Golden opportunities to work with the best-managed agency


Cupid’s Escorts is an established female-owned and operated companionship agency that has built a solid reputation for being honest, reliable, and ethical. We understand what your needs are as a woman, and we will always make sure that you are comfortable working on our team. If this is your first time becoming a companion, if you’re looking to switch from another agency, or you want to return after an absence, we will guide you through the process to make sure this is the right choice for you.

Cupid’s Escorts is made up of a team of highly organized and professional women who believe in empowerment, education, and fun. We are here for you in every way possible. We are not just your agency sending you on calls; we are your support while you lay the foundation for your future.

Our business model is often copied by other other agencies, but they cannot compare with our unparalleled reputation and service.

At Cupid’s, we strive to help you build a better work/life balance and provide you with the full support you need to be financially independent, achieve your personal and professional goals, or find additional ways to enrich your life. Cupid’s Escorts strongly believes in achieving your best in everything that you do, we believe that every woman should have the power to make their lives better.

Joining Cupid’s Escorts agency can open up many doors for you; it’s up to you which one you choose to walk through.

Jillian Hollander

Jillian Hollander
Owner of Cupid’s Escorts

“All your dreams can come true if you have the courage to pursue them.”

Walt Disney


Women who work with Cupid’s Escorts enjoy their status as one of the most prestigious companions in the country. To see what Cupid’s can offer you in representation, we invite you to contact us directly and in confidence via email: hiring@cupidsescorts.ca

Please note that due to the high volume of applications we receive, we ask that you include a detailed description of yourself, your experience that is relative and non-relative to this industry, as well as some non-nude photographs for our consideration. Emails that do not contain the requested information will not be considered/responded to, so please be sure to include this. No phone calls, please.

All information is kept confidential.

Please note that we do not re-schedule interviews under any circumstance.

Perks of being a Cupid’s Escorts companion

Starting from day 1
  • A higher-than-average hourly wage, one of the highest in the industry
  • The flexibility of a schedule that you decide on; you decide on what hours you want to keep and how long you wish to be on schedule each day; you’re in charge!
  • We offer training for ladies who are new to escorting
  • Complimentary photo shoot by a female professional photographer in a proper studio with many perks like a gifted set of lingerie from high end brands for you to keep and a hair stylist on site, Cupid’s photoshoots standout more than other agencies because of our attention to detail
  • A safe and empowering environment that strives to be stress-free; we believe in work/life balance
  • The benefit of working with very experienced and organized all-female staff that understands your needs
  • Personal drivers that only drive one to two ladies at a time
  • We do not have an office that you are required to wait for your calls at, nor will you have to wait in a driver’s car all evening between calls
  • Full respect of your boundaries and limitations; with an understanding that these may change
  • Amazing Search Engine Optimization that has kept us on the front page of Google and other search engines for maximized exposure
  • A very loyal following of clientele who know who we are and what we represent, we have one of the most solid reputations in the industry and have been the leader in this industry for over two decades
  • Access to our exclusive library with dozens of titles about sex-work, relationships, money management and how to make the best of your time in and out of this industry
  • We offer complimentary self-defence workshops to our staff every quarter
  • Exclusive partnership with a highly regarded cosmetic clinic and spa that offers 30% off injectables and 50% off skin treatments to all employees
  • We are the “Fully Booked” agency; we are here to maximize your time and will book you as much as you are comfortable with
After 6 months of continuous employment
  • We will match your RRSP contribution by 25% at tax time
  • Should you be a student or wanting to return to an academic program, Cupid’s will do what we can to help build your future; we will pay 50% up to $3,000 toward your tuition per year
  • We will pay 50% of your plastic surgery (up to $2,000 per year), this includes breast implants, teeth whitening, Botox/fillers as well as most cosmetic procedures
  • Cupid’s Escorts will gift you $3,000 towards your purchase of a new home or investment property to help with overwhelming costs of buying in the Toronto area
  • Cupid’s is very proud to offer a Parental Benefit of $100 for your first child and $50 for each additional child per month to help with the of being a parent, this benefit is available immediately after you begin employment with Cupid’s

“There is no time like the present to change your life for the better.
We will be there to help along the way.”

Jillian Hollander
It is with deep regret that I submit my resignation! I will be heading back to home, soon will be my last day with Cupids, the agency I've come to love. Of course, the agency is nothing without the people who work for it, and so I want to say thank you for a great summer. It was profitable and very very fun. I'll especially miss Tom and William; they kept me company and made me laugh during what would otherwise have been many very dull miles to Mississauga, Brampton, Airport, even Whitby for %&# sake. And thanks to you, Jillian Hollander, for being our "Toronto mom," for looking out for us, keeping us safe, happy and for listening to all our concerns. If it weren't for you, I'd never have gotten back into the biz in the first place. You are a real gift to all your staff who find themselves at your company, no matter what their background or personal pressures.

Compliments from Juliette
I worked for Cupid's for 6 months and thoroughly enjoyed my experience. It was my first time working in the industry and I don't regret it one bit. Jillian was very supportive and compassionate towards both my physical and emotional well being, and the drivers were so easy to get along with. If I ever decide to return to escorting, Cupid's is the only place I'll call. I wouldn't want to work for anyone else.

Compliments from Melissa
I really love this job. I'm finding it to be a lot of fun. I really don't think I would have had such a great experience doing this if I worked for another agency. Thanks Jillian!

Compliments from Jessica
I would just like to let you know I have decided to retire from the business and focus on perusing my passion. I wanted to say thank you so much for the opportunity. You are one of the most reasonable, fair and understanding bosses I have ever had. It has been a pleasure working for you and I wish you and your business all the best in the future.

Compliments from Lilith
Thank you for the wonderful opportunity to work and showing me the positive side of the business.I'm going to miss u all guys (phone girls, drivers, and especially a fun fairy like you). I hope I am welcomed back if needed.

Compliments from Rose
Due to changing circumstances within my personal life, it gives me great sadness to resign from your agency and the industry. It has been an amazing 5 months working for you and has time ever flown by! I'd like you to know how much I appreciated the opportunity to work for you, and will never be able to express my gratitude. I loved working within this industry mostly because the agency and the people working within it were incredible. Together we all functioned as a family with similar goals. It was an experience that has left imprints on my heart :) I hope in the future if life decides to throw me more curve balls I will be able to slap on my heels and join your team again. As I said from the moment I walked into your office, and as I say leaving, there is no other woman I would want to work for other than you. Again, many thanks :) and I hope to see you around Madame Jillian ;)

Compliments from Serena
It was fate that I landed in your hands - I am more of a woman leaving Toronto then I was when I met you that night. I will never be to truly thank you enough for all that you have done for me. An infinite amount of doors have opened because of you. Thank you a million times;

Compliments from Lauren
I don't know what you took in school Jillian but you should have a PhD in caring you have been so excellent to us Cupid Girls. Thank you!

Compliments from Olivia
Working at Cupid's was honestly the best thing that has happened to me. It was the answer to all my problems. All the wonderful people I've met while working here were some of the most amazing, hardworking, inspiring, strong people I've ever known and I'm thankful beyond words that I was able to work in such a great position. I really wish there was another way.

Compliments from Yumi
I want to thank you for your kindness, support and everything you have done. There is a reason you are the best in the business and I am fortunate that I got to work with you. I wish you and the rest of the team nothing but the best.

Compliments from Anastasia

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