Chief of Staff, Skyward

On behalf of our portfolio company, Skyward, we are seeking a dynamic, highly motivated Chief of Staff to support their CEO and leadership team in navigating a fast-paced startup environment focused on innovation and impact.

Skyward is a dynamic Canadian startup on a mission to make the world safer. Our cutting-edge technology can stop lightning and prevent out-of-control wildfires, protect communities, and avoid 5% of global GHG emissions. We combine science, big data, and machine learning to tackle one of nature's most unpredictable and devastating forces; lightning. If you’re passionate about making a real-world impact, we want you on our team!

Mission: Skyward’s mission is to save lives, ecosystems, and communities by preventing lightning from causing out-of-control fires on high-risk days. In Canada, in 2023, lightning caused 93% of area burned, community evacuations, billions in fire-fighting costs, and released an “India’s worth” of greenhouse gas (3x Canada’s entire economy). Hotter and drier forests, as a result of climate change, are making lightning more deadly. Preventing lightning wildfires is the lowest cost option globally for emissions reductions.

Role Overview:

We seek a dynamic, highly motivated Chief of Staff to support our CEO and leadership team in navigating a fast-paced startup environment focused on innovation and impact. This role blends strategic planning, strong operational execution, and relationship-building with internal teams and external partners. The ideal candidate thrives in ambiguity, is highly adaptable, and excels at driving organizational efficiency while fostering a positive company culture.

This is a high-impact role with significant exposure to all aspects of the business, requiring someone who is proactive, detail-oriented and capable of big-picture thinking and executing with precision.

Key Responsibilities:

Operational Excellence

• Anticipate challenges and proactively identify solutions to organizational bottlenecks.

• Ensure the leadership team stays focused on high-impact priorities by streamlining processes and driving accountability.

• Plan and manage weekly executive meetings, ensuring objectives are met.

• Maintain oversight of KPIs to ensure company goals are on track

Strategic Planning & Partner Engagement

• With the CEO translate high-level strategies into actionable plans that drive outcomes

• Grow revenue by supporting the CEO with proposals, closing deals, and managing partners

• Manage cross-functional initiatives and key projects that align with the strategic priorities.

• Serve as a liaison between the CEO and both internal teams and external stakeholders, ensuring alignment and smooth communication.

Communication & Relationship Building

• Act as an extension of the CEO by representing the company in meetings/ communications

• Prepare internal and external communications on behalf of the CEO, including presentations, reports, and email correspondence.

• Build and maintain strong relationships with internal stakeholders and external partners, ensuring the company’s culture of collaboration is upheld.

Culture & Team Development

• Foster a positive, inclusive culture by promoting the company’s core values and driving employee engagement initiatives.

• Lead efforts to build scalable processes that enable the team to operate efficiently and grow

• Mentor team members and encourage collaboration to drive innovation and efficiency.

Travel & Flexibility

• Be prepared for extensive summer travel to remote locations and year-round business and partner-related travel as required by the company’s needs.

Key Attributes & Qualifications:

Must-Have Attributes

• Strategic Thinker: Able to quickly assess situations, connect dots and recommend actions

• Operations & Detail-Oriented: Follows through on tasks, asks follow-up questions, and ensures things are done right.

• Planner: Anticipates needs, keeps projects on track, and manages timelines effectively.

• Excellent Communicator (Speaker & Writer): Confident in representing the CEO and communicating effectively across all levels.

• People Person: Naturally builds trust and rapport with people across different teams, partners, and stakeholders.

• Builder: Thrives in a startup environment and enjoys creating new processes, systems, and culture from the ground up.

• Self-Motivated: Takes initiative without needing external motivation or supervision.

• Under-Promises and Over-Delivers: Consistently meets or exceeds expectations.

• Fast Learner: Quickly absorbs new information and adapts to changing circumstances.

• Curious: Constantly seeks to uncover hidden insights and improve processes.

• Focused: Keeps the leadership team focused on the most impactful priorities.

• Travel-Ready: Comfortable with extensive travel requirements, particularly in summer.

• Nimble & Flexible: Adapts quickly to changing priorities and thrives in dynamic environments.

• Hustle: Demonstrates a strong work ethic, persistence, and determination to get things done.

Preferred Qualifications

• Experience in startups or fast-paced environments.

• Background in operations, project management, or consulting.

• Fire or aviation industry experience is a plus but not required.

• Bachelor’s degree required; advanced degrees or certifications are a bonus.

What We Offer:

• World-Changing Mission: Contribute to groundbreaking solutions to reduce wildfires

• Personal Growth: As an early team member, you can contribute and grow significantly

• A Collaborative, Fast-Paced Culture: Work alongside passionate individuals

• Competitive Compensation & Benefits: Market compensation with the fun of a startup!