Head of Technical Support

At EdSights, we're building the technology for higher education to understand what students are actually thinking and feeling, so they can act before small struggles become big problems. We call it Student Voice Intelligence: engaging students in real-time, AI-powered conversations, uncovering the real drivers of attrition, and delivering those insights to power student success and enrollment workflows. Today, we partner with 300+ colleges and universities across the country. We're backed by an $80M investment from JMI Equity and are in a phase of rapid execution and expansion. This is an opportunity to do meaningful, hands-on work at a high-growth startup tackling one of higher education's most urgent challenges: helping more students persist from enrollment through graduation. You’ll join a driven, thoughtful team that values ownership, moves quickly, and cares deeply about building products that make a measurable difference for students. “EdSights has perhaps the world’s most valuable data set on what college students need to navigate their academic lives.” - The Washington Post The Opportunity EdSights is hiring its first Head of Technical Support to build and lead our technical support function from the ground up. You’ll handle tickets directly while laying the operational foundation the team will eventually scale on. What You’ll Do Build the Function Design EdSights’ technical support function: service model, escalation paths, SLAs, and operating principles. Select and implement a ticketing platform (e.g. Zendesk, Freshdesk, Intercom) and own the full rollout. Launch or revamp a customer-facing help center with self-service content (articles, FAQs, how-to guides) in partnership with Customer Education. Implement and manage an AI chatbot integrated with the help center, configuring deflection flows and iterating on resolution rates. Define support tiers (T1: general inquiries, T2: technical/product, T3: engineering escalations) with clear ownership and handoff criteria. Own Performance & Quality Own core KPIs (CSAT, response time, resolution time, ticket backlog) and report regularly to leadership. Implement a QA process to review tickets, identify coaching opportunities, and continuously improve technical accuracy. Analyze support trends to surface recurring issues, product gaps, and documentation needs for CX and Product. Lead & Scale the Team Serve as the sole technical support resource in the near term while building the infrastructure for future growth. Define the hiring roadmap: when to add headcount, what roles to hire, and skills needed at each stage. Build onboarding and training programs including product curricula, shadowing structures, and ramp milestones. Develop Deep Technical Expertise Become the internal authority on EdSights’ Retain and Admit products - how they work, where they break, FAQ, how to triage. Triage and resolve complex issues involving APIs, integrations, and data flows; use logs and tools like Hex for diagnosis. Maintain visibility into known product gaps and bugs; communicate proactively with affected customers and the CX team. Collaborate Cross-Functionally Partner with Implementation and Partner Success to ensure smooth handoffs from onboarding to ongoing support. Work with Engineering to define escalation paths for bugs, logging standards, and customer status communication. Collaborate with Product to ensure customer-reported issues are documented, prioritized, and tracked to resolution. What We’re Looking For 4 to 7 years in technical support leadership within a B2B SaaS environment. Proven track record building or significantly scaling a support function, including tooling decisions and process design. Experience at an early- or growth-stage company where operating without established processes is the norm. Hands-on experience implementing a ticketing platform including workflows, automations, and reporting. Comfort working with APIs, webhooks, and integrations. Experience managing a customer-facing knowledge base and familiarity with AI chatbot/virtual agent platforms. Strong command of support KPIs with the ability to build reports and translate ticket data into cross-functional insights. Exceptional written communication skills; able to explain complex issues clearly to non-technical users. Confident working cross-functionally with Engineering, Product, and CX; able to advocate for customers and present to leadership. Experience supporting platforms with AI, NLP, or data analytics components. Familiarity with higher education and FERPA data privacy considerations is a plus. The Process Async Video Interview - Your application will be reviewed by humans, if we’d like to learn more we will send you a link for a quick video interview through Willo. Recruiter Screen/Intro - You’ll chat with Mary, our Head of Talent, to discuss the role, your background, and logistics. Hiring Manager Interview - You’ll meet with Meg, VP of CX, to dive deeper into role-specific experience and expectations. Customer Experience Interview - You’ll meet with 2 leaders on the CX team to continue to chat about your experience. Product/Engineering Interview - You’ll meet with a cross-functional leader from product/engineering. References - We’ll ask for 3 references. Ideally, 1 to 2 will be previous managers. Offer! Why join EdSights? Make a real impact in higher education — Be part of a mission you can be proud of to help colleges and universities better support students through AI-driven insights, real-time engagement, and student-centered technology. Join a values-driven, collaborative culture — Be part of a kind, inclusive, “no-ego” team that prioritizes trust, transparency, and respect. Grow with a fast-scaling EdTech company — EdSights is ranked on Inc. 5000 for rapid growth and innovation. Enjoy flexibility and competitive benefits — Remote-friendly work, unlimited PTO, paid parental leave, competitive compensation, new Apple hardware, 401k matching, and strong health and wellness benefits. EdSights provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, gender expression, veteran status, or any other protected characteristic under applicable law. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.