2

Remote Caribbean Jobs in Wisconsin (NOW HIRING)

This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed ... the Caribbean. Salary: 110K + Commission OTE: Up to 220K including base salary What your impact ...

New

This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed ... the Caribbean. Salary: 110K + Commission OTE: Up to 220K including base salary What your impact ...

New

This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed ... the Caribbean. Salary: 110K + Commission OTE: Up to 220K including base salary What your impact ...

New

This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed ... the Caribbean. Salary: 110K + Commission OTE: Up to 220K including base salary What your impact ...

New

This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed ... the Caribbean. Salary: 110K + Commission OTE: Up to 220K including base salary What your impact ...

New

This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed ... the Caribbean. Salary: 110K + Commission OTE: Up to 220K including base salary What your impact ...

New

... and the Caribbean. Preference will be given to candidates who can work in EST timezone. Salary ... Remote work and more! About Iatric Systems: Iatric Systems, an independent business unit of Harris ...

... and the Caribbean. Preference will be given to candidates who can work in EST timezone. Salary ... Remote work and more! About Iatric Systems: Iatric Systems, an independent business unit of Harris ...

... and the Caribbean. Preference will be given to candidates who can work in EST timezone. Salary ... Remote work and more! About Iatric Systems: Iatric Systems, an independent business unit of Harris ...

... and the Caribbean. Preference will be given to candidates who can work in EST timezone. Salary ... Remote work and more! About Iatric Systems: Iatric Systems, an independent business unit of Harris ...

... and the Caribbean. Preference will be given to candidates who can work in EST timezone. Salary ... Remote work and more! About Iatric Systems: Iatric Systems, an independent business unit of Harris ...

... and the Caribbean. Preference will be given to candidates who can work in EST timezone. Salary ... Remote work and more! About Iatric Systems: Iatric Systems, an independent business unit of Harris ...

... and the Caribbean. Preference will be given to candidates who can work in EST timezone. Salary ... Remote work and more! About Iatric Systems: Iatric Systems, an independent business unit of Harris ...

... and the Caribbean. Preference will be given to candidates who can work in EST timezone. Salary ... Remote work and more! About Iatric Systems: Iatric Systems, an independent business unit of Harris ...

... Caribbean. Salary: 70K-80K AI & Innovation Mindset We are committed to leveraging emerging ... Remote work and more! About Cayenta: Cayenta is a leading provider of enterprise resource ...

... Caribbean. Salary: 70K-80K AI & Innovation Mindset We are committed to leveraging emerging ... Remote work and more! About Cayenta: Cayenta is a leading provider of enterprise resource ...

... Caribbean. Salary: 70K-80K AI & Innovation Mindset We are committed to leveraging emerging ... Remote work and more! About Cayenta: Cayenta is a leading provider of enterprise resource ...

... Caribbean. Salary: 70K-80K AI & Innovation Mindset We are committed to leveraging emerging ... Remote work and more! About Cayenta: Cayenta is a leading provider of enterprise resource ...

... Caribbean. Salary: 70K-80K AI & Innovation Mindset We are committed to leveraging emerging ... Remote work and more! About Cayenta: Cayenta is a leading provider of enterprise resource ...

... Caribbean. Salary: 70K-80K AI & Innovation Mindset We are committed to leveraging emerging ... Remote work and more! About Cayenta: Cayenta is a leading provider of enterprise resource ...

next page

Showing results 1-20

Remote Caribbean information

What kinds of remote jobs are commonly available for professionals based in the Caribbean?

Professionals living in the Caribbean can often find remote opportunities in fields such as customer service, information technology, digital marketing, virtual assistance, and education. Employers typically seek candidates with reliable internet connectivity and the ability to work independently, often on teams that span multiple time zones. Daily responsibilities vary by role but usually involve virtual collaboration, clear communication, and a high level of self-motivation. Working remotely from the Caribbean allows flexibility and work-life balance but also requires adaptability to different business cultures and schedules. Career advancement depends on performance, upskilling, and sometimes pursuing additional certifications relevant to the chosen industry.

What are the key skills and qualifications needed to thrive in the remote Caribbean position, and why are they important?

There is no recognized real-world professional occupation with the job title "Remote Caribbean." As such, there are no core skills, qualifications, technical tools, certifications, or relevant soft skills associated with this job title. Individuals seeking employment should refer to specific roles related to their field of interest, such as remote customer service, remote project management, or remote IT support, and reference the skills required for those specific positions. Using accurate and established job titles ensures job seekers pursue roles with clear expectations and career pathways.

What is a remote Caribbean job?

A Remote Caribbean job allows you to work remotely while living in the Caribbean, either as a freelancer, remote employee, or digital nomad. These jobs typically require stable internet access and can range from tech and customer support roles to marketing and consulting. Many Caribbean nations offer remote work visas, making it easier for professionals to live and work legally.

