Enterprise Customer Success Manager

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 an Enterprise Customer Success Manager to help define and build what customer success looks like at Rewind. This is a foundational role for someone who thrives at the intersection of strategy and execution.

As our founding CSM, you’ll report directly to the CRO and partner closely with enterprise and upper mid-market customers to ensure they realize the full value of Rewind. You’ll play a critical role in designing and scaling our customer success function, including building the systems, playbooks, and best practices that will support long-term growth.

You’ll own the end-to-end customer experience, from pre-sale testing/onboarding through to renewal, with a focus on driving value, satisfaction, and retention. Along the way, you’ll collaborate closely with Sales/Account Management, Sales Engineering, Product, Marketing and Support to ensure a seamless and successful customer journey.

This role is ideal for someone with strong B2B SaaS customer success experience who excels in early-stage environments and is energized by building from the ground up, bringing structure, shaping strategy, and creating impact where it doesn’t yet exist.

What you’ll do

Enterprise customer partnership & value realization

• Manage relationships with a portfolio of enterprise and upper-mid market customers, serving as their primary strategic partner at Rewind

• Guide customers through pre and post sale testing, implementation, adoption, and ongoing success planning to ensure they achieve value from Rewind’s platform

• Conduct regular business reviews, success planning sessions, and executive check-ins with key stakeholders.

Customer health, retention & growth

• Develop and own strategies to improve customer health, long term retention and customer satisfaction

• Partner with Account Managers to identify cross-sell opportunities across Rewind’s other supported integrations (ex. expanding from Jira to GitHub coverage)

Customer insights & cross-functional collaboration

• Act as the voice of the customer internally, sharing insights that help shape product priorities and improvements.

• Partner closely with Sales during handoffs and expansion opportunities to ensure a seamless customer experience.

• Collaborate with Product and Engineering teams to surface feedback and influence roadmap discussions.

• Work with Marketing and Support teams to develop resources that help customers adopt and succeed with Rewind.

Customer success strategy & playbook development

• Design and implement the foundational customer success playbook, including onboarding frameworks, engagement models, and lifecycle strategies

• Define what great customer success looks like at Rewind by establishing processes, success metrics, and best practices

• Build repeatable approaches for enterprise onboarding, value realization, and account health monitoring

• Identify tools, systems, and workflows needed to support a scalable CS organization
  

What you’ll bring

• 4+ years of experience in Customer Success, Implementation, Account Management, or a related role within a B2B SaaS environment

• A builder’s mindset with the ability to create structure, processes, and playbooks from the ground up with minimal oversight

• Strong agentic fluency

• Experience managing a renewable book of business in a SaaS company

• Proven ability to manage enterprise accounts with multiple stakeholders

• Excellent relationship-building skills, with the ability to engage both operational and executive audiences

• A data-informed approach to managing customer health, retention, and growth

• Ability to collaborate cross-functionally with Sales, Product, Engineering, and Marketing teams

• A proactive, ownership-driven mindset with strong accountability and follow-through

Location and working hours

This role is remote within Canada (Eastern Time Zone) .

Compensation Philosophy
The actual base salary will vary based on various factors, including market and individual qualifications objectively assessed during the interview process. The listed range above is a guideline, and the base salary range for this role may be modified.

If your expectations are above this range, it may be because your experience aligns with a more senior level. In some cases, we’re open to hiring at a higher level for the right person and are committed to paying competitively and fairly.

If your experience is closer to an earlier career stage, we may still consider your application. In that case, we would evaluate the role at a different level within our levelling framework, which would correspond to a salary below the range shown.

Pay is just one part of the overall compensation at Rewind.

Why join Rewind

At Rewind, you’ll help shape the future of data protection for thousands of businesses. We’re performance-driven, innovative, and not afraid to challenge what’s possible. You’ll join a team that values trust, accountability, and respect for people’s time — and encourages every employee to experiment, think critically, and grow.

We support innovation through experimentation — including smart use of AI tools — and believe the best ideas come from those who aren’t afraid to push boundaries.

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

• $2000/year wellness/home office allowance

• $5000/year professional development 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.

AI Usage

Our recruitment process may include the use of artificial intelligence–enabled tools to help manage and review applications efficiently. These tools assist our team, but hiring decisions are ultimately made by human reviewers.