Technical Support Specialist

Crimson Education is the world's leading college admissions consulting firm, with over 1,490 Ivy League offers and 2,410 to the US Top 15. We help ambitious students gain admission to the world's top universities through expert-led guidance and proven, data-driven strategies. Crimson students are 7x more likely to get into the Ivy League than their peers. We were recently featured on the front page of the Wall Street Journal .

Crimson is the only college admissions consultancy that brings together:

• Former Ivy League and Top 20 admissions officers to rigorously review and refine applications
• Professors and PhD teaching fellows from leading universities to guide students through original, independent research - with pathways to selective peer-reviewed publication or conference presentation
• Past ISEF winners and judges who coach students to compete for state, national, and international science fair awards
• Capstone project mentors who help students design and scale leadership initiatives with real-world impact, measurable outcomes, and credible external validation

We're backed by leading VC firms, including Tiger Global, Heal Partners, IceHouse Ventures, and Movac, and recently closed a USD $40M Series D funding round at a USD $640M valuation. We now operate across 21 markets worldwide, including the US, Canada, UK, Singapore, Japan, Hong Kong, Australia, and New Zealand.

The Role

What are the main responsibilities for this role?

• Investigate, triage, and resolve complex technical support tickets escalated from operational teams (Operations, Customer Support, Strategy & Tutoring).
• Perform deep-dive troubleshooting across web, mobile, database records, and third-party integrations (e.g., Zoom, Google Workspace, Slack, Payment/Invoicing gateways).
• Execute safe operational interventions (e.g., session feedback resets, duration adjustments, user permission fixes, data reconciliation) following standard operating procedures (SOPs).
• Identify recurring failure patterns and automate manual admin workflows to reduce turnaround time.
• Replicate bugs, gather detailed technical telemetry (logs, network requests, payload traces), and file high-quality bug reports for Core Tech engineers.
• Participate in sprint triage meetings and advocate for bug fixes and UX improvements based on ticket volume trends.
• Maintain and expand technical runbooks, internal troubleshooting guides, and self-serve documentation for frontline support and operational teams.
• Assist in testing new product releases and validating critical bug fixes in staging and production environments.

What skills and experience are required?

• 2+ years of experience in technical support, application support, or systems operations within a SaaS, EdTech, or fast-growing digital platform environment.
• Strong familiarity with modern AI tools, LLMs (e.g., ChatGPT, Claude, Cursor), prompt engineering, or AI-powered workflows; enthusiastic about leveraging AI to 10x support productivity.
• Solid understanding of web architectures, REST APIs, JSON payloads, and browser developer tools (Network/Console inspection).
• Proficiency in SQL to trace and verify data records.
• Familiarity with third-party SaaS integrations, especially Salesforce, Zoom, Slack bots/apps, Google Workspace/SSO, Stripe, etc.
• Experience with ticket tracking and incident management tools (e.g., Zendesk, Jira, Linear, Slack).
• Strong problem-solving mindset: you love dissecting ambiguous issues, tracing root causes, and finding efficient solutions.
• Excellent written and verbal communication skills in English, with the ability to clearly explain complex technical or AI behaviors to non-technical stakeholders.
• High empathy, calm under pressure, and a strong sense of ownership over user satisfaction.

Nice to Have

• Rich experience with Salesforce.
• Basic scripting/automation skills (e.g., Python, JavaScript/TypeScript, SQL, or shell scripts).
• Hands-on experience debugging AI agent workflows, API integrations, or vector/RAG systems.
• Experience working in remote, asynchronous, cross-timezone teams.
• Background or strong passion for EdTech.

Why work for Crimson?

• Rapidly growing start up, with a flexible working environment where you will be empowered to structure how you work
• Limitless development and exposure - our internal promotions/role changes made up 33% of all recruitment last year
• $1000 individual training budget per year, we love to 'Level Up' (it's one of our core values)!
• Psychologist on staff
• Insightful fireside chats and workshops to help support our high-performing and ambitious team
• Radical Candor is a feedback approach we live by
• We're a global player with 28 markets (and growing) across the globe. Most roles have the option to work from one of our many offices or remotely!

If you're passionate about growing in a fast-paced, collaborative environment and want to work with cutting-edge technology, then we'd love to hear from you!

Please keep an eye on your spam/junk email folder for correspondence from Team Tailor.