Director of Software Engineering (AI/ ML / SAAS - Startup) Location: Downtown Toronto, Full-Time | Hybrid 4 days We are looking for a Software Engineering Leader (Director or experienced Senior Manager) to build and scale our Toronto engineering office. This is a unique opportunity to help grow a cutting-edge AI-driven SaaS company. In this role, you will grow the Toronto site into a high-performing engineering organization. You’ll provide technical oversight, lead delivery, and establish a strong, collaborative culture. While focused on leadership, you’ll remain close enough to the technology to mentor engineers and contribute to key technical decisions. You will work directly with the VP of Software and collaborate with teams in California to ensure alignment on engineering direction, execution, and product vision. Key Responsibilities Build & Scale the Toronto Office Hire and develop a team of 20–30 engineers (frontend, backend, ML/AI, data, devtools). Create a strong, high-performance engineering culture. Stay Technically Engaged Maintain technical credibility and participate in architecture and design discussions. Provide guidance on systems, design, and engineering best practices. Recruit talent through strong relationships with Canadian universities and local markets. Coach engineers, develop future leaders, and uphold engineering excellence. Lead Delivery Across Value Streams Own end-to-end product delivery from planning to adoption. Partner with product, AI, and chip teams on roadmap execution. Ensure communication and alignment across distributed teams. Establish effective engineering rituals and cross-site collaboration practices. Ideal Experience Leadership experience (Sr. Manager, Director) managing 15+ engineers. 10+ years in software engineering with progression from developer → tech lead → leader. Technical depth in cloud-native systems, SaaS platforms, and AI/ML environments. Strong track record delivering complex products and scaling engineering teams. Skilled in hiring, mentoring, communication, and cross-site collaboration. What We Offer A pivotal opportunity to build and scale the Toronto engineering office. Direct collaboration with senior and cross-disciplinary engineering leadership. Strong connections to top Canadian universities and research institutes. Competitive salary and early-stage equity. A high-trust, low-ego culture focused on ownership, innovation, and collaboration. Level & Growth Path We are targeting Director-level candidates. However, strong Managers or Senior Managers who meet the criteria and are ready for the next step are encouraged to apply. The role can be scoped as Manager or Senior Manager with a performance-based promotion path as the site grows. Technical Skills Cloud-Native Architecture SaaS Platforms AI/ML Systems Distributed Systems Software Design & Architecture SDLC & Agile Execution Delivery & Execution Roadmap Ownership End-to-End Product Delivery Cross-Site Communication Execution Planning System Reliability & Best Practices Soft Skills Strategic Thinking Communication Culture Building High-Performance Teaming Stakeholder Alignment Screening Questions How many engineers have you directly managed at one time? Have you scaled a team or site before? If yes, how large and in what timeframe? Describe your experience with cloud-native systems (AWS, GCP, Azure, etc.). What exposure do you have to AI/ML systems or data-intensive architectures? Provide an example of a product or feature you led from planning to launch. How do you ensure delivery alignment across distributed or cross-functional teams? What role have you played in recruiting and onboarding engineers? How do you coach engineers toward technical leadership? Apply sasha@talenttohire.com Follow us at https://www.linkedin.com/company/talenttohire #J-18808-Ljbffr
Managing Partner | Contract Surety
Employment Type: Full-time
Workplace Type: Remote (Hybrid option for Ontario)
Compensation: $150,000 – $500,000+ per year (Commission, profit share, and vested equity)
About Ai Insurance Organization
Ai Insurance Organization’s Managing Partner Program is Canada’s premier turnkey path to brokerage ownership. We’re seeking an experienced Contract Surety Producer ready to take the next step into business ownership.
With exclusive Lloyd’s Coverholder status, direct market access, and mentorship from industry leaders, this is your opportunity to transition from top producer to Managing Partner — building equity in your own brokerage without restrictive franchise fees or barriers.
