Experienced Customer Support Specialist – B2B SaaS and Cloud Data Protection

At arenaflex, we're passionate about protecting 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. As a Customer Support Specialist, you'll be on the front lines of a fast-paced support team where project work is the norm, change happens quickly, and every team member is empowered to shape how support works at scale.

About arenaflex

arenaflex is a rapidly growing company backed by top investors, including Insight Partners, Inovia, Bessemer, and Atlassian Ventures. We're proud to be recognized as one of Canada's 50 fastest-growing technology companies (2023 Deloitte Fast 50). Our mission is to provide top-notch data protection solutions that meet the evolving needs of businesses worldwide.

Thriving at arenaflex

We're a team that thrives in a fast-paced, ever-changing environment. 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.

Job Description

As a Customer Support Specialist, you'll be responsible for delivering thoughtful, high-quality customer support via email, live chat, and phone when necessary. You'll take full ownership of issues from initial report to resolution, escalating only when needed and always with full context. You'll support a variety of users, including technical and non-technical personas, across a global B2B customer base.

Key Responsibilities

* Delivering thoughtful, high-quality customer support via email, live chat, and phone when necessary

• Taking full ownership of issues from initial report to resolution, escalating only when needed and always with full context
• Supporting a variety of users, including technical and non-technical personas, across a global B2B customer base
• Managing your workload with autonomy—balancing fast triage with deep problem-solving as needed
• Working closely with Engineering, Product, and other internal teams to flag bugs, clarify expected behavior, and relay customer insights
• Contributing to internal and external documentation, macros, and process improvements
• Participating in team initiatives and special projects that improve how support operates
• Collaborating with your peers to build a strong, inclusive support culture grounded in accountability and continuous learning

What We’re Looking For

* At least 1–3 years of experience in customer support, ideally within a B2B SaaS startup or scale-up

• Experience working with mid-market or enterprise customers—especially in contexts where premium support or SLAs were in place
• Excellent communication skills - clear, empathetic, and appropriately technical based on audience
• A proactive, ownership-driven mindset. You spot inefficiencies, raise ideas, and take initiative to improve
• Comfort with ambiguity, change, and wearing multiple hats in a growing environment
• Technical curiosity—enough to dig into product behaviors, replicate customer issues, and provide actionable context to engineering

Bonus Points If You…

* Have experience supporting billing issues such as invoicing, payment errors, or subscription changes

• Have worked with tools like Zendesk, Salesforce, Slack, Stripe, or Jira
• Have contributed to help centers, internal knowledge bases, or automation projects

Additional Information

* Where You’ll Work: Our organization follows a hybrid work structure where employees work from the office three days/week. This role will be based out of our Toronto office.

• How arenaflex 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, including flexible work hours, employee stock options, health benefits, three weeks vacation, seven life leave days, two Level Up days for professional development, one volunteer day, summer Fridays, office closed during the holiday break in December, four weeks sabbatical after four years with us, paid parental leave, $5,000/year professional development allowance, and $1,000/year wellness/home office allowance.

Join Our Team

We're 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. Apply for this job