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Remote Technology Leadership Jobs in Wisconsin (NOW HIRING)

... technology leader. This is a pivotal leadership position responsible for driving the AI-centric ... This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed ...

... technology leader. This is a pivotal leadership position responsible for driving the AI-centric ... This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed ...

... technology leader. This is a pivotal leadership position responsible for driving the AI-centric ... This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed ...

... technology leader. This is a pivotal leadership position responsible for driving the AI-centric ... This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed ...

... technology leader. This is a pivotal leadership position responsible for driving the AI-centric ... This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed ...

Senior Director - Client Data Solutions

Wauwatosa, WI · On-site +1

$103K - $139K/yr

As a senior member of the Client Technology leadership team, this role works closely with Product ... Remote - United States Work set up: Monday to Friday - FTE Skills: Are you Strong experience in ...

Senior Director - Client Data Solutions

Wauwatosa, WI · Remote

$103K - $139K/yr

As a senior member of the Client Technology leadership team, this role works closely with Product ... Remote - United States Work set up: Monday to Friday - FTE Skills: Are you Strong experience in ...

Working closely with IT project teams, technical leaders, and business partners, the Change Manager ... We embrace a remote-first culture through our Flexible Workplace. Most employees hold Home-Flex ...

Showing results 21-40

Remote Technology Leadership information

What is the difference between Remote Technology Leadership vs Remote Software Development Manager?

AspectRemote Technology LeadershipRemote Software Development Manager
Primary FocusStrategic technology vision, innovation, and team oversightManaging software development projects, teams, and delivery
Required SkillsLeadership, strategic planning, technical expertise, communicationProject management, coding knowledge, team coordination
Work EnvironmentHigh-level collaboration with executives and tech teamsHands-on management of development teams and timelines
Common CertificationsIT leadership, cloud certifications, PMPAgile, Scrum, PMP, technical certifications

Remote Technology Leadership focuses on setting strategic tech direction and leading teams at a high level, while Remote Software Development Managers oversee day-to-day project execution and team management. Both roles require technical knowledge, but differ in scope and responsibilities.

What are the key skills and qualifications needed to thrive as a remote technology leader, and why are they important?

To thrive as a Remote Technology Leader, you need a strong background in IT management, software development, or systems architecture, often supported by a relevant degree and leadership experience. Familiarity with collaboration tools like Slack, project management platforms such as Jira or Asana, and cloud-based systems is essential, and certifications like PMP or Agile Scrum Master can be advantageous. Outstanding communication, emotional intelligence, and the ability to build trust and motivate distributed teams are crucial soft skills. These competencies enable effective oversight, drive innovation, and ensure alignment across remote teams for organizational success.

What is remote technology leadership?

Remote technology leadership refers to managing and guiding technology teams or projects from a location outside of a traditional office environment. Leaders in this role oversee technical strategy, project execution, and team collaboration using digital communication tools and platforms. They are responsible for ensuring that remote teams remain productive, aligned with business goals, and equipped to handle challenges unique to distributed work. Effective remote technology leaders foster a strong team culture, prioritize clear communication, and leverage technology to support team success.

What are some common challenges remote technology leaders face, and how can they effectively address them?

Remote technology leaders often encounter challenges such as maintaining clear communication across distributed teams, ensuring alignment on project goals, and fostering a strong team culture without in-person interaction. To address these challenges, leaders frequently leverage collaboration tools, set up regular video meetings, and establish transparent processes for tracking progress and sharing feedback. Additionally, creating opportunities for virtual team-building and encouraging open communication channels help build trust and keep team members engaged, even when working from different locations.
What job categories do people searching Remote Technology Leadership jobs in Wisconsin look for? The top searched job categories for Remote Technology Leadership jobs in Wisconsin are:
What cities in Wisconsin are hiring for Remote Technology Leadership jobs? Cities in Wisconsin with the most Remote Technology Leadership job openings:
Infographic showing various Remote Technology Leadership job openings in Wisconsin as of August 2026, with employment types broken down into 73% Full Time, 11% Part Time, and 16% Contract. Highlights an 100% Remote job distribution.

(Remote) Vice President of Research & Development

Harris

Remote

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 29 days ago


Harris Computer rating

8.5

Company rating: 8.5 out of 10

Based on 10 frontline employees who took The Breakroom Quiz

78th of 242 rated software companies


Job description

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


What Harris Computer employees say

Pay

Benefits

Hours and flexibility

Workplace

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About Harris Computer Systems

Sourced by ZipRecruiter

Harris Computer Systems, based in Ottawa, ON, CA, is an established player in the field of public sector software technology. Since its inception in 1976, the company has been striving to make clients' operations more efficient through reliable, practical, and flexible software solutions. Its extensive portfolio primarily serves utility, healthcare, public sector, and educational institutions, contributing to the betterment of public services through technology. Harris strongly believes in the value of forward-thinking technology and the power it has to drive progress for the public sector. This methodology is entirely in line with their mission to ensure customer success by providing reliable, practical, and robust software solutions.

Industry

Accounting services

Company size

1,001 - 5,000 Employees

Headquarters location

Ottawa, ON, CA

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