What You’ll Do
Own & Grow Your Business – Lead your own surety-focused brokerage practice under the Ai Insurance platform.
Build a High-Value Portfolio – Develop relationships with contractors, developers, lenders, and project owners nationwide.
Deliver Expert Bonding Solutions – Structure bid, performance, labour & material, and maintenance bonds for complex projects.
Recruit & Mentor – Build your own team of producers and CSRs to support your growth.
Leverage Infrastructure – Access our HubSpot CRM, Vertafore SIG, digital marketing, and operational support to scale efficiently.
Collaborate with Underwriters – Negotiate competitive terms with top-tier surety markets.
What You Bring to the Table
Active RIBO License (in good standing) – Required
5+ Years of Contract Surety Experience – Proven production track record in mid-to-large accounts
Strong business development and leadership skills
Established network in the construction industry
CRM proficiency (HubSpot preferred); Vertafore SIG experience an asset
Entrepreneurial mindset with the drive to build and lead your own brokerage
Why Become a Managing Partner with Ai Insurance Organization?
???? Lucrative Earnings – Commission up to 90% on new business + renewal income + profit share
???? Equity Ownership – Vest in your book of business and brokerage over time
???? Exclusive Market Access – Lloyd’s Coverholder + leading contract surety markets
???? Comprehensive Benefits – Health, dental, disability, and life insurance
???? Mentorship & Support – Hands‑on guidance from Canada’s top insurance leaders
???? Turnkey Marketing – Digital campaigns, branding, and lead generation built in
???? Work from Anywhere – Remote‑first with hybrid option for Ontario
Join the A-Team
If you’re a proven contract surety producer ready to take the leap from producer to owner, apply today and become a Managing Partner with Ai Insurance Organization.
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A leading insurance network provider in Canada is seeking seasoned insurance professionals to join their Managing Partner network. Candidates should have over 5 years of experience in the insurance industry and own a book of business with a minimum of $3M GWP. This opportunity emphasizes building a legacy with unmatched market access, proven success models, and comprehensive support to grow a successful insurance franchise. #J-18808-Ljbffr
A leading AI-driven SaaS company in Toronto seeks a Director of Software Engineering to build and scale their engineering office. You will grow a talented team of engineers while maintaining technical oversight. This pivotal role offers a competitive salary and potential equity in a high-trust culture focused on innovation. Ideal candidates have strong leadership skills, experience managing technical teams, and a solid background in cloud-native, AI, and SaaS technologies. #J-18808-Ljbffr
Are you ready to take control of your future? We’re looking for seasoned insurance professionals to join our growing Managing Partner network. If you have over 5 years of experience in the insurance industry and own a book of business with a minimum of $3M GWP, this is the opportunity you've been waiting for. Who We Are: As an industry leader, we provide unparalleled support to partner owners. Our proven Managing Partner model is designed to help you succeed by offering access to exclusive markets, top-tier insurance products, and extensive business development resources. We understand the challenges brokers face, especially in today’s rapidly changing environment, and we're here to help you overcome them. Why Join Us? Unmatched Market Access: Gain entry to exclusive markets and products, giving you a competitive edge and the ability to offer more to your clients. Proven Success Model: Low startup costs, high earning potential, and continuous support. Ownership Opportunity: Retain significant ownership of your business while benefiting from our industry expertise and resources. Comprehensive Support: From marketing assistance to lead generation, our support infrastructure is designed to help you grow your business efficiently. What You Need: Experience: A minimum of 5 years in the insurance industry, with a deep understanding of both personal and commercial lines. Book of Business: Own a book of business with a minimum of $3M GWP. Entrepreneurial Spirit: A desire to take charge of your career and build a successful insurance franchise. Ready to Make Your Move? This is your chance to step into a role where your experience and business acumen can truly shine. Our program is not just about running an office; it’s about building a legacy. If you’re ready to break free from the constraints of traditional brokerages and start your own thriving business, we want to hear from you. #J-18808-Ljbffr
