4 Chief Technology Officer jobs in Mississauga

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 , 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.

#LI-Hybrid 
 #LI-DNI

Powered by JazzHR

ZsW8F7mYUS

• 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.

• 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

• 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.
. click apply for full job details

ABOUT THE CITY OF TORONTO

The City of Toronto is the fourth-largest city in North America and the fourth-largest government in Canada, with a highly diverse and multicultural population. In addition, the City of Toronto has several agencies and corporations, including the Toronto Police Service, Toronto Public Library, and the Toronto Transit Commission, which make up the broader municipal organization.

Consistently ranked one of the world’s most livable cities, Toronto is home to more than 2.9 million people whose diversity and experiences make this great city Canada’s leading economic engine and one of the world’s most diverse and livable cities.

THE OPPORTUNITY

Toronto is a global leader in technology, finance, film, music, culture, and innovation, consistently ranking at the top of international rankings due to investments championed by its government, residents, and businesses. In its pursuit of modernizing City services through strategic investment, digital transformation, and a culture of innovation, the Technology Services Division collaborates with all City Divisions, agencies, boards and corporations to deliver client-centric business solutions and secure, reliable IT infrastructure.

Embarking on a transformative journey, the Technology Services Division is reshaping its culture and service delivery approach, focusing on four key priorities:

1.   Lead the delivery of digital transformative technologies through modern enterprise capabilities with resilience across public and divisional-facing platforms

2.   Deliver User-Centric Solutions: Provide end-to-end solutions that provide ease of use and are accessible and flexible in serving the needs of the public

3.   Harness data to drive action and engagement across platforms, processes and experiences

4.   Empower Stakeholders: Engage and empower teams to foster a culture of agility and innovation while driving platform /product roadmaps

Reporting directly to the Chief Technology Officer, the Deputy Chief Technology Officer, Digital Business and Enterprise Applications, brings hands-on experience with Agile delivery, DevOps, and building modern, scalable digital systems. You'll be leading the development of digital platforms that support both internal operations and the services residents rely on every day, while leading the platform and architecture roadmap to deliver on our vision.

Beyond digitizing our services, you will shape the City’s digital delivery approach, drive enterprise transformation, and embed a strong culture of excellence and continuous improvement. Your work will improve the digital experience and journey for both staff and the residents of Toronto.

IDEAL CANDIDATE PROFILE

The successful candidate will be a visible, hands-on leader with a deep understanding of delivery digital transformation at scale. They will bring empathy, curiosity and a collaborative spirit, with the ability to engage deeply with both technical and non-technical teams, ask the right questions and build trust across a large, complex organization. This role requires more than setting direction; it calls for someone who actively shapes the path forward with their teams, translates strategy into action, clarifies expectations and ensures real progress on transformation initiatives.

This is not a traditional, policy-focused leadership role. It is executional and delivery-driven. The ideal candidate is politically astute, comfortable in high-accountability environments and skilled at aligning with peers across departments while navigating sensitivities around contracts, governance and council priorities. They must be able to coach cross-functional teams, develop delivery capability and shift the culture from a transactional service model to one of shared ownership. This is a role for a seasoned leader who leads by doing, builds credibility quickly and demonstrates what is possible through both vision and action.

The Deputy CTO will have significant autonomy to shape priorities and lead change, supported by a talented team of over 200 technology professionals. This is a senior leadership role with broad influence across the organization and the opportunity to directly impact service delivery for millions of residents.

KEY RESPONSIBILITIES

Digital Delivery and Agile Systems Leadership:

·   Drive the design, build, and continuous delivery of digital systems and platforms that power core city services.

·   Champion Agile, DevOps, solution design and development capability to accelerate delivery while building team capabilities, modern development practices and platform maturity.

·   Build out and execution of a City-wide enterprise digital roadmap across key customer touchpoints for key services, with the goal of digitizing key touchpoints.

·   Co-leadership of programs with key divisions (Customer Experience, Housing, Parks and Recreation, etc.) with the goal of driving efficiency and enhanced experience for the public.

·   Oversee architecture, solution design, and platform governance across the TSD division.

Modernization, Continuous Improvement and Enterprise Architecture:

·   Lead the strategy, delivery, and implementation of large-scale corporate programs, including digital services, divisional application development, public-facing services, solution architecture and design services.

·   Works across divisions to adopt modern delivery practices to deliver with agility and efficiency, including continuous development/improvement tools, adoption of modern platform development, quality engineering, security and release management practices.

·   Drive rapid response programs aligned to Council and Mayoral priorities, advancing capabilities across teams and divisions to deliver with speed and agility.

·   Lead change across the way we work; develop new standards across platforms, delivery capabilities, and lead the evolution of Technology Services architecture to serve emerging needs.

Strategic Partnerships and Leadership:

·   Collaborate across City divisions and Council to align digital priorities with the needs of the public and strategic business goals.

·   Co-leads key division and platform roadmaps, inclusive of application lifecycle management, modernization and decommissioning plans.

·   Collaborates with finance and procurement teams to optimize vendor relationships and negotiate favourable contracts for the City of Toronto.

·   Works closely with the CTO, peers, and City leadership to identify and capitalize on opportunities where technology can add value to support program operations and strategic objectives.

Culture and Team Leadership 

·   One Team: Cultivating a sense of unity where each member understands their purpose and impact.

·   Performance and Resiliency: Building high performance and resiliency through modelling standards, trust, transparency, and respect.

·   Creativity and Innovation: Encouraging creativity and innovation by welcoming diverse perspectives, promoting healthy debate, and questioning the status quo.

·   Equity and Accountability: Respecting each other's ideas and leaning into equity and accountability, creating a sense of independence and ownership.

REQUIRED SKILLS, QUALITIES AND EXPERIENCE

·   Post-secondary education in business administration, engineering, computer science, information technology or an equivalent combination of education and experience.

·   Must have 10+ years of experience leading technology teams in the delivery of large-scale enterprise applications through transformation stages to modern platforms, cloud-based technologies and digital programs.

·   Proven track record of working with business partners in developing strategic, technology and user-centric programs through project and program delivery roadmaps.

·   Experience in helping teams deliver enterprise and domain-level architecture planning programs while delivering solution design services to teams.

·   Considerable experience leading a high-performing team through change, ensuring continued successful service delivery.

·   Experience and knowledge of transforming teams into new ways of working across modern technologies (cloud, SAAS, AI) and methodologies (Agile/SAFE, CI/CD, DevOPS, etc.).

·   Effective communication skills with the ability to communicate with both technical and non-technical stakeholders, senior leaders, and governing bodies.

·   Proven success in managing large projects, development and support streams with a high degree of employee and stakeholder satisfaction.

EQUITY, DIVERSITY, AND INCLUSION

The City is an equal opportunity employer, dedicated to creating a workplace culture of inclusiveness that reflects the diverse residents that we serve. Learn more about the City’s commitment to  employment equity .

ACCOMMODATION

The City of Toronto is committed to creating an accessible and inclusive organization. We are committed to providing barrier-free and accessible employment practices in compliance with the Accessibility for Ontarians with Disabilities Act (AODA). Should you require Code-protected accommodation through any stage of the recruitment process, please make them known when contacted and we will work with you to meet your needs.  Disability-related accommodation during the application process is available upon request . Learn more about the City’s  Hiring Policies and Accommodation Process .

HOW TO APPLY

To apply to this exciting opportunity, email your resume to:

Marty Greenaway, Consultant

Feldman Daxon Partners    

E:

T:

The City of Toronto supports a hybrid work model for this position, with flexibility based on operational and leadership needs.