a client problem
- Help the team move between the big strategic question and the tactical details required to execute it
- Teach and share your thinking so that the team's strategic capability continues to grow

Build and run the A/B testing roadmap
- Develop testing plans that move each client's marketing and fundraising forward
- Look beyond which version won and ask why it won
- Turn individual tests into broader learning that can strengthen work across the entire client portfolio

Understand the human behind the data
- Bring genuine curiosity about donor psychology and human behaviour to the work
- Look beyond dashboards and results to understand what may have caused someone to respond, give again, disengage or change their behaviour
- Use those insights to form hypotheses, design better tests and improve the donor experience

Own and evolve the HEARTS framework™
- Deepen the IP itself and build fluency across the team and our clients
- Help HEARTS become the shared language for how generosity experiences are interpreted and evaluated at Generosity X

Present and lead in the room
- Bring analysis into regular client reviews every two months, alongside additional quarterly reviews, annual strategy sessions, in-person strategy days, management presentations and board-level sessions as required.
- Translate complex analysis into a clear story and a practical path forward
- Be comfortable offering a point of view, explaining the evidence behind it and holding your position when appropriately challenged

Use AI to make the work better
- Step comfortably into AI-enabled reporting and strategy workflows already being used at Generosity X
- Look for opportunities to improve those systems rather than simply following them

Build what's next
- Help standardize offerings such as website audits and strategic roadmaps
- Build recent initiatives alongside the Founder
- Identify opportunities, solve problems and move ideas forward without waiting for a fully built playbook
- Help shape the strategy function as Generosity X grows

Eventually, build the team This is a new role and an emerging function. You won't walk into a large team on day one.

You'll begin by being close to the work yourself. As the function grows, you'll have the opportunity to help define the roles around you, coach the craft and build a team capable of carrying the work forward.

What We’re Looking For

You should bring





- 8+ years of relevant experience in fundraising, direct response or marketing strategy or 5+ years of strong agency-side experience
- At least 2 years of experience presenting to executives, boards or other senior stakeholders
- Strong technical marketing instincts and the ability to move comfortably between strategy and execution
- Confidence personally working with data and analysis rather than simply managing others who do it
- A solid grasp of acquisition economics: you know what a new donor costs, what they’re worth over time and when a channel pays back
- Experience with experimentation, testing and using results to shape future strategy
- Genuine curiosity about donor psychology and human behaviour. You want to understand why something worked, not just that it worked
- Experience using AI as part of real workflows, processes, analysis, automation or problem-solving, beyond basic chatbot use
- The ability to communicate complex analysis clearly and credibly to clients
- Comfort working independently in a fast-moving, remote and highly asynchronous environment
- Strong alignment with Generosity X's values

Previous people-management experience is welcome but not required. We're more interested in whether you have the capability and desire to grow into leadership as this function grows. You May Thrive Here If…

You can spend the morning on a three-year donor strategy and the afternoon working out why one campaign behaved unexpectedly.

When something works, you want to know why. New ideas and technology energize you.

You're comfortable moving things forward before every process is built.

At Generosity X, you'll have real autonomy. When the Founder asks, "How could we make this better?", you see it as collaboration, not criticism.

Most of all, you're ready to build this function from the ground up.

Overview of Benefits

- Three weeks of paid vacation
- Additional time off from December 25–31
- Health Spending Account and Wellness Spending Account
- Paid Fridays off from May 1 through the August long weekend, without moving to a compressed workweek
- Quarterly in-person retreats to connect, grow, learn and collaborate
- A culture where you're trusted to lead, not just execute

Working Conditions Generosity X has core collaboration hours of 9am-3pm, Mountain Time, and your working schedule will need to provide consistent availability during that window.

Travel of up to 20% should be expected.

While candidates across Canada will be considered equally, being located in Calgary may provide occasional opportunities to work alongside Matt in person.

How to Apply

Please upload your resume, and send your cover letter to [email protected]. We'd particularly love to understand why this role interests you and what you've built, tested or improved that you're proud of.

At Generosity X, we are dedicated to fostering a workplace culture that embraces diversity, equity, and inclusion. As an equal opportunity employer, we welcome and encourage applications from individuals of all backgrounds and abilities. Accommodations are available upon request throughout the recruitment process.

Artificial intelligence Statement: Vocare Union takes a personal, relationship-focused approach to recruitment. AI may support our work, while our recruiters make candidate assessments and recommendations. Generosity X may use AI to screen or assess applicants during its hiring process.

Vocare Union is the search team supporting Generosity X through this recruitment process.

📌 Head of Marketing Strategy & Insights (Canada)
🏢 Vocare Union
📍 Canada