What are popular job titles related to Remote Caribbean jobs in Wisconsin? For Remote Caribbean jobs in Wisconsin, the most frequently searched job titles are:
What cities in Wisconsin are hiring for Remote Caribbean jobs? Cities in Wisconsin with the most Remote Caribbean job openings:
Infographic showing various Remote Caribbean job openings in Wisconsin as of August 2026, with employment types broken down into 78% Full Time, 11% Part Time, and 11% Contract. Highlights an 100% Remote job distribution.

(Remote) Sr Account Executive

Harris

Remote

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 2 days ago

New


Harris Computer rating

8.5

Company rating: 8.5 out of 10

Based on 10 frontline employees who took The Breakroom Quiz

77th of 242 rated software companies


Job description

A division of Harris; Systems & Software is seeking a Senior Sales Executive to drive net-new growth within a defined territory. This role is responsible for identifying, engaging, and converting municipal utilities through complex, RFP-driven sales cycles.

The Senior Sales Executive owns the full sales process from initial outreach through contract execution. This includes developing a qualified pipeline, building relationships with utility stakeholders, and leading competitive pursuits. The role requires strong business acumen, disciplined forecasting, and the ability to navigate long-cycle enterprise sales.

The ideal candidate is a self-starter who is comfortable creating opportunities, engaging senior decision-makers, and leading structured evaluations to close.

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: 110K + Commission

OTE: Up to 220K including base salary

What your impact will be:
  • Identify and pursue net-new municipal utility opportunities within a defined territory
  • Build and maintain a qualified pipeline aligned to company growth targets
  • Lead sales cycles from initial engagement through RFP, evaluation, and contract execution
  • Develop and maintain accurate forecasts for bookings and pipeline progression
  • Maintain accurate and timely CRM (Salesforce) updates across all opportunities, including pipeline stage, stakeholder context, and next steps to ensure forecast accuracy and visibility
  • Establish and grow relationships with key stakeholders within target accounts
  • Partner with Technical Sales Engineers to deliver tailored demonstrations and technical validation
  • Collaborate with Product, Professional Services, and leadership to position solutions effectively
  • Represent the company at industry events, conferences, and customer meetings
  • Build and maintain strong relationships with strategic third-party partners
  • Participate in relevant internal and external meetings and functions
What we are looking for:
  • 7+ years of experience in enterprise software sales, with a focus on net-new business development
  • Demonstrated success managing full-cycle, complex sales processes
  • Experience leading customer presentations and executive-level discussions
  • Experience working with multi-stakeholder buying committees
  • Strong communication, interpersonal, and presentation skills
  • Experience using CRM systems (Salesforce preferred)
  • Bachelor's degree or equivalent experience
What would make you stand out:
  • Experience selling to municipal utilities, public sector, or regulated industries
  • Familiarity with CIS, billing, AMI, or customer service platforms
  • Experience with RFP-driven sales environments
  • Experience selling complex, configurable enterprise software solutions
Competencies
  • Strong business and sales acumen
  • Effective communication and presentation skills
  • Ability to deliver clear, compelling presentations to technical and non-technical audiences
  • Relationship-building and stakeholder management
  • Negotiation and closing discipline
  • Organizational and planning skills
  • Persistence and resilience in long-cycle sales environments
How Success Is Measured
  • Achievement of bookings and revenue targets
  • Growth of qualified net-new pipeline
  • Forecast accuracy and pipeline visibility
  • Advancement of opportunities through RFP and evaluation stages
  • Strength of relationships within target accounts
  • Quality and consistency of CRM documentation
Work EnvironmentThis role operates in a remote work environment with regular interaction with internal teams and customers. The position requires the ability to work independently while maintaining strong collaboration across Sales, Technical, and Delivery teams.TravelThis position is remote and requires travel to customer sites, industry events, and internal meetings as needed.Physical DemandsThis is primarily a sedentary role requiring regular use of a computer and communication tools. Occasional travel may require lifting materials up to 20 pounds.Equal Employment OpportunityHarris Computer is an equal opportunity employer and is committed to creating an inclusive environment for all employees.Other DutiesThis job description is not intended to be a comprehensive list of all responsibilities. Duties and responsibilities may change based on business needs.

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!

About Systems & Software
Systems & Software, a subsidiary of Harris Computer and part of Constellation Software, has been serving utilities and municipalities since 1973. Headquartered in Vermont, the company provides the enQuesta CIS platform to manage billing and utility operations for electric, water, gas, wastewater, solid waste, and property taxes. Our solutions enable utilities to manage complex rate structures, streamline operations, and enhance customer service, all without the need for custom code or disconnected systems. With cloud-based deployment, SOC 2 Type II certification, and interoperability with meter data systems, GIS, and financial tools, Systems & Software delivers stability, security, and flexibility that utilities can trust. Our commitment to ongoing investment ensures continuous innovation and a strong partnership with our customers across North America.

About Harris:

Harrisis 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

Get the full story on Breakroom


Harris Computer Systems logo

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

Social media