Retail Sales District Manager

WinsAbove; Toronto; On-site; CAD 230,000 - 290,000; Full time

Job summary

WinsAbove is looking for a District Manager to lead the launch of Toast's Canadian retail sales team based in Toronto. This role involves driving sales, managing a new team, and shaping the go-to-market strategy while working closely with various teams to meet client needs.

The ideal candidate will have 5+ years in sales, with a strong leadership background and a passion for inspiring others. Total targeted cash compensation is between CAD $230,000 and $290,000.

Qualifications

• 5+ years of sales experience in a sourcing and/or closing role.
• 3+ years of leadership experience.
• Proven track record of success.

Responsibilities

• Hire, develop, and manage a quota-achieving sales team.
• Conduct coaching and solution proposal crafting with your team.
• Utilize Salesforce to drive productivity and analyze conversion rates.

Skills

Sales experience

Leadership

Motivation

Entrepreneurial mindset

Tools

Salesforce

Job description

After years of building an innovative POS platform for restaurateurs, Toast is expanding its offerings into other food and beverage concepts such as convenience stores, grocery stores, and bottle shops. This role will require a founder’s mindset as we grow Toast’s presence in this new vertical with a new offering: the Toast Retail platform. We are looking for a District Manager to spearhead our Canadian Retail launch – starting by personally selling, shaping the GTM motion, and then building a sales team. Toast offers an all-in-one platform that helps restaurateurs and retailers operate their business, increase sales, engage guests, and keep employees happy.

As a Founding District Manager, you will be one of the first sales leaders of our Canadian Retail Sales team and pivotal to the growth of the Toast brand in Canada. Reporting to the Regional Vice President of Retail Sales, you will help launch our Canadian presence, drive early wins, and then help build and scale the sales team. You’ll work closely with enablement, onboarding, and product teams to understand Retail operators’ unique needs and build solutions that help Retailers thrive. We’re looking for a passionate, entrepreneurial leader to launch and grow the Toast brand in this new market.

You will be managing and supporting field based account executives. Candidates must live local to Toronto or be willing to relocate.

A day in the life (Responsibilities)

• Hire, develop, motivate, and manage a quota-achieving sales team
• Coach your team on a full cycle sales process. This includes coaching on how to conduct efficient discovery meetings, live demos, and craft a solution proposal that best meets the prospective customer’s needs
• Spend time coaching and empowering your team through field visits that include walk-ins, prospecting, trade shows, and local business partnerships to help exceed quotas
• Partner and collaborate with peers and parallel teams across the business to ensure that expectations set during the sales process are met in delivery
• Strategically utilize Salesforce (our CRM) and other technology to drive productivity, report on forecast deal pipelines, and analyze conversion rates
• Accountable for the new business growth across your assigned district

What you’ll need to thrive (Requirements)

• 5+ years of sales experience in a sourcing and/or closing role
• 3+ years of leadership experience
• Proven track record of success
• Passionate with the ability to inspire and motivate those around them
• Entrepreneurial, self-motivated, creative, and flexible with the ability to perform well under pressure

What will help you stand out (Nonessential Skills/Nice to Haves)

• Management experience building customer-facing, quota-achieving full cycle sales teams
• Experience working in a tech environment
• Experience working in a fast-paced, high growth environment
• Experience working in a retail environment
• Proven track record of creating a winning culture that performs at a high level

Total Targeted Cash: $230,000 – $290,000 CAD

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