Remote Apple Technical Advisor Jobs in Wisconsin

Cayenta, a division of Harris; is seeking a Vice President of Research & Development who is a business-focused technology leader.

This is a pivotal leadership position responsible for driving the AI-centric transformation of our core product suite and the evolution of a large, tenured engineering organization.

The central challenge is to master the balance between two competing priorities: executing the strategic, multi-year roadmap for our next-generation CayentaOne platform while supporting the operational realities of a large, profitable install base. The leader who succeeds will do so by embedding practical AI at every level of the R&D organization-from accelerating our own development lifecycle to delivering intelligent, high-value features for our customers.

Success in this role requires a strategic business partner for the EVP who can translate technology initiatives into P&L impact, lead a complex cultural change, and instill a culture of pragmatic, AI-driven innovation.

This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed, approximately 50%. Candidates must hold a current, valid passport and be legally eligible to travel internationally. This includes either passport based visa exemption or possession of any required travel visas for entry into Canada, the United States, and the Caribbean.

Salary:

130K - 200K CAD

91K - 141K USD

AI & Innovation Mindset

We are committed to leveraging emerging technologies to improve how we work, serve our customers, and drive business outcomes. The successful candidate will demonstrate curiosity and a willingness to actively adopt and leverage AI tools to improve workflows, solve problems, and increase efficiency. Candidates should be comfortable using AI enabled technologies, including copilots, chat based AI assistants, and automation tools, as part of their everyday work while maintaining appropriate judgment, security, and compliance standards.

What your impact will be:

Drive the AI-Powered Transformation

• Own the execution of the corporate AI mandate within Cayenta, moving the organization from activity to measurable P&L impact.
• Translate AI capabilities into revenue-generating or cost-saving initiatives. You will be accountable for the business case and ROI of our AI investments.
• Accelerate the CayentaOne roadmap by championing and implementing AI-assisted development (AI-DLC) practices to modernize our legacy stack faster.
• Oversee the product strategy for Cayla, evolving it from a feature into a core, agentic AI platform that becomes a key competitive differentiator.

Serve as a Strategic Business Partner

• Act as the key technical advisor to the EVP and GM, translating complex concepts into business terms to inform executive decision-making.
• Own and articulate the business case for the technology roadmap, defending strategic priorities with executive peers in Sales, Professional Services, and Support.

Lead Technical & Product Execution

• Manage the entire R&D P&L, balancing the budget between market-driven features, managing technical debt, and strategic AI and platform investments.
• Instill a sense of urgency and an agile, metrics-driven approach to development, improving velocity and predictability without sacrificing quality.

Lead a Resilient Change-Ready Team

• Lead, mentor, and inspire a 70-person organization, assessing talent and structure to align the team with our AI-first strategic goals.
• Win the trust of skeptics and create a path forward for a tenured team, fostering a culture of pragmatic innovation, accountability, and continuous improvement.

The Profile We're Looking For

You are a business leader who excels in a technical domain. You see AI as a tool to solve business problems, not as a research project.

What we are looking for:

• A proven track record as a trusted technology partner.
• Demonstrated experience moving AI initiatives from ideation to live production with measurable P&L impact. You must be able to articulate how you have used AI to either grow revenue or reduce costs.
• Deep, hands-on experience leading the multi-year modernization of a mature, revenue-generating enterprise software product. You have the "scar tissue" to prove it.
• High emotional intelligence (EQ) with demonstrated success turning around or re-energizing a change-resistant engineering culture.
• Financial acumen and an understanding of how to run R&D with P&L discipline, preferably within a company with a similar operational model to Harris.

What we can offer:

• 3 weeks' vacation and 5 personal days
• Comprehensive Medical, Dental, and Vision benefits starting from your first day of employment
• Employee stock ownership and RRSP/401k matching programs
• Lifestyle rewards
• Remote work and more!
• A Challenge with Impact: This is a difficult and complex role. Success will fundamentally change the trajectory of the business unit and have a visible impact on our P&L.
• Autonomy & Accountability: You will have the autonomy to run your organization, with full accountability for its performance and outcomes.
• Compensation: The compensation package includes a competitive base salary ($130,000 - $200,000 CAD), a bonus structure tied to business unit performance.

About Cayenta:

Cayenta is a leading provider of enterprise resource management solutions in the local government, utility and financial industries. Cayenta's products, services and customer relationships provide the foundation for continued innovation and growth.

About Harris:

Harris is a leading provider of mission critical software to the public sector in North America. As a wholly owned subsidiary of Constellation Software Inc. ("CSI", symbol CSU on the TSX), Harris has become the cornerstone for CSI's investment in utility, local government, school districts, public safety, and healthcare software verticals. Our success has been realized through investments in our proprietary software and market expertise. This focus, combined with acquiring businesses that build upon or complement our offerings, has helped drive our success. Harris will continue to growth through reinvestment - both in the people and products that we offer and making investments in acquiring new businesses.

#LI-remote