Head of Sales

1 week ago

Markham, Ontario, Canada Prospects by Sports Illustrated Full time $60,000 - $100,000 per year

We're Hiring: Head of Sales – Youth Hockey Tournaments (Remote)

Location:

Remote (Canada or USA)

Type:

Full-Time | Base $60,000 + Bonus (OTE $80K–$100K+)

Start Date:

As soon as we find the right all-star

Company Description

Prospects by Sports Illustrated (PSI) is a premier youth sports organization running elite AA and AAA hockey tournaments across North America. Backed by the credibility of the Sports Illustrated brand, PSI delivers professional-grade tournaments like the All-Star Challenge, The Cup, Mo Cup, Coffey Cup, and the Canadiens Cup—each designed to spotlight top players while giving them a weekend they'll never forget.

We've hosted teams from across Canada, the U.S., and Europe, built a robust media content engine, and earned the trust of thousands of coaches and families.

Now we're looking for a closer to help us grow. That's where you come in.

Role Description

We're seeking a high-energy, strategic Head of Sales who isn't afraid to get on the phone, connect with coaches, network with decision-makers, and close deals fast.

This is not a passive "order-taker" role. You'll drive registrations for multiple PSI tournaments, work closely with marketing to align messaging and media, and become the trusted voice for our events with hockey programs across North America.

What You'll Be Doing

  • Prospect & Close: Build and manage a pipeline of AA & AAA hockey coaches and team contacts.
  • Phone-First Sales: Get people on the phone quickly and turn interest into registration.
  • Follow-Ups & Funnels: Use our CRM tools to stay on top of every lead, deadline, and division.
  • Coordinate with Marketing: Guide the creation of social graphics, PDFs, email templates, videos, and other tools to help you close deals.
  • Network & Sell Big: Pitch bundles, multi-team discounts, and full circuit commitments.
  • Collaborate Across Departments: Communicate with tournament directors, registration managers, and media/content teams to ensure a seamless handoff and experience.

What Makes You a Fit

  • You're a closer — you can sell on the phone, via email, in DMs, or face-to-face.
  • You move fast — you follow up, create urgency, and stay in front of leads.
  • You know the sports world — ideally hockey, youth sports, or events (or you've sold into it).
  • You're a strong communicator — written, verbal, video, and confident in your own voice.
  • You love systems — CRM tools, follow-up workflows, and pipeline tracking don't scare you.
  • You're coachable — this is a growing company; we learn fast and iterate constantly.

Compensation & Perks

  • $60,000 Base Salary (CAD or USD depending on location)
  • Performance Bonuses tied to registrations, returning teams, and upsells
  • Year 1 OTE: $80,000
  • Year 3 OTE: $100,000+
  • Flexible remote work
  • Travel opportunities to some of the top tournaments in North America
  • Hands-on experience working with one of the most exciting youth sports brands in the industry

How to Apply

Send us:

  • Your resume
  • A short video (under 2 mins) introducing yourself and why you'd crush this role
  • A 1-paragraph pitch: How would you follow up with a coach who expressed interest in the Mo Cup but hasn't registered?

Email to:

Cayla Tverberg –

Subject Line: Head of Sales – [Your Name]

Bonus if You Have:

  • Sold in youth sports, travel teams, tournaments, or camps
  • Played competitive hockey
  • Worked with platforms like EventConnect, HubSpot, or Streak
  • Created sales tools in Canva, Google Docs, or Loom

  • IT Sales Manager

    1 week ago

    Markham, Ontario, Canada Venture Computers of Canada Inc. Full time $120,000 - $150,000 per year

    Role Overview:The IT Sales Manager is responsible for driving revenue growth by leading the sales strategy and execution for IT products and services. This role involves managing a team of sales professionals, developing client relationships, and collaborating with technical teams to deliver tailored solutions that meet customer needs.Key...

