Who you are

- Sales experience: you have 4+ years selling enterprise software to SMB and mid-market accounts

- Quota performance: you have a track record of meeting and exceeding quota

- Product and domain expertise: you love becoming an expert, sell consultatively, and teach prospects something at every touchpoint

- Negotiation skills: you have a proven ability to lead complex negotiations involving bespoke commercial and pricing agreements

- Exceptional communication: you communicate incredibly well, both remotely and in person

- Executive presence: you enjoy getting in the room with economic buyers and working with complex organizations to find and close great-fit deals

- Autonomy: you do your best work in a highly ambiguous, fast-paced environment

- Technical fluency: you are comfortable communicating the value of technical B2B SaaS solutions to technical stakeholders

What the job involves

- 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

- Sourcing and closing full sales cycles for $25K to $100K opportunities

- Working with companies of up to 1,000 employees

- Winning highly competitive deals by positioning Rootly as the incident management and on-call platform of choice for 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 and present ROI analyses

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

Perks

- Medical, dental, vision, and life coverage for you and your dependents

- Flexible PTO, plus company holidays, team off-sites, and a year-end shutdown to recharge

- Meaningful equity in a high-growth company, and 401(k) matching for US employees

- Hybrid work (we hire across the US, Canada, Europe, and Singapore)

- Free lunches at HQ
- Fast-moving, high-impact environment where you have autonomy to own big problems from day one

- Top-tier hardware and tools, plus an annual stipends for home offices

📌 Mid Market Account Executive (Toronto)
🏢 Rootly
📍 Toronto