Montreal Outreach Plan

The execution plan for the discovery outreach defined in the Montreal Nonprofit Market Analysis (section 7). The market analysis holds the strategy and target list; this document holds how we are actually reaching people, the active tracks, and the field materials.

Approach: warm paths through personal connections, in-person conversations, and door-by-door reconnaissance. No cold email. Chip's Montreal network is the primary channel; LinkedIn is used to reach bridge people, never to cold-message community-sector directors.

Goal: five discovery conversations covering both beachhead segments, at least one umbrella body, and one funder-side voice. Every conversation runs the 10-question discovery script from the market analysis. Kill criteria from section 7.3 apply.

Started: July 29, 2026.

1. The Five Conversation Slots

Funder-side backup: Fondaction impact investments contact, or Centraide via referral once slot 1 resolves.

2. Operating Rules

These came out of the first outreach cycle and apply to all future messages.

1. Warm beats cold, always. A first-degree connection never spoken to is still cold; prefer an intro through someone who knows both sides.
2. Forwardable-note pattern for intros. Ask first ("can you intro us?"), and only after the yes send a short note the connector can forward as is. Never send the note before the yes. The connector adds their own endorsement line on top; the note carries the facts they would otherwise get wrong.
3. One ask per message with busy connectors. Follow-up asks (introductions to other organizations) wait until the first ask is resolved.
4. No calendar link in a first message. The link goes in the second message, after they agree, as a courtesy. For senior contacts, propose two or three concrete times instead of a link.
5. French by default for community-sector and social economy contacts. English only where the contact's own presence is anglophone.
6. Research framing, not sales. Every first conversation is framed as learning how organizations report to funders. The product is one transparent sentence, then questions. Demo only if asked, live, never as something they can use tomorrow.
7. Dose the pipeline. About three new asks at a time; open a new track when an active one goes quiet for 3 to 4 days. This sector is small and networked; volume reads as spray-and-pray.

3. Active Tracks

Track 1: YMCAs of Québec (Pascale Audette, President and CEO)

The largest multi-program community organization in the province (~$51M revenue, 950+ staff, 71,000+ people served a year), one year into a strategic refocus, holding federal (IRCC), provincial, Centraide, and foundation funding at once. The CEO is tech-native (Disney, Behaviour Interactive, Carebook, AgeTech Capital, Real Ventures investment committee), which makes this a peer conversation about impact measurement from the buyer's top floor.

Angle: how a $51M org proves impact across four funder types; what she wished nonprofits could show her when she was on the investing side. Not a sales target; the value is the funder map, sector intros, and possibly a program-level pilot much later (the ZAD newcomer-youth program and employment services fit the measurement model best).

Track 2: Communautique (Cassie Rhéaume, Executive Director)

Communautique's mission is digital adoption in the Quebec community sector, which makes its ED the single best-placed person to explain why software succeeds or dies inside an organisme communautaire. New in the role (March 2026), previously ED of TECHNOCompétences.

Angle: the tech-adoption failure map (budget, French, staff digital literacy, board approval), a direct test of the French-admin blocker from the market analysis, and a credibility bridge into RIOCM and TIESS circles. Communautique is also a plausible distribution partner in the network-pricing model.

Track 3: PME MTL économie sociale (Javier M. Vaquero)

Five years directing social economy financing at PME MTL (2020 to 2025), previously entrepreneurship coordinator at a Carrefour jeunesse-emploi. He has read the grant applications and annual reports of the exact organizations in the Tier 1 list, from the funder's chair.

Angle: does measured impact actually move financing decisions; what insertion enterprises really track about trainees and in what tools; named referrals into CEIQ members and the CJE network. This track can fill conversation slot 4 by itself.

Log.

