Head of Sales

Homewise - Toronto, ON (30+ days ago)

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Are you passionate about technology and high-growth startups? Are you a proven strategic thinker and team leader? Eager to make a difference and build a business? If so, this position may be for you. This is a rare opportunity to get in on the ground floor of a new business in a hot market.

Our team at Homewise is adding a Head of Sales position for someone who can build and develop an internal sales team, help acquire new growth avenues and be part of growing our relationship platform, while helping us exceed sales targets.

What you’ll be doing:
Reporting directly to the CEO, you will manage a team of Mortgage Advisors to increase our close rates, build structure/operations and drive a positive culture for growth. Further, you will be working to build partnerships with industry referral partners, while nurturing current relations. All to while enabling us to grow our business and team across the country and eventually the world.

Key responsibilities include:

  • You will hire, train and develop a sales team (Mortgage Advisors) that can create value and provide a best in class experience for clients
  • You will coach all revenue-driving Homewise employees on sales methodologies, working hand in hand with the team to understand how to nurture employee development
  • You will take responsibility for our conversion numbers, and devise a strategy and execution plan in order to reach our company revenue goals
  • Manage processes for inbound client deal flow with internal team
  • You will experiment and optimize on our current sales process, learning from mistakes along the way to derive process improvements across the organization
  • You will become an authority on selling into medium and large Real Estate Brokerages and Developers, learning the ins and outs of the business as we grow and managing relationships
  • You will quickly and efficiently scale our business to expand into new markets
  • You will roll up your sleeves and ride along on deal calls when necessary
  • You will lead weekly sales meetings that teach, engage, educate and motivate your team and eventual team(s) to maximum performance
  • You will listen to the needs of the market and share insights with product and marketing teams
  • You will create programs, process, and influence product strategy to empower multiple cross-functional teams to deliver relationship and operational excellence
  • You will develop and implement best practices to maximize conversion rates, forecasting accuracy, and customer-centric engagement
  • You will create reporting cadences/KPIs, consumable by both your direct reports and executives
  • Collaborating with other Senior Leadership on strategic initiatives and operational improvements

About you:

  • 5+ years of sales experience in a leadership role
  • Highly analytical and quantitative and used to making decisions based on deep analytical thinking
  • Experience growing a sales organization from 5 to 30 at a rapid pace
  • Experience in building quotas, comp plans, territories and performance management policies
  • Consistent track record of success against team quotas
  • Expertise at developing, implementing, and improving a high impact renewal sales process
  • Passionate about process improvements, and able to see those through to completion
  • Entrepreneurial mentality
  • An authority at CRM management and other sales stack tools
  • Self-starter who can own projects from start to finish with minimal guidance
  • Self-aware and understands personal limitations to ask for help when needed
  • BONUS: Experience in the mortgage, real estate or lending industry
  • BONUS: Experience working in supremely entrepreneurial environments

What we offer:

  • An opportunity to be part of the leadership team of a fast-growing startup
  • Equity options to be part of the success that you help generate
  • Lead change and growth strategies that have a direct impact on business success
  • Competitive compensation package with meaningful equity
  • Amazing growth opportunities

Job Type: Full-time

Salary: $80,000.00 to $140,000.00 /year


  • sales: 5 years (Preferred)


  • Toronto, ON (Preferred)