Technical Support Engineer

Wispr Flow is making it as effortless to interact with your devices as talking to a close friend.

Today, Wispr Flow is the first voice dictation platform people use more than their keyboards — because it understands you perfectly on the first try. It’s context-aware, personalized, and works anywhere you can type, on desktop or phone.

In 2026, in addition to dictation, we're focused on building native actions — an agentic framework that understands you, and works reliably.

We’re a team of AI researchers, designers, growth experts, and engineers rethinking human-computer interaction from the ground up. We value high-agency teammates who communicate openly, obsess over users, and sweat the details. We thrive on spirited debate, truth-seeking, and real-world impact.

We're grown our revenue +150% every quarter for the last 4 quarters, and have raised $81M from Tier 1 VC firms and other well-known angels.

About the Role

We're looking for a Technical Support Engineer who doesn't just close tickets. You deliver an 11-star experience to every single customer, regardless of their plan or what they pay. Every person who reaches out should come away feeling genuinely delighted, not just helped.

You'll be on the front lines solving real problems for Wispr Flow users while shaping how customers feel about our product in their inbox, in their app store reviews, and in every conversation they have about us. How our customers talk about Wispr matters deeply, and you'll play a direct role in earning that trust.

This isn't a role where someone hands you a script for every situation. You'll write your own, often with the help of AI. You'll need creativity, technical depth, and the judgment to know when a problem needs a workaround, when it needs a bug report, and when it needs you to build something entirely new to fix it.

What You'll Do

• Resolve customer support tickets across billing, account, product, and technical issues with speed, empathy, and precision

• Deliver a consistently delightful experience to every customer, every time. Free users and enterprise accounts alike

• Advocate for customers internally by surfacing product gaps, recurring pain points, and feature requests to product and engineering teams

• Stay close to customer sentiment across support channels, app store reviews, social media, and community forums. Understand how customers feel about Wispr and proactively address what shapes that perception

• Investigate and triage bugs end-to-end: reproducing issues, pulling logs, tracing root causes, and writing clear bug reports that engineering can act on immediately

• Use AI tools to accelerate your workflow: drafting responses, analyzing patterns, diagnosing issues, and building lightweight automations that make the whole team faster

• Manage ticket queues with attention to SLAs, priority tiers, and customer impact

• Contribute to internal knowledge bases, support documentation, and process improvementsIdentify trends across tickets and translate them into actionable insights for product, engineering, and leadership

• Collaborate cross-functionally with security, compliance, billing, and engineering to resolve complex customer issues

What We're Looking For

• High agency: you see a problem and fix it without waiting for permission or a playbook, then you document what you found so the rest of the team can learn from it and build on it

• AI-native workflow: you already use AI daily to move faster, write better, solve harder problems, and automate repetitive work; strong prompting skills are a must

• Technical depth: you're comfortable reading logs, navigating developer tools, understanding APIs, and debugging software issues even if you're not writing production code

• Pattern recognition: you spot the signal in the noise; when the same issue shows up three different ways, you connect the dots

• Customer obsession: you believe every customer deserves an 11-star experience; you don't adjust your effort based on what someone pays

• Clear communication: you write concise, accurate responses that respect the customer's time and technical level

• Creative problem-solving: when the standard answer doesn't exist, you build one

• Comfort with ambiguity: you don't just tolerate fast pivots and shifting priorities, you're genuinely excited by them. This is an early-stage startup where extreme flexibility isn't a nice-to-have, it's the job. Things move fast here and you should be able to not just keep up, but thrive because of it.

A note on experience: We care far more about how you think than where you've worked. If you've spent your career in hospitality, retail, teaching, or any other field where you learned to genuinely care for people, solve problems creatively, and stay composed when things get hectic, you might be exactly who we're looking for. Tools can be learned quickly; curiosity, customer instinct, and high agency can't be taught. If this role excites you but your resume doesn't look like a traditional tech support background, we'd still love to hear from you.

Nice to Have

• Experience with support tooling like Pylon, Intercom, or Zendesk

• Familiarity with Sentry, Linear, Notion, or similar engineering/ops tools

• Background in Saas, developer tools, or AlExperience with Stripe billing or enterprise account management

• You've built automations, internal tools, or workflows that made a support team more effective

Why Wispr

You'll join a small, high-impact team where your work directly shapes how customers experience our product and how they talk about it. Customer sentiment isn't a metric we check quarterly; it's something we actively build with every interaction. We move fast, we care deeply about craft, and we believe the best support engineers are some of the most important people in the company.

We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request.

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