Chief Executive Officer (Fundraise-First) (Canada)

Chief Executive Officer (Fundraise-First) (Canada)

17 Aug
|
Icons of Real Estate
|
Canada

17 Aug

Icons of Real Estate

Canada

JOB TITLE: Chief Executive Officer (Fundraise-First)

COMPANY: Icons of Real Estate

LOCATION: Remote — Latin America or Eastern Europe strongly preferred

EMPLOYMENT TYPE: Full-Time

ABOUT ICONS OF REAL ESTATE

Icons of Real Estate is a fast-growing podcast production platform and SaaS marketplace serving real estate professionals across the United States. We operate 100+ active podcasts, book approximately 100 agent guests per week, and run a two-sided marketplace connecting podcast hosts with real estate agent guests. Our platform (The HUB) manages the full production and booking pipeline for our clients.

We're a lean, profitable, remote-first business with a clear strategic vision: scale aggressively and position the company for a significant exit with the right strategic acquirer in the real estate technology space.

THE OPPORTUNITY

This is not a typical CEO hire.

We are looking for an experienced operator who wants to step into a CEO role, spearhead a $1M growth raise as their first act, and then run the company through to a strategic exit — with a meaningful financial reward tied to the outcome.

Here's the structure:

- Phase 1 (0–4 months): You lead and close a $1M growth round within 120 days, leveraging your existing investor relationships and ours. During this phase, we provide a $2,000–$3,000/month draw to keep you focused exclusively on this role. Upon successful close of the round, you receive a $40,000 milestone bonus paid immediately.
- Phase 2 (post-raise): Full-time CEO role kicks in at $8,000–$9,000/month base salary, funded from the raised capital.
- Exit bonus: A meaningful performance bonus tied to the company's sale price, structured as a percentage of proceeds above a baseline valuation. On a strong exit, this is a life-changing number.

This structure is intentionally designed for someone who is motivated by upside and outcome — not salary. If you need a market-rate base salary from day one, this is not the right fit.

WHAT YOU WILL DO

- Spearhead and close a $1M growth round within 120 days,



leveraging your existing investor relationships
- Take full operational ownership of the business — team, platform, clients, and growth
- Work directly with the founding team to execute the growth strategy: paid acquisition, product development, and partnerships
- Drive the company toward a strategic acquisition, managing relationships with potential acquirers and M&A; advisors
- Build and lead a distributed remote team across multiple time zones

WHAT WE ARE LOOKING FOR Non-negotiables:

- You have personally been through at least one company acquisition, ideally on the sell side — you know what due diligence looks like from the inside
- You have direct experience raising capital — angel, seed, or growth round — and have active investor relationships you can activate
- You have run a lean remote team of 5–20 people and are comfortable operating without a large support structure
- You are available to commit full-time to this role

Strongly preferred:

- Background in SaaS, media, marketplace, or real estate technology
- Based in Latin America or Eastern Europe (for time zone compatibility with an Australian founding team and US client base)
- Existing network in the US real estate or proptech space

WHAT YOU GET

- $2,000–$3,000/month draw during the fundraising phase (Phase 1)
- $40,000 milestone bonus paid immediately upon successful closing of the funding round
- $8,000–$9,000/month base salary (post-raise)
- Meaningful exit bonus tied to sale proceeds above a baseline — structured to reward growth you create, not the value already built
- A transparent, defined path to a significant exit event within 12–24 months
- Full operational authority to run the business

HOW TO APPLY Send a message or apply here. Please include a short note covering:

1. One raise you have personally led or co-led (amount, structure, outcome)
2. One acquisition you have been part of (your role, outcome)
3. Why this specific structure appeals to you

Send to [email protected] We are moving quickly. First conversations will happen within the week.

📌 Chief Executive Officer (Fundraise-First) (Canada)
🏢 Icons of Real Estate
📍 Canada

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