Remote Legal Software Sales Jobs in Wisconsin (NOW HIRING)

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.

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