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Added 11 mins ago
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IT Senior Analyst, Enterprise Applications - HCM Process & Solutions
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IT Senior Analyst, Enterprise Applications - HCM Process & Solutions
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Director, Engineering
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Toronto, ON
- $150,000 to $176,000 CAD / year
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Town Web

Senior Support Engineer

Remote, Canada

Remote

Salary of $85,000 to $105,000 a year, depending on experience · Full-time

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Job details

Pay: Salary of $85,000 to $105,000 a year, depending on experience
Job type: Full-time
Workplace: Remote
Posting language: English
Posted: Oct 5, 2026

Original job description

Senior Support Engineer

Town Web · HeyGov · ClerkMinutes. Remote, Central US hours. $85,000 to $105,000 a year. Open to candidates in the United States, Canada, the United Kingdom, and Ireland.

About us

We make municipal software built for clerks: websites residents can use, forms and payments that replace stacks of paper, and meeting minutes drafted after every meeting. More than 1,300 local governments rely on us, from counties and cities to villages and towns. We have local government clients in almost every state in the U.S.

Our clients are municipal clerks and the government teams around them. They keep city hall running and rarely get thanked for it. Your job is to make working with us the easy part of their week.

The role

This is the senior seat on our Client Success team. We are hiring you to raise the standard of our support: fix what is broken, write down how it should work, and show what great looks like.

Our AI agent now answers repeatable, well-documented questions. What is left is the work that only a person can do: own a client's problem from the first message to the confirmed fix, build a relationship a clerk trusts, and turn what you learn into better documentation and a better product.

This is not a ticket-closing job. Think of a great 5-star hotel that puts slippers by the bed before you ask. We want a clerk to finish a conversation with you and tell the clerk in the next town about the great experience they had. If that takes three calls, take three calls.

It is also a technical job. You will work with our developers every day. When something breaks, you work out where it lives before anyone else has to. Is the problem on the events calendar on the client's homepage, or in the calendar widget embedded on a department page? Is the wrong speaker name only in the transcript, or is it also in the finished minutes? You reproduce it, write it up so a developer can act without a follow-up question, stay on it until it ships, and tell the client yourself.

You need both halves. A brilliant troubleshooter who is short with a clerk will not work here. Neither will a lovely person who forwards every problem to a developer.

Your first 90 days

Learn all of our products well enough to teach them
Take over every open escalation and close or schedule each one
Rebuild the path from support to our developers so nothing leaves the queue untracked
Find the ten questions clerks ask most and fix each at the source: an article, a Fin answer, or a product change

What you will do

Raise the standard

Design how issues move from support to developers, and keep that path working
Set the bar for replies, calls, and write-ups, and coach teammates by example
Turn what you fix into playbooks the team and Fin can follow

Delight clients

Make every interaction feel personal, warm, and unhurried, especially for less technical users who would rather talk to a person than read a help article
Step in when the AI agent or the documentation is not enough, and make sure the client feels heard and helped, not processed
Treat client sentiment as the real measure of success, not ticket speed
Look for small moments to go above and beyond, and share what works so it becomes how the whole team operates

Own the problem from start to finish

Be the named person on an account when things go wrong: one owner, one plan, regular updates, until the client says it is fixed
Step in early when an account shows strain (repeat tickets, a rough launch, a frustrated message) and run the recovery. Get on a call, write down what is open, set dates, follow through
Make sure nothing sits untracked once it leaves the support queue

Diagnose, then escalate

Work out which product and which layer an issue lives in before you hand it to a developer
Reproduce it, capture the steps with screenshots or a recording, and file it in Linear with everything a developer needs
Check on your open Linear issues, chase what is stuck, and confirm the fix with the client
Use Claude, connected to our code repository, to trace where a behavior comes from. For small, well-understood fixes, draft the change for a developer to review

Knowledge base and AI support

Inherit and maintain the help center for all of our products. It is what our AI agent (Fin, in Intercom) answers from
Write and improve articles from real, recurring questions, on a weekly rhythm measured against live ticket volume
Write troubleshooting guides that separate look-alike problems, so the next person, or Fin, can tell them apart
Tune Fin: review where it failed, fix the article, and teach it to ask a clarifying question when a request could mean two things
Record short training videos so clients can learn at their own pace

Support and onboarding

Handle the conversations Fin cannot resolve across Town Web (websites), HeyGov (forms, payments, reservations, campaigns), and ClerkMinutes (agendas, transcripts, minutes)
Help new clients through onboarding with the projects team so they reach value quickly
Talk with clerks by phone and video every week. Get on a call whenever a situation needs a human voice

Account care

Build real relationships with your assigned accounts
Understand what each client is trying to accomplish, what they use, what they do not know we offer, and where they will need help before they ask
Run proactive, recurring check-ins instead of waiting for tickets. For example, reach out a few weeks after go-live to review how their forms are performing
Use product usage data to spot clients who are not getting full value yet
Meet clients in person. Join us at clerk conferences and marketing events a few times a year. We cover all travel & lodging expenses

Spot opportunity

Tell clients about services they do not use yet (digital forms, payments, .gov domains, accessibility, training) without it feeling like a pitch
Flag possible expansion and renewal opportunities to the sales team

Training

Get clients to real proficiency with the product, not just past their immediate question
Work with Product Managers to co-host webinars about new features and training

Tools you will use: Intercom and Fin, Linear, Claude, our help center, screen recording, Zoom phone.

