Want to know if this job is worth applying to?
Toronto, Ontario, Canada
Remote only
Vice President, Product Strategy & AI Innovation
Salaray Range: 160,000-165,000 CAD
SUMMARY
The Vice President, Product Strategy & AI Innovation is responsible for defining and executing the company's product, market, and innovation strategy. Reporting directly to the President, this executive role serves as the business leader for the company's software portfolio and is accountable for ensuring product investments drive customer value, competitive differentiation, revenue growth, profitability, and long-term market leadership.
The VP will lead the transformation of the organization from traditional software development practices to a product-led, specification-driven, AI-enabled operating model. This leader will establish the strategic vision for the company's next generation of commercial construction and field service management solutions, including the development of an AI-first, agentic ERP platform.
The role is accountable for determining what should be built, why it should be built, and how product investments align with corporate objectives. Engineering leadership remains accountable for how solutions are technically designed, developed, and delivered.
TECHNICAL SKILLS
Strategic Thinking
Business Acumen
Market Insight
Product Vision
Financial Analysis
Executive Communication
Change Leadership
Innovation Leadership
Customer Centricity
Organizational Alignment
Decision Quality
Talent Development
Results Orientation
KEY RESPONSIBILITIES
Product Vision & Corporate Strategy - Develop and maintain a multi-year product strategy aligned with corporate growth objectives. - Define and communicate the long-term vision for the company's software portfolio and AI-first platform strategy. - Identify emerging market opportunities, customer needs, industry trends, and competitive threats. - Lead strategic planning activities related to product investments, innovation initiatives, and market expansion. - Serve as a key member of the executive leadership team contributing to overall corporate strategy.
Product Portfolio Leadership - Own product portfolio prioritization and investment decisions. - Establish portfolio governance processes to evaluate product opportunities based on strategic fit, customer impact, ROI, and competitive advantage. - Define product lifecycle strategies including growth, expansion, modernization, and retirement decisions. - Ensure all major product initiatives have clearly defined business cases, success metrics, and measurable outcomes.
AI & Innovation Leadership - Lead the company's AI transformation strategy. - Define the roadmap for AI-enabled workflows, autonomous agents, predictive analytics, and intelligent business automation. - Evaluate emerging technologies, partnerships, and acquisition opportunities that support the company's innovation objectives. - Establish frameworks for responsible, scalable, and commercially viable AI adoption across products and internal operations.
Product-Led Operating Model - Build and institutionalize a specification-driven product development process. - Establish standards for customer discovery, product requirements, solution specifications, acceptance criteria, and outcome measurement. - Create alignment between Product, Engineering, Customer Success, Professional Services, Sales, and Marketing. - Ensure product decisions are driven by customer outcomes, market opportunities, and business objectives.
Customer & Market Intelligence - Maintain direct relationships with strategic customers and industry leaders. - Lead customer advisory boards, product councils, and market research initiatives. - Develop deep understanding of commercial construction, HVAC, plumbing, electrical, mechanical, and field service industries. - Translate market intelligence into strategic product opportunities.
Commercial Leadership - Partner with Sales and Marketing on go-to-market strategy, positioning, packaging, pricing, and competitive differentiation. - Analyze product profitability, growth opportunities, and investment returns. - Support strategic customer engagements and major account opportunities. - Contribute to annual planning, budgeting, and forecasting activities.
Organizational Leadership - Lead Product Management, Product Operations, Business Analysis, User Experience, and Product Innovation functions. - Develop high-performing product leaders capable of translating business strategy into executable product plans. - Foster a culture of accountability, customer obsession, innovation, and continuous improvement. - Build cross-functional alignment across the organization.
KEY PERFORMANCE INDICATORS
- Annual Recurring Revenue Growth - Product Gross Margin - Product Adoption Rates - Customer Retention and Net Revenue Retention - Customer Satisfaction and NPS - Product Portfolio ROI - Strategic Initiative Success Rate - AI Product Adoption Metrics - Time from Concept to Approved Specification - Innovation Pipeline Value
QUALIFICATIONS
Education - Bachelor's Degree in Business, Engineering, Computer Science, Technology Management, or related field. - MBA or equivalent executive business education strongly preferred.
Experience - 10+ years of progressive leadership experience in software, SaaS, ERP, or technology businesses. - Demonstrated success leading product strategy and business transformation initiatives. - Experience managing product portfolios and investment decisions. - Strong understanding of software economics, recurring revenue models, and enterprise software markets. - Experience with AI-enabled products, automation technologies, and emerging software platforms preferred. - Experience serving commercial construction, field service, trades, ERP, or operational software markets is highly desirable.
Leadership Competencies - Strategic Thinking - Business Acumen - Market Insight - Product Vision - Financial Analysis - Executive Communication - Change Leadership - Innovation Leadership - Customer Centricity - Organizational Alignment - Decision Quality - Talent Development - Results Orientation
SUCCESS PROFILE
The successful candidate is a business strategist first, product leader second, and technology innovator third. They possess the ability to connect market opportunities, customer outcomes, financial performance, and technology investments into a unified product strategy that drives sustainable competitive advantage and long-term enterprise value.
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.