Retail Sales District Manager

United States Digital Space LLC; Toronto; Hybrid; CAD 230,000 - 290,000; Full time

Job summary

ToastTab is seeking a Founding District Manager to launch our Canadian Retail presence from Toronto, leading a field-based team and shaping the GTM motion. You will report to the Regional VP of Retail Sales and help recruit, train, and scale the sales organization in Canada.

You will collaborate with enablement, onboarding, and product teams to tailor solutions for Retail operators and drive early wins. A founder’s mindset is essential to thrive in this high-growth, hybrid environment.

Qualifications

• 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.

Responsibilities

• Hire, develop, motivate, and manage a quota-achieving sales team.
• Coach your team on a full cycle sales process, including discovery meetings, live demos, and solution proposals.
• Spend time coaching through field visits, walk-ins, prospecting, trade shows, and local business partnerships to exceed quotas.
• Partner and collaborate with peers to ensure expectations set during the sales process are met in delivery.
• Strategically utilize Salesforce 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.

Skills

Sales leadership

Team management

Strategic selling

Tools

Salesforce CRM

Job description

After years of building an innovative POS platform for restaurateurs, the company 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 the company’s presence in this new vertical with a new offering: the the company 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. the company 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 the company 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 the company 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

AI at the company

At the company, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits athttps://careers.toasttab.com/the company-benefits.

The estimated Total Targeted Cash compensation range for this role is listed below. Total Targeted Cash for this role includes base salary, commission, and bonus (if eligible). This role qualifies for uncapped commissions. The starting salary will be determined based on skills, experience, and geographic location. In addition to cash compensation, our total rewards components include benefits and equity (if eligible).

Total Targeted Cash

$230,000—$290,000 CAD

How the company Uses AI in its Hiring Process

Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. To learn more: https://careers.toasttab.com/ai-in-hiring

Our Approach to Hybrid Working

We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region:https://careers.toasttab.com/locations-the company

Diversity, Equity, and Inclusion is Baked into our Recipe for Success

At the company, our employees are our secret ingredient—when they thrive, we thrive.The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.

We Thrive Together

We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-the company.