Chief Operating Officer

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 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.