Executive Assistant to CEO

EXECUTIVE ASSISTANT | Full-time, permanent

Works onsite in Calgary, AB

Work schedule:

8:00 AM - 4:30 PM

Mandatory in-office days are Monday, Tuesday, and Friday

Remote optional days are on Wednesday and Thursday

We’re looking for a highly experienced, proactive Executive Assistant to serve as a trusted partner to Chantelle Little, Founder & CEO of Tiller.

The right candidate will own key initiatives, bring structure to complex priorities, and operate with strong judgment, discretion, and autonomy. You’ll act as an extension of the CEO, anticipating needs, managing critical workflows across sales and operations, and ensuring nothing important falls through the cracks.

You thrive in a fast-paced environment, think several steps ahead, communicate clearly, and take pride in delivering high-quality work with minimal oversight. You’re comfortable managing confidential information, navigating ambiguity, and making decisions that reflect the CEO’s voice and Tiller’s values.

Tiller operates under a hybrid work model with in-office collaboration on Mondays, Tuesdays, and Fridays, and optional remote work on Wednesdays and Thursdays. From time to time, this role will require additional in-office presence to fully support the CEO’s priorities and agenda.

• Own and execute a broad range of administrative responsibilities and strategic special projects that directly enable the CEO to lead and scale Tiller effectively.
• Exercise strong judgment to ensure communications, decisions, and follow-ups reflect the CEO’s voice, leadership style, and Tiller’s principles.
• Manage inbound calls, route appropriately, and ensure timely follow-up.
• Prepare high-quality reports, documents, spreadsheets, and presentation materials as needed.
• Provide sophisticated calendar and time management, proactively resolving conflicts, protecting focus time, and ensuring the CEO’s time is spent on the highest-impact priorities.
• Partner closely with the CEO to keep her well-informed of upcoming commitments, deadlines, and responsibilities. Act as a "barometer" for internal and external dynamics, flagging issues, risks, and opportunities early.
• Anticipate and prepare for meetings, conferences, and offsites by gathering background materials, confirming logistics, preparing agendas, and ensuring the CEO is fully prepared. Attend select meetings to support execution and follow-through.
• Support sales operations, including:
  Assisting with proposal and pitch deck preparation, Maintaining and updating prospect data in Hub Spot, Supporting the sales pipeline and ensuring key actions don’t fall through the cracks.
• Support recruiting initiatives by scheduling interviews, organizing candidate materials, managing assessments, and ensuring a strong candidate experience throughout the process.
• Lead and continuously improve new employee onboarding, ensuring a smooth, thoughtful, and well-organized experience for new hires.
• Oversee software setup, access, and upgrades for new and existing employees in coordination with internal teams.
• Manage office operations, including coordination of maintenance and purchasing supplies and equipment as needed.
• Assist in vendor research, selection, and coordination to support smooth business operations.
• Support the completion of grant applications and other business-related submissions as required.
• Provide support for internal and external events, marketing initiatives, and team activities.
• Build strong, trusted relationships across the organization and externally, acting as a culture carrier and ambassador for Tiller.

• Have 5+ years of experience providing dedicated support to a senior-level executive, ideally in a fast-paced or agency environment.
• Operate with the highest level of integrity, discretion, and professionalism, particularly when handling sensitive or confidential information.
• Are a strong team player who builds trust quickly and collaborates effectively across functions.
• Welcome feedback and view it as an opportunity for growth and improvement.
• Are a true self-starter who can work independently, identify gaps, and take ownership without needing step-by-step…