Chief Executive Officer, ProviderSoft at Jonas Software in Remote

Chief Executive Officer, ProviderSoft Location: Remote - USA Job Description: ProviderSoft is hiring a CEO to own a profitable, established vertical SaaS business end to end. Full P&L. Real autonomy inside a Constellation Software business. The outgoing CEO is stepping up to a Group Leader role and will be the new CEO's direct manager and a resource through the transition. This is a planned succession, not a turnaround. You will not be managing layers of middle management or navigating corporate politics. You will be making real decisions, close to customers, close to the product, with a team small enough that your leadership directly shapes culture and outcomes. About ProviderSoft ProviderSoft has spent two decades building software for early childhood developmental therapy agencies, a stable and specialized niche where our customers serve children and families who depend on quality care. We are profitable and capital-efficient, with a loyal customer base and a 20-plus year operating track record. Our mission is to empower Early Childhood Development providers with the software, service, and expertise they need to achieve operational excellence, so they can deliver the highest quality care to children and families in their communities. We organize the business around three pillars: **Software, Service, and Expertise.** The next CEO must champion all three. About Jonas Software and Constellation ProviderSoft is part of PYXiS, a portfolio within Jonas Software, one of Constellation Software's (TSX: CSU) operating groups. Constellation is one of the world's largest acquirers and operators of vertical market software businesses, with a decentralized model that gives BU CEOs real autonomy. Strategy, capital allocation, hiring, and product direction are owned at the BU level, not dictated from above. Accountability is direct and real, and so is the autonomy. The new ProviderSoft CEO will report to the Group Leader of a four-business group within the PYXiS portfolio. What you'll own Strategic leadership - Develop and execute a multi-year strategy that accelerates growth and deepens the competitive moat. P&L. - Full ownership of the budget and financial performance, including ARR growth, retention, margins, and capital allocation. Team development - Coach and mentor the Senior Leadership Team across Engineering, Sales & Marketing, and Customer Success. Build a cohesive executive team that co-owns the company's success. Product strategy - Partner with engineering leadership to own the product vision and roadmap, ensuring it aligns with market needs and drives growth. Go-to-market execution - Oversee the revenue engine end to end (Sales, Marketing, and Customer Success) from lead generation through retention and expansion. Stakeholder management - Serve as the primary interface with the Group Leader, providing transparent reporting on performance, strategy, and key initiatives. What you'll work on first Supporting the Director of Sales & Marketing in maturing the go-to-market engine. A Director of Sales & Marketing and BDR function are in place. The work ahead is turning that foundation into a repeatable, predictable system that fills the funnel and moves prospects to close. Target market expansion into California and Massachusetts is in flight. Driving AI adoption across the business. Vertical SaaS is being reshaped by AI across product, development, customer-facing operations, and internal operations. The next CEO needs to ensure ProviderSoft keeps pace and captures every advantage AI offers, in every part of the business. Driving the product through a strategic modernization period. A legacy core platform is generating revenue and serving customers well today. Reducing technical debt and building the foundation for AI-native product capability is the work of the next several years. Sharpening the leadership team. Recently bolstered with directors in R&D and Sales & Marketing, the SLT must continue evolving from departmental leaders into an integrated executive team operating with clear KPIs and a consistent operating cadence. Who you are Must-haves: People-first leader. You have directly managed cross-functional teams and built real trust with the people you lead. You can point to specific examples (names, situations, outcomes) of developing talent and maintaining healthy culture in small teams. This is a hands-on environment. There is nowhere to hide from leadership gaps. Technical credibility with AI fluency. You can engage meaningfully with engineering on architecture, technical debt, and modern development approaches. You are already using AI in your own work and have a point of view on how it reshapes vertical SaaS in product, operations, development, and customer value. P&L awareness. You have had meaningful exposure to business economics, including revenue, margins, retention, and capital allocation. You do not need to have owned a full P&L, but you understand how operational decisions connect to financial outcomes. Comfort with capital-efficient, profitable business models matters more than venture-backed, growth-at-all-costs experience. Builder mentality. You have taken something from messy to structured. A team, a process, a product area. Not just a maintainer. Preferred: Vertical market SaaS experience (any niche) Familiarity with acquisition-driven operating models (Constellation, Roper, Volaris, etc.) Track record of legacy system modernization Experience operating in small, high-autonomy environments where the CEO answers support tickets sometimes #LI-PP1 Business Unit: ProviderSoft 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.