  • Analyst, Sales and Business

    1 day ago

    Markham, Ontario, Canada MOBIS PARTS CANADA Full time

    About MOBIS Parts Canada (MPCA):MOBIS Parts Canada ("MPCA") is a technological leader in the automotive industry, specializing in the distribution of parts for Hyundai Motor Company and Kia Motors. With a strong commitment to collaboration, ingenuity, and a promise to bring safety and happiness to our customers, MPCA is dedicated to constant evolution and...

  • Field Sales Engineer

    2 days ago

    Markham, Ontario, Canada Quanser Full time $80,000 - $120,000 per year

    Job Title:   Field Sales EngineerLocation:    Markham, OntarioType of job:  Full-time, PermanentStart Date:  January 2026Quanser has an immediate need for Field Sales Engineer to join our teamOUR PROMISE TO YOUWe offer a fast-paced, dynamic, and creative environment where your opinions and ideas can make a difference. People who thrive here are all...

  • Specialist, Sales

    1 day ago

    Markham, Ontario, Canada Gordon Food Service Full time $28,000 - $42,000 per year

    Welcome to Gordon Food Service We are excited that you are thinking about opportunities with us, and we have an amazing story to share. Here's a quick glance of who we are and the impact you could have on the food service industry. There's a seat at our table for you...InnoServ provides installation, preventative maintenance, servicing and measures...

  • Meat Supervisor Trainee

    7 days ago

    Markham, Ontario, Canada T&T Supermarket Full time $40,000 - $60,000 per year

    Company Introduction: T&T Supermarket Inc. was founded in 1993 with two stores in BC. Since then, it has expanded rapidly and is now Canada's largest Asian supermarket chain with 31 stores across the country: 13 in BC, 7 in Alberta, 10 in Ontario, and 1 in Quebec. The Company's continuous expansion is going to bring more new stores in the next couple of...

  • Meat Supervisor Trainee

    5 days ago

    Markham, Ontario, Canada T & T Supermarket Full time $40,000 - $70,000 per year

    Reporting to the Meat Department Head (or his/her delegate), the Meat Supervisor is responsible for supporting the Department Head and Assistant Department Head in providing guidance, supervision and sets as a good example for Meat Assistants to follow.T&T Supermarket Inc. was founded in 1993 with two stores in BC. Since then, it has expanded rapidly and is...

  • Franchise Business Consultant

    1 week ago

    Markham, Ontario, Canada b2e3e319-b046-4c46-affe-0ca74780b7d8 Full time $60,000 - $100,000 per year

    Location: Markham, OntarioJob DescriptionWhat is the role?Reporting to the Regional Director, the Franchise Business Consultant ("FBC") is responsible for all operational activities and sales results in the district. Key areas of focus will be successful district system wide sales growth while meeting financial and operational objectives.Key...

  • Senior Manager, Sales, Ontario General Insurance Market, I

    1 day ago

    Markham, Ontario, Canada TD Full time $105,400 - $158,000 per year

    Work Location:Markham, Ontario, CanadaHours:35Line of Business:Personal & Commercial BankingPay Details:$105,400 - $158,000 CADTD is committed to providing fair and equitable compensation opportunities to all colleagues. Growth opportunities and skill development are defining features of the colleague experience at TD. Our compensation policies and practices...

  • Senior Manager, Sales, Ontario General Insurance Market, I

    2 days ago

    Markham, Ontario, Canada TD Full time $105,400 - $158,000

    Work Location:Markham, Ontario, CanadaHours:35Line of Business:Personal & Commercial BankingPay Details:$105,400 - $158,000 CADTD is committed to providing fair and equitable compensation opportunities to all colleagues. Growth opportunities and skill development are defining features of the colleague experience at TD. Our compensation policies and practices...

  • Skate Instructor

    1 day ago

    Markham, Ontario, Canada City of Markham Full time $30,000 - $40,000 per year

    The City of Markham is proud to be recognized for the 5th consecutive year as one of Canada's Best Employers by Forbes and Statista Inc. In 2025, the City of Markham is ranked 2nd among municipalities in Canada and 12th overall for Government Services. The recipient of multiple environmental awards, we are recognized for our innovative sustainability and...