Executive Assistant to the 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 About the role 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. What you get to do: 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 HubSpot, 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. You may be a fit for this role if you: 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 direction. Demonstrate excellent problem-solving and decision-making skills, even with incomplete information. Maintain a positive and solutions-focused mindset when navigating challenges. Are highly organized, detail-oriented, and thorough, without losing sight of the bigger picture. Communicate clearly and effectively in writing and verbally. Are skilled at researching, synthesizing information, and reporting insights clearly. Have experience working in a Mac-based environment. Are comfortable using tools such as Google Docs, Sheets, Slides, Slack, HubSpot, and similar platforms. Compensation Competitive base salary commensurate with skills and experience. Annual compensation reviews against external benchmarks. Performance-based bonus structure rewarding impact and excellence. Health and Dental (premiums shared 50/50) Long-term disability (employee paid) Life and Critical Illness Insurance Emergency Travel Medical Employee & Family Assistance Program Group RRSP and TFSA with access to a Certified Financial Advisor Our Culture We’re a team that believes better B2B SaaS growth comes from sharper thinking, creative execution, and being truly accountable to results. We’re small enough to move fast, but big enough to give you room to grow. You’ll work closely with smart, collaborative people that value both strategy and execution. And you’ll be part of a culture where experimentation, honesty, and continuous learning are how we get better every day. #J-18808-Ljbffr