Regional Sales Manager, Canada

SquareTrade is the fastest growing company of its kind. We’re revolutionizing a $30b industry with service innovation and attention to customer satisfaction. We partner with some of the largest, most sophisticated retailers and carriers in the world (The Home Depot, Walmart, Target, Amazon, Costco, and T-Mobile to name a few), consistently win industry awards, have received tens of thousands of 5-star reviews… and we’re just getting started. A member of the Allstate family, SquareTrade has headquarters in San Francisco and London.

The Regional Sales Manager is a key role within the SquareTrade Field Operations team. Reporting to the Senior Manager, Field Operations, this role is pivotal in working with key stakeholders including, but not limited to, Partner Field stakeholders, Channel Sales Leads, and SquareTrade channel partners to grow partner performance within a defined Canadian territory.

The ideal candidate is a highly motivated and relationship-driven field sales professional who thrives in a dynamic environment. They are comfortable working independently while collaborating effectively with a broad range of stakeholders, from frontline associates and store partners to senior leadership within partner organizations and internal teams. This individual is adaptable, agile, and proactive in identifying opportunities, adjusting priorities as business needs evolve, and building strong partnerships that drive territory performance and business results.

The role works closely with partner senior leadership, store partners, frontline associates, Account and Field Leadership, and internal business partners to strengthen SquareTrade mindshare, execute partner initiatives, and deliver insights that improve territory performance.

Responsibilities

• Execute the partner playbook within a defined Canadian territory and deliver timely business insights to each contact.
• Work with Account and Field Leadership to prioritize contact strategy and partner initiatives within the territory.
• Influence SquareTrade mindshare at channel senior management levels through product and sales analysis, acting as a thought partner on territory performance and business opportunities.
• Build relationships with partner senior leadership, store partners, and frontline associates in the territory to provide ongoing support for SquareTrade services.
• Operate independently with a high degree of ownership, sound judgment, and initiative to identify opportunities, address gaps, and drive territory performance.
• Demonstrate agility in a dynamic field environment by adjusting priorities, responding to changing partner needs, and adapting quickly to evolving business conditions.
• Travel up to 80% of the time for partner meetings, store visits, field engagement, and territory execution.

Requirements

• Ability to communicate effectively in written and verbal formats to relay key business opportunities, strategy, and performance insights.
• Demonstrated organizational skills and ability to prioritize work and operate effectively in a dynamic organization.
• Energy and initiative to recognize tasks that need to be accomplished and take action to fill gaps where necessary.
• Ability to work in a cross-functional environment across all levels of the organization.
• Flexibility to work in a hybrid field environment, including virtual meetings and in-person store visits.
• Demonstrated ability to effectively manage day-to-day responsibilities while balancing long-term projects, partner initiatives, and territory priorities.

• 7+ years of work experience in areas related to retail channels, client relationship building, field sales, and/or sales operations.
• Proven presentation and public speaking skills.
• Proficiency with PowerPoint and Excel.
• University or college qualification preferred, or equivalent combination of education and relevant experience.
• Ability to travel up to 80% of the time.

At SquareTrade you'll have access to:

• Medical, dental and vision coverage
• Up to 5% company match into RRSP
• $100/month budget to help prioritize your physical wellbeing
• $80/month stipend to subsidize connectivity costs
• 20 days Vacation
• Tuition reimbursement up to $5,250 per year to further your personal educational advancement desires

SquareTrade estimates the possible base compensation for this role, to be in the range : $90K - $120K

This position is posted to fill an existing vacancy.

The candidate(s) offered this position will be required to submit to a background investigation.

SquareTrade is proud to be an Equal Employment Opportunity employer. We are committed to creating an inclusive work environment for all employees. We celebrate diversity and encourage applications from all qualified individuals regardless of race, religion, color, national origin, sex, gender identity, gender expression, sexual orientation, age, marital status, veteran status, or ability status. It is the Company’s policy to employ the best qualified individuals available for all jobs. Therefore, any discriminatory action taken on account of an employee’s ancestry, age, color, disability, genetic information, gender, gender identity, gender expression, sexual and reproductive health decision, marital status, medical condition, military or veteran status, national origin, race (include traits historically associated with race, including, but not limited to, hair texture and protective hairstyles), religion (including religious dress), sex, or sexual orientation that adversely affects an employee's terms or conditions of employment is prohibited. This policy applies to all aspects of the employment relationship, including, but not limited to, hiring, training, salary administration, promotion, job assignment, benefits, discipline, and separation of employment.

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