Director, Sales

Toronto or Remote (Canada)

Full Time Executive-level / Director
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Wealthsimple
Wealthsimple is the simple way to grow your money like the world's most sophisticated investors. No-maintenance portfolios, expert investment advisers and low fees.
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Wealthsimple is on a mission to help everyone achieve financial freedom, no matter who they are or how much they have. Using smart technology, Wealthsimple takes financial services that are often confusing, opaque and expensive and makes them simple, transparent, and low-cost. We're the company behind some of Canada's leading digital financial products, and are growing faster than ever.
Our team is reimagining what it means to manage your money. Smart, high-performing team members will challenge you to learn and grow every day. We value great work and great ideas — not ego. We're looking for talented people who love a fast-paced environment, and want to ship often and make an impact with groundbreaking ideas.
We’re a remote-first team and output is more important than face time, so where you choose to work is up to you — as long as you have internet access, you can work from anywhere in Canada. Be a part of our Canadian success story and help shape the financial future of millions — join us!
Read our Culture Manual and learn more about how we work.
About Wealthsimple Work
Wealthsimple Work is a modern group retirement offering for employers and their employees. With Work, employers can easily offer employees regular contributions to their retirement savings through a Group RRSP plan, and employees can add to this plan through Wealthsimple’s award winning app. Most group retirement plans are costly and have lacklustre engagement. WS Work is on a mission to change this with a low-cost, no-effort offering that employees actually love to use.
Wealthsimple Work is seeking an accomplished Sales leader to scale our 5-person sales team. We are looking for somebody with experience scaling revenue and building a go-to-market machine at SaaS software startups with an SMB / mid-market focus. With a superior product and a growing number of happy early customers, this role is the key to us succeeding as a business. This person will be responsible for both scaling our team through hiring, training, and managing a team of Account Executives and Business Development Representatives and scaling our processes to support them.

In this role, you will have the opportunity to:

  • Grow the team and structure it as you see fit for our market
  • Own our quarterly new revenue target and work with the team meet goals
  • Use metrics to refine our sales pitch and process until we have a well oiled GTM machine
  • Roll out a training program for existing and future members of the sales team to improve the performance of the team on an ongoing basis
  • Partner with Marketing to accelerate our overall go-to-market efforts
  • Work cross-functionally to guide market positioning and to provide feedback for product development

What we're looking for:

  • Extensive Sales experience, with past experience growing sales teams, preferably with Series A-C startups
  • Track record of leading sales teams in SaaS software and demonstrated followership amongst your teams
  • Demonstrated ability to sell a complex product
  • Fluency with financial and investing concepts (though you do not need to be an investing expert by any means) 
Job perks/benefits: Startup environment
Job region(s): North America
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