Customer Experience Specialist

Remote (United States)

Job Details

Location: United States

Workplace: Remote

Employment Type: Full-Time

Experience: 2+ years in technical SaaS support, software customer success, or a comparable customer-facing technical support role

Schedule: 8:00 AM - 5:00 PM local time (Eastern, Central, Mountain, or Pacific Time)

Core Areas: Customer Experience Management, Technical SaaS Support, Software Troubleshooting, Root Cause Analysis, Customer Education, Knowledge Base Management, AI-Assisted Support, Customer Issue Resolution

Compensation: Starting at $65,000 annually with potential adjustments based on experience and qualifications

About the Role

This Customer Experience Specialist opportunity focuses on delivering high-quality technical SaaS support, resolving complex software issues, and helping customers use business software effectively. The position manages customer interactions across chat, email, phone, and screen-sharing sessions, taking ownership of support requests from initial contact through resolution. Key responsibilities include technical troubleshooting, customer education, issue investigation, and identifying opportunities to improve the overall customer experience.

The role combines hands-on problem-solving with AI-assisted support workflows, customer training, and knowledge management. Working with Pylon, AI agents, and cross-functional teams, the specialist investigates software configurations, data relationships, integrations, and unexpected system behavior. The position also supports users of association management software (AMS), develops educational resources, and translates recurring customer issues into actionable improvements for product development and support operations.

What You'll Do

• Manage customer support conversations in Pylon across live chat, email, phone, and screen-sharing sessions, maintaining ownership from initial response through complete resolution.
• Deliver technically accurate, timely, and personalized assistance while helping customers understand solutions and build confidence using the software.
• Investigate and troubleshoot complex software issues involving customer configurations, data relationships, system integrations, and unexpected application behavior.
• Perform root cause analysis using available technical resources, troubleshooting tools, and internal knowledge to identify practical, sustainable solutions.
• Use AI agents and AI-powered tools to research customer questions, investigate technical problems, draft responses, and analyze support information.
• Evaluate AI-generated results, apply independent judgment to verify accuracy, and contribute to improving AI-assisted support workflows.
• Collaborate with Onboarding, Customer Success, software developers, and other internal teams to investigate escalations, communicate technical findings, and resolve customer issues.
• Advocate for customer needs by sharing feedback, clarifying recurring challenges, and helping internal teams understand the impact of product issues.
• Educate customers on software functionality, recommended workflows, and effective product usage to strengthen adoption and self-service capabilities.
• Lead or co-host customer Office Hours, webinars, live training sessions, and individual educational conversations.
• Create, update, and maintain Help Center articles, internal knowledge base documentation, troubleshooting guides, and other educational resources as product functionality evolves.
• Identify recurring support questions, customer friction points, and patterns that indicate opportunities to improve documentation, software functionality, and the support experience.
• Translate customer insights into actionable recommendations and contribute to initiatives that prevent repeat issues and improve customer outcomes.
• Experiment with new support tools, workflows, and processes to increase efficiency, reduce repetitive work, and create more capacity for meaningful customer interactions.
• Balance competing support priorities, determine when deeper investigation or escalation is appropriate, and maintain consistent follow-through on customer commitments.
• Develop strong product expertise and continuously improve technical troubleshooting, customer education, and support practices.

Qualifications

Required Experience

• At least 2 years of experience in technical SaaS support, software customer success, or a comparable customer-facing role involving technical troubleshooting.
• Experience investigating and resolving complex software problems, identifying underlying causes, and explaining technical findings to nontechnical customers.
• Experience conducting one-on-one or group customer conversations, explaining software concepts, answering questions, and helping users learn unfamiliar functionality.
• Experience working remotely and collaborating asynchronously using communication and project management tools such as Slack, Zoom, and Jira.
• Experience managing customer-facing responsibilities independently, prioritizing competing requests, and taking ownership of issues through resolution.

Required Skills

• Exceptional written communication skills, including the ability to explain technical concepts clearly, adapt messaging to different audiences, and provide personalized, actionable responses in asynchronous support environments.
• Strong technical curiosity and independent troubleshooting capabilities, with a methodical approach to investigating software behavior, asking diagnostic questions, and using available resources before escalating issues.
• Practical experience using AI tools to research information, solve problems, or improve workflows, including the ability to critically evaluate AI-generated output and apply human judgment.
• Customer-focused problem-solving skills, including the ability to understand underlying customer goals, explore alternative approaches, and recommend effective solutions when an initial request cannot be fulfilled as expected.
• Ability to explain technical findings to nontechnical audiences and guide customers through software features, troubleshooting steps, and unfamiliar concepts.
• Strong ownership, sound judgment, and follow-through when managing customer issues, balancing speed with thoroughness, and determining when to investigate further, request assistance, or escalate.
• Ability to identify patterns across customer interactions, connect information from multiple sources, and recognize opportunities to prevent recurring problems.
• Initiative and adaptability when testing new tools, incorporating feedback, learning new systems, and improving existing customer support processes.
• Strong organizational skills and the ability to manage multiple priorities independently in a changing work environment.
• Willingness to continuously develop product knowledge, technical expertise, and customer education capabilities.
• Authorization to work in the United States and availability to work from 8:00 AM to 5:00 PM in the applicable local U.S. time zone.

Preferred Qualifications

• Experience with QuickBooks Online, Pylon, association management software (AMS), or CRM platforms.
• Familiarity with the association industry and software used to manage association operations and member relationships.
• Experience supporting Novi AMS is strongly preferred.

Benefits

• Fully paid family health, dental, and vision insurance.
• Generous paid time off and paid holidays.
• Family-friendly leave policies.
• 401(k) retirement plan with employer matching contributions.
• Home office equipment and support for remote work.
• Professional development opportunities, including certifications, continuing education, and career advancement.
• Opportunities to contribute ideas and influence customer support processes, tools, and the overall customer experience.
• Remote-first working environment with an emphasis on flexibility and work-life balance.