Senior Technical Support Specialist; Seattle - Hybrid Seattle

Senior Technical Support Specialist (Seattle - Hybrid)

Location:

Seattle

Reports to:

Esha Joshi, Cofounder and Chief Customer Officer

Yoodli is the AI roleplay simulator redefining how individuals and teams master communication. We’re building a new category: AI Roleplays, an experiential learning platform that helps people improve through lifelike simulations powered by generative AI.

Think of it as the batting cage before the big game - but for communication. Whether it’s a sales pitch, manager feedback session, or media interview, Yoodli provides private, judgment‑free, just‑in‑time coaching. Leaders at companies like Google, Databricks, Snowflake, Ring Central, Toastmasters, and BDO use Yoodli to ramp reps faster, improve message delivery, and reduce coaching burden on frontline managers. The result is stronger performance, greater team readiness, and a more scalable path to impact.

We’ve raised over $20M, are doubling our team in 2025, and are headquartered at the beautiful Pier 70 in Seattle.

We’re hiring a Senior Technical Support Specialist to be both a frontline problem‑solver and a strategic builder of Yoodli’s AI‑first support experience.

You’ll handle customer tickets directly, especially the trickiest, most technical issues, while also spotting patterns, building playbooks, and working with Rev Ops and Engineering to make sure we never have to solve the same problem twice. You’ll help define what “AI‑first support” means at Yoodli, ensuring our customers get fast, reliable answers while our team scales efficiently.

This role is perfect for someone who enjoys rolling up their sleeves in the queue but also wants to shape the bigger system - mentoring teammates, improving processes, and embedding AI into the way support works.

• Frontline Support & Complex Customer Escalations
  • Provide hands‑on customer support, including troubleshooting integrations, errors, and unexpected behaviors
  • Act as the senior escalation point when frontline teammates hit blockers
  • Investigate customer‑reported problems by reviewing logs, configurations, and product behavior
  • Provide clear explanations, fixes, or workarounds, and elevate to Engineering when necessary
  • Communicate clearly and empathetically with customers, even on complex technical issues
• Build Scalable Systems
  • Translate recurring customer problems into playbooks, automation, or product improvements
  • Partner with Rev Ops to integrate tools, workflows, and AI‑driven support capabilities into the broader GTM stack
  • Document technical solutions and maintain a knowledge base that empowers teammates and customers
• Drive AI‑First Support
  • Identify patterns in tickets and proactively design ways to automate them (e.g., AI‑driven answers, smarter routing)
  • Collaborate with leadership to define what “AI‑first support” means at Yoodli and bring it to life
  • Ensure customers get fast, accurate, and consistent answers
• Cross‑Functional Collaboration
  • Work closely with frontline Support and product specialists to upskill them with playbooks and repeatable processes
  • Partner with Engineering on P1 escalations, ensuring they’re prioritized and framed correctly
  • Act as a bridge between customer insights, product signals, and operational systems

We’re looking for someone with:

• 4–7 years of experience in technical support, support engineering, or solutions consulting
• Can dig into logs, configs, APIs, and integrations (but don’t need to be a production engineer!)
• Balance technical depth with customer empathy – you explain complex issues simply and clearly
• Naturally mentor peers, improve processes, and raise the bar for the team around you
• Think like a systems builder: solving problems once and making them disappear for everyone
• Thrive in a startup environment where you own problems end‑to‑end

• Experience with AI‑powered support tools (e.g., Intercom bots, AI ticket routing, GPT knowledge bases)
• Familiarity with SaaS Rev Ops / GTM stacks (Hub Spot, Gong, etc.)
• Track record of reducing escalations, shortening resolution times, or scaling support through automation
• Exposure to enterprise SaaS support environments with strategic accounts

• Competitive compensation ($80,000–$120,000) + meaningful equity
• High‑impact, mission‑driven work with direct customer feedback loops
• Work with a humble, driven, deeply collaborative team
• Hybrid schedule: 3 days in‑office at our Seattle HQ (lunch included) + 2 days remote
• A product you’ll use and believe in – every single week

Does this role sound like a good fit? Email us at gtm-hiring. Please include the role’s title in the subject line and attach or link to your resume.