Co-Founder and Chief Technology Officer (CTO)

R Labs; Toronto; Hybrid; CAD 250,000 +; Full time

Job summary

A leading venture builder in Toronto is seeking a visionary Co-Founder and CTO to launch Proptimize, an AI-powered platform designed to enhance commercial property development. You will be responsible for architecting the technology, leading product development, and ensuring effective market alignment. This hybrid role offers equity ownership and the chance to make a significant impact on housing affordability in Canada.

Benefits

Equity ownership through founders’ shares

Monthly stipend as Entrepreneur in Residence

Access to funding and mentorship

Qualifications

• Proven track record of successfully building and scaling technology platforms.
• Experience architecting complex data integration systems.
• Strong background in AI and ML, particularly in generative design.

Responsibilities

• Architect the core technology platform.
• Lead AI and machine learning development.
• Automate proposal generation.

Skills

Machine learning and AI

Generative BIM

Complex data integration

Geospatial technology

Full-stack architecture

Real estate or construction tech experience

Job description

Who we are

At R-LABS Canada Limited Partnership (“R-LABS”), we build purpose driven companies to solve major problems in real estate and housing. We are launching our next innovative company, Proptimize (currently in stealth mode). To do so, we need an innovative Co-founder to partner with us to take this venture to the next stage.

This posting is not for an employment role at R-LABS, but an opportunity to co-found a new company created through our venture building model. Founders will act as Entrepreneurs in Residence (EIRs) until the new startup is incorporated. This is a hybrid role.

What we need

We are looking for a visionary Co-Founder and Chief Technology Officer (CTO) to lead the development and scaling of Proptimize. You will validate and launch Proptimize, a new venture with the mission to empower commercial property owners to maximize the value of their assets, while playing a meaningful role in solving Canada's housing affordability crisis. This is a rare opportunity to partner with a leading venture builder to launch a new company from the ground up, guiding it through validation, funding, and commercialization.

Today, many property owners want to unlock the full potential of their properties for future generations, but often do not know what can be built under current zoning, what financing options are available, or which trusted redevelopment experts to work with.

Proptimize is an AI-powered technology platform designed to solve these problems by integrating complex real estate datasets and bi-directional API integrations with our industry partners to automatically determine the highest and best use of properties through scenario analysis and optimization using generative BIM design to produce financial proformas complete with construction costs and timelines. The platform will automatically generate detailed proposals that brokers and developers can present to commercial property owners while seamlessly connecting qualified project leads to trusted redevelopment partners, including architects, builders, lenders, and entitlement consultants.

As Co-Founder and CTO, you will be the technical visionary behind the company, responsible for architecting and building the core technology platform, leading product development, and establishing the technical foundation for scale. You will work in close collaboration with R-LABS and an experienced network of investors, industry experts, and real estate professionals.

This is a hybrid role working 2-3 days per week onsite at our office by Union Station.

Who you are

You are a technical leader and strategic thinker, with a proven track record of successfully building and scaling technology platforms. You have experience architecting complex data integration systems, scenario modelling and optimization to solve real-world problems. You have a strong background in AI and ML, particularly in generative design, computer vision, or spatial analysis that positions you to revolutionize how real estate development decisions are made.

You have experience making strategic technology decisions that drive innovation and business growth. You excel in translating complex technical concepts into business value, building and leading high-performing engineering teams, and creating scalable technology architectures. Your approach combines deep technical expertise with the ability to execute complex projects and deliver results.

Ideally, you have subject matter experience in proptech, construction technology, GIS and mapping platforms, or real estate data analytics. You understand the intricacies of municipal data, property analysis, and development planning. You have a strong network in the technology space, with established relationships among data providers, technical talent, and technology partners.

Above all, you are passionate about emerging technologies, real estate innovation, and the opportunity to create a meaningful impact on housing affordability. You are driven by the chance to transform how redevelopment decisions are made using artificial intelligence and generative design.

What’s in it for you

Purpose and impact. This is a rare opportunity to build transformative technology in an industry primed for disruption. Proptimize will leverage the most advanced AI and generative design technologies to revolutionize how property development decisions are made, directly impacting housing affordability across Canada.

Influence. You will shape our Minimum Viable Product (MVP) from day one. Within your first three months, you will lead the development of a prototype that takes a real property, analyzes its zoning, creates two to three redevelopment options, runs the financials, and generates a clear, client-ready proposal. Your technical stack will involve integrations with tools like Dynamo, GIS, Revit, and machine learning frameworks. You will build this foundation alongside our partners at R-LABS.

