Digital / Scaled Customer Success Manager

One-to-Many Customer Success | Digital Programs | Portfolio Segmentation | Builder

About Petal

Petal is a Canadian healthcare technology company transforming how healthcare organizations and physicians manage their work. Our solutions support critical healthcare workflows, and Customer Success plays an important role in ensuring our customers adopt our solutions, realize meaningful value, and continue to grow with Petal.

As our Customer Success organization evolves, we are building a new way of serving a broad portfolio of customers—one designed around scale, digital engagement, customer signals, and targeted human intervention.

We are looking for someone who has done this before.

About the Role

We are looking for a Digital / Scaled Customer Success Manager to build and own our one-to-many Customer Success motion for a pooled portfolio of customers.

This is not a traditional 1:1 CSM role.

You will not manage a small book of enterprise customers through recurring meetings, QBRs, and individually tailored success plans. Instead, you will be responsible for driving Customer Success outcomes—adoption, engagement, retention, value realization, and expansion—across a broad portfolio of customers through scalable programs and digital engagement.

The scaled motion is not already built.

You will help create it.

You will assess the portfolio, define meaningful customer segments, identify the signals that indicate customer health, risk, opportunity, or the need for human intervention, and build the programs and journeys that allow us to engage customers at the right time and in the right way.

You will also help define when a customer should remain within the pooled model and when its complexity, risk, growth potential, or strategic importance warrants transitioning to an assigned CSM.

We are specifically looking for someone who has previously built, implemented, or materially evolved a digital, pooled, or one-to-many Customer Success motion.

Prior experience doing this work is a requirement for the role.

What This Role Is — and What It Is Not

This role IS:

• Building a one-to-many / digital Customer Success motion.

• Managing customer outcomes across a broad pooled portfolio.

• Segmenting customers based on meaningful business and customer signals.

• Designing lifecycle journeys and engagement programs.

• Building digital and 1 programs that drive adoption, retention, value, and growth.

• Determining when customers need direct human intervention.

• Creating triggers and plays based on usage, health, lifecycle, risk, engagement, and opportunity.

• Using data, technology, automation, and AI to increase the reach and impact of Customer Success.

• Testing programs, measuring results, learning, and iterating.

• Building processes and infrastructure where they do not yet exist.

This role IS NOT:

• A traditional named-account CSM position.

• A role centered around managing a small portfolio of enterprise customers.

• A calendar filled primarily with recurring 1:1 customer meetings and QBRs.

• A role where every customer receives the same CSM cadence.

• A Customer Support queue.

• A fully established Digital CS program that you will simply inherit and execute.

• A position for someone waiting for the playbooks, journeys, segmentation, programs, and processes to already exist.

If your Customer Success experience has primarily been managing a named portfolio through 1:1 relationships, this role will be meaningfully different.

If you have built Customer Success programs that allow one CSM to influence the outcomes of many customers simultaneously, we want to hear from you.

What You'll Build

Portfolio Segmentation & Coverage Model

You will help determine how our pooled portfolio should be managed.

This includes:

• Assessing the existing customer portfolio and identifying meaningful segments.

• Defining differentiated engagement strategies by customer segment, lifecycle stage, behavior, need, and opportunity.

• Establishing which customers should receive digital, 1, triggered, or direct CSM engagement.

• Identifying signals that indicate when a customer requires intervention.

• Helping define criteria for when a pooled customer should transition to assigned Customer Success coverage.

• Continuously refining segmentation and coverage based on customer behavior and results.

The objective is not simply to categorize customers. It is to determine what Customer Success experience each customer needs and how we can deliver it efficiently.

Digital & One-to-Many Customer Success Programs

Design, launch, and continuously improve scalable programs that help customers achieve value without relying primarily on individual CSM meetings.

Programs may include:

• Lifecycle communications

• Digital onboarding and enablement

• Adoption campaigns

• Webinars

• Office hours

• Customer education

• Self-service resources

• Product adoption programs

• Renewal readiness programs

• Risk mitigation campaigns

• Customer advocacy and reference programs

• Expansion and growth campaigns

• Trigger-based customer outreach

You will determine which programs are needed based on customer data, behavior, feedback, and business priorities—not simply create programs for the sake of activity.

Customer Signals, Health & Intervention

Help build the intelligence behind our scaled Customer Success motion.

You will:

• Identify the customer signals that matter.

• Monitor product adoption, engagement, support activity, lifecycle stage, customer sentiment, renewal timing, growth signals, and other relevant indicators.

• Help develop customer health and risk frameworks.

• Define triggers for automated engagement.

• Define triggers for direct CSM intervention.

• Identify customers whose risk, complexity, strategic value, or growth potential warrants reassessment of their coverage model.

• Build repeatable plays for common customer situations.

The goal is to move from “Who should I contact today?” to a system that helps Customer Success understand who needs attention, why, and what should happen next.

Customer Success Outcomes

Although the engagement model is different, this is still fundamentally a Customer Success role.

You will be accountable for helping drive:

• Customer adoption

• Engagement

• Value realization

• Retention and renewal readiness

• Risk identification and mitigation

• Customer satisfaction

• Advocacy and references

• Expansion identification and customer growth

Scaled Customer Success does not mean less Customer Success. It means finding smarter and more repeatable ways to achieve those outcomes across a larger customer population.

