Mid-Market Account Executive

Job Description

Position Title

Mid-Market Account Executive (Insurance Strategy)
Type: Hybrid Full-Time

About Our Client

Our client is an innovative Canadian technology company transforming how insurance brokerages operate through advanced communications and data intelligence solutions. With over a decade of industry impact they have evolved beyond traditional telecom services into a leader in conversational AI and risk management platforms tailored specifically for the insurance sector.

Their mission is to help brokerages reduce operational friction mitigate compliance risk and scale efficiently without increasing headcount. By converting everyday voice interactions into structured actionable insights they address two of the industrys most expensive challenges: errors and omissions (E&O) exposure and process inefficiency.

This organization is at the forefront of AI-driven transformation in a traditionally conservative industry offering employees the opportunity to work on meaningful high-impact this role you will engage directly with senior decision-makers and play a key part in shaping how modern brokerages evolve.

Key Responsibilities

As the Mid-Market Account Executive you will drive business transformation by helping insurance brokerages adopt innovative solutions that improve efficiency reduce risk and unlock growth.

Strategic Sales Execution

You will manage the full sales cycle from initial outreach through to closing and long-term account development.
You will build trusted relationships with prospects by aligning solutions to measurable business outcomes rather than product features.

Business Case Development & Value Selling

You will develop ROI-driven business cases that quantify the cost of inaction including lost productivity and potential compliance risks.
You will confidently present financial and operational value to senior stakeholders such as Principals and financial decision-makers.

Consultative Discovery & Problem Solving

You will lead in-depth discovery conversations to uncover operational inefficiencies and hidden profit leakage.
You will identify opportunities where AI-driven automation can improve workflows documentation accuracy and compliance tracking.

Stakeholder Engagement & Multi-Threading

You will build alignment across multiple stakeholders including leadership operations and IT teams.
You will tailor messaging to address technical operational and financial priorities across the organization.

Sales Process Leadership & Deal Orchestration

You will guide prospects through a structured buying journey using mutual action plans to maintain momentum and clarity.
You will act as a project leader throughout the sales cycle ensuring all stakeholders remain engaged and aligned.

AI Advocacy & Market Education

You will educate clients on how conversational AI creates a competitive advantage in modern brokerage environments.
You will position technology as a strategic asset for CRM automation compliance and operational visibility.

Qualifications

To succeed in this role candidates should demonstrate:

Education & Experience:

Post-secondary education in business finance or a related field is considered an asset.
57 years of experience in consultative B2B sales ideally within mid-market or complex solution environments.

Technical Skills:

Strong ability to build and present financial models including ROI and cost-benefit analyses.
Experience using CRM platforms and familiarity with structured sales methodologies such as Challenger Gap Selling or Sandler.

Key Competencies:

Strong consultative selling skills with the ability to diagnose and solve complex business challenges.
Excellent communication and storytelling abilities to translate technical solutions into clear business value.
High level of accountability with a data-driven approach to managing pipeline conversion rates and performance.
Proactive mindset with the ability to manage multiple stakeholders and drive deals forward effectively.

Nice-to-Have Experience:

Industry experience within insurance or financial services.
Exposure to technical integrations particularly involving voice/AI data and systems such as Agency Management Systems (AMS).

Compensation & Benefits

Base Salary: $85000 $105000 CAD
On-Target Earnings (OTE): $170000 CAD
Commission Structure: Uncapped commission with significant accelerators for over-performance
Work Model: Hybrid with required proximity to London Ontario for monthly in-person meetings
Career Growth: Opportunity to sell a high-impact differentiated solution in a rapidly evolving AI-driven market
Earnings Potential: Strong upside for high performers in a value-based sales environment

Apply Today

Quote Job Reference #84437. Submit your resume directly to Nicole Brown via email at . No cover letter required.

About Us

Executrade is one of Western Canadas most comprehensive full-service recruitment firms with over 50 years of expertise in connecting talented professionals with leading organizations.

We are proud to apply principles of diversity equity and inclusion in all our recruitment practices ensuring equal opportunities for all candidates. Our commitment to these values enables us to match organizations with a diverse range of top talent fostering workplace cultures that thrive on innovation collaboration and respect.

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