"Alerted.org

Executive Assistant Aspira | Leadership About Aspira

For forty years, Aspira has been the market-leading software and services provider for the great outdoors, primarily for state and provincial parks and wildlife agencies. As part of our constant evolution, we're executing an aggressive multi-year transformation to accelerate revenue growth, optimize cost structures, and maximize shareholder value while expanding our market position.

The leadership team has reset the company’s core values to drive our transformation: Customer Obsession, Forward Momentum, One Team One Dream, Radical Transparency, Win with Integrity, and Excellence guide everything we do.

The Ideal Candidate

As the Executive Assistant to the CEO, you’ll serve as a trusted partner in managing the CEO’s time, communications, and priorities. This is not a traditional EA role — it blends high-level executive support with strategic collaboration, making it ideal for someone who thrives in fast-paced, dynamic environments and has an interest in SaaS, outdoor recreation, or hospitality technology.

Key Responsibilities

Executive Support

• Manage and optimize the CEO’s complex calendar across global time zones.

• Coordinate extensive travel logistics, including client visits, conferences, and team offsites.

• Prepare briefing materials, agendas, and itineraries for meetings and trips.

• Handle confidential communications and sensitive matters with discretion and professionalism.

Operational Support

• Monitor and help manage day-to-day business operations alongside the CEO.

• Track follow-ups from leadership meetings and ensure accountability across departments.

• Collaborate with product and engineering leads to ensure smooth execution of strategic priorities.

Strategic Partnership

• Serve as a thought partner to the CEO on client engagement, industry trends, and growth opportunities in the outdoor recreation, parks, and hospitality sectors.

• Draft communications, presentations, and internal/external updates with a clear and compelling voice.

• Support relationship-building efforts with key clients and stakeholders, including pre/post-meeting documentation and insights.

Cross-Functional Coordination

• Liaise with internal teams (Product, Engineering, Marketing, Client Success) to gather information and facilitate decision-making.

• Represent the CEO’s perspective and priorities when appropriate.

Qualifications

• Experienced executive assistant or chief-of-staff-level support (5+ years preferred), ideally in SaaS, tech, or industries related to outdoor recreation or hospitality.

• Exceptionally organized, proactive, and adaptable — thrives in ambiguity and can juggle multiple priorities with grace.

• A natural communicator with strong writing and interpersonal skills.

• Emotionally intelligent with high discretion, integrity, and judgment.

• Comfortable with technology tools like Microsoft Outlook, Teams, Slack, and project management systems.

• Passionate about outdoor spaces, travel, or parks/hospitality is a huge plus.

• Able to travel occasionally to support the CEO at events or offsites.