VP of Strategic Accounts

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a VP of Strategic Accounts based in Canada.

This executive sales leadership role focuses on building and expanding strategic relationships with major organizations in the insurance and technology sectors. You will own complex enterprise sales cycles, from initial engagement and discovery through negotiation and long-term account growth. The position requires a consultative approach, combining business strategy, technical understanding, and executive-level relationship management. You will collaborate closely with cross-functional teams to shape solutions that address complex customer challenges and deliver measurable outcomes. This is an opportunity to influence go-to-market strategy, establish trusted partnerships, and contribute to the growth of an innovative AI-driven platform. The ideal candidate thrives in a fast-paced environment, enjoys building from the ground up, and has a proven ability to close high-value enterprise opportunities.

Accountabilities:: The VP of Strategic Accounts will be responsible for driving enterprise growth by developing strategic customer relationships, leading complex sales initiatives, and partnering with internal teams to deliver successful outcomes. Key responsibilities include:

Own the complete sales cycle for strategic enterprise prospects, including relationship development, discovery, executive alignment, negotiations, and closing.

Build trusted relationships with senior stakeholders across complex organizations, including business leaders, technology teams, operations teams, and executives.

Develop account strategies for priority customers by identifying key decision-makers, mapping organizational structures, and creating tailored value propositions.

Lead consultative conversations that connect business challenges with innovative technology solutions and measurable business outcomes.

Collaborate with engineering, product, marketing, and customer success teams to ensure effective customer onboarding, adoption, and expansion.

Represent the organization in executive-level discussions, clearly communicating the value of AI-powered solutions to business and technical audiences.

Share market insights and customer feedback to influence product strategy and go-to-market initiatives.

Contribute sales expertise, methodologies, and best practices to support the continued growth of the strategic accounts function.

Requirements:

The ideal candidate is an experienced enterprise sales professional with a strong track record of managing complex B2B technology sales cycles and building relationships with senior stakeholders. Required qualifications include:

8–10+ years of experience in quota-carrying enterprise or strategic B2B SaaS sales roles, with demonstrated success closing large, complex opportunities.

Proven ability to navigate lengthy sales cycles involving multiple stakeholders and executive decision-makers.

Strong consultative selling skills with the ability to translate technical solutions into business value.

Experience selling into regulated or complex industries such as insurance, financial services, healthcare, fintech, or enterprise technology is highly valued.

Demonstrated stability, consistent performance, and the ability to develop deep expertise over time.

Ability to operate effectively as a senior individual contributor within a fast-moving, scaling environment.

Strong executive presence, communication skills, and confidence engaging both technical and business audiences.

Self-driven, resourceful mindset with the ability to create strategies, processes, and playbooks rather than rely on established frameworks.

Passion for innovation, continuous learning, and solving challenging customer problems.

Benefits:

The role offers a competitive compensation package and the opportunity to work in a high-growth environment. Benefits include:

Base salary target of $170,000–$200,000.

On-target earnings (OTE) ranging from $340,000–$400,000.

Stock options as part of the overall compensation package.

Comprehensive benefits and additional employee perks.

Fully remote work flexibility.

Opportunity to work with innovative AI-powered technology transforming the insurance industry.

High-impact role with significant ownership and visibility across the organization.

Collaborative environment focused on learning, innovation, and customer success.

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