Head of Data & AI, Jonas Software
Enterprise management software solutions
Be an early applicant
Enterprise management software solutions
501-1000 employees
Be an early applicant
501-1000 employees
Company mission
To be the branded global leader across the 40+ vertical markets.
Role
Who you are
- Expert-level Snowflake knowledge, including data modelling, performance optimisation, and advanced features
- Strong Python skills for data engineering, ML, and AI development
- Proven experience building and deploying machine learning models
- Hands-on experience with embeddings, vector databases, and AI/LLM-driven systems
- Strong understanding of modern data engineering practices (ELT, orchestration, versioning)
- 5+ years’ experience in data engineering, data science, or ML-focused roles
- Demonstrated leadership of data or analytics engineering teams
- Proven track record delivering production-grade data and AI platforms
- Experience working closely with senior technical leadership (CTO, Head of Engineering, etc.)
Desirable
- Background in data science or applied machine learning
- Experience enabling AI agents or intelligent automation
- Familiarity with cloud-native architectures and MLOps practices
What the job involves
- The Head of Data & AI is a senior technical leadership role responsible for shaping and delivering Gladstone’s data and AI capabilities. Reporting directly to the CTO, this role combines hands-on technical leadership with collaboration across product, engineering, and commercial teams to build a secure, scalable data and AI platform.
- You will lead a small team of data and analytics engineers, while helping embed machine learning, AI agents, and advanced analytics into real customer workflows — ensuring data and AI are applied thoughtfully, responsibly, and with clear business impact
- Own the Data & AI Platform — Design and evolve a modern, scalable data platform centred on Snowflake to power analytics, AI models, and agent-based workflows
- Enable AI-First Products — Build and operationalise machine learning models, embeddings, and vector stores that support AI agents and intelligent customer experiences
- Lead a High-Impact Team — Develop and mentor a small team of data and analytics engineers, setting technical direction and delivery standards
- Bridge Strategy and Execution — Translate business and product goals into robust data and AI solutions that deliver measurable value
- Own the design and evolution of Gladstone’s data and AI platform, with Snowflake as the core analytical and ML data store
- Build and maintain scalable data pipelines, models, and data products to support analytics, AI, and multi-tenant use cases
- Design, train, and deploy machine learning models, embeddings, and vector stores to enable AI agents and intelligent workflows
- Lead and mentor a small team of data and analytics engineers, setting technical standards and delivery priorities
- Partner with Product, R&D, and Infrastructure to embed data and AI capabilities into customer-facing platforms
- Ensure data quality, security, governance, and performance across the data and AI estate
- Provide clear technical insight, progress updates, and recommendations directly to the CTO
- Technical Authority — Deep expertise with the credibility to lead architectural and modelling decisions
- Hands-On Leadership — Comfortable building while leading others
- Strategic Thinking — Able to connect data and AI capabilities to product and business outcomes
- Execution Excellence — Delivers reliable, production-grade solutions
- Collaboration & Influence — Works effectively across technical and non-technical teams
Our take
Jonas Software is an investment and software management company that focuses on the vertical markets, meaning markets that develop software for specific needs rather than general use. Founded in 1990, the company rose to prominence when it was acquired by Constellation Software in 2003 and now oversees more than a hundred companies that it itself has acquired over the years. Now it operates in over 40 vertical markets across more than 30 countries.
Investing smaller amounts in niche companies has paid off for Jonas, many of its investments later becoming large markets and leaders in their industry. For instance, Jonas’s expansion into the world of fitness membership software preceded the explosion of digital fitness apps. Other notable investments have included Jonas’s Clubhouse Online, a mobile app that helps book slots and reservations for golf club services in the mid-noughties, preceding the rise in online hospitality booking.
Throughout the 2020s, Jonas has expanded further into the hospitality, compliance and manufacturing sectors, merging its acquisitions with property management and online marketing companies to compete against the likes of Amadeus and Oracle. In a bid to expand and compete against younger yet larger companies, Jonas is restructuring its less profitable assets.
Freddie
Company Specialist at Welcome to the Jungle
Insights
5% employee growth in 12 months
Company
Company benefits
- Great Benefits Package: Competitive benefits package for all employees. We provide resources that help you be the best version of yourself.
- Growth Opportunities: We strive to provide our team with opportunities to increase their knowledge so they can build an enriched career.
- Competitive Salary: Attractive compensation package, including competitive salary and bonus opportunity.
Company HQ
Markham, ON
Leadership
Barry Symons
(CEO)Spent 11 years with Constellation Software (Jonas’ parent company). They joined Constellation in its infancy and grew with the organization, culminating in their role as Chief Financial Officer, helping lead Constellation’s successful IPO.
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