TestGorilla: Senior Demand Generation Manager
July 29, 2026Toptal: STEP Platform Developer/Engineer — MDM | Remote
July 29, 2026
Headquarters: Remote
URL: https://retr.app/
Why this role matters now
A loan officer’s business runs on relationships. Ours runs on making sure RETR never gets in the way of theirs.
When something breaks for a customer, a real deal is on the line, and what they need is a person who understands both the product and their business. That person is you.
Most support jobs are a treadmill: you answer the question, the question comes back, you answer it again. Here the work compounds. A good answer becomes an article, the article teaches our AI, and the question stops coming. We measure which articles resolve and which fail, so you can watch the queue shrink because of something you wrote.
What you’ll do
• Be the first human a customer talks to, across email, chat, and phone, for individual and enterprise accounts alike
• Answer the hard half. Our AI handles the routine questions; what reaches you is the ambiguous, the technical, and the high-stakes
• Write and improve the knowledge base articles that make the AI better and the queue smaller. We measure which articles resolve and which fail, and we fix the ones that fail
• Build real fluency in mortgage and real estate workflows, deep enough to explain our product in the customer’s language rather than ours
• Take actions that carry weight: refunds, cancellations, and billing corrections in Stripe
• Surface product friction to Engineering with enough evidence that it gets fixed, then tell the customer when it ships
• Hand inbound leads to Sales cleanly. Support does not sell, but Support is often the first to touch a future enterprise deal
The first 90 days
Two things in this job reach customers at scale without a human in between: the knowledge base, which feeds our AI, and our enterprise accounts. A knowledge base article that is 80 percent right makes the AI wrong for everyone who asks. So neither one is handed to you on a calendar date. Both are handed over when you have earned them.
Days 1 to 14. Product and customer mastery. Learn what every search does and why a customer would use it. Read every knowledge source we have. Study the queue, open and closed. Start answering emails and chats.
Days 15 to 30. Triage with ease. Route what you cannot answer to the right place. Start taking phone calls, which demand faster answers than anything written.
Day 30. You can run the inbox alone, handle refunds and cancellations, and walk a customer through troubleshooting without help. You will run a mock demo of the platform with your manager playing the customer.
Day 60. You start owning knowledge base articles. If a customer asks something twice, you write it.
Day 90. Full coverage, including enterprise, to the white-glove standard those customers expect. The test that matters: your manager can be offline for a week and nothing breaks.
We would rather ramp you properly than throw you at enterprise in week three and apologize to a customer for it.
The team
Two people. You report to our Customer Support Manager. She reports to our COO. That is the org.
You will also work directly with Engineering on bugs and escalations, with Customer Enablement on onboarding, and with Sales on inbound leads. We are twelve people. Everyone reaches across.
The stack
• Support. HubSpot for tickets, SLAs, and reporting. Aircall for phone. Stripe for billing.
• AI. An AI agent handling first-line resolution, tuned against a knowledge base you will help own.
• Product. The RETR platform: search, lists, exports, alerts, and enterprise account management.
What we’re looking for
• 1 to 3 years in a customer-facing role, ideally at a B2B SaaS company
• Genuine patience and real critical thinking. Most of what reaches you will not have an obvious answer
• You explain the why behind an issue rather than just the fix, because that is what builds trust
• Sharp attention to detail in how you document requests, troubleshooting steps, and interactions, plus the instinct to see a problem before it lands
• You would rather fix the root cause than close the ticket
• Comfort with support tooling and a willingness to learn new systems quickly
• Curiosity about AI as a tool you shape, not a threat you resent. A meaningful part of this job is making the machine better
Bonus. Familiarity with the mortgage or real estate industry, or another regulated and technical field.
How we operate
Three philosophies we run by:
• Give more than you get.
• Lead with value.
• Do the right thing.
Five values behind them: Honesty. Integrity. Fairness. Accountability. Excellence.
You’ll love this job if you already operate this way. If you don’t, we’re not the right fit for you.
“Give more than you get” is the one that shows up most in this job. It is the difference between answering the question a customer asked and answering the question they were actually trying to solve. We may not always be able to go the extra mile, but we can always go the extra inch.
What we offer
• $52,000 to $58,000 base salary. National band, no geo-adjustment
• Fully remote, US-based
• Company-paid medical at 100% of your individual premium
• Dental, vision, life, short-term and long-term disability employer-provided
• 401(k) with match: 100% of your first 1% plus 50% of your next 5%
• 15 days PTO plus 13 paid holidays, including Christmas Eve and the day after Thanksgiving
• $100 weekly meal stipend, $100 monthly wellness stipend
• Full home office setup: laptop, monitors, camera, peripherals provided
What we don’t offer
• Big-tech RSUs. We’re bootstrapped. No stock grants.
• Bureaucracy. We’re small and we like it that way.
• A ticket queue you disappear into. What you learn from customers reaches the people who build the product, in the same week.
• A script to hide behind. Our customers are people building businesses, not numbers in a queue, and we answer them that way.
How to apply
Send a resume and a short note to jobs@retr.app answering one question: tell us about a question you got asked so many times that you did something about it. What did you change, and did it work?
We read every application. If there’s a fit, we’ll set up a conversation.
We’re an equal opportunity employer. We welcome candidates of all backgrounds, experiences, abilities, and perspectives. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.
More at retr.app.
To apply: https://weworkremotely.com/remote-jobs/retr-customer-support-specialist
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