As the Customer Experience Leader, you will design systems to enhance customer activation and retention, manage the customer journey, and drive organizational growth through data and empathy.
About PushPress
PushPress is building the Intelligent Industry Ledger for boutique fitness.
We’re transforming how boutique gyms operate — and how the entire $100B fitness industry connects, transacts, and grows. Trusted by 5,000+ gyms and 500,000+ members, PushPress processes over $500M annually and is backed by Altos Ventures and Mucker Capital.
We're evolving from a traditional business system of record into an AI-powered Industry Ledger — an intelligent infrastructure layer that brings order to a highly fragmented boutique fitness industry. By unifying disconnected operators, workflows, and data into a single platform, we’re enabling faster decisions, new business models, cross-gym collaboration, and network effects that increase the value of every studio in our client base.
We’re a global team of builders, operators, and fitness fanatics on a mission to level the playing field for fitness entrepreneurs. If you're ready to help reshape an industry — let’s talk.
About the Role
As the Customer Experience Leader at PushPress, you’ll design and lead a world-class CX organization that fuels activation, retention, and long-term growth by helping every customer unlock the full value of the PushPress platform.
You’ll architect the systems, processes, and team structures that deliver seamless onboarding and exceptional support, setting every gym owner up for success from day one. This role blends strategy and execution: you’ll zoom out to design scalable frameworks, then zoom in to optimize the workflows and incentives that power the customer journey.
You’ll thrive here if you’re an empathetic operator who can think like an architect, act like an owner, and lead with data, all while keeping the human element at the core of the experience.
What You'll Do
- Champion customer success and value creation - keep gym owners at the center of every decision, ensuring their success drives our retention and growth metrics.
- Design and scale the CX organization - advance the structure, workflows, and roles needed to support growth. Continue the evolution from a generalist team to specialized pods for onboarding, support, and enablement.
- Own the end-to-end customer journey - manage the experience from sales handoff to activation to long-term support and advocacy. Partner closely with R&D, Sales, and Growth to create a seamless, high-impact customer experience across all touchpoints.
- Drive activation, adoption, and retention - define success metrics, shorten time-to-value, and proactively identify churn risks. Build programs and incentives that motivate customers and teams toward adoption and expansion.
- Translate insight into action - break down complex customer and operational problems into clear components, prioritize effectively, and turn customer pain points into actionable roadmaps for both the CX organization and Product.
- Build and sustain operational excellence - establish a strong operating cadence, translate company goals into team-level objectives, and develop a high-performing CX organization positioned for long-term success.
- Make data actionable - monitor key KPIs and adjust as needed (activation rate, P90 time to resolve, time-to-value, cost to serve) to guide staffing, process improvements, and automation investments. Collaborate with RevOps and Finance to model ROI and efficiency gains.
- Reduce friction through systems and tools - work with R&D to simplify complex workflows in the onboarding and support experience, deploying AI or automation to scale without losing the human touch.
- Lead with empathy and accountability - build a culture centered on clarity, urgency, and ownership, reinforcing our core tenets. Empower the team to support non-technical SMB owners with patience and confidence while balancing operational efficiency with genuine care.
What You'll Bring
- 8+ years of professional experience in Customer Experience, Onboarding, or Support leadership roles within SaaS, ideally vertical SaaS or SMB-focused.
- Excellent communicator, people leader, and system thinker who balances empathy with execution.
- Proven ability to lead organizational transformation through scale - evolving team structures, systems, and culture while keeping the customer at the center.
- Metrics-driven operator experienced in defining and acting on KPIs that guide CX performance with an aptitude for quick experiments to drive improvements.
- Experience designing comp plans, spiffs, or incentives that align behavior with customer outcomes.
- Strong cross-functional collaborator who thrives working with Product, Sales, and RevOps.
- Strong executive communicator and storyteller who connects CX metrics to company strategy and board-level outcomes.
- Financially fluent - can model headcount needs, cost-to-serve, and CX ROI to inform strategy.
- Embraces a culture of Radical Candor - welcomes feedback, coaches others openly, and fosters growth through honest, respectful dialogue.
Preferred Skills and Experience
- Experience in fast-scaling vertical SaaS companiesFamiliarity with AI and automation tools in onboarding or support.
- Experience blending PLG and sales-assisted onboarding models.
- Background in fitness, wellness, or SMB SaaS industries.
- Tools: Intercom, Zendesk, HubSpot, ChurnZero, or similar CX systems.
- Experience with SQL or data modeling for analytics and reporting.
Benefits and Perks
- Health Care Plan (Medical, Dental & Vision)
- Retirement Plan (Company Sponsored 401k with Match)
- Life Insurance
- Flexible Paid Time Off (and Public Holidays)
- Family Leave (Maternity, Paternity)
- Work From Home Stipend
- Equity Incentive Plan
- Company Issued Laptop
#LI-EJ1
PushPress is dedicated to fostering an inclusive and dynamic workplace. We’re all about leveling up, and that means we don’t tolerate any form of discrimination or harassment. We’re committed to provide equal opportunities, regardless of race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability, genetic info, veteran status, or any other legally protected characteristic.
At PushPress, we’re dedicated to helping both our technology and our team reach peak performance. Whether it’s with your proactive approach, eye for detail, or drive to make a meaningful impact, we’d love to hear from you. At PushPress, we’re all about pushing boundaries and achieving new personal bests—come join us and be part of our fitness-tech journey!
Top Skills
Churnzero
Hubspot
Intercom
SQL
Zendesk
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