Business Unit:InitiativesTravel Required:Up to 30% travel across North AmericaCompany SummaryConstellation Dealership Software provides mission-critical software to some of the largest, most successful dealerships in North America, UK and Australia. We value long-term relationships with our clients, with most of our revenues flowing from recurring revenues. We are part of Constellation Software Inc., a Canadian-listed corporation with an average compound growth rate of 28% per annum over the last 10 years. Constellation’s mission is to acquire, manage, and grow market‑leading vertical market software businesses that develop specialized, mission‑critical software solutions for the specific needs of the industries they serve.Position SummaryThe Innovation Manager will lead our Voice & Communications initiative — a cloud‑based VoIP platform built for dealerships across equipment, RV, marine, powersports, and related segments — from early‑stage development through real‑world adoption, commercial launch and growth. This initiative replaces legacy dealer phone systems with a modern, AI‑enabled communications platform integrated with dealership management and CRM systems.This is a hands‑on product management role that requires direct engagement with dealerships to understand communication workflows, validate product‑market fit, and guide the solution through pilot and rollout phases across diverse operating environments. The role operates with an entrepreneurial, Lean Startup mindset, balancing product development, customer adoption and overall business viability.You will define the product direction, shape AI‑enabled capabilities such as call transcription, summarization, and intelligent routing, and partner closely with Engineering to deliver a practical, scalable solution across dealership verticals. In parallel, you will drive pricing, packaging and go‑to‑market efforts, ensuring the initiative delivers measurable value to customers while meeting financial objectives.This role is accountable for both product quality and business outcomes and is expected to operate as a startup within Constellation — driving the initiative from concept through sustained growth.Key ResponsibilitiesDevelop the business plan for the Voice & Communications initiative and own adoption, revenue growth, and overall financial performance, including how AI‑driven capabilities contribute to differentiation and value.Build and validate financial models — pricing, cost structure,



and expected returns — and present go/no‑go recommendations to Executive Leadership at key stage gates.Engage directly with dealerships to understand communication workflows, validate product‑market fit, and identify early adopters; lead pilot programs andwork through implementation, pricing and adoption challenges.Participate in early‑stage sales efforts — customer conversations, pilot agreements and initial deployments — helping secure founding customers and refine the go‑to‑market approach.Define the product vision and core capabilities of the VoIP platform, including AI‑enabled functionality such as call transcription, summarization, intelligent routing and workflow automation, ensuring AI delivers practical, measurable value within dealership operations.Drive the transition from pilot to broader deployment, evolving the solution from MVP to a scalable offering by improving onboarding, usability, reliability and AI performance based on customer feedback and usage.Define and refine pricing and packaging, and continuously evaluate performance across adoption, revenue, cost efficiency and the impact of AI‑driven capabilities.Required QualificationsBachelor’s degree in Business Administration, Computer Science, Finance or a related discipline, or equivalent experience.Experience in Product Management, Business Development or a similar role with ownership of a product or initiative from concept through delivery and adoption.Experience working directly with customers or end users to understand workflows, validate solutions and drive adoption.Strong understanding of business processes with the ability to identify opportunities for product or service improvements.Experience with VoIP, UCaaS or cloud communications platforms strongly preferred.Familiarity with AI‑driven capabilities such as transcription, natural language processing or workflow automation and the ability to apply them in practical business use cases.Experience in dealership, ERP or vertical SaaS environments is an asset.Entrepreneurial mindset; thrives in lean, startup‑style initiative environments with limited process and high ownership.Strong cross‑functional influencer; able to move engineering,



commercial and executive stakeholders without direct authority.AI product craft — specifies features precisely, evaluates output quality rigorously, decomposes multi‑agent workflows and diagnoses failure modes before they reach production.Sound judgment on trust and compliance — designs human‑in‑the‑loop checkpoints, call‑recording consent flows and escalation rules appropriate for mission‑critical dealer software; communicates trade‑offsclearly to leadership.Financial discipline — builds financial models, translates platform and AI costs into dealer subscription pricing and applies the same rigor to per‑call token spend as to any other line item.Salary Range (Ontario & BC Only)The estimated base salary range for this role is CAD$100,000 - CAD$150,000 plus commission yearly. We include salary ranges in job postings only where required by applicable pay transparency laws, based on the jurisdictions in which the role may be performed. The posted range is a good faith estimate and reflects factors that are subject to change. Final offer amounts may vary based on job‑related factors, including work location, candidate experience and expertise and other relevant considerations.Human‑Centered, AI‑SupportedWe may use AI tools to support and streamline parts of our recruitment process, such as scheduling and note‑taking. AI helps us work more efficiently and consistently, but it never replaces human judgment. All hiring decisions are made by people not machines. Interviews are conducted by real team members who want to get to know you and your experience. AI is used to reduce bias, improve fairness and streamline processes while keeping human connection and individual stories at the heart of our process.We recognize the value and importance of diversity and inclusion in our communities and in the workplace. We celebrate diversity and one of our goals as an employer is to create an inclusive work workplace for all employees. We are an equal opportunity employer and do not discriminate against any employee or applicant because of race, religion, sex, sexual orientation including gender identity or expression, pregnancy, national origin, age, marital status, veteran status, disability status or any other category or characteristic protected by law.Applicants with disabilities who would like to require a reasonable accommodation related to any part of the application process may contact us at [email protected].#J-18808-Ljbffr

📌 Innovation Manager - C$100,000 - C$150,000 A Year (Winnipeg)
🏢 Constellation Dealership Software
📍 Winnipeg