Enterprise Sales Director - Strategic, Retail

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Enterprise Sales Director - Strategic, Retail based in Canada.

This role is designed for a senior enterprise sales leader who thrives on building strategic partnerships and closing complex, high-value opportunities. You will lead some of the most important customer engagements, working with executive stakeholders and shaping commercial strategies. The position combines consultative selling, business transformation, and deep customer relationship management. You will help organizations redefine customer experiences through advanced AI-powered solutions. Operating in a fast-moving environment, you will influence sales strategy while collaborating closely with cross-functional teams. This is an opportunity to play a key role in scaling innovative technology adoption with leading retail brands.

Accountabilities:: As an Enterprise Sales Director, you will own strategic sales initiatives, manage complex enterprise opportunities, and drive meaningful business outcomes through trusted customer partnerships. You will be responsible for leading large-scale deals, shaping commercial strategies, and representing the value of AI-driven customer experience solutions.

Lead complex enterprise sales opportunities involving multiple business units, regions, and stakeholders, creating effective deal strategies and managing execution from discovery through close.

Build and maintain trusted relationships with C-suite executives, senior decision-makers, and operational teams within strategic retail accounts.

Act as a strategic advisor to customers, understanding business challenges and positioning solutions that deliver measurable impact.

Design and negotiate sophisticated commercial agreements, including pricing strategies, deal structures, and risk management approaches.

Influence account strategy and contribute to broader sales methodologies, processes, and best practices.

Collaborate with internal teams across product, engineering, customer success, and leadership to ensure successful customer outcomes.

Leverage AI-powered tools throughout the sales lifecycle, including account research, personalized outreach, meeting preparation, forecasting, and pipeline management.

Represent the organization with executive-level communication, precision, and credibility in high-stakes customer conversations.

Requirements:

The ideal candidate is an experienced enterprise sales professional with a proven ability to manage strategic accounts, navigate complex buying environments, and deliver significant revenue growth. You should combine strong commercial judgment with excellent communication skills and the ability to build lasting executive relationships.

10+ years of experience in enterprise or strategic sales, managing large and complex customer accounts.

Proven success closing multi-million-dollar, multi-stakeholder enterprise deals across multiple regions or business units.

Experience managing significant sales quotas and leading complex sales cycles involving high-value contracts.

Strong track record of building trusted relationships with C-level executives and senior business leaders.

Deep expertise in enterprise deal structuring, negotiation, pricing strategy, and commercial risk management.

Exceptional executive communication, storytelling, and presentation skills.

Ability to operate independently in a fast-paced, high-growth environment with strong ownership and accountability.

Experience selling technology solutions, SaaS platforms, AI products, or enterprise software is highly preferred.

Strong understanding of AI technologies and the ability to communicate their business value to both technical and non-technical audiences.

Experience working alongside founders or executive leadership teams in strategic customer engagements is a plus.

Benefits:

The role offers a comprehensive benefits package designed to support professional growth, personal well-being, and long-term success.

Flexible unlimited paid time off.

Medical, dental, and vision coverage for employees and eligible family members.

Life insurance and disability benefits.

Retirement plan options depending on country of employment.

Parental leave support.

Fertility and family-building benefits.

Wellness and lifestyle benefits, including discretionary benefit allowances.

Access to a collaborative, innovative, and AI-focused work environment.

Opportunities to work with leading global brands and influence the future of customer experiences.

Eligible employees may participate in equity programs according to applicable policies and plans.

How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best!  Why Apply Through Jobgether?    Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.     #LI-CL1