Chief Technology Officer

Job not on LinkedIn

🕒 5 days ago

🌐 Canada, United States – Remote

🇨🇦 Canada – Remote 🇺🇸 United States – Remote

⏰ Full Time

🔴 Lead

👨‍💼 Chief Technology Officer (CTO)

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Jonas Software

WebsiteLinkedInAll Job Openings

1001 - 5000 employees

🏗️ Construction

💼 Consulting

🏥 Healthcare

Construction • Consulting • Healthcare

Jonas Software is a prominent acquirer of vertical market software companies, with a rich history of over 20 years. The company focuses on mission-critical software solutions across various industries, aiming to provide business tools and a network for growth. Jonas Software operates under a decentralized structure, allowing acquired companies to maintain their autonomy while tapping into Jonas's extensive experience and best practices. They adhere to a 'buy & hold forever' strategy, ensuring long-term stability and a permanent home for acquired businesses. With more than 130 successful acquisitions under its belt and being part of Constellation Software, Jonas Software emphasizes preserving the legacy and culture of the companies it acquires, fostering a culture of sharing and leveraging expertise in vertical market software.

📋 Description

• Own technology strategy, software engineering, architecture, infrastructure, DevOps, and delivery across the organization • Set product direction and roadmap prioritization, aligning technology investment with commercial priorities • Lead platform and eCommerce modernization, including migration off the legacy platform, and recommend target architecture and delivery path • Establish CI/CD pipelines, observability, automation, and cloud and hosting modernization roadmaps with migration controls and rollback readiness • Embed AI tooling into development through automated testing, smarter code review, and faster iteration cycles • Own cybersecurity, IT general controls, compliance, business continuity, disaster recovery, and technology risk governance • Document institutional knowledge through documentation and runbooks • Lead, develop, and retain a distributed 14-person engineering organization spanning internal, offshore, and external partner resources • Evaluate and prioritize commercially viable customer-facing AI capabilities • Maintain selective involvement in strategic customers, major escalations, product advisory discussions, and technically complex opportunities • Provide periodic Board and executive exposure on modernization, technology investment, strategy, cybersecurity, and risk • Establish AI-DLC maturity baselines and timelines and lead adoption of AI-enabled workflows • Complete technology, product, and delivery assessment within the first 60 days • Deliver target architecture and funded modernization roadmap by 120 days, with CI/CD and observability infrastructure deployed • Make AI-assisted development standard practice within the first 120 days • Show measurable modernization progress, stronger delivery predictability, improved product execution, and increased resilience within 12 months

🎯 Requirements

• Prior Chief Technology Officer, VP of Engineering, or equivalent executive accountability for a software organization • 15+ years of progressive technology experience, including 10+ years leading software development teams • Hands-on experience modernizing legacy systems, including demonstrated leadership of a POS or eCommerce platform modernization and/or a migration off legacy platforms • Track record building or deploying CI/CD pipelines, observability systems, and automation in resource-constrained environments that demanded ruthless prioritization and speed • Experience leading distributed teams across internal, offshore, and external partner resources • Executive oversight of cybersecurity, technology risk, operational resilience, and business continuity • Technical depth paired with business fluency, able to connect engineering decisions to business outcomes and hold credible conversations with the President about business impact • Preferred: retail technology, point-of-sale, eCommerce, or payments experience • Preferred: beverage-alcohol, grocery, or specialty retail industry experience • Preferred: cloud modernization leadership on AWS, Azure, or Google Cloud • Preferred: adjacent experience in vertical SaaS, fintech, ERP, or other high-availability transaction environments

🏖️ Benefits

• Base salary plus revenue sharing • Long-term incentive: 20% stock option match, subject to the applicable plan terms and vesting schedule • Medical, dental, and vision coverage • Retirement program • 4 weeks PTO • Flexible work arrangements • Fully remote work across the United States and Canada • Annual corporate leadership training (global)

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