Dating Coach for Men


Were you meant to be cupid?


About Us

Dashing Date is a Canada-wide speed dating events and matchmaking company. 2020 marks our 8th year in business! We create seamless dating experiences and introduce single professionals looking for a serious relationship to potential partners. We are currently hiring a Chief Matchmaker to manage and develop our client base in Montreal, Toronto and Ottawa. This position is commission-based.

What type of person embodies a Chief Matchmaker?

  • People feel great comfort in the presence of a Dashing Date Matchmaker. They trust opening up and sharing their hearts desires.
  • A Dashing Date matchmaker loves to listen and help. They have a knack for connecting people due to their innate intuitive character.

What are the responsibilities of a Chief Matchmaker?

  • Scheduling and conducting face-to-face meetings with clients who are looking to work with a matchmaker.
  • Reviewing client questionnaires and doing in-depth assessments of who could be a good match for whom.
  • Phone calls, emails, and customer relationship management.
  • Setting up blind dates for clients (venue selection, reservations, feedback follow-ups)
  • Providing dating advice, coaching, and guidance to clients.
  • Administrative tasks (lots of email, use of CRM, database research and more).
  • At least 2 hours per day is needed to get started.

We’re hiring someone…

  • who believes in our vision and what we do
  • self-motivated with a strong work-ethic
  • warm and relatable
  • reliable and dedicated
  • who is looking for an awesome side-hustle
  • who understands and loves the hustle
  • who can devote 15 hours or more per week
  • with a large professional and/or personal network
  • who networks often and meets lots of new people
  • who has a laptop and smart phone (Macbook and iPhone? Bonus!)

(There are a number of things we didn’t list here, such as, impeccable communication skills, web savviness and being well-dressed/ presented among other necessary and valued attributes. We figure, all this goes without saying).

*If you are awesome and people love you, and you have the flexibility to commit to the position requirements, this could be an opportunity for you.*

Don’t apply unless you’re serious and qualified.

Our business is growing rapidly. This means, following training, you will be handed clients from the get-go. You will not only begin with existing clients but also a list of potential clients, those who have expressed an earnest interest in our matchmaking services. You will have access to valuable data and resources and the ability to earn from Day 1.

Connect Humans. Apply here:

Dashing Date Chief Matchmaker Application! Please note, you will need to upload at least 2 recent photos, so please have them ready.