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About the Role

Aspire Software is seeking a Chief Operating Officer (COO) to provide critical operational and commercial leadership to a software business unit. The role involves developing and implementing strategic plans across sales & marketing, customer support, and professional services, with a focus on AI-forward execution and operational excellence to achieve growth objectives.

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, and 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.
• Drive revenue growth by 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 CRM and other internal tools to increase forecasting capability, implement targets, and provide actionable insights to the executive team and board of directors.
• Create and implement KPIs for the sales team to measure performance and productivity (e.g., CAC / LTV).
• Develop performance dashboards and establish reporting processes (measure NRR and MRR trends).
• Work with sales leaders in establishing quotas, budgets, compensation plans, and pricing optimization.
• Manage key relationships with large accounts.
• Attend trade shows and panels.
• 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.
• Ensure profitable project delivery by monitoring billable utilization, staff OPEX, and contribution margin.
• Establish strategies to increase NRR.
• Track results on a monthly basis with the Head of Professional Services.

Requirements

• 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 is a plus.
• A natural ability to lead performance and financial health in a business.
• 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.

Skills

• AI strategy development
• Sales & Marketing strategy
• Customer Support management
• Professional Services delivery
• Financial goal setting
• Performance management
• CRM utilization
• KPI development
• Customer success program execution
• Project profitability monitoring
• Net Revenue Retention (NRR) strategies
• Leadership
• Communication
• Organizational skills
• Problem-solving
• Goal setting
• English proficiency

Location

• Canada

Work Type

• Full-time

Experience Level

• 5+ years of management experience
• P&L management experience
• SaaS Vertical Market experience

Education Level

• Bachelor's degree or equivalent
• MBA or advanced degree

Salary/Compensations

• Competitive salary and bonus structure based on performance.

Benefits

• Health insurance
• 401(k) with company match
• Paid time off
• Opportunities for professional development and career advancement.

About the 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.