Founder Associate – Content, Technology & Operations

$60,000–$80,000 + performance incentives | Full-time | Primarily in person

You may be surprised to find this opportunity on Indeed - we almost did not post it here.

Most of our search is happening privately through investors, executives and strategic business partners. But exceptional people do not always come through the obvious channels, so we decided to cast the net wider.

Want to hear directly from the person you would be working with?

A short message from Rae Ostrander, Founder & CEO:

https://drive.google.com/file/d/1Xi8uA8nJg1OI-gKjCfqLn43qSZzRQWmH/view?usp=sharing

We are looking for one highly driven, highly resourceful person to work closely with the founder and CEO of Contrast Asset Management and Tortoise.

This is not a traditional assistant role.

You will help build the infrastructure around a growing founder-led business — content, video, technology, AI, investor experience, research, projects and executive operations.

That may mean setting up a studio, building a better content system, helping develop what we should be talking about, improving a CRM process, supporting an investor, organizing an event, researching an idea or taking something that is still half-formed and helping turn it into something real.

You do not need to arrive knowing how to do all of it. You do need to want to figure it out.

What are we building?

At Contrast, we invest in multifamily real estate and believe strong returns come from better operations, better decisions and better execution.

Through Tortoise, we are building something broader around investing, financial education and personal growth.

The traditional financial path is becoming harder for a lot of people.



Home ownership is increasingly out of reach. Inflation can quietly erode progress. And some of the strategies people were told to rely on simply are not producing the financial outcomes they expected.

Over 25 years of operating an investment company, we have never been particularly interested in the conventional financial playbook because, even when it worked, it was not always the best way to obtain meaningful and life-changing results.

Today, the problem is bigger.

The old playbook was never perfect. For a growing number of people, it may no longer be enough.

Our founder has also worked with Robert Kiyosaki and other financial education and training organizations, helping shape an approach that challenges conventional thinking around investing, financial independence and how people build long-term financial security.

We believe there is a real opportunity to take that experience, combine it with new technology, better education and better investment options, and build something both meaningful and highly successful.

This should matter to you personally too. We are not looking for someone to simply create content about investing, financial education and personal growth from the sidelines. We want someone who is genuinely interested in improving their own financial future. Someone willing to learn, test ideas,



challenge assumptions and put some of what we teach into practice.

You do not need to arrive as an expert. But you should want to become much more knowledgeable than you are today. The best communication does not come from memorizing the message. It comes from understanding it, believing in it and living enough of it to know why it matters.

Who are we looking for?

Someone ambitious enough to want responsibility.

Curious enough to keep learning.

Confident enough to have an opinion.

Humble enough to change it.

Someone great with people, comfortable with technology, interested in business and energized by creating something that did not exist before.

Someone who actively seeks feedback and wants to improve not only at work, but as a person.

Our culture is closer to a high-performance team than a traditional corporate office.

High standards. Low bureaucracy.

We want to compete, improve and perform — and we want people around us who want the same.

Starting compensation is $60,000–$80,000 plus performance incentives.

Create value, take on more responsibility and your opportunity should grow with it.

If this sounds unusually interesting for something you found on Indeed, we would like to hear from you.

Apply with your resume or LinkedIn profile and tell us one thing:

What about this opportunity made you want to learn more?

Pay: $60,000.00-$80,000.00 per year

Application question(s):

- In 2–4 sentences, what specifically about this prospect made you want to apply?
- Are you able to work full-time, primarily in person in Cambridge Ontario?

Work Location: Hybrid remote in Cambridge, ON

📌 Founder Associate – Executive Support, Content & Technology (Cambridge)
🏢 Contrast Asset Management
📍 Cambridge