Reports to: Sr. Manager, Customer Success Operations

Primary Collaboration: Customer Success team members, customers, and internal technical/support partners.

About Pathwise

Pathwise (formerly TransAct) is a leading provider of cloud-based operational solutions built for the K–12 education community. With more than 30 years of experience and a team that includes former district administrators and transportation directors, we build software that solves the real challenges of running school operations.

About the Role

The Customer Success Specialist serves as a technical problem solver and trusted advisor for our K–12 customers. This role requires someone who enjoys troubleshooting complex software issues while communicating technical concepts in a clear, calm, and customer-friendly manner. Success in this position comes from balancing strong technical aptitude with exceptional customer service and relationship-building skills.

This is a hands-on support role in a fast-paced SaaS environment where priorities shift quickly, customer needs are time-sensitive, and collaboration across Product, Engineering, and Customer Success is essential.

Preferred Schedule

This position is intended to provide customer support during our Eastern Time evening support window. The anticipated schedule is 11:00 a.m. to 8:00 p.m. Eastern Time, Monday through Friday, including a one-hour unpaid meal period.

Our busiest support season occurs during the summer and Back-to-School months, when responsiveness, teamwork, and adaptability are especially important.

Key Responsibilities

• Diagnose and troubleshoot software-related issues reported by customers, ensuring timely and accurate resolution.
• Serve as a technical resource capable of independently troubleshooting complex customer issues before escalation.
• Translate technical information into clear, customer-friendly communication.
• Confidently guide customers through complex software workflows while maintaining a high level of customer satisfaction.
• Effectively de-escalate customer concerns through active listening, empathy, and solution-oriented communication.
• Support a high-volume technical support environment while maintaining quality and responsiveness.
• Provide technical support through chat, email, and phone.
• Support both initial implementation and ongoing day-to-day customer use cases.
• Be available to work the anticipated schedule of 11:00 a.m.–8:00 p.m. ET, Monday through Friday, with flexibility to adjust work hours occasionally based on business needs, customer demand, or peak seasonal support periods.
• Gather relevant information and document detailed incident reports in the ticketing system, maintaining comprehensive records of customer interactions and solutions.
• Collaborate with cross-functional teams, including software developers, to escalate and resolve complex issues requiring further investigation.
• Conduct in-depth analysis of software-related problems, identify patterns, and propose proactive solutions to improve product functionality and stability.
• Create and maintain technical documentation, including FAQs, troubleshooting guides, and knowledge base articles, to support customer self-service.
• Continuously expand technical knowledge and stay current on software advancements, industry trends, and support methodologies.
• Maintain accurate customer account records and system data to support operational excellence.
• Strive to achieve and exceed KPIs such as response time, first-call resolution rate, and customer satisfaction ratings.
• Proactively monitor customer engagement and platform utilization to identify opportunities for increased adoption and customer success.
• Conduct customer check-ins and training sessions to reinforce best practices and support long-term platform utilization.
• Serve as a customer advocate by gathering feedback and partnering with internal teams to improve the customer experience.
• Manage relationships with an assigned portfolio of customer accounts and serve as a primary point of contact throughout onboarding and ongoing support.
• Perform other duties as assigned
• Build customer confidence by communicating technical solutions clearly, professionally, and with empathy, particularly during high-impact customer situations.

Required Qualifications

• Bachelor's degree or equivalent combination of education and experience.
• 2+ years of experience in customer success, account management, customer support, client services, or a related field.
• Excellent written and verbal communication skills.
• Strong interpersonal and relationship-building abilities.
• Exceptional organizational and time management skills.
• Ability to manage multiple priorities in a fast-paced environment.
• Proficiency with CRM and customer management systems.
• Strong problem-solving and critical-thinking skills.
• Demonstrated technical aptitude with the ability to troubleshoot software applications independently.
• Ability to explain technical concepts to both technical and non-technical users.
• Experience supporting SaaS software in a technical customer support environment.
• Comfortable managing multiple technical issues simultaneously while maintaining a positive customer experience.
• Ability to build rapport and maintain professionalism during challenging customer interactions.

Preferred Qualifications

• Experience supporting K–12 education, transportation, communications, SaaS, or technology solutions.
• Experience conducting customer onboarding, training, or implementation activities.
• Familiarity with customer success metrics and retention strategies.
• Experience using CRM, ticketing, and customer support platforms such as Salesforce, HubSpot, Zendesk, Jira, or similar systems.
• Experience supporting cloud-based software applications (SaaS).

Key Competencies

• Customer Focus
• Communication
• Relationship Building
• Problem Solving
• Accountability
• Collaboration
• Adaptability
• Attention to Detail
• Time Management
• Technical Aptitude
• Customer De-escalation
• Critical Thinking
• Learning Agility

Success in the Role

Success in this role is reflected when customers view their Customer Success Specialist as a trusted partner who is responsive, knowledgeable, proactive, and committed to helping them achieve their goals while maximizing the value of their investment in Pathwise solutions.

The ideal candidate is energized by a fast-paced, high-volume support environment where customer needs evolve quickly. They enjoy solving technical problems, communicating confidently with customers, and adapting to changing priorities while maintaining a calm, solution-oriented approach. They build customer trust through responsiveness, technical expertise, clear communication, and a commitment to delivering an exceptional customer experience.

A person in this role is successful when they:

• Develop strong relationships with assigned customers and become a trusted resource.
• Ensure customers successfully adopt and utilize Pathwise products and services.
• Respond promptly to customer inquiries and see issues through to timely resolution.
• Troubleshoot complex software issues while clearly communicating technical concepts to customers with varying levels of technical expertise.
• Balance technical problem-solving with empathy, professionalism, and exceptional customer service.
• Identify potential risks early and partner with internal teams to address concerns before they impact the customer experience.
• Maintain high levels of customer satisfaction and engagement.
• Effectively coordinate cross-functional resources to meet customer needs.
• Demonstrate strong product knowledge and confidently guide customers through best practices.
• Contribute to customer retention by consistently delivering a positive customer experience.
• Gather meaningful customer feedback to help influence product and service improvements.
• Maintain accurate account documentation and proactively manage customer communications.

Key Indicators of Success

• Achievement of customer satisfaction (CSAT) target
• Strong customer retention and renewal rates within assigned accounts.
• Timely resolution and follow-through on customer issues.
• Demonstrated growth in customer adoption and utilization of Pathwise solutions.
• Positive customer feedback and relationship strength.
• Effective collaboration with Product, Engineering, Support, and Operations teams.
• Consistent achievement of individual and team customer success goals.

Benefits & Perks

• Medical plans that include PPO and HMO options
• Health Savings Account (HSA), Flexible Spending Account (FSA), and Health Reimbursement Arrangement (HRA) options, where applicable
• Dental and vision insurance
• 401(k) plan with company matching contributions
• Company-paid life and disability insurance
• Paid time off, flex time, and a generous company holiday schedule
• Paid parental leave

Work Environment

This is a remote position requiring prolonged periods of computer and telephone use. Employees must be able to effectively communicate with customers and colleagues through video conferencing, email, chat, and phone. Occasional travel may be required.

Equal Employment Opportunity

Pathwise is an Equal Opportunity Employer. We are committed to creating an inclusive environment for all employees and applicants. All qualified applicants will receive consideration for employment without regard to race, color, religion, creed, sex, pregnancy, childbirth or related medical conditions, sexual orientation, gender identity or expression, national origin, ancestry, age, disability, genetic information, marital status, military or veteran status, or any other characteristic protected by applicable federal, state, or local law.