QuickMail: Technical Customer Support

The role

We are hiring a technical customer support person with an owner’s mentality.

You will own support for QuickMail and Mailflow, our deliverability add-on. There is no first or second line. You are the first and last person our customers talk to.

Customers count on you to solve their problems and find the real cause when something breaks. You work closely with engineering, and you tell the founder what we need to know to make the product better: where the friction is and where the opportunities are.

The role covers the help desk, system health checks, testing new releases before they ship, and leading the weekly team meeting. It takes excellent communication, solid technical understanding and sharp critical thinking.

This is not a script-reading job. Most tickets involve deliverability, DNS records, LinkedIn automation or campaign setup. You dig into customer accounts in our Support Dashboard, reproduce the issue, then decide what to do and how to explain it to the customer.

We are a remote team spread across time zones. Most routine tasks have a written guide with a checklist, so you know what done looks like. You are expected to refine and improve those processes. When something new comes up, you work out the most efficient way to handle it.

If you want a lot of autonomy across many areas, real responsibility and a fast-paced environment, this role is for you.

What work looks like

You own two things: customers get unstuck fast, and the product stays reliable

Every day

• ⁠Set the day’s support priorities and work the Help Scout queue for QuickMail and Mailflow. Triage, resolve, and dig deeper when a ticket needs it.
• ⁠Check the support dashboard: job queue, event-stream latency, blacklist status, newly purchased domains. If something is off, investigate, diagnose, and drive it to resolution.
• ⁠Review fraud alerts and disable accounts that are scams or abusing the platform.

Delighting customers

• Comfortable jumping on calls with customers, building rapport fast. and set them up for success.
• ⁠Update the changelog and help articles based on what shipped and what customers asked.
• ⁠Share customer feedback with the team, ask happy customers for reviews and case studies, and watch NPS for testimonial candidates.

Making support smarter with AI

• ⁠Improve the AI support agent. Review its answers, fix the docs it drew from when it is wrong, and contact the customer when its reply was off.
• Write and maintain automated tests, built with AI, that try to break staging before customers do.
• ⁠Use the MCP connections we have in place (Helpscout, GitHub, Postmark, and others) to get an accurate picture of support and find the next thing worth improving.

Keeping the product solid

• ⁠Gatekeep releases. New fixes and features land on staging every week. Test them, confirm when staging is ready to ship, and think through how existing and new users will be affected.
• Report bugs as GitHub issues with everything the developer needs: steps to reproduce, screenshots or a Loom, and any GraphQL or console errors.
• ⁠Captain red alerts. When a core feature breaks (emails not sending, login down), confirm it, alert the team on Slack or Telegram, update the status page every 30 minutes, keep affected customers informed, and drive the fix. Then run the retrospective so it does not happen twice.

Running the week

• ⁠Lead the weekly team meeting in MonsterOps: issues written up, to-dos done, numbers updated.
• ⁠Keep rock status and KPIs current in MonsterOps.

Tools you’ll use: Helpscout, our Support Dashboard, Sidekiq, GitHub, Slack, Telegram, MonsterOps, Outline, MxToolbox, Postmark, Bento, TidyCal, Fathom, Visual Code and Claude.

Who you are

• You build rapport fast. You are warm, positive, and relatable in writing and on calls.

• You are a good communicator. Externally, you can show warmth, empathy and care. Internally, you are able to communicate clearly and concisely about important things.
• You can operate with minimal instructions. You understand a short brief without every detail spelled out. You can prioritize well (especially when you have a lot on your plate), and get things done without hand-holding.
• You are comfortable on video. You are natural on live calls with Zoom and Meet, and on recorded video through tools like loom.
• Your teammates can always count on you. You say what you’ll do and you do what you said.
• You act with a constant sense of urgency. You can execute fast and find new ways to improve your productivity.
• You are resourceful. You use all the tools at your disposal to get great results.
• You have a low ego. You don’t take offense easily and you handle disagreement as a discussion, not a personal attack.
• Growth mindset. You are positive about new workflow/process/product/tool changes. You love giving and receiving positive and negative feedback without getting defensive.
• Hours that overlap with East coast US and UK, where most of our customers are.

A plus if you have

• Have experience with customer facing, or if you don’t have it, tell us why you are perfect for this role.
• Working knowledge of deliverability and LinkedIn outreach. Warmup, DNS, inbox rotation, DKIM, SPF, Outlook and Gmail technical setup, . We can teach this, but a head start helps.
• Comfort with agency setups. Workspaces, guest seats, inbox purchases and what happens when an agency loses a client.
• Light data skills. You can pull numbers from Help Scout or our MCP to back up what you report.
• An eye for happy customers. You notice them and ask for testimonials and case studies at the right moment.

How we work together

You’ll work directly with me, the founder, and with our lead developer.

Working with me can be intense. Here is what that looks like in practice:

• My replies are short and can come across as harsh. If something I wrote lands badly or isn’t clear, ask me.
• My direction can change. I may say one thing, then something different a few days later as I learn more. When that happens, check what changed and adapt.
• I prefer information to be short and to the point. Lead with what matters, then give more details if I ask.
• I can stay frustrated about a problem until it’s solved. That’s something I’m aware of and working on. You’ll do well here if you can stay calm and focused when the pressure is on.
• We often think fast and interrupt each other when discussing ideas. If that would bother you, this role probably isn’t for you.

This role suits someone with high emotional intelligence, who doesn’t take things personally, asks when something is unclear, and keeps many things moving at once.

Your schedule can be flexible. If you have a martial arts class every Thursday at 3 pm, go and make up the time later. In return, on the rare occasion we need your help on a weekend, we ask you to be flexible too.

• Contract type (full-time or part-time)
• Compensation: $2,500 to $4,000 USD per month, depending on experience and location. US-based hires will work as independent contractors (1099).
• Start date: negotiable