Chief Operating Officer

About this role

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.

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