Chief Operating Officer

Aspire Software

Chief Operating Officer leading operational and commercial strategies for Aspire Software. Overseeing business development, customer success, and financial health.

Posted 4/27/2026full-timeRemote • 🇺🇸 United StatesLeadWebsite

About the role

Key responsibilities & impact

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
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
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 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

Requirements

What you’ll need

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 and the USA

Benefits

Comp & perks

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.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

AI strategy developmentfinancial managementsales performance managementcustomer project deliveryCRM optimizationKPI developmentP&L managementbusiness intelligenceFP&A processescustomer acquisition strategies

Soft Skills

leadershipcommunicationorganizational skillsproblem-solvinggoal-orientedentrepreneurial spiritcross-functional team managementanalytical skillscustomer success managementtraining facilitation

Certifications

Bachelor’s degreeMBAadvanced degree