Chief Operating Officer

Aspire Software; Toronto; On-site; CAD 180,000 - 260,000; Full time

Benefits offered by this job

Health insurance

401(k) with company match

Paid time off

Professional development opportunities

Job summary

Aspire Software, an operational arm of Valsoft Corp, is seeking a Chief Operating Officer to lead the group’s operations and commercial functions in Canada. You will shape strategy across sales & marketing, customer care and professional services, driving AI-enabled growth and operational excellence.

The COO will own long‑range plans, oversee P&L, and build a robust communications framework with the executive team and board. A proven SaaS leader with an entrepreneurial mindset is essential.

Qualifications

• Bachelor’s degree or equivalent; MBA or advanced degree preferred.
• 5+ years of direct cross‑functional team management with P&L in a SaaS business.
• Experience implementing AI automation in Sales/Marketing/Support.
• Strong financial acumen and ability to drive growth.
• Willingness to travel 30%.
• Authorized to work in Canada.

Responsibilities

• Lead AI strategy across non‑R&D departments.
• Own long‑term financial and operational goals.
• Develop vision, growth, and profitability strategies.
• Hands‑on day‑to‑day operations including sales, services and support.
• Manage key relationships with large accounts.
• Attend trade shows and panels.

Skills

Cross-functional leadership

Strategic planning

AI automation

Growth mindset

Leadership

Education

Bachelor’s degree or equivalent

MBA or advanced degree

Tools

CRM platforms

Job description

DescriptionAspire Software is looking to hire a

DescriptionAspire 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 proven entrepreneurial spirit and pace‑setter traits
• Broad financial acumen across the organization (e.g., understanding financial documents, business intelligence, FP&A processes, etc.) is mandatory
• History of developing and implementing successful strategies for net new customer acquisition and market penetration
• Ability to structure, analyze, and solve complex business problems, as well as deliver impact against concrete business goals
• Excellent Leadership, communication, and organizational skills
• A 'roll up the sleeves' attitude towards problem‑solving is essential
• Goal‑oriented with comfort in setting measurable goals for others and him/herself
• 30% travel required for internal and customer meetings
• At least a professional level of English, both written and verbal, is mandatory.
• Must be legally authorized to work/travel in Canada

Why Join Aspire?

• Competitive salary and bonus structure based on performance.
• Health insurance, 401(k) with company match, and paid time off.
• Opportunities for professional development and career advancement.