Vice President of Strategic Accounts

About the Role

This executive leadership position involves spearheading the development and expansion of strategic relationships with leading companies in the insurance and technology sectors across Canada. The VP of Strategic Accounts will direct comprehensive enterprise sales cycles, from initial outreach through negotiation and ongoing account growth. The incumbent will employ a consultative approach combining business acumen, technical knowledge, and executive relationship management. This role collaborates extensively with multidisciplinary teams to tailor solutions addressing complex client challenges, with measurable business impacts. This position offers a chance to influence go-to-market strategies, forge trusted partnerships, and contribute to scaling an innovative AI-driven platform.

Primary Responsibilities

• Lead end-to-end sales processes for strategic enterprise clients, including relationship building, discovery, executive alignment, negotiations, and closing deals.
• Establish and maintain trusted partnerships with senior leaders, including business, technical, operations, and executive stakeholders within complex organizations.
• Craft account strategies by identifying key decision-makers, mapping organizational structures, and tailoring value propositions for priority customers.
• Conduct consultative discussions that link business challenges to innovative technology solutions delivering measurable outcomes.
• Work closely with engineering, product, marketing, and customer success teams to ensure smooth onboarding, adoption, and expansion within customer accounts.
• Represent the company in executive-level dialogues, clearly articulating the value of AI-powered solutions for both business and technical audiences.
• Provide market insights and client feedback to shape product development and go-to-market strategies.
• Contribute sales expertise and best practices to grow the strategic accounts function effectively.

Candidate Requirements

• A minimum of 8 to 10 years in quota-bearing enterprise or strategic B2B SaaS sales roles with a proven record of closing complex, high-value deals.
• Demonstrated capability to manage long sales cycles involving multiple stakeholders and executive decision-makers.
• Strong consultative selling skills with the ability to translate technical offerings into compelling business value.
• Experience in regulated or complex fields such as insurance, financial services, healthcare, fintech, or enterprise technology is highly advantageous.
• Track record of consistent performance, stability, and developing deep expertise over time.
• Ability to operate autonomously and effectively as a senior contributor in a fast-paced, growing company environment.
• Excellent executive presence with superior communication skills, engaging confidently with both technical and business leaders.
• Self-motivated with a resourceful mindset, adept at creating strategies, processes, and frameworks rather than depending on established ones.
• Passion for innovation, continuous development, and tackling challenging customer issues.

Compensation and Benefits

• Base salary range between $170,000 and $200,000 annually.
• On-target earnings (OTE) estimated between $340,000 and $400,000 per year.
• Equity participation through stock options included in the compensation package.
• Comprehensive benefits and additional employee perks.
• Fully remote working arrangement.
• Opportunity to contribute to groundbreaking AI technology transforming the insurance industry.
• High-impact role with significant ownership and visibility within the organization.
• An engaging, collaborative, and innovation-oriented work environment focused on learning and customer success.

Additional Information

This position is listed by a partner company who will manage all applications and subsequent hiring steps. Applications are evaluated using AI-assisted processes for quick and unbiased candidate screening; however, final hiring decisions are human-led. The candidate's personal information will be processed in compliance with applicable data privacy regulations, including GDPR. AI tools may be utilized for application assessment but do not replace recruiter or hiring manager judgment.