Chief AI Officer - JD Group

Jonas Software

6d • Remote

About The Position

Chief AI Officer (CAIO) CORA - JD Group Location: Remote (North America)— with periodic travel required for portfolio visits and acquisition diligence. About CORA Group CORA Group is an operating group of Jonas Software under Constellation Software Inc. (TSX:CSU). We acquire, strengthen and grow vertical market software companies across a range of industry-specific segments (e.g., Healthcare, LegalTech, Moving & Storage, Collections & Recovery, Food Service, Construction, Loyalty, and many more). Our “buy-and-hold forever” model delivers long-term value, operational discipline, and entrepreneurial freedom. We operate with short decision lines, decentralized business unit leadership, and expect strong ownership of results. Role Summary This Is a Transformation Mandate — Not a Strategy Role We are seeking a results-driven Chief AI Officer (CAIO) to lead the full-scale transformation of our business units from SLDC (Software-Led Delivery Capability) to AI DLC (AI-Driven Delivery Capability) by year-end. This is not a strategy-only role. We need a hands-on builder and operator who will take full accountability for delivering measurable transformation outcomes. The CAIO will begin with two key business units and lead the phased rollout across multiple BUs within our VMS portfolio. This role owns the mandate, the roadmap, and the results. We are not looking for pilots. We are not looking for slide decks. We are looking for measurable transformation. The Mission Convert two priority BUs to AI-driven delivery within months Architect and deploy a scalable AI operating model across all BUs Embed AI into core workflows: delivery, operations, client lifecycle, and decision-making Drive quantifiable gains in margin, productivity, quality, and speed Institutionalize AI as a core enterprise capability — not a side initiative You will own roadmap, execution, adoption, governance, margin expansion and performance. What This Role Requires Proven track record leading enterprise AI transformation at scale Experience operationalizing AI in production environments across multiple business units Demonstrated P&L impact from AI implementation Experience in SaaS, VMS, workforce tech, or complex enterprise platforms strongly preferred Ability to operate at both board-level strategy and hands-on execution depth Strong change leadership across cross-functional teams You must be equally comfortable setting enterprise vision and working directly with product, engineering, and operations teams to ship outcomes. What Success Looks Like By year-end: Two BUs fully operating under AI-driven delivery models Enterprise AI playbook built and scaling Tangible margin expansion and efficiency gains AI embedded into how we operate — not layered on top The Profile Enterprise transformer Operator first, strategist second Comfortable with accountability and hard deadlines Decisive, data-driven, commercially sharp Energized by building what does not yet exist Why This Role Matters This is a defining leadership role with direct CEO partnership and enterprise-wide impact. You will not inherit an AI function. You will build it — and deliver it. Compensation & Benefits Competitive base salary + performance-based bonus tied to group and strategic outcomes. Long-term incentive opportunities reflecting Constellation’s “buy-and-hold” philosophy. Flexible work options, comprehensive benefits, professional development support Strong career path within Jonas/CORA/Constellation — with lateral and upward opportunities across a portfolio of software companies. Why Join Us? Play a pivotal role in shaping AI adoption across a growing portfolio of vertical software companies. Operate at the intersection of strategy, growth, and innovation — without losing sight of business unit-level performance and people development. Join a culture that values autonomy, transparency, empowerment and long-term thinking. Access deep operational knowledge and AI expertise from across the Constellation Software network. Business Unit: CORA Corporate Scheduled Weekly Hours: 40 Number of Openings Available: 1 Worker Type: Regular More About Jonas Software: Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain. Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.” We are committed to technology, product innovation, quality, and exceptional customer service. Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees. Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index. At Jonas we have long realized that our greatest asset is our employee base. As such we strive to provide our team with a fantastic working environment and an enriching career, which we know will translate into world class service to our valued clients. This allows Jonas Software to maintain and extend our lead as the premier software and services provider in each of our markets. If being part of a growing organization that moves at a fast pace and constantly strives to get better each and every day is what you are looking for, then we want to hear from you. Everyone has heard the sports analogy “to be the best, you have to beat the best”; well at Jonas Software we have tweaked that slightly to fit vertical market software. We believe to be the best you have to hire and retain the best!!! Jonas Software is an Equal Opportunity Employer. If you need accommodation for a disability at any stage of the application process or want more information on our accommodation policies, contact recruitment at [e-mail] or 905-470-4600 Jonas Softwareis part of a CSI group of companies. << Back to Career Site

Requirements

• Proven track record leading enterprise AI transformation at scale
• Experience operationalizing AI in production environments across multiple business units
• Demonstrated P&L impact from AI implementation
• Experience in SaaS, VMS, workforce tech, or complex enterprise platforms strongly preferred
• Ability to operate at both board-level strategy and hands-on execution depth
• Strong change leadership across cross-functional teams
• You must be equally comfortable setting enterprise vision and working directly with product, engineering, and operations teams to ship outcomes.

Responsibilities

• Convert two priority BUs to AI-driven delivery within months
• Architect and deploy a scalable AI operating model across all BUs
• Embed AI into core workflows: delivery, operations, client lifecycle, and decision-making
• Drive quantifiable gains in margin, productivity, quality, and speed
• Institutionalize AI as a core enterprise capability — not a side initiative
• Own roadmap, execution, adoption, governance, margin expansion and performance.

Benefits

• Competitive base salary + performance-based bonus tied to group and strategic outcomes.
• Long-term incentive opportunities reflecting Constellation’s “buy-and-hold” philosophy.
• Flexible work options, comprehensive benefits, professional development support
• Strong career path within Jonas/CORA/Constellation — with lateral and upward opportunities across a portfolio of software companies.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed