Technical Support Specialist

EasyLlama is transforming the HR compliance industry by reinventing outdated and uninspiring training solutions and adapting them for the mobile-first generation. Our engaging, fun, and interactive training helps millions of employees worldwide build a safer, more positive, and inclusive workplace. As we continue to set the standard in compliance solutions, our vision extends far beyond training—we aim to partner with thousands of organizations to reduce employee risk and foster a more inclusive and secure environment for all. With world-class customer reviews—boasting a 96% rating on G2 from over 100 reviews—and industry-leading NPS and Customer Satisfaction scores, EasyLlama is proud to have earned the trust of over 5,000 clients, including brands like Shake Shack, WeightWatchers, Sephora, JiffyLube, and Y Combinator. Our mobile-friendly platform delivers on-demand, self-paced, and bite-sized solutions that meet employees where they are, increasing engagement and retention. At EasyLlama, we are not just transforming compliance training—we are challenging the status quo. We have a strong culture of collaboration, innovation, and getting things done. Our CORE values DRIVE is how we work at EasyLlama. Weʼre Doers, Resourceful, Impactful, Valued Partners, & Excellence-Focused. We are Doers . We proactively make things happen. We are Resourceful. We treat time, money, and energy as valuable. We are Impactful . We prioritize what matters. We are Valued Partners . We put customers & teammates first. We are Excellence-Obsessed . We always deliver excellent work. From CEO to newest hire, DRIVE asks us to take ownership, solve problems, prioritize what matters, support teammates, and deliver high- quality work. When we live these values, our product choices, customer interactions, hiring, and promotions all help us live out our mission: to build safer and more productive workplaces. About the Role We’re hiring a Technical Support Specialist to own escalated, technically complex customer issues. You’ll step in when problems go beyond standard support—owning investigations, troubleshooting integrations, and working cross-functionally to drive resolution. You’ll act as the bridge between Customer Success, Product, and Engineering, ensuring issues are clearly understood and efficiently resolved. This role also supports pre-sales and onboarding, helping prospects and new customers navigate technical questions and set up for success. This is a high-ownership IC role that requires strong technical problem-solving, clear communication, and the ability to operate across teams. What You’ll Do Own and resolve escalated technical support issues, including integrations and complex product behavior Troubleshoot across systems, APIs, and third-party tools to identify root causes Act as the primary liaison between Support, Product, and Engineering on technical issues Clearly document issues, reproduce bugs, and communicate context to internal teams Ensure timely resolution and consistent follow-through on all escalations Support pre-sales conversations by answering technical questions from prospects Partner with Customer Success during onboarding to guide customers through technical setup Identify recurring technical issues and drive improvements to: Documentation and help center content Internal troubleshooting workflows Product feedback loops Maintain clean, accurate records in support and CRM systems Who You Are 3–5 years in Technical Support, Solutions Engineering, or similar role Strong troubleshooting skills across integrations, APIs, and SaaS tools Ability to clearly communicate technical concepts to both technical and non-technical audiences Highly organized with strong attention to detail Comfortable working cross-functionally with Product and Engineering teams Proactive and resourceful — you take ownership of problems and drive them to resolution Nice to Have Experience working with APIs, webhooks, or integration platforms Familiarity with tools like HubSpot, Linear, or similar SaaS ecosystems Experience in a B2B SaaS environment Exposure to pre-sales or onboarding support What Success Looks Like Escalated technical issues are resolved quickly and thoroughly Clear communication between Support, Product, and Engineering Reduced repeat issues through improved documentation and feedback loops Prospects and new customers feel confident in technical setup and capabilities Why This Role Matters This role ensures that complex technical issues don’t slow down customers or the business. You’ll play a critical part in resolving high-impact problems, improving the product through feedback, and supporting customers at key moments—from evaluation to onboarding. What to Expect The interview process at EasyLlama takes about 3-4 weeks and will include cross-functional stakeholders of the role. Here's what the interview process looks like: Recruiter Screen Hiring Manager Interview Peer Interview Executive Interview Reference Checks How We'll Take Care of You $75K – $95K Base salary + Bonus potential Flexible, fully remote environment Competitive employer-sponsored health insurances 401(k) + company matching Professional development reimbursements Quarterly remote work stipend *The EasyLlama herd is fully remote, with employees distributed across the US. We are currently hiring in the following approved* states: AR - Arkansas CA - California CO - Colorado CT - Connecticut FL - Florida IL - Illinois LA - Louisiana MA - Massachusetts MI-Michigan MN - Minnesota NJ - New Jersey NY - New York NC - North Carolina OH - Ohio OR- Oregon PA - Pennsylvania TN - Tennessee TX - Texas VA - Virginia WA - Washington WI - Wisconsin * EasyLlama reserves the right to change the list of approved states at anytime. *To ensure the best employee experience, we offer competitive compensation packages, comprehensive benefits, an annual wellness stipend, PTO, 401k with company matching, and monthly team events to nurture connection! At EasyLlama, we strive to walk the walk. We are helping make workplaces all over the globe safer and more inclusive, including our own. We honor employees and candidates from all walks of life and all experiences, regardless of race, ethnicity, veteran status, disability, sexual orientation, gender identity or religion. *Applies to full time (W2) employees.