• July 29: French LinkedIn DM sent. Warm reply the same day, on paternity leave, reconnect end of August.
• August 18: follow-up with the Sondely link and the calendar. Booked September 2, postponed for health, rebooked for September 4.
• September 4: in person, about 50 minutes. The conversation covered how PME MTL evaluates and finances social economy enterprises, so the funder-side questions of the brief are answered and are not asked again.
• September 9: he sent, unprompted, the list he had promised. Social economy enterprises: Insertech, Cuisine Collective Hochelaga-Maisonneuve, La Transformerie, Cyclo Nord-Sud, Théâtre Denise-Pelletier. Funders: PME MTL, RISQ, Fiducie du Chantier de l'économie sociale, Cap Finance, Fondaction. Impact bodies: Sillons, Fondation McConnell, Fondation Saputo, Fondation Chagnon. He knows the organizations and offered to help with whichever one Chip picks.
• Read against the market analysis: Insertech (CEIQ member, computer refurbishing, Centraide-funded) and CCHM (insertion enterprise, 14-month program, RISQ-financed) are beachhead segment 1 and Tier 1. The other three enterprises are outside the target segments. The funders and foundations are the funder-side backup and can be approached directly; Sillons is a methodology body closer to TIESS than to a funder.
• September 16: reply sent asking for one thing, an introduction to Insertech's direction for a 30-minute research conversation on how they follow participants and report to funders. One ask per message; CCHM waits for this one to resolve. Message text in the CatalyzeUp inbox (javier-insertech.md).

Track 4: Connector (Sylvain Carle)

Personal relationship; ex-Real Ventures, now impact investing. Carries the Track 1 intro. Once that resolves, one follow-up ask: contacts at Centraide, TIESS, or Fondation du Grand Montréal. His investor view on the funder-pays and network-pricing hypotheses is also worth capturing.

4. Door-by-Door: Reconnaissance Routes

Walk-ins are reconnaissance, not the meeting. The goal at each stop: see the waiting room, note the funder logos and the languages on the walls, and leave with the name of the direction générale plus a reason to follow up. Best window: Tuesday to Thursday, 9:30 to 11:30 AM. Bring nothing to sell.

Front-desk line: "Je développe un outil de mesure d'impact pour les organismes communautaires, je suis de Montréal, et je veux comprendre comment les organismes rendent des comptes à leurs bailleurs avant de finir le produit. J'aimerais parler à la direction. Est-ce que je peux laisser mes coordonnées?"

Cluster A: La Petite-Patrie (metro Beaubien), the umbrella cluster

If Track 3 produces a CEIQ name first, use it; a referenced visit beats a cold one.

Cluster B: Centre-Sud, homelessness and youth

Cluster C: Settlement direct targets

Downtown bonus when nearby: YES Employment + Entrepreneurship, 666 rue Sherbrooke Ouest, suite 700. Anglophone, Tier 1, and a natural skills-volunteering entry (founder mentoring).

What to observe at every stop

• Funder logos posted (Centraide, PSOC, city, foundations): who they report to
• Languages on posters and forms: the translation reality on the ground
• Waiting room traffic: program scale
• Bulletin board: current programs, AGA dates, hiring
• Whether the front desk knows how outcomes are tracked (sometimes they just say)

Sequencing: Cluster A first, Cluster C second, Cluster B third, YES opportunistically.

5. The Helping-Hands Route

Slower, deepest discovery: skills-based volunteering instead of job applications. Three forms that fit this sector:

1. Founder mentoring at YES Montreal or a Carrefour jeunesse-emploi (their programs recruit exactly this profile).
2. Tech/data volunteering for one organization during funder-report season, which means seeing the actual spreadsheet they file.
3. Board service: small orgs recruit tech-profile board members at their fall AGAs.

This route produces the most honest relationship with the sector and the ground truth on reporting pain, at the cost of speed.

6. Conversation Protocol

Every discovery conversation runs the 10-question script from the market analysis, section 7.3. Answers are recorded verbatim, one row per organization. Per-contact briefs (who they are, tailored questions, landmines) are working documents kept outside this docs site, alongside the live track status.

After 10 conversations: review against the kill criteria and update or rebuild the segment priorities in the market analysis.

7. What Outreach Must Not Outrun

From the market analysis, restated because it gates everything: discovery conversations can run now, but no paid pilot until the gating release ships (French/Spanish admin console, localized notification emails, PDF export; see Platform Localization). The two highest-leverage demo gaps to close in parallel: side-by-side attempt comparison UI and a Program Impact Baseline template.