Digital Customer Success Manager

ScalePad • Markham, ON

10d • Remote

About The Position

At ScalePad, we are building more than software; we are building confidence and clarity for the people who manage the technology businesses rely on every day. Our mission is to help MSPs evolve into MVPs (their clients’ most valuable partner). Our tools turn them from reactive service providers into strategic advisors through a consistent, scalable Customer Success motion. Our product suite unifies risk insights, client planning, and service delivery so MSPs can have smarter conversations, show clients their value, and grow their revenue. We are creating a workplace where curious, growth-minded people can do their best work, where ideas are valued, progress is shared, and everyone belongs. Together, we are creating a future where MSPs don’t just keep businesses running, they help them thrive. We believe that when our partners succeed, we all do. With offices in Vancouver, Toronto, Montreal, and Phoenix and a global-first mindset, ScalePad has grown into a category leader trusted by 12,000+ partners across 60+ countries. We’ve been recognized for our products and corporate culture by MSP Today, G2, and Great Place to Work™.

Requirements

• 1+ years in B2B customer success, account management, or professional services, working with accounts of various sizes.
• Demonstrated ability to manage a large, diverse portfolio without dropping threads
• Comfort owning commercial conversations: renewals, growth, mid-term risk, and a monthly performance target.
• Sharp prioritization instincts. You can triage a full inbox and a full book simultaneously and make good calls about what needs you today vs. next week.
• Strong written and verbal communication — your emails are clear, your calls are focused, your follow-up is timely.
• Working experience with HubSpot and Gainsight (or a comparable CS/CRM stack).
• Actively uses AI tools to manage workload — whether that’s drafting outreach, surfacing risk signals, building automations, or triaging priorities. This isn’t a nice-to-have. If you’re still doing everything manually, this role will feel like a mismatch.

Nice To Haves

• Experience managing a portfolio of 1,000+ customers.
• Familiarity with digital-first CS motions — scaled engagement, automated journeys, and the judgment to know when to go high-touch.
• A track record of contributing to CS process improvement — not just following playbooks, but identifying where they break and fixing them.

Responsibilities

• Serve as the primary point of contact for digital customers, managing inbound requests across education and training, contract and billing inquiries, and escalations, including responding to in-app “speak to someone about your account” requests and ensuring timely, effective resolution.
• Proactively engage high-impact customers identified through customer scoring, while monitoring early signals of disengagement to intercept at-risk customers before cancellation and drive preemptive churn mitigation.
• Lead revenue retention conversations, and owning digital deal execution end-to-end, including renewals, and upsell opportunities, and identifying cross sell opportunities for the AE team.
• Own churn-save decisions independently for digital customers, enabling faster response times and improved retention outcomes without reliance on manager approvals.
• Act as the bridge between automated digital engagement and personalized customer interactions, ensuring continuity in the customer experience while triaging partners to the appropriate internal teams (Support, Technical CSMs, Billing, Product) as needed.
• Close the loop on partner feedback by following up on feature requests, reinforcing engagement and trust in the product roadmap, while identifying systemic product or billing issues from inbound trends.
• Track and report on key segment metrics, including churn rate, save rate, and expansion MRR, and share structured insights such as monthly product feedback reports to inform cross-functional improvements.

Benefits

• Share in our success through our Employee Stock Ownership Plan (ESOP) and RRSP matching.
• Parental leave programs are in place to support you and your family when it matters most.
• Join opt-in mentorship programs and learn directly from founders and senior leaders who’ve scaled multiple SaaS ventures and spent decades in the MSP industry.
• Access an annual professional development budget to level up your skills, your career, and your impact.
• Work with brand new, top-of-the-line hardware and equipment so you can do your best work, whether you’re at home or in one of our hubs.
• Roles at ScalePad are structured as remote or hybrid, with hub locations in Vancouver, Toronto, Montreal, and Phoenix. Specific work models are outlined in each posting.
• Receive a monthly stipend to help you create an effective hybrid or remote work environment.
• Take care of yourself with 100% employer-paid benefits.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 101-250 employees