Service Initiative Manager

Job Title: Service Initiative Manager
Location: Remote (USA/Canada)
Travel: Up to 35%
Department: Product & Innovation

Who We Are

Dealer Information Systems (DIS) is a market-leading provider of Dealer Management Software (DMS), serving Agriculture, Construction, Truck Refrigeration, and Lift Truck dealerships across North America. As part of the Constellation Software family, DIS focuses on building mission-critical, customer-centric, and profitable software products that deliver measurable value to our customers.

The Role: Service Initiative Manager

DIS is seeking a strategic and driven Service Initiative Manager to lead the continued evolution and growth of one of our flagship service-focused software solutions. This role is ideal for a business-minded product or initiative leader with a passion for customer success, operational efficiency, and long-term product strategy.

You will be responsible for guiding the modernization of the product, working cross-functionally to evaluate and enhance its value proposition, and identifying opportunities to broaden its impact across our dealership network. This includes supporting product re-platforming efforts, exploring how technologies like AI can drive workflow improvements, and working closely with Sales, Support, and Product teams to ensure the solution delivers measurable results.

This is a long-term strategic initiative with strong executive support, offering the opportunity to shape the future of service workflows across industries DIS supports. The ideal candidate brings a mix of product thinking, operational insight, and customer empathy – along with a strong ability to lead cross-functional efforts from concept to execution.

Key Responsibilities:

Product Modernization & Re-platforming

• Partner with Product and Engineering teams to guide the modernization and re-platforming of the service solution

• Ensure enhancements align with long-term business strategy and real-world service workflows

• Prioritize investment areas such as performance, usability, reliability, and system integration

Market Strategy & Value Expansion

• Deeply understand dealership operations to identify unmet needs and opportunities for increased adoption

• Reassess the product’s value proposition and refine packaging, positioning, and messaging as needed

• Collaborate with Sales and Marketing to ensure go-to-market efforts effectively highlight product strengths and drive growth

AI Integration & Innovation

• Identify practical, high-impact opportunities to embed AI into service workflows (e.g., scheduling, diagnostics, summarization)

• Partner with internal innovation and development teams to scope, test, and deliver AI features that improve productivity and user experience

Cross-functional Leadership & Execution

• Drive alignment across Product, Development, Sales, Support, and Customer Success teams to execute against shared goals

• Define clear success metrics, delivery milestones, and feedback loops to maintain forward momentum

• Maintain end-to-end visibility into the initiative’s progress and remove blockers as needed

Customer Engagement & Insight Gathering

• Engage directly with dealerships to capture insights, validate enhancements, and build strong customer relationships

• Leverage real-world feedback to inform product roadmap decisions and prioritize development efforts that deliver measurable impact

Required Experience:

• Familiarity with field service operations, dealership workflows, or B2B service management tools

• Demonstrated ability to lead complex, cross-functional initiatives from concept through execution

• Proven success working directly with customers or end users to shape product direction and improve adoption

Preferred Qualifications:

• 5+ years of experience in product management, initiative leadership, or strategic program roles within software or technology companies

• Experience with software modernization or re-platforming efforts

• Exposure to AI technologies and their application in business workflows (e.g., intelligent automation, summarization, diagnostics)

• Background in SaaS, enterprise software, or vertical market software is a plus

Skills & Traits:

• Strategic thinker with strong product instincts and a passion for solving real-world problems

• Excellent communicator with the ability to align stakeholders across Product, Engineering, Sales, and Support

• Analytical mindset: comfortable using data, feedback, and market insight to drive decisions

• Highly organized and self-directed; able to manage ambiguity and maintain momentum

• Customer-centric and outcomes-driven – focused on delivering measurable value

Why Join DIS?

• Take ownership of a live, high-potential product with early traction

• Act as the driver of business growth with real autonomy and impact

• Work in an entrepreneurial environment backed by the stability of a global software leader