About the Role
This is a ground floor opportunity to be one of the first Mid Market Account Executives at Rootly and shape our trajectory. You will experience what being at a scrappy startup is like. You will help lay the foundation for the entire sales process and grow revenue by:

Building a book of business across North America that results in 100% quota attainment in your first year with Rootly

Successfully sourcing and closing full sales cycles for $25-100k opportunities

Working with companies of up to 1,000 employees

Winning highly competitive deals by positioning Rootly as the Incident Management & On-Call platform of choice to mid market buyer segments

Designing and presenting product narratives and insights to executives within named accounts

Working with company leaders from multiple functions to lead product workshops and prepare/present ROI analyses

Leading and contributing to team projects to develop and refine our sales process

What You'll Need

4+ years selling enterprise software to SMB and Mid Market accounts

Track record of meeting & exceeding quota

Loves becoming a product and domain expert. You sell consultative and teach prospects something at every touch point

Evidence of proven ability to lead complex negotiations involving bespoke commercial and pricing agreements





Is an incredible communicator, remotely and in-person

Enjoys the challenge of getting in the room with economic buyers and working with complex organizations to find and close great fit deals

Functions optimally in a highly ambiguous and fast-paced environment with autonomy

Is comfortable communicating the value of technical B2B SaaS solutions to technical stakeholders

Benefits

Competitive compensation and early equity in a fast-growing, venture-backed company.

Comprehensive medical, dental, and vision coverage.

3 weeks vacation, plus unlimited sick and mental health days, and a company-wide end‑of‑year shutdown to recharge.

$500 stipend for home office setup.

Unlimited token usage and access to AI tools.

A fast-moving, high‑impact environment where your leadership and ideas directly shape the future of the company.

Rootly is an equal prospect employer. We aim to create an environment where every team member at Rootly feels like they belong so they can have a greater impact on our business and customers. We do not discriminate on the basis of race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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📌 Mid Market Account Executive (Ontario)
🏢 XYZ Venture Capital
📍 Ontario