Mid Market Account Executive

XYZ Venture Capital; Toronto; Hybrid; CAD 169,971 - 254,957; Full time

Benefits offered by this job

Competitive compensation

Medical, dental, vision coverage

3 weeks vacation, unlimited sick days

Home office stipend $500

Unlimited AI tools access

Year-end shutdown

Job summary

Rootly seeks a driven Mid Market Account Executive to build a North America book of business and close substantial $25–$100k deals. You will present ROI analyses to executives and work with cross-functional leaders to shape the sales process. Candidates thrive in ambiguity, excel in complex negotiations, and communicate technical SaaS value effectively.

You will contribute to a fast-moving, high-impact team with equity potential and a strong emphasis on learning the product inside out.

Qualifications

• 4+ years selling enterprise software to SMB and Mid Market accounts.
• Track record of meeting & exceeding quota.
• Sell consultatively and become a product/domain expert.
• Proven ability to lead complex negotiations with bespoke agreements.
• Excellent communicator, both remotely and in-person.
• Experience engaging economic buyers in large organizations to close fit deals.
• Thrives in ambiguous environments with autonomy.
• Able to articulate value of technical B2B SaaS to technical stakeholders.

Responsibilities

• Build a book of business across North America achieving 100% quota in your first year.
• Source and close full sales cycles for $25-100k opportunities.
• Engage with companies of up to 1,000 employees.
• Position Rootly as the Incident Management & On-Call platform of choice to mid market buyers.
• Design and present product narratives and ROI analyses to executives.
• Collaborate with leaders from multiple functions to lead product workshops and ROI discussions.
• Lead and contribute to team projects to develop and refine our sales process.

Skills

Enterprise software sales

Quota attainment

Consultative selling

Negotiation

Strong communication

Stakeholder management

Autonomy

Technical SaaS knowledge

Job description

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 opportunity 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.