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Chief Operating Officer

Job in Toronto, Ontario, C6A, Canada
Listing for: Aspire Software
Full Time position
Listed on 2026-09-25
Job specializations:
  • Management
    Operations Management, General Management
  • Business
    Operations Management
Salary/Wage Range or Industry Benchmark: 180000 - 260000 CAD Yearly CAD 180000.00 260000.00 YEAR
Job Description & How to Apply Below

Description
Aspire Software is looking to hire a

Description
Aspire Software is looking to hire a Chief Operating Officer (COO) for one of our Software Business Units! This position provides critical operational and commercial leadership to a company within a growing software vertical. You will be responsible for developing and implementing the business’s strategic plan spanning sales & marketing, customer support, and professional services. The COO must identify, define, and execute the strategies required to achieve the growth plans and operating objectives with a focus on improving operational excellence.

This person should bring an AI-forward mindset to executing our growth plans.

Here is a little window into our company
:
Aspire Software, an operational arm of Valsoft Corp, operates and manages a portfolio of wholly owned software companies, providing mission‑critical solutions across multiple verticals. Implementing industry best practices in a decentralized model has allowed Aspire to become a hub for creating rapid growth by reinvesting in its portfolio.

Group Responsibilities
  • Develop and implement an AI strategy for non‑R&D departments
  • Own the long‑range, annual and quarterly financial and non‑financial goals
  • Develop and communicate a clear vision of goals and objectives, strategies, philosophies about growth, revenue generation and profitability, customer care agenda.
  • Be hands‑on in day‑to‑day operations including sales performance, sales opportunity management, forecasting, services resourcing, customer support, and customer project delivery
Sales & Marketing
  • Drive revenue growth, working with the sales team to identify new opportunities and execute growth strategies including cross/upsell and entering adjacent markets
  • Develop and implement best in class sales operations and sales infrastructure to enable effective scale and ensure process discipline
  • Develop and maintain competitive intelligence programs, generating industry trend reports to inform new feature and product development
  • Improve use of a CRM and other internal tools to increase forecasting capability, implement targets, and provide actionable insights to executive team and board of directors
  • Create and implement KPIs for sales team to measure performance and productivity (ex: CAC / LTV); develop performance dashboards and establish reporting process (measure NRR and MRR trends)
  • Work with sales leaders in establishing quotas, budgets, compensation plans and pricing optimization
  • Management of key relationships with large accounts is mandatory
  • Attend trade shows and panels
Customer Care/Customer Success
  • Execute an effective, long‑term customer success program for clients
  • Implement and maintain client support initiatives
  • Facilitate both in‑house and client training sessions
  • Monitor and document Customer Success metrics, including program usage, satisfaction levels, ticket throughput, and resolution
  • Coordinate the administration of annual customer satisfaction surveys (NPS) and other communication tools
Professional Services
  • Ensure we are delivering profitable projects by monitoring billable utilizations, staff OPEX and contribution margin
  • Establish strategies to increase NRR
  • Track results on a monthly basis with the Head of Professional Services
About You
  • Bachelor’s degree or equivalent, preferably in a technical or business discipline, MBA, or advanced degree
  • 5+ years of direct cross‑functional team management experience and P&L management within the SaaS Vertical Market, preferably in Travel & Leisure
  • Experienced with AI Automation efficiencies in Sales/Marketing/Support/Professional Services
  • Hardware sourcing and integrated payment processing experience a plus
  • A natural ability to lead performance and financial health in a business
  • Bring a…
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