About the Onboarding Team
The Onboarding Team is responsible for getting new PushPress customers set up, activated, and confident across all products. We focus on delivering a consistent, high-quality experience that drives Time to First Value and reduces early churn.
We are a globally distributed, async-first team. We value direct, respectful communication and strong ownership. Our goal is to remove friction from the customer journey so gym owners can get to work faster.
About The Role
The Customer Onboarding Specialist is the first human connection new PushPress clients have after signing up, and that moment matters. This is a full-stack onboarding role, meaning you work across the entire PushPress product suite — gym management, CRM and marketing automation, and website services — onboarding customers on individual products, multiple products, or all of them together depending on what they’ve purchased. This role is responsible for guiding new customers through setup, accelerating Time to First Value, and setting the foundation for long-term success.
You own the onboarding experience from kickoff through launch. Some customers are setting up one product. Others are standing up multiple products simultaneously, which means sequencing setup tracks, managing dependencies between platforms, and adapting your approach when priorities shift. You bring strong product knowledge, clear communication, and disciplined follow-through from day one. With a significant portion of churn occurring in the first six months, this role plays a direct role in retention and customer confidence.
What You'll Do
Guide new clients through setup of PushPress products, including key configurations, integrations, and initial workflows.
Deliver onboarding through a mix of one-on-one calls and Intercom-based support.
Educate clients on workflows aligned to their business goals and operating model.
Track onboarding progress and proactively follow up to remove blockers.
Collaborate with Support and Operations teams to identify and close onboarding gaps.
Review and update Help Docs and customer training material to improve onboarding clarity.
Identify early churn signals and escalate risks to Support or Operations teams.
Provide how-to guidance via chat for customers in the onboarding phase.
Develop deep product expertise across the PushPress platform and stay current on new releases, feature updates, and best practices.
Lead scaled onboarding programs and own early churn identification and mitigation strategies.
How Success Is Measured
Time to Complete Onboarding — duration from contract signing to account launch.
Onboarding CSAT — client satisfaction score for the onboarding experience.
Early Retention — measured against churn reduction targets in the first six months.
What You'll Need
Strong working knowledge of the PushPress product suite, including platform configuration and core workflows.
Experience leading customer onboarding, implementation, or setup projects in a SaaS environment.
Comfort delivering onboarding over video, screen share, and live troubleshooting sessions.
Strong project management skills with consistent follow-up and milestone ownership.
Clear, confident communication with the ability to explain technical concepts simply.
High attention to detail and disciplined use of systems and tracking tools.
Empathy and calm under pressure when supporting customers who feel overwhelmed.
Core Skills and Qualities
Ability to context-switch fluidly between calls, chat support, and follow-up work throughout the day.
Comfort screen sharing across desktop and mobile environments during live onboarding.
Proven ability to manage multiple onboarding timelines at once without losing quality.
Strong written and verbal communication that builds trust and momentum.
Comfort working in CRM systems to track progress, risks, and outcomes.
Ability to adapt onboarding approaches to different business models and client needs.
Ownership mindset with accountability for outcomes, not just meetings completed.
Comfort working asynchronously with cross-functional partners.
Must Have Background
Two or more years of experience in SaaS onboarding, implementation, or client-facing roles.
Demonstrated ability to manage customers through multi-step, multi-week setup processes with consistent follow-through.
Nice-To-Have Background
Experience building or improving onboarding playbooks, content, or automation.
Background in SMB ownership and management, especially gyms and fitness operaitons.
Understanding how fitness businesses operate and having the skills to educate, understand and question practices based on the software’s capabilities
Experience supporting CRM pipelines, lead management, or messaging workflows.
Two or more years of experience in gym ownership, gym management, or fitness operations.
Tools and Systems
Daily tools: Intercom, HubSpot, Zoom, Slack, Google Workspace.
Familiarity with PushPress products preferred but not required.
What We're Looking For
Product mastery. You invest in learning the full PushPress suite deeply and can articulate its value clearly to any audience.
Accountability. You own client milestones end to end. Success doesn’t stop when the call ends.
Contribution. You proactively improve the process — whether that’s updating a help doc, flagging a gap in the playbook, or suggesting a better workflow.
Continuous learning. You stay current on product changes and look for ways to sharpen your onboarding approach over time.
This Role Is Not
A reactive support role. You are proactively driving customers toward activation, not waiting for them to ask for help.
A scripted role. Customers come in with different products, different business models, and different levels of readiness. You adapt in real time, not just follow a checklist.
A role where the job ends at kickoff. Success means the customer is live, confident, and using the product — not just that the first call happened.
Scenario-based onboarding exercises focused on real customer setups.
Review of communication style, clarity, and confidence during live walkthroughs.
Discussion of how you manage timelines, blockers, and competing priorities.
Assessment of ownership, urgency, and customer-centered decision making.
Top Skills
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory



