About The Media Firm.
The Media Firm. is a Toronto-based content marketing agency specializing in high-performing content for premium brands across the Greater Toronto Area: real estate professionals, builders, and design-focused brands.
In addition to client work, we operate a growing real estate media platform with strong audience reach (100k+ followers) across Instagram, TikTok, and YouTube. This platform runs its own content pipeline (submissions, property content, brand partnerships) on the same operational standard we bring to every client account.
Role Overview
You run the lead generation, outreach, and automation operation for The Media Firm. You find the right people, build the system that works them, and develop the relationships that turn cold contacts into long-term partners.
The foundation is in place. Your job is to organize it, expand it, and run it. That means sourcing and generating leads, building and managing drip campaigns, running email and text outreach and automation sequences, maintaining pipeline hygiene, and handing qualified relationships to leadership at the right moment.
The primary audience is real estate agents, brokers of record, and brokerages across Canada. Everything else is secondary: contractors, construction professionals, custom home builders, pre-construction developers, interior designers, architects, landscape designers, mortgage professionals, brand partners, influencers, and potential sponsors. You understand the difference in value and path for each profile and bring clear recommendations on how to approach them.
Bonus scope: email newsletter management for the platform.
You own this function. You lead the strategy and execution. Leadership stays in the loop to ensure everything aligns with the brand.
Core Responsibilities
System Architecture and Foundation (AI-Assisted)
- Audit and organize the existing CRM structure across Follow Up Boss (GTA) and Instantly.ai (national), then build it out properly from there
- Build and maintain a clean contact tagging structure so every lead is organized by location, profile type, and relationship stage
- Use Claude to map automation logic before activating it: what triggers what, what follow-up applies to each segment, and what a qualified hand-off looks like
- Document your system and present it for alignment before execution begins. Come with a complete recommendation, not a question
Outreach Execution and Pipeline Management (AI-Assisted)
- Source and generate leads from realtor.ca, Clay, and other channels. Route every contact into the correct platform with the correct tags from day one
- Run cold email and text outreach through Instantly.ai for national contacts. Manage GTA contacts through Follow Up Boss
- Use Claude to personalize outreach at scale: sequence writing, lead research, contact analysis, and message refinement
- Build and manage drip campaigns and automation sequences that reflect where each contact is in the relationship
- Maintain clean pipeline records: no duplicates, no stale tags, no contacts sitting in the wrong stage
Optimization and Reporting (AI-Assisted)
- Track performance at the sequence level, segment level, and contact level
- Use Claude to surface patterns in engagement and conversion data. Bring the analysis and the recommended fix together, do not wait to be asked
- Identify high-value contacts across multiple opportunities and flag them for expanded outreach
What We're Looking For
- Proven experience in lead generation, outreach, or CRM work with results you can speak to specifically: not what you managed, but what it produced
- Strong systems thinking: you can design a contact structure and automation workflow before executing it, not after the fact
- Hands-on experience with cold email and automation platforms such as Instantly.ai, Apollo, Lemlist, or similar
- CRM fluency in Follow Up Boss, Go High Level, HubSpot, or equivalent: you can build pipelines, set up automations, and keep records clean without being trained from scratch
- Daily, fluent use of Claude or comparable AI tools as a core part of your workflow. This is not a bonus skill, it is the foundation of how this role operates
- Organized, proactive, and self-directed. You manage your own pipeline, flag issues before they become problems, and deliver without hand-holding
- You treat the work as yours. When you find a problem, you come with the recommendation, not just the observation
Bonus Experience
- Direct experience with Follow Up Boss or Go High Level automation workflows
- Background in real estate, real estate media, or working alongside agents and brokerages in Canada
- Experience building and scaling outreach systems from scratch, not inheriting a built one
- Existing relationships in the Canadian real estate or home industry
- Email newsletter management experience
Compensation
Commission-based. Structure and earning potential will be discussed during the interview.
Why Join The Media Firm.
- Own a function that sits at the center of a growing media platform with 100,000+ followers and an expanding roster of industry professionals across Canada
- Work inside an AI-first operation built for speed and output
- A flexible, remote role with real earning potential tied directly to your performance
- A path to expanded scope and growth for the right person who delivers
Send a short note on your outreach and automation background and why this role interests you. Generic applications will not be reviewed.
Pay: $17.20-$24.50 per hour
Benefits:
- Casual dress
- Company events
- Work from home
Application question(s):
- Share one specific example of a lead generation system or CRM workflow you built from scratch. Not managed. Built. Include the tools you used and the results it produced.
- Describe one specific way you have used Claude or another AI tool in your outreach work. Name the task, what you asked the AI to do, and what you changed or added yourself.
- You are stepping into an outreach operation that has a foundation but needs to be reorganized and expanded. Before you contact a single lead, what do you fix or build first and why?
Experience:
- Lead generation: 2 years (required)
- CRM software: 1 year (required)
- Email marketing: 1 year (required)
- Lead Automation: 1 year (required)
Work Location: Remote
