Head of Customer Experience & Success Management (CXSM)
Member Solutions | Remote (Canada preferred) | Full-time
Quick Facts
Location: Remote: Canada preferred; USA considered
Compensation: $130K–$150K CAD + performance incentives tied to Net Revenue Retention (NRR) improvement
Start Date: May 2026
Direct Reports: Retention Lead, Growth Lead, Marketing Specialist, Sales Rep (part-time, with path to full-time as lead volume grows)
Tools: HubSpot CRM, Slack, GitHub, Google Workspace, AI tooling
Onboarding Sponsor: Chief Growth Officer (first 60 days)
The Role
You will be the Head of Customer Experience & Success Management (CXSM), reporting to the President. This is a leadership role with direct ownership of retention, revenue growth, customer success, and team performance.
This is not a "build a team from scratch" role. You are inheriting an active operation with real clients, real churn, and real urgency. You will take over revenue and CX operations within your first two weeks, freeing the Chief Growth Officer (CGO) to focus on technology strategy and platform migration. You are the bridge between product innovation and client retention.
The CGO will serve as your onboarding sponsor for the first 60 days — your operational anchor while you're getting up to speed. The team is energetic and client-passionate — genuinely motivated to make a difference. What they need is structure, clear priorities, and a leader who can channel that energy into systems that compound.
The platform migration is also underway — hundreds of client sites moving to a modern stack over the coming months. You are the client-facing voice of that transition: coordinating communication, managing expectations, and keeping clients confident through the change. It's organized work, not a crisis.
The first 90 days are hands-on operator time. Pick up the phone, talk to clients, personally handle cancellation calls. You can't build systems around what you haven't experienced firsthand.
You should be using AI daily to move faster, make better decisions, and scale your impact. If your instinct is to hire more people before improving systems, this role will not be a fit.
Be honest with yourself before applying. This is a turnaround, not a cruise ship. The business needs someone who can stop the bleeding while building the systems that create long-term growth. If you thrive in ambiguity, prefer to move fast, and get energy from fixing broken things, keep reading.
About Member Solutions
Member Solutions, part of Constellation Software (TSX: CSU), is a leader in billing and member management solutions for membership-based businesses across the United States and Canada. With over 30 years of expertise, we serve hundreds of martial arts studios and support fitness facilities, gymnastics clubs, dance studios, shooting ranges, and more.
At Member Solutions, we don't just provide software. We live by our unique ‘software for life’ philosophy. It’s a commitment to our clients for life. We believe in building long-term partnerships, genuinely understanding their businesses, and empowering them to create stronger communities, one member at a time. As a Client Success Manager, you will be at the forefront of this mission.
Our software products and managed billing services help businesses streamline operations, ensure timely and accurate invoicing and collections, and maintain compliance with relevant laws and regulations.
As a remote-first company with deep roots in Pennsylvania, Member Solutions is rapidly expanding across North America. This growth presents exciting career opportunities for those ready to scale with us.
The competitive landscape is active — ZenPlanner, Spark, Kicksite, Dojo Muscle, and others are competing for the same studio owners. The right candidate walks in knowing they're playing defense on an installed base, not just growing from zero.
What You'll Do
Revenue & Sales Oversight
Own the inbound sales pipeline and coordinate with the shared Sales Rep
Build the upsell motion through the GrowthIQ product suite (AI-powered lead generation, webchat, SMS, SEO optimization) — GrowthIQ has early traction but no proven playbook yet. You're building it.
Build and iterate the upgrade playbook (e.g., identify eligible accounts, run the conversations, close the deals)
Design and deploy AI-assisted sales workflows (e.g., lead qualification, follow-ups, personalization at scale)
Continuously experiment with messaging, scripting, and outreach systems to improve conversion rates
Report weekly on pipeline, conversion, and revenue metrics
Customer Experience & Retention
The retention math here is clear: keeping an existing client creates more value than winning a new one. If you understand why that's true in SaaS, you'll immediately see where the leverage is in this role.
