Navigate Complexities. Create Change. Together. This is our purpose at CUPS.

Our unique integrated approach to care empowers people to work holistically to create and achieve goals that support their well-being and builds readiness to navigate and access support in the community. As a formative presence, we work together to build better systems and a stronger community.

Clients depend on us, supporters trust us, and partners count on our collaboration. We do not take this responsibility lightly – we are accountable for our words, our actions, our relationships, and most importantly, ourselves. Through a compassionate lens, we afford every person dignity in their interactions with us.

We proactively seek opportunities for continuous learning with open minds and transformative spirits. Through our culture, rooted in our values, we will achieve our purpose and ambition.

The Opportunity

We are looking for an Executive Assistant to join our at CUPS.

You'd be joining a small, high-functioning Senior Leadership Team, working most closely with a CEO who leads with big energy, warmth and a relationship-first style. The right person for this role builds an authentic, trusted connection with that outgoing approach, while bringing their own natural strength in structure to the partnership sharp planning and preparation skills, clear written communication, and confident meeting facilitation that keeps things on time and outcome-focused. You'll also work across leaders with genuinely different paces and styles, from direct and fast-moving to measured and detail-focused to collaborative; reading those cues and adjusting your approach is core to making this role work.

This is more than an administrative role: it's the administrative branch of the Senior Leadership Team. You'll be an active partner in keeping projects, decisions and communications moving, and you'll take an active hand in how the building itself runs day to day spotting facilities issues, keeping meeting rooms and common spaces in good order, and connecting problems to the leader who can solve them, before they become bigger problems.

- Location: Onsite, CUPS - 1001 10 Ave SW, Calgary
- Reports to: Chief Executive Officer
- Contract type: Permanent
- Schedule: Full-time, Mon to Fri, 37.5 hours per week
- Starting salary: $66,300.00 - $69,800.64

Key Responsibilities Support the CEO and Senior Leadership Team

- Own calendar management, meeting coordination, and travel logistics, prioritizing time and access based on organizational impact.
- Track timelines, deliverables, action items and follow up on behalf of the CEO and SLT and hold people to them.
- Draft, review and edit executive correspondence, communications and briefing materials.
- Represent the CEO and SLT in stakeholder communications, exercising judgment on what to resolve directly and what to escalate.
- Anticipate needs and prepare briefing notes and background in advance of every meeting, encounter and external engagement.
- Plan and run meetings that are well-organized, time-effective and outcome-focused, from agenda design through to action tracking.




- Take ownership of discrete workstreams within special projects and strategic initiatives, driving them to completion with minimal oversight.

Support Governance and the Board of Directors

- Serve as the primary administrative contact for the Board and support the Board Chair in governance activities.
- Schedule Board and committee meetings, prepare and distribute materials, and produce accurate, qualified minutes and action summaries.
- Own end-to-end preparation for Board duties meeting logistics, Board handbook maintenance, minutes and correspondence anticipating what Directors need before they ask.
- Onboard new Directors and manage committee meeting logistics, including videoconferencing and boardroom arrangements.
- Exercise discretion and political awareness in all Board-facing work.

Lead Our Office and Admin Team

- Directly lead the CUPS Office Manager, a direct report, ensuring the day-to-day office from mail and meeting room readiness to kitchen upkeep and event support- run smoothly in service of CUPS Directors and Strategic Managers, while coaching them to embody CUPS values and grow as a strong leadership-support partner.
- Maintain active, ongoing oversight of how the building functions day to day, monitoring meeting room booking processes, staying ahead of facilities issues, and fielding common staff requests, then routing what needs attention to the right leader.
- Create an approachable, caring and trauma-informed environment for workers, clients and guests.
- Act as an ambassador of CUPS' mission and values, both internally and externally.

Build Relationships Across CUPS

- Develop collaborative, accountable working relationships with colleagues across CUPS to strengthen communication flow and cross-departmental understanding.
- Build genuine, trusted relationships with Board members, administrative partners and external stakeholders, reading relationship and organizational dynamics accurately and responding with discretion.
- Play an active role in planning and executing CUPS events and volunteer engagements, partnering with event leaders from concept through delivery.

Employment Requirements

- A completed 1-year certificate in Professional Administration, Business Administration, Information & Records Management or a related field, plus 5+ years of progressively responsible administrative experience supporting senior management or executive levels; OR a 2-year diploma in a related field plus 3+ years of equivalent experience.
- 3–5 years of direct experience supporting senior and executive leaders, with demonstrated growth in responsibility.
- Advanced proficiency with Microsoft Office (Outlook, Word, Excel, PowerPoint, Teams) and experience managing calendars, correspondence,



briefing materials and executive workflows.
- Preference given to candidates who have supported a CEO, executive leader, or similar senior office.
- Class 5 Driver's License and access to a vehicle required for events, off site meetings and other duties as needed

What You Bring

- Solid analytical and problem-solving skills; you independently identify issues, assess options, and recommend solutions.
- Proven experience managing complex, competing workflows with exceptional discernment, prioritization and execution.
- Highly motivated, self-directed, and equally effective independently and as part of a team.
- Comfortable being the connective tissue between an energetic, relationship-driven CEO and the structure, documentation and follow-through that keeps the organization running smoothly.
- Strives to make others successful and connects authentically with people across every level of the organization.

Work Conditions

- Exposure to stories of trauma, emotionally complex, and sensitive client situations.
- Frequent handling of confidential and highly sensitive organizational and client information.
- Infections waste conveys being exposed to regulated medical waste which this role would not be exposed to under any regular circumstances.
- Exposure to a community healthcare environment, including contact with individuals experiencing acute or chronic health conditions
- Manual dexterity required to use desktop computer and peripherals.
- Work is characterized by frequent interruptions, changing priorities, and competing deadlines.
- Intermittent physical activity including walking, standing, sitting, and lifting (minimum 35lbs)

CUPS envisions a Calgary where everyone is respected and can live healthy, fulfilling lives. To do this, we’re building a culture of inclusion and belonging, guided by our values and a commitment to truth and reconciliation. If you're passionate about supporting Calgarians and expanding our impact, we’d love to hear from you. We value lived experience, including from folks who reflect the clients we serve, as much as formal qualifications. For accommodations during the recruitment process, contact [email protected].

Ready to Join Us?

Submit your resume and cover letter, including your salary expectations.

We thank all applicants for their interest; only those selected for interviews will be contacted.

Pay: $66,300.00-$69,800.64 per year

Application question(s)

- What prompted you to apply to CUPS?
- How many years of direct experience do you have supporting C-Suite or Senior Executive leaders (e.g., CEOs, VPs, Executive Directors)?
- Which of the following best describes your completed post-secondary education and relevant experience?
- Do you possess a valid Class 5 Driver’s License and have regular access to a reliable personal vehicle for attending events and off-site meetings?
- What are your salary expectations?
- For your application to be considered, you must submit a cover letter outlining your motivation for this role. Have you attached a copy of your cover letter?

Work Location: In person

📌 Executive Assistant (Calgary)
🏢 CUPS
📍 Calgary