Equity and compensation. As a Co-Founder, you will receive equity ownership through founders’ shares, ensuring that your contributions are directly tied to the success of the company. During the initial development stages, you will receive a monthly stipend as an Entrepreneur in Residence (EIR). Additionally, you will earn a competitive salary once the company is incorporated.

Support and stability. You won’t be building alone. Proptimize is supported by R-LABS, an experienced venture builder in real estate innovation. You will have access to funding, mentorship, and strategic resources from day one.

As Co-Founder and CTO, you will:

• Architect the core technology platform. You will design and build Proptimize’s AI-driven platform, integrating datasets including parcel fabric, zoning regulations, modular housing component configurations, construction costing, city utility footprints, market data, permits and approvals, and macroeconomic indicators.
• Lead AI and machine learning development. You will develop and deploy ML models that perform the highest and best use analysis, generate generative BIM design options, and build accurate financial proformas with construction cost modelling.
• Automate proposal generation. You will build systems that automatically produce investor-grade proposals that brokers and developers can present directly to landowners, streamlining the entire redevelopment pipeline.
• Establish data partnerships and integrations. You will build relationships with municipal data sources, real estate data providers, modular housing construction partners, and construction cost databases to ensure access to robust and reliable data feeds.
• Build and lead the engineering team. You will recruit and oversee your team, including full-stack developers, ML engineers, data engineers, and DevOps specialists, to bring the platform to market.
• Drive product innovation. You will shape the technical evolution of the Proptimize platform, ensuring it aligns with market demand and scales effectively.
• Ensure platform reliability and security. You will establish a robust cloud infrastructure and security protocols to ensure platform reliability, performance, and data integrity at scale.
• Be the public face of the technology. You will communicate Proptimize’s technical capabilities and vision to investors, partners, and industry stakeholders, building credibility and visibility for the company’s technology leadership.
• Invest in success. Once incorporated, you will have the opportunity to further invest in Proptimize and benefit from its growth and success.

Technical expertise you bring:

• Machine learning and AI. Experience developing, deploying, and scaling ML models, particularly in generative design, computer vision, or spatial analysis
• Generative BIM. Proficiency with parametric modelling, Building Information Modelling (BIM), and automated design generation
• Complex data integration. Ability to unify and process large, heterogeneous datasets across varied formats and sources
• Geospatial technology. Experience with GIS platforms, spatial databases, and location-based analytics
• Full-stack architecture. Expertise in designing and scaling cloud-based systems, APIs, and data pipelines
• Real estate or construction tech experience. Experience with proptech platforms, site planning, massing studies, zoning and permitting systems, and redevelopment workflows

Join us.

We welcome and appreciate candidates with a range of backgrounds and experiences, including women, persons with disabilities, Black, Indigenous and People of Colour (BIPOC), the LGBTQ2SIA+ community, and other equity-seeking groups.

If you have 70% of the qualifications we are looking for, express your interest here. Please let us know what accommodations or assistance we can provide you during the application process by emailing [e-mail], and we will be happy to assist you.

What you can expect from our interview process:

• A virtual interview with a Talent Advisor to discuss your interest in joining Proptimize as a CTO and Co-Founder.
• A technical deep-dive session with the Head of Technology of R-LABS and technical advisors to discuss platform architecture and AI/ML approach.
• An in-person interview with the Managing Director from R-LABS to explore technical vision and team fit.
• An opportunity to complete two assessments: Clifton Strengths to identify your natural talents and Kolbe to evaluate how you apply these strengths in action.
• A final in-person interview with the CEO and Co-Founder of Proptimize, and CEO and Founder of R-LABS, to address any remaining questions and finalize partnership terms.

About R-LABS.

R-LABS (“Our Labs”) is a partnership of innovative corporations and game-changing entrepreneurs focused exclusively on problems in real estate and housing. Through our proprietary venture-building platform, R-LABS co-creates and helps cultivate companies with new business models to generate a positive impact on the community and build considerable value. R-LABS = Return on Society + Return on Investment.

The only one of our kind, R-LABS is the real estate industry’s venture-builder. Innovation is a crucial part of our operation, and is central to our ecosystem focused on making a sustainable high impact. We are a startup factory launching and supporting fast-moving companies that benefit from our expertise, networks, funding and leadership. Real estate and housing are essential to everyone but have complicated challenges that require innovative action. We draw upon granular insights and deep knowledge to address the many interrelated industry problems to bring about transformative change.

For more information about R-LABS, their ventures, partners, and teams, please click here.

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