Founding GTM Associate

The Opportunity

Charitability builds finance-first and intelligence-first automation tools for local governments, funders, and mission-driven institutions. We've been operating for multiple years in this sector, with real revenue and a growing client base across multiple product lines.

Preside (getpreside.ai) is an AI-powered intelligence layer on top of municipalities' existing systems of record — making council minutes, bylaws, agendas, and institutional knowledge searchable in natural language with source citations. Preside is live with test cities and actively expanding across Ontario.

Financial Viability (financialviability.ai) is an ML-powered financial risk and organizational monitoring system for funders, social finance lenders, and grantors — helping the institutions that deploy capital to non-profits understand the financial health of the organizations they fund.

Our childcare suite serves the municipal Service System Managers (SSMs) across Ontario who administer public child care funding under Canada's CWELCC program — covering more than 30% of all cities in Ontario, with clients collectively managing over $350 million in funding. The suite includes our financial reconciliation platform, a multi-site operator reporting tool, and what we believe is the only municipally deployed agentic financial cost audit system in Canada.

Preside and Financial Viability will be your highest priorities as our first GTM hire. You'll also help us scale the broader portfolio. You'll work directly with the co-founders to own outbound, content, events, vendor list strategy, and growth experimentation — using the best AI tools on the planet as your co-workers.

That's the deal: more ownership, more impact, more risk, more upside.

What You'll Work On

Scaling Preside's outbound motion. We have live outbound email sequences running to clerks, CAOs, and directors at Ontario municipalities. You'll own the day-to-day: wave orchestration, A/B testing messaging, reply triage, and reporting on what's working.

Building Financial Viability's early demand generation. New product, new audience (foundations, social finance lenders, community foundations, grant program administrators). You'll help shape how we introduce this product to the market — content, outreach, association engagement, and early conference presence.

Vendor lists, procurement registrations, and institutional channels. Selling to municipalities and foundations means navigating vendor registration systems, procurement portals, and sector associations. You'll own getting us listed and building relationships with the gatekeepers.

Events and field marketing. Municipal conferences, sector conferences for foundations and social finance, procurement showcases, and targeted roundtables. You'll scope, plan, and execute our event presence.

Content that compounds. Case studies from real deployments, thought leadership for municipal clerks and CAOs, financial health frameworks for funders. You'll draft, iterate with AI, and publish — always grounded in what we've learned from real customers.

Building the GTM system itself. Just as our engineering team builds agentic development workflows, we want our GTM function to be AI-native from day one. You'll help build automation pipelines for lead research, personalization, reply handling, and experimentation tracking.

Who You Are

This role is defined less by your resume and more by how you think about going to market in 2026. We're not looking for someone who just uses AI tools. We're looking for someone who builds their entire workflow around them — and who understands that selling to mission-driven institutions is a fundamentally different game than selling to commercial software buyers.

The Non-Negotiables

* You live in AI tools. Claude, ChatGPT, Gemini, Grok — not as writing assistants, but as thought partners, research agents, and automation layers. You use them to build strategies, analyze markets, draft sequences, and automate the boring parts of your day.

* You understand institutional buying. Selling to a city clerk is not selling to a startup CTO. You get that decisions take time, require multiple stakeholders, and are shaped by procurement rules rather than feature demos. You're energized by long cycles and relationship sales, not frustrated by them.

* You think in experiments. You're our first growth hire. We don't know the exact right way to win these markets — we're exploring and experimenting. You thrive on hypothesis-driven outreach, small bets that compound, and the discipline to measure, learn, and iterate. You don't just ship activity.

* You have extremely high agency. Nobody is going to tell you what to work on every day. You'll be given priorities and outcomes, and you'll figure out the path. You're comfortable with ambiguity and wired to make progress without hand-holding.

* You know how to write well — and how to edit. A lot of this work will be done in partnership with AI. That makes your taste the bottleneck. You can tell the difference between a good sentence and a bad one, between a convincing pitch and a generic one, and you'll push back on AI output until it's right.

* You're thoughtful about digital channels. You don't assume digital ads are the answer to every problem. For the markets we sell into, they usually aren't. You're skeptical of generic growth playbooks and curious about what actually works in regulated, institutional sectors.

What Sets You Apart

These aren't expected for a new grad — but any of them will catch our attention:

* A public policy, public administration, political science, MPA, nonprofit management, or journalism background — or anything that has given you a real understanding of how government or mission-driven organizations operate from the inside.

* Student government, campaign volunteering, nonprofit co-ops, or civic engagement. Signals that you find institutional work interesting rather than exhausting.

* Any experience running outbound campaigns — even for a student org, a side project, or a cause. If you've touched Instantly, Apollo, Clay, or Lemlist, tell us.

* Content creation you're proud of. A newsletter, a blog, a podcast, a social following — any sustained writing or publishing practice.

* You're drawn to meaningful civic work and excited about joining a company doing genuinely innovative things in a space that actually matters.

Why Charitability

* Real impact. Every customer you help us land is a municipality that runs more efficiently, a funder that makes better decisions, or a non-profit that gets better support. This is civic tech that actually matters.

* Foundational role. You're our first dedicated GTM person, building the playbook with the co-founders from scratch. Your decisions will shape how we sell for years.

* AI-native GTM at the frontier. Our engineering team is building one of the most advanced agentic AI products in regulated government markets. You'll have the same mindset and tooling available on the GTM side. The goal is a GTM function that operates at the scale of a much larger team — because the AI is doing the leverage.

* Path to permanent. This role is structured as a 6-month fixed-term contract with a clear conversion path to a permanent role, including equity, based on performance and company growth. We're not hiring you to do a short project — we're hiring you hoping you'll stay and grow with the company.

How to Apply

Apply here: https://script.google.com/a/macros/charitability.ca/s/AKfycbz1qzRmKcDXsvZTqQqoxVtxrCZ9sY6W4zZBUlS37skk5NqQ9NE6dgk5k5wOBSpV7tvZ/exec

You'll answer three short questions — the same ones we'd ask in a first call — plus a few quick multi-selects so we can learn about your background, the tools you use, and how you think about AI. We don't need a cover letter, just a resume.