Technology, Automation & AI

Technology will be an important part of how we build this motion.

You will help identify opportunities to use technology, automation, and AI to:

• Detect customer signals and patterns.

• Prioritize accounts requiring attention.

• Trigger customer journeys and engagement.

• Personalize communication at scale.

• Reduce repetitive manual CSM work.

• Create and maintain customer education and self-service experiences.

• Surface risk and expansion opportunities.

• Measure program effectiveness.

You do not need to be a software engineer.

You do need to be technically curious, systems-oriented, and comfortable building or prototyping workflows using modern Customer Success, CRM, automation, and AI tools.

We are looking for someone who asks, “How could we build this?” rather than immediately assuming another team needs to build it for them.

Required Experience

• 5+ years of experience in Customer Success, Digital Customer Success, Scaled Customer Success, SaaS, or a closely related customer-facing function.

• Direct experience building, implementing, or materially evolving a digital, scaled, pooled, or one-to-many Customer Success motion. This is required.

• Demonstrated experience managing customer outcomes across a broad portfolio without relying primarily on 1:1 customer relationships.

• Experience designing and executing 1 or digital Customer Success programs.

• Experience with customer segmentation and differentiated engagement strategies.

• Experience using customer data and signals to prioritize engagement and intervention.

• Demonstrated experience improving adoption, retention, customer value, and/or expansion through scalable Customer Success strategies.

• Experience creating repeatable processes, plays, customer journeys, or lifecycle programs.

• Strong analytical and operational capabilities.

• Experience working cross-functionally with teams such as Product, Sales, Support, Marketing, Operations, and Professional Services.

The Builder We're Looking For

You will likely thrive in this role if you:

• Have built something similar before and can explain exactly what you personally built.

• See 300 customers and immediately think about segmentation, signals, journeys, triggers, and programs—not 300 meetings.

• Know the difference between managing a large portfolio efficiently and building a true scaled Customer Success motion.

• Can determine what should be automated, what should be 1, and what still requires human engagement.

• Enjoy starting with an imperfect environment and creating structure.

• Are comfortable testing an approach, measuring its impact, and changing it when it doesn't work.

• Think in systems and repeatable motions rather than individual workarounds.

• Are comfortable working with data and technology.

• Can move between strategy and hands-on execution.

• Take ownership without waiting for someone else to define every step.

Strong Assets

The following are valuable, but not required:

• Experience in healthcare technology or healthcare SaaS.

• Experience working with physicians, clinicians, or healthcare organizations.

• Bilingualism in French and English.

• Experience with Customer Success platforms, CRM systems, lifecycle automation, or digital adoption tools.

• Hands-on experience using AI or automation to build Customer Success workflows.

• Experience building a scaled CS motion from the ground up in a growing or evolving organization.

How Success Will Be Measured

Success will ultimately be measured by customer and business outcomes, including:

• Adoption and engagement across the pooled portfolio.

• Customer retention and renewal outcomes.

• Customer health and risk reduction.

• Expansion signals and growth opportunities generated.

• Customer satisfaction and advocacy.

• Effectiveness of digital and 1 programs.

• Percentage of customers successfully served through scalable motions.

• Effectiveness of intervention triggers.

• Increased Customer Success capacity and efficiency.

• Successful identification of customers requiring assigned coverage.

• Measurable reduction in unnecessary manual or repetitive CSM activity.

What Success Looks Like

Within your first year, we want to be able to look at our pooled Customer Success portfolio and clearly answer:

Who are our customers?

How should they be segmented?

What Customer Success experience should each segment receive?

What signals tell us a customer is healthy, at risk, ready to grow, or needs human intervention?

Which programs can drive adoption, value, retention, and growth across many customers simultaneously?

When should a customer move from pooled to assigned coverage?

What should technology and automation handle—and where does human Customer Success create the most value?

And most importantly:

Is our scaled Customer Success motion producing measurable customer and business outcomes?

You won't be joining to inherit the finished answer.

You'll be joining because you've built this before and can help us build it here.

Petal’s position on remote working

In our opinion, a company cannot claim to be modern, innovative and have the well-being of their team at heart, without attempting to integrate remote working to the level that their business model allows them to. Petal employees continue to benefit from the option of teleworking up to the maximum flexibility permitted by the nature of the position and the smooth running of operations.

Our benefits

• Recurring hybrid work allowance.

• Compensation that recognizes your contribution.

• 4 to 6 weeks of paid vacation per year.

• 5 paid personal days per year.

• A group RRSP / DPSP plan with employer contribution.

• A complete group insurance plan, from day 1.

• An annual wellness allowance.

• Access to the Lumino Health™ telehealth application.

• Flexible work hours and more.

Petal is an active participant in the equal opportunity employment program, and members of the following target groups are encouraged to apply: women, people with disabilities, aboriginal peoples and visible minorities. If you are a person with a disability, assistance with the screening and selection process is available on request.

A quick important note: We’ve noticed that some external websites are posting our job openings under incorrect job titles. To find our real opportunities and join our team, please make sure to apply through our official careers page or our trusted partners. We can’t wait to hear from you!