Who you are

- 3+ years of experience managing a Mid-Market or commercial sales team in a B2B SaaS environment
- A track record of hitting and exceeding team quota as a sales manager

- Experience as a top-performing individual contributor before moving into management — you know what great looks like on the ground

- Strong coaching instincts; you know how to identify what's holding a rep back and how to fix it

- Experience managing the full sales cycle, from outbound prospecting through to close

- High business acumen; you understand how to position value to technical buyers and business leaders alike

- Comfortable operating in a high-growth, fast-moving environment where not everything is figured out yet

- Experience selling into DevOps, engineering, or ITOps personas is a strong plus

- Familiarity with Salesforce, Outreach or similar sales tools

What the job involves

- This is a ground floor opportunity to build and lead Rootly's Mid-Market sales motion. As the first Manager, Mid-Market Sales, you won't just manage a team, you'll help shape the playbook, the culture, and the trajectory of one of our highest-priority segments

- You will lead, coach, and develop a team of Mid-Market Account Executives responsible for building pipeline, running full sales cycles, and closing new business across North America. Your success will be measured by your team's quota attainment, their development, and the processes you put in place to help them consistently win

- This role reports directly to our VP of Sales

- Lead, coach,



and develop a team of Mid-Market Account Executives to consistently meet and exceed quota

- Own team performance metrics; pipeline coverage, conversion rates, cycle times, and forecast accuracy while using data to drive coaching and process improvements

- Run regular 1:1s, pipeline reviews, and deal strategy sessions that level up your team's skills and close rates

- Partner closely with Marketing, RevOps, and CS to build a seamless end-to-end motion from top of funnel through to close

- Hire and onboard new AEs as the team scales, building a high-performance culture from day one

- Bring structure, repeatability, and creativity to a segment that is still being defined; you'll write the playbook as much as you'll run it

- Actively participate in key deals and strategic conversations, acting as an executive sponsor and resource for your team in the field

- Report on team performance and share insights with leadership on a regular cadence

Benefits

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

- Adaptable 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

📌 Manager of Mid-Market Sales (Toronto)
🏢 Rootly
📍 Toronto