Sales Director

The New Network; Ontario; Remote; CAD 100,000 - 130,000; Full time

Job summary

A leading Canadian SaaS company is seeking two Regional Sales Directors to drive growth in Eastern and Western Canada. This senior role requires independent new business development skills and experience in the insurance sector, offering a flexible remote work environment with comprehensive benefits.

Benefits

Extended health, dental, and vision care

Generous time off

Professional development allowance

Equity participation

Qualifications

• 5 or more years of B2B SaaS sales experience, ideally in insurance or insurtech.
• Strong understanding of the Canadian insurance landscape.
• Proven ability to manage the full sales cycle independently.

Responsibilities

• Identify and engage prospective clients in your region.
• Build and manage a healthy pipeline from first contact through close.
• Deliver customized demos and communicate value at the executive level.

Skills

B2B SaaS sales experience

Understanding of the Canadian insurance landscape

Communication skills

Independence in managing sales cycle

Job description

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Co-Founder & CEO at The New Network | Talent Whisperer | Culture Builder | Trusted Partner of Tech Scale-Ups

We’re partnering with a growing Canadian SaaS company that’s transforming how insurance gets done. They’re expanding nationally and hiring two Regional Sales Directors, one for Eastern Canada and one for Western Canada, to help drive the next phase of growth.

The company offers a modern, flexible software platform built specifically for the insurance industry. Designed to support carriers, mutual insurers, MGAs, and brokerages, their technology helps clients streamline operations, improve responsiveness, and scale more efficiently in a competitive market.

About the role

This is a senior role focused on new business development. As Regional Sales Director, you’ll take ownership of your region and lead the full sales process from prospecting and relationship building to presenting tailored solutions and closing deals. You’ll work independently while collaborating with internal teams to deliver a high-quality buyer experience.

This is a fully remote position with travel for conferences and client meetings as needed. You’ll be part of a collaborative, distributed team that values autonomy, connection, and shared success.

What you’ll do

• Identify and engage prospective clients in your region across target segments
• Build and manage a healthy pipeline from first contact through close
• Deliver customized demos and clearly communicate value at the executive level
• Coordinate with Product, Marketing, and Implementation teams to ensure smooth handoffs and consistent messaging
• Share insights from the field to help refine go-to-market strategies
• Represent the company at industry events and within the insurance community

What you’ll bring

• 5 or more years of B2B SaaS sales experience, ideally in insurance or insurtech
• Strong understanding of the Canadian insurance landscape
• Proven ability to manage the full sales cycle independently
• Excellent communication skills, including the ability to engage C-level stakeholders
• A self-driven, accountable approach and comfort working in a fast-paced environment
• Ability to absorb technical information and translate it into business value
• Experience in a scaling SaaS environment is a strong asset.

Why this might be the right fit for you

• A product with strong market traction and meaningful differentiation
• A high-trust, remote-first culture with real support and flexibility
• Benefits include extended health, dental, and vision care, EFAP, generous time off, professional development allowance, and equity participation

If you're an experienced SaaS sales professional looking to own your region and make a measurable impact, we’d love to hear from you.

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales and Business Development

• Industries

  Software Development and Insurance

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