Senior Sales Executive (Contractor)

We’re seeking a strategic, results-driven sales professional who is passionate about selling Saas solutions and who has a deep understanding of the Life Insurance industry, from both Carrier and Distribution perspectives.

Reporting directly to the President, this remote role is perfect for a self-starter with a hunter mentality who thrives in consultative sales and is eager to make a direct impact.

Key Responsibilities

• Target Outreach and Pipeline Development: Proactively target and build relationships with key decision makers, including Technology, Innovation and Strategy Departments across enterprise organizations to develop and maintain a strong sales pipeline across Canada and the U.S.
• Sales Cycle Leadership: Guide prospects through the sales cycle, from discovery calls and needs assessment to solution demonstrations, proposal development, negotiation and closing.
• Account Management: Collaborate closely with internal stakeholders to manage key accounts, anticipate business needs, design business solutions to support client success and build long-term relationships.
• Revenue Growth: Drive business success by delivering value add solutions and achieving quarterly goals.
• Market Engagement & Brand Development: Actively leverage social selling platforms to build a professional brand, engage with prospective client content, and establish initial familiarity before direct outreach.
• Rigorously track and manage all sales activities and forecasts within the CRM system to ensure consistent follow-up and pipeline health; identify and secure new clients to consistently meet or exceed business objectives.
• Represent illustrate inc at industry events, strengthening professional connections, and promoting our solutions.
• Marketing Expertise: Support brand development, market awareness, and demand generation initiatives.
• Maintain in-depth knowledge of illustrate inc products and how they deliver business value.

What You Bring

• Experience: 5+ years of software solution sales experience, preferably in the North American Life Insurance industry or in technology sales solutions
• Industry Expertise: Strong understanding of enterprise IT solutions, with the ability to engage decision-makers (Directors, VPs, CIOs, and business leaders).
• Proven Success: Track record of selling software solutions through consultative, ROI-driven approaches.
• Communication Skills: Exceptional verbal and written communication skills, with experience in proposal development and client presentations.
• Sales Leadership: Ability to develop and execute sales strategies that drive value for clients and the organization combined with demonstrated relationship building and closing skills.
• Marketing Savvy: Well developed understanding and experience with B2B marketing tools and techniques. Demonstrated experience optimizing data analytics to identify new opportunities and drive business results.
• Flexibility: Ability to travel across North America and work remotely.

What We Offer

• Impactful Role: A key position in a dynamic, growth-driven company at the forefront of innovation.
• Earning Potential: Competitive compensation, with significant earning opportunities based on production and sales performance results.
• Professional Growth: Work alongside industry leaders and expand your expertise in a rapidly evolving field.