Enterprise Account Executive

Rootly; Toronto; On-site; CAD 111,064 - 166,597; Full time

Benefits offered by this job

Competitive compensation

Equity in the company

Comprehensive medical, dental, vision coverage

3 weeks vacation plus unlimited sick days

$500 stipend for home office setup

Job summary

A growing technology firm is seeking an experienced Enterprise Account Executive in Toronto, Canada. You will shape the sales process, drive revenue through building relationships and closing high-value deals. The ideal candidate has over 7 years in enterprise software sales with a proven quota achievement record, exceptional communication skills, and a consultative selling approach. Join us for competitive compensation, equity, and a range of benefits including comprehensive health coverage and a flexible environment.

Qualifications

• 7+ years selling enterprise software to SMB and enterprise accounts.
• Proven ability to lead complex negotiations.
• Experience with enterprise software quotas of at least U$1M+.

Responsibilities

• Build a book of business across North America.
• Source and close full sales cycles for U$50-150K+ ARR opportunities.
• Design and present product narratives to executives.

Skills

Enterprise software sales

Negotiation skills

Communication skills

Consultative selling

B2B SaaS understanding

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’d 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 Enterprise 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 U$50-150K+ ARR opportunities
• Winning highly competitive deals by positioning Rootly as the Incident Management & On-Call Platform of choice to enterprise buyers 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

• 7+ years selling enterprise software to SMB and enterprise accounts
• Has owned enterprise software quotas of at least U$1M+
• 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.