Dating Coach for Men

Welcome Future



Dashing Date is a well-established Canadian speed dating company, headquartered in Montreal, that is in its 9th year of business. We specialize in organizing high-quality, expertly curated virtual dating experiences for single professionals who are serious about meeting someone.

Our team is driven, friendly and passionate about the dating space and helping people find love! We work hard, with integrity and a positive mindset. We challenge and question everything, including our own work and processes. We stay ahead of the curve and are always ready to embrace change!

Our team values open and honest communication and is always willing to hear each other out. We love cracking jokes and bringing joy to the workplace. We’ve designed our jobs so that we can all work remotely, from the comfort of our own homes. Most importantly, we really are a team (even when we’re working separately), which means that we are always there to encourage and support each other.

Dashing Date started as a speed dating company back in 2012 and within a couple of years, we were offering matchmaking services too! The matchmaking division grew very organically, clients who were serious about meeting someone but couldn’t always make it out to our events started to request one-on-one set-ups so, that’s just what we did! Our matchmaking services are now available in three cities, Montreal, Toronto and Ottawa.


We’re hiring a Chief Matchmaker

We’re excited to welcome a new member to our team who will lead our Matchmaking Department and be integral to its growth in 2022! If you have an entrepreneurial spirit and want to grow an already blossoming business into something big and beautiful, this role could be the perfect fit for you.

Here are just some of the perks to kicking off your matchmaking career with us:

  • Begin your new position with a roster of already active and paying clients.
  • Recruit clients only from hot, confirmed leads.
  • Grow the business as if it were your own.
  • 90% of communication with clients is handled by email and text message.
  • Only work with clients you’re excited about and feel a connection with.
  • Benefit from rigorous marketing and ad campaigns already in place.
  • Work from the comfort of your own home.
  • Flexible schedule.
  • Receive constant guidance and support.
  • Bring your own personality and flair to your work.
  • Unlimited earning potential.
  • Generous commission structure.
  • Full training will be provided to bring you up to speed.


Something you should know is that most matchmaking jobs require you to go out and find the clients. What makes Dashing Date exceptional is that because we’re a speed dating company first and foremost, we have new clients entering our database every month!

No cold calling or expired leads are part of this mix! You will only work with and recruit clients who are already in our database and who have expressed interest in our matchmaking services.


Possesses an entrepreneurial spirit.
Is looking for a project with amazing potential and is ready to give their 200%.
Is a self-starter who is reliable and hard-working.
Is driven by results and can deliver without being micro-managed.
Is forward-thinking and takes initiative.
Works with integrity and honesty.
Acts intuitively, with kindness and empathy.
Has excellent time management skills and is punctual and reliable.
Is incredibly organized.
Communicates clearly and effectively with flair and personality, both spoken and written.
Excels at grammar, spelling, and punctuation and is a word fanatic.
Is fun, energetic, and confident.
Celebrates the wins – big or small – and enjoys the process as much as the outcome.

The J.O.B.

matchmaking job computer image

Tasks & Responsibilities

Builds clientele through email/text and marketing programs.
Hits ambitious monthly quotas.
Sells the service with ease, finesse and professionalism.
Researches our database regularly and recruits new clients.
Identifies potential partners among our client databases.
Writes witty, fun and captivating client profiles.
Writes engaging, bubbly and professional emails.
Sets up blind dates (including all logistical requirements).
Reviews matchmaking questionnaires.
Manages customer service (90% of which is via email).
Develops and maintains solid relationships with existing clients.
Organizes and maintains an accurate and informative timeline about each client.
Develops custom dynamic email sequences for efficient follow-ups with clients.


Your own laptop (preferably a MacBook and in good condition)
Your own smartphone (updated and in good condition)
Easily reachable and responsive
Navigates and learns new software platforms and digital tools* with ease and curiosity
Able to start, manage, and complete projects independently
Identifies and prioritizes competing tasks and responsibilities
Experience managing projects and timelines
Handles unexpected or challenging situations with ease, elegance and finesse
Fluent in English (French is a bonus)
Enjoys never-ending humdrum day-to-day administrative tasks!

*We currently use WordPress, Active Campaign, Asana and Gmail extensively, among other platforms

It would also be an asset if you have any of the following

Worked in the dating industry in some capacity
Can provide dating and relationship advice and tips
A background in psychology
Experience creating strategic and engaging marketing campaigns
Are great with creative copywriting and content creation
Enjoy sales – and you’re great at closing the deal!


This role is 100% commission-based and offers a generous and competitive commission structure with unlimited earning potential.

There is no base salary or hourly pay.

If you’re qualified and serious...

Please submit your personalized cover letter (specific to this role) and your C.V. by email to: jobs@dashingdate.com

Include your name and “I love matchmaking” in the subject line.

Qualified candidates will be asked to submit a video application. You can jump to the front of the (interview) line by submitting your video application asap. Click here for instructions.