Lead the retention function: every cancellation gets a structured save conversation
Design, implement, and iterate the save flow (structured cancel intervention with playbooks by cancel reason)
Build and iterate AI-assisted save flows (e.g., dynamic scripts, objection handling, cancel interception)
Roll out the automated results report as a retention weapon (when clients see their ROI, they stay longer)
Own exit interviews for every lost account (eliminate the "unknown" cancel reasons)
Use AI to analyze churn data, identify patterns, and proactively intervene before cancellations occur
Run proof calls with top-tier accounts: "Here's what your site did this month"
Team Leadership
Directly manage the Retention Lead, Growth Lead, Marketing Specialist, and Sales Rep
Run weekly CX standups, 1:1s, and team communication
Coach with candor: set clear expectations, give direct feedback, build trust fast
Introduce AI leverage across the team, improving output per head, not just adding capacity
Build coverage plans for team transitions, including managing through a direct report's upcoming parental leave — a known short-term challenge with a clear runway
Marketing & Customer Messaging
Own all client-facing communication: upgrade announcements, feature launches, email campaigns
Oversee the Marketing Specialist on campaign execution and customer messaging
Position new platform capabilities (AI features, modern sites, results reporting) in language clients care about
Use AI to generate, test, and iterate messaging across campaigns (email, SMS, web)
Build systems for rapid experimentation and continuous improvement in customer communication
Partner Channel
Take ownership of key partner relationships — referral pipeline, co-marketing, beta testing
Build the partner channel from 2–3 referrals/month toward a repeatable, measurable engine
Track whether partner-referred accounts retain better and use that data to invest accordingly
Identify opportunities to use AI in partner enablement, co-marketing, and lead sharing workflows
Across all areas, you are expected to identify and seize opportunities to use AI to automate, accelerate, and improve outcomes — and to ship those improvements continuously.
What You'll Own — KPIs
While managed manually on Day 1, you are expected to build systems, leveraging AI where appropriate, to enable real-time monitoring and drive continuous improvement across each.
Metric & What It Means
Monthly churn rate: Reduce cancellations through structured, system-driven save flows and proactive retention
Save flow success rate: % of cancel attempts that result in a save or downgrade vs. full loss
GrowthIQ upsell pipeline: Conversations started, conversions closed, MRR added through product upgrades
Client NPS / satisfaction: Measured through proof calls, exit interviews, and engagement with results reports
Partner referral volume: New accounts sourced through partner relationships and repeatable partner workflows
Net revenue retention (NRR): The north star — are we retaining and expanding revenue from existing clients?
Exit interview capture rate: % of cancels where we know exactly why they left with structured, analyzable data
CGO bandwidth recovered: Within 30 days, the CGO should not be pulled into any client-facing issue
Who You Are
Required
5+ years in B2B SaaS in customer success, account management, or revenue leadership
2+ years managing a team — you have hired, coached, and held people accountable
Experience driving SaaS retention metrics: churn reduction, save rate, NRR, NPS/CSAT
Player-coach mentality — you will personally handle cancel conversations and proof calls, not just manage dashboards
Comfort with data — you can build a weekly dashboard, segment a client base, and make decisions from metrics
Strong communicator — you write clearly, present confidently, and have difficult conversations without avoiding them
Bias for speed — you ship before it is perfect and iterate based on results
AI-specific expectations:
- You already use AI tools daily (e.g., ChatGPT, Claude, Zapier, Make) and will be expected to use and build on this stack
- You think in systems, regularly looking for ways to automate, augment, or eliminate manual work
- You can point to specific examples where you used AI tools to improve an outcome — a process you automated, a decision you made faster, a workflow you redesigned. Hands-on experience with AI is expected; you don't need to have written code.
Preferred
Experience in the fitness, martial arts, or wellness vertical — you understand studio owners
Background in vertical market SaaS — you know what it means to go deep in a niche
Experience at a Jonas Software, Constellation Software, or PYXiS Software portfolio company
Deep familiarity and hands-on experience with AI-powered SaaS products (lead generation, conversational AI, automated reporting)
Experience in a turnaround or high-change environment — you have walked into a business that was declining and helped reverse it
Why This Role Matters
This role exists because the turnaround has two fronts — and one person cannot lead both. The technology front (platform migration, AI-first architecture, cost restructuring) is led by the CGO and Interim CTO. The revenue and customer front needs its own leader. That is you.
Real ownership. You are not a middle manager. You own retention, revenue growth, and the customer relationship for the entire business. Your decisions show up in the P&L.
AI-first product differentiation. The platform is being rebuilt with AI at the core — automated results reporting, AI-powered lead generation, conversational agents. You are selling and retaining around genuinely differentiated technology.
Vertical market depth. Fitness and martial arts studio owners are a passionate, loyal customer segment. When you solve their problems, they tell every other studio owner they know.
Constellation Software backing. Startup-level autonomy with the stability and resources of a $75B+ parent company. Long-term hold means long-term thinking. No one is optimizing for a Series B exit.
Direct impact on business trajectory. Every saved account, every upsell, every proof call that keeps a client — it compounds. You will see the numbers move because of what you did.
A career-defining proving ground. Turnarounds build leaders faster than stable businesses. You will touch every dimension of a SaaS operation — retention, revenue, product, migration, team. Success here is visible, and within PYXiS and Jonas, that visibility opens doors.
How to Apply
Send your resume and a brief note on why this role interests you. We value directness over polish — tell us what you have done, not what you aspire to do.
#LI-PP1
Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.
Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.” We are committed to technology, product innovation, quality, and exceptional customer service.
Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.
Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.