Mid Market Account Executive

Rootly; Toronto; Hybrid; CAD 90,000 - 135,000; Full time

Benefits offered by this job

Competitive compensation

Equity in the company

Comprehensive medical, dental, and vision coverage

3 weeks vacation and unlimited sick/mental health days

$500 home office stipend

Access to AI tools

Job summary

A dynamic tech startup in Toronto is seeking a Mid Market Account Executive to establish a book of business across North America. This role entails sourcing and closing full sales cycles for opportunities valued between $25,000 and $100,000. The ideal candidate will have over four years of experience in selling enterprise software, a proven track record of exceeding quotas, and the ability to communicate effectively with both technical and economic buyers. This position offers competitive compensation, comprehensive benefits, and a chance to have a significant impact on the company's growth.

Qualifications

• 4+ years selling enterprise software to SMB and Mid Market accounts.
• Track record of meeting & exceeding quotas.
• Ability to lead complex negotiations.
• Comfortable communicating with technical stakeholders.
• Excellent communicator, both remotely and in-person.
• Thrives in ambiguous, fast-paced environments with autonomy.

Responsibilities

• Build a book of business across North America.
• Source and close full sales cycles for $25–100k opportunities.
• Win highly competitive deals in mid-market segments.
• Lead product workshops and present ROI analyses.
• Design and present product narratives and ROI analyses to executives in named accounts.
• Lead product workshops across functions and contribute to ROI analyses.
• Help develop and refine the sales process through team projects.

Skills

Consultative selling

Complex negotiation

Communication skills

B2B SaaS knowledge

Autonomy in fast-paced environments

Autonomy

Job description

About Rootly

At Rootly, we are on a mission to be the go-to way companies respond when things go wrong, helping every organization be more reliable. We do this by building an industry‑leading incident management platform that allows companies around the world consistently and quickly resolve incidents. We are not simply transforming an industry, we are carving an entirely new +$B segment ourselves and need incredible talent to achieve this ambitious goal together.

Customers love Rootly. Some of the fastest‑growing companies around the world such as NVIDIA, Figma, Canva, Tripadvisor, Squarespace and more rely on Rootly to power their critical incident management process. They obsess over our delightful enterprise‑ready platform and unique partnership model. See why our customers have reviewed us 5 stars on G2.

Investors love Rootly. We are backed by some of the most respected funds in the world from Y Combinator to operators like the CTO of Dropbox and GitHub. We would be happy to disclose our entire funding and profitability picture live during the interview. As a culture, we relentlessly put transparency first. We conduct monthly financial reviews as a team so everyone has a pulse on the health of the business and publish what we are building in our weekly changelog.

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
• Evidences 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

Why Rootly?

We’re not just another startup. We’re building something category‑defining and want teammates who crave ownership, love solving hard problems, and thrive in a high‑bar, high‑impact environment.

Here’s what you can expect when you join Rootly:

• Competitive compensation and early equity in a fast‑growing, venture‑backed company.
• Comprehensive medical, dental, and vision coverage.
• 3 weeks of 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.

If this sounds like the kind of challenge and opportunity you’re looking for, apply now and let’s build something great together.

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.