Senior Sales Representative

5+ years

What we do

Heyday is on a mission to revolutionize retail by bringing the in-store experience to the favourite messaging channels of every type of customer. Heyday’s platform helps retailers and brands sell and support from a distance with its next-generation conversational AI solution that combines the power of live chat and automation. With Heyday, brands can enable memorable, convenient, and always-on experiences for their customers, while freeing their teams to focus on high-value interactions. 

Who you'll be working with

At Heyday, we're a fun mix of passionate and smart developers, designers, marketers, product managers, salespeople, and analysts. With our diverse skills and expertise, we work together as one team, while doing our best work. Here we emphasize collaboration, transparency, integrity and empathy.

What you’ll do

Since we are growing and expanding into new markets you’ll be in charge of sourcing, contacting, nurturing and closing businesses located in that market. We need you to own your business within our business and help us grow and define our go to market approach. 

Your main responsibilities:

  • You’ll research prospective accounts in target markets, pursue leads and follow through to a successful agreement
  • You’ll find creative ways to reach decision makers and communicate our service offering
  • You’ll maintain HubSpot CRM for accurate & timely sales pipeline and sales activity reporting 
  • You’ll build industry awareness of Heyday and our services through networking and relentless presentation and demonstration efforts
  • You’ll prepare quotes and contracts that are aligned with your customers objectives as well as Heyday’s capabilities and delivery schedule.
  • You’ll learn about the industry and the competitive landscape and keep the internal development teams aware of potential missing features
  • You’ll achieve sales activities targets and well as revenue targets

What you’ll need

You’ll need to be bursting with self-confidence, love presenting and enjoy reaching out to people in an industry that is quite competitive (although we are the best! :-) We will value your drive, your creativity, your open mindedness and your flexibility as we are a fast moving start up.


  • You have 5 years of relevant sales experience  
  • You have worked in the B2B tech industry for at least 2 years
  • You master English and are an excellent communicator and listener 
  • You are comfortable with CRM, particularly HubSpot
  • You have a hunter profile and an upbeat go-getter attitude
  • Taking initiatives is part of who you are

If you are interested in this position but do not meet all the requirements, do not hesitate to contact us and write to us to explain what interests you about this opportunity and how your experience is relevant to the role!

Also, be sure to follow us on LinkedIn, Facebook and AngelList to stay up to date on any new Heyday career opportunities. 

Why Join Heyday?

You’ll work on an innovative product. You’ll learn new skills and grow your expertise while being constantly challenged in a fast-paced work environment. But you won’t do it all alone, and you’ll be able to count on the support of your team to help you do your best work! Although we are a fast-growing start-up, we understand the importance of having a work-life balance, and you'll be surprised to see how much we can accomplish while remaining calm and positive :)

To ensure your well-being at Heyday, here's what we offer:

  • Group insurance including Dialogue (telemedicine application) from day one and paid 50% by Heyday!
  • Here, everyone starts with 3 weeks of vacation.
  • Of course, flexible work hours  ;)

We are currently working remote, but when it's safe again, you'll enjoy working on the 14th floor of a building that offers a breathtaking view of Mont-Royal and downtown - at the corner of Saint-Laurent & Rachel! 

We thank all applicants for their interest; and we will do our best to reply to all of you in a timely manner.

Difference help us grow

Heyday is an equal opportunity employer that values diversity. Here you will feel like you belong regardless of your ethnicity, religion, colour, national origin, gender, sexual orientation, age, marital or disability status. We seek different perspectives, experiences and opinions. We embrace diversity because we genuinely believe that it helps us grow and innovate. 

Let us know if you’ll require assistance during the application process.

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