How we work

Delight over deflection. The goal is happy, successful clients, not fewer conversations
Ownership over routing. A hard case is yours until it is resolved
Diagnose before you escalate. A developer should never have to ask what the client actually saw
Documentation is the foundation everything else runs on, not an afterthought
Teaching over ticket-closing. Proficiency, not just an answer

Who you are

You like people, and it shows. Clerks are often not technical, sometimes stressed, and now and then upset. You pick up the phone gladly and leave them calmer than you found them
Hospitable by nature. A background in hospitality or another service-first field is a plus
You have done support somewhere known for it. The standard we have in mind is Basecamp: competent, calm, and trusted to make the call
Technically deep. You read the error, open the browser console and the network tab, check a DNS record, find your way around WordPress, and follow the trail into the code with Claude's help
At home with developers. You know what a good bug report contains and you have filed plenty
High autonomy. You decide, act, and report. You do not wait to be told
A clear, warm, precise writer, with clients and across teams
A natural teacher, patient with less technical users
Able to see the whole account, not just the ticket in front of you

Who you might be

Someone who worked the Genius Bar at an Apple Store and misses solving problems for a person, not a queue
Someone who learned support at a company known for it, such as Basecamp, Automattic, or Help Scout
A hotel or hospitality professional who moved into software and kept the instincts
A former municipal or deputy clerk who was always the one who figured out the software. You already know our clients' world
Or maybe none of these! If the rest of this page sounds like you, we certainly want to hear from you

This is not the job for you if

You would rather work a queue than talk to people
You find non-technical users frustrating
You want to hand a problem to a developer and move on
You need someone to tell you what to do next

Work style

Independent and ownership-driven. You do not need heavy oversight to perform
Comfortable wearing several hats across products and brands
Comfortable in a lean, documentation-first team
Proactive rather than reactive with accounts

What success looks like

Clients describe working with us as a great experience
No client has to ask who is handling their problem. They already know it is you
Issues you file get fixed without a developer asking for more detail
Tickets stop recurring, not just get answered
Help center articles created or improved every week, and Fin resolving more each month
Repeat questions turned into product fixes or automation
Expansion and renewals tied to the accounts you touch
Account relationships that are trusted, not just responsive
The rest of the team gets better because you are on it

Experience

Five or more years in technical support or support engineering at a software company, working directly with engineers
An issue tracker used daily: Linear preferred, Jira or similar is fine
Intercom or similar support tooling, including work with an AI support agent
A knowledge base you wrote that other people relied on
AI tools such as Claude already part of your daily work
Nice to have: government or municipal software, WordPress-based websites, hospitality or other service-first work
Able to travel within the US a few times a year. Not required, but very helpful to understand our customers better.

How to apply

Apply through Workable. You will answer two short questions in writing and record a two-minute Loom video teaching us one thing

Complete the Culture Index survey. You can do it right after you apply. We only review candidates who have completed it

Interview with our Head of Client Success

Paid take-home exercise built from real client situations

Conversation with our CTO and founder, including a short role-play call with a clerk who needs help

Offer letter, if selected

Salary of $85,000 to $105,000 a year, depending on experience
20 paid vacation days, plus public holidays for your country of residence
Fully remote, working Central US hours
Internet stipend
Gym membership or wellness stipend

We do not offer a health plan or a 401(k) today. The salary range reflects that.

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More about this job

Responsibilities

You will own client issues from start to finish, acting as the primary point of contact to resolve technical problems and build trusted relationships. Additionally, you will improve documentation, maintain the help center, and collaborate with developers to ensure product fixes are implemented effectively.

Requirements

The role requires five or more years of experience in technical support or support engineering at a software company. Candidates must possess strong troubleshooting skills, experience with issue trackers and AI tools, and the ability to communicate effectively with non-technical users.

Skills

Technical support
Customer success
Troubleshooting
Documentation
Intercom
Linear
Claude
WordPress
Relationship management
Communication
Project management
Training
Data analysis
Software support
Problem solving

Benefits

Paid vacation days
Internet stipend
Gym membership
Wellness stipend

Remote locations

United States
Canada
United Kingdom
Ireland

Remote locations (standardized)

Canada
Ireland
United Kingdom
United States

Visa sponsorship

Not detected in the job text

Keywords

Senior Support Engineer
Client Success
Municipal software
Technical support
Intercom
Fin
Linear
Claude
WordPress
Documentation
Troubleshooting
SaaS
Remote work
Customer experience
Onboarding
Account management
API
DNS
Browser console
Network tab
Webinars
Product training
Government technology
Hospitality
Service-first

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