Manager, Mid Market Sales

XYZ Venture Capital; Toronto; On-site; CAD 120,000 - 160,000; Full time

Benefits offered by this job

Equity

Medical coverage

Vacation

Home office stipend

AI tools access

Fast-paced environment

Job summary

Rootly is seeking a Manager, Mid‑Market Sales to build and lead our Mid‑Market sales motion in North America. You’ll shape the playbook, culture, and trajectory of this high‑priority segment, while coaching and developing a team of Account Executives responsible for pipeline, full sales cycles, and new business.

You will report to the VP of Sales and collaborate with Marketing, RevOps, and CS to ensure a seamless end-to-end motion, from prospecting to closing, enabling high growth and quota

Qualifications

• 3+ years managing mid-market or commercial sales teams in B2B SaaS.
• Proven track record of meeting/exceeding team quota as a sales manager.
• Experience transitioning from individual contributor to management.

Responsibilities

• Lead, coach, and develop Mid‑Market Account Executives to meet and exceed quota.
• Own pipeline metrics, forecast accuracy, and cycle times; drive coaching based on data.
• Run regular 1:1s, pipeline reviews, and deal strategy sessions.
• Partner with Marketing, RevOps, and CS for end-to-end motion from top of funnel through to close.
• Hire and onboard new AEs as the team scales; build a high‑performance culture.
• Shape the playbook and actively participate in key deals as executive sponsor.
• Report on team performance and share insights with leadership.

Skills

Sales leadership

Coaching

Data-driven coaching

Full sales cycle

Account management

Education

Bachelor’s degree in business/related field

Tools

Salesforce

Outreach

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 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.

What You'll Do

• 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

What You'll Need

• 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

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.