Mid-Market Account Executive (DevOps)

Rewind; Canada; Hybrid; CAD 70,000 - 100,000; Full time

Job summary

A rapidly growing technology company is seeking a Mid-Market Account Executive to manage the sales process and drive revenue from mid-market customers. This hybrid role, based in Toronto, involves collaborating with various teams to deliver impactful solutions and support customer needs. The ideal candidate has 3–5 years of B2B SaaS closing experience and is comfortable in fast-paced environments, focused on customer satisfaction and proactive engagement.

Benefits

Flexible work hours

Employee stock options

Health benefits

3 weeks vacation

Paid parental leave

$5000/year professional development allowance

Qualifications

• 3–5 years of B2B SaaS closing experience with consistent quota achievement.
• Proven success managing full-cycle sales with mid-market customers.
• Experience selling to DevOps, IT, or engineering teams is a plus.

Responsibilities

• Own the entire sales process for mid-market accounts—from discovery to close.
• Drive net new revenue by closing new mid-market customers.
• Support the Product team with feedback from prospects.

Skills

B2B SaaS closing experience

Strong discovery and closing skills

Growth mindset

Comfort in high-velocity sales environments

Job description

Rewind is a service that protects the critical data that powers businesses of all sizes. Our focus is on backing up data that lives in the cloud — in apps like Jira, GitHub, Confluence and Shopify. We are backed by Insight Partners, Inovia, Bessemer and Atlassian Ventures and are proud to be recognized as one of Canada’s 50 fastest growing technology companies (2023 Deloitte Fast 50). We invite you to read our startup story to learn where we came from and where we’re going.

Read about our mission, story and values here. To find out more about our perks, click here. Some of our blogs might help you get a better understanding of what we do here. You can find them all here.

Thriving at Rewind

We embrace the fast‑paced, ever‑changing nature of startup life. If you love working with speed, agility, and creativity, you’ll feel right at home here. Here’s what it takes to succeed with us:

• Team-First Mentality: We put teamwork at the core of everything we do, believing that we are better when we are together. Success is shared, and when the team wins, we all win.
• Performance-Driven Mindset: We are proactive, goal‑oriented, and focused on delivering tangible, high‑quality results. We go beyond meeting expectations — we aim to exceed them.
• Flexible Work-Life Approach: We encourage balance and understand the need to recharge. While we stay agile for urgent needs, we make sure there’s time to recover and enjoy life.
• Customer Centricity: Our commitment to customers shapes everything we do. We listen, build relationships, and innovate — from our dedicated customer support team to our engineers, everyone at our company is focused on solving problems that matter most to our users.
• Taking Initiative: We value ownership and proactive problem‑solving. We encourage team members to think creatively, take ownership, and lead improvements. Your ideas and actions drive our success.
• We Make Time for Fun: We work hard and make time to enjoy the journey. It’s not just about hitting milestones—it’s about making the experience rewarding along the way.

About the role

We’re looking for a Mid‑Market Account Executive to join our growing Sales team. In this role, you’ll own the full sales cycle—from discovery through to close—primarily selling to DevOps and IT leaders within the office of the CTO, CIO and CISO.

This role combines inbound and outbound sales. You’ll benefit from a strong pipeline of opportunities generated through free trials via our SaaS marketplace listings (Atlassian, GitHub, monday.com), our BDR team and a strong Solution Partner program. Supplementing these leads through your own opportunity creation through targeted prospecting and relationship development will be key. With major cloud migration shifts (Atlassian Data Center End of Life) recently announced, you’ll be well‑positioned to capture a massive market opportunity, as some of the largest companies in the world transition their business‑critical applications to the cloud, ultimately, requiring the protection that Rewind provides.

What you’ll do

Sales process management

• Own the entire sales process for mid‑market accounts—from discovery to close, including infosec and legal reviews.
• Collaborate with Sales Engineering to deliver impactful demos, guided trials & POCs.
• Keep opportunities updated daily in Salesforce for visibility and forecasting accuracy. AI use is encouraged!

New business generation

• Drive net new revenue by closing new mid‑market customers.
• Work closely with our Business Development team to strategize and deploy creative outbound prospecting strategies to generate pipeline from net‑new target accounts.
• Build relationships, with the support of our Partnerships team, within top solutions partners to identify and generate interest from new prospects.

Market engagement & feedback

• Support the Product team with feedback from prospects to help shape product direction.
• Share learnings with the broader Sales team to improve our collective approach.
• Attend industry events and meet with customers on‑site as needed.

What you’ll bring

• 3–5 years of B2B SaaS closing experience with consistent quota achievement.
• Proven success managing full‑cycle sales with mid‑market customers.
• Strong discovery and closing skills, with a naturally curious approach to customer needs.
• A growth mindset and creative approach to pipeline generation.
• Comfort operating in fast‑changing, high‑velocity sales environments.

Nice to have

• Experience selling to DevOps, IT, or engineering teams.
• Familiarity with SaaS ecosystems such as Atlassian, GitHub, or monday.com.
• Experience in or exposure to data protection, backup, or security products.

Location and working hours

This is a hybrid role based in Toronto, with flexibility to work from home several days per week. Occasional travel for customer meetings or industry events will be required.

Why join Rewind

Rewind is built on trust, accountability, and respect for people’s time. We’re customer‑obsessed, constantly innovating, and comfortable challenging the status quo. Here, you’ll be encouraged to think differently, push boundaries, and make a meaningful impact. We also believe in giving back—to our customers, our teammates, and our communities. If you’re looking for a place where you can grow, solve real problems, and help shape the future of data security and backup, Rewind is the place for you.

How Rewind Will Support You

We know that enjoying the journey is just as important as reaching our goals. We work hard to create a positive, inclusive environment where fun and laughter are part of our everyday routine. We also offer a variety of benefits to support your success both at work and in your personal life, which includes but is not limited to:

• Flexible work hours
• Employee stock options
• Health benefits
• 3 weeks vacation
• 7 life leave days
• 2 Level Up days for professional development
• 1 volunteer day
• Summer Fridays and office closed during the holiday break in December
• Paid parental leave
• $5000/year professional development allowance (you can take courses, buy books, attend conferences, cover certifications, etc)
• $1000/year wellness/home office allowance

Rewind is committed to building an inclusive, supportive place for you to do the best and most rewarding work of your career. We value how each new hire is an opportunity for us to bring in a different perspective, and we are always eager to further diversify our company. We strongly encourage candidates of all different backgrounds and identities to apply.