Administration and Operations Coordinator 

12 month contract

(25 hours per week)

Start date: as soon as possible

Location flexible

About Head to Head

Head to Head promotes mental resilience and overall wellness through mentorship programs that are led by 30+ Olympians nationwide. Over 15 school/club/camp visits per month take place in BC, AB, SK, MB, ON and QC; all of which are guided by the Head to Head curriculum. Founded by 2X Olympian, World Championship Medallist, and 2016 Olympic Swim Team Captain, Martha McCabe; Head to Head offers year-long mentorship programs to schools, camps, and clubs, corporate speaking engagements and partnerships, and half day swim clinics. Head to Head Olympian mentors are supported through financial compensation, networking opportunities, and professional growth opportunities as they transition to their life after sport.

Job Summary

Head to Head is seeking administrative and operational support to organize, and coordinate all programs across Canada . The best candidate is extremely detail oriented, has a natural mindset for creating streamline systems and organizing processes to help increase efficiency.  The role includes resource preparation for all club and school mentorship programs, so an eye for design and competence with software and technology is important. This role requires an exceptionally motivated person who can demonstrate self-driven initiative and understands the importance of precision. Excellent communication, customer relation, and writing skills are necessary. This job is very flexible, and is largely completed from home/remotely. As such you are required to have your own personal laptop and a quiet place to work. You will be reporting directly to the Founder and President of Head to Head and will be required to complete the majority of work between ~ 10AM and 2PM EST M-F.

What will you be doing?

Event Administration

● Coordinating logistics for each event, including pool bookings, creating Eventbrite pages,  writing email content, preparing email campaigns, creating promotional images, answering FAQs and inquiries,  preparing materials for Olympian and onsite leads at events, and collecting feedback from post event surveys

● Ensuring event logistics and details are all accounted for. This included booking pools, checking in with facilities, ensuring schools have all required materials for upcoming visits, confirming Olympian actions completed, and much more.

● Compiling attendee information and communicating directly with Olympian and onsite leads and updating current messaging as well as overseeing event registrations and maintaining connections with attendees and any sponsors across all events

● Storing, preparing, and shipping all materials for clinics (putting together clinic materials - printing and hole punching workbooks, labeling workbooks, compiling all materials needed and mailing to onsite staff)

● Proactively seeking improvements for all materials, processes and templates in place

● Being onsite, or finding onsite leads for swim clinics as a customer facing employee


● Building out, and managing a system to track all Olympian visits, social posts, school, club, and camp needs, and ensuring all stakeholders are communicated with regularly and receiving the materials they need (ie. videos, workbooks, promotional pieces, check ins, etc.)

● Email outreach: using templates of past emails and contacts, sending out upcoming information and/or setting up phone calls for Founder with new potential customers

•Creating promotional materials, sharing information with all contacts in Head to Head database for that location (working with Mailshake software)

● Tell the story of Head to Head by recapping the month’s activities in the monthly newsletters for Head to Head (with Active Campaign CRM software). This includes tracking events; past and upcoming, while seeking other important information in the youth wellness space around resilience and wellness.

● Enhancing existing brochures, information materials, and building new resources (with Canva)

● Ability to problem solve, and go above and beyond customer and partner expectations

● Going above and beyond in any client facing obligations, which includes collecting feedback, servicing customers and fulfilling partnership agreements. Keeping partners up to date with Head to Head events, opportunities and ensuring contests, and shared content is posted in a timely manner is one of many important tasks to be completed.

What are we looking for in you?

• Very detail oriented, organized, experienced in administrative work, and has an ability to manage and prioritize conflicts

• Excellent self-management skills. Must be able to work under minimal supervision and prioritize own work to meet objectives and deadlines - extremely driven to exceed expectations

• Strong attention to detail and accuracy, with an appreciation for the implications of errors to all involved including the brand of Head to Head

• Comfortable building processes and systems and thrive when provided with large amounts of information and detail to sort through and clarify

• Proven communication (both verbal and written), listening, and interpersonal skills are critical (previous client facing roles is a strong asset)

• Experience with digital software tools such as Mailshake, CRM systems, Canva is considered an asset

• Preference given to bilingual (French/English) speakers with event and administrative experience

All interested candidates please contact Founder and President, Martha McCabe at with a cover letter outlining how you meet the role description, resume, and 2 references (name, email and phone number) from past employers. Applications will be considered on a first come first serve basis and this role will stay open until the right candidate is found. 

Thank you!