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

Skilled 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-solvingis 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.

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📌 Chief Operating Officer (Ontario)
🏢 Valsoft
📍 Ontario