About Routeware, Inc. Routeware is the industry leader in providing software and data analysis that enables public and private enterprises to improve the effectiveness of their waste and recycling programs. Our solutions help organizations save time and money, increase efficiency, improve safety and help make our world a greener place. Based in Portland, Oregon, the company employs a distributed team across North America and the UK. Our brands, products, and services provide an all-in-one platform to municipal and private waste haulers and other fleet services. As part of an essential and growing industry, we seek solution-oriented team players who want to positively impact the environment. Our work environment is collaborative, dynamic, fast-paced, and fun with a strong appreciation for innovation and initiative. Our Mission: Transform waste collection to drive a better future for generations to come. Our Values: Adaptability - The waste industry and technology are ever-changing, and the Routeware team never stops adapting to be at the forefront of technology innovation, supporting our customers to stay ahead. Mission-driven - At Routeware, it matters to us that our work has a lasting positive impact on our customers' outcomes, our fellow team members' well-being, and the long-term sustainability of our environment. Human-first - While technology drives our products; the real, live, caring people at Routeware are the true drivers of meaningful outcomes for our customers. POSITION OVERVIEW We are seeking a Supervisor of Technical Support to provide both frontline customer support and leadership within our support team. This role is ideal for an internal candidate who has demonstrated the ability to serve as a lead, mentor, and point of operational oversight—even without formal management experience. The Supervisor will balance hands-on customer interactions with guiding and developing team members, ensuring that technical issues are resolved efficiently and service quality remains high. KEY RESPONSIBILITIES Customer Support & Technical Expertise Provide direct, high-quality technical support to customers across our products and services. Troubleshoot complex technical issues and serve as an escalation point for team members. Maintain deep product knowledge and continuously develop expertise to support evolving technologies. Team Leadership & Mentorship Act as a mentor and role model for support team members, sharing best practices and encouraging skill development. Provide daily operational oversight, including queue management, case assignment, and issue prioritization. Offer coaching, informal training, and constructive feedback to strengthen team performance. Operational Oversight Monitor support activity and ensure service level agreements (SLAs) and quality standards are met. Assist in documenting processes, troubleshooting guides, and knowledge base articles. Partner with the Head of Support Operations to identify trends, escalate systemic issues, and recommend process improvements. Monitor support activity and ensure SLAs and quality standards are met, driving measurable outcomes such as response times, resolution rates, and customer satisfaction targets. Cross-Team Collaboration Work closely with Product, Engineering, and Customer Operations teams to advocate for customer needs and provide feedback on recurring issues. Support communication between support staff and other departments to ensure alignment and resolution of escalations. Contribute to strategic support initiatives, helping to shape processes, tools, and customer experience improvements in partnership with leadership. QUALIFICATIONS BENEFITS Comprehensive benefits (medical with HSA option, vision, dental, and life insurance) Paid parental leave Medical and Dependent FSA 401K match Unlimited PTO Ten company holidays 1 Volunteer day Summer Friday's Routeware is an Equal Opportunity Employer and prohibits all forms of discrimination or harassment. At Routeware, we are committed to the principle of equality, and all employment decisions are based on job requirements, business needs, and individual qualifications, without regard to race, color, religion or belief, national, social or ethnic origin, sex (including pregnancy), age, physical, mental or sensory disability, HIV Status, sexual orientation, gender identity and/or expression, marital, civil union or domestic partnership status, past or present military service, family medical history or genetic information, family or parental status, or any other status protected by the laws or regulations in the locations where we operate.