Head of Customer Advocacy

• Headquarters: Remote
• URL: https://retr. app/
• Why this role matters right now

As a product‑led company, our growth comes from customers who adopt the product, love it, and bring more of their team onto it.

That puts this role directly on the growth path: onboarding, adoption, renewal, and expansion all run through it.

We're looking for someone who will own the customer from the day they sign, build the playbook that makes value repeatable, and hire the team that runs it.

If you're energized by getting customers to real value fast and turning that into something a team can do at scale, you'll fit in well here.

• What you’ll do
• Own every customer after the sale: onboarding, adoption, health, renewal, and growth
• Figure out why our best accounts grew, turn it into a playbook, and build the team that runs it
• Own renewals end to end, with no surprises the company doesn’t see coming
• Win enterprise trials, which is where we win or lose an account
• Bring down churn in our self‑serve base through product and automation, not headcount
• Scale customer support as the base grows, holding quality to our standards
• Know our customers better than anyone in the company, and keep Sales close wherever that knowledge should turn into a conversation
• Hire and lead the customer team
• The first 60 days
• Days 1 to 14. Live in the accounts. Learn the product, the industry, and the book. Go through every account that grew and find out what actually drove it.
• Days 15 to 30. There’s more than one growth path in this base. Name them. Test them. Prove a couple. By day 30 you have a playbook hypothesis with evidence behind it.
• Day 30. Start hiring while you’re still refining. It doesn’t need to be finished. It needs to be 80% right.
• Day 60. First success managers in seat, book split, playbook running with your team.
• The team

Success, Enablement, and Support report to you. You’ll hire your first success managers inside 60 days. You report to our COO.

• What we’re looking for
• You’ve built a customer success function from scratch, not just run one somebody else built
• You can talk about your retention and expansion numbers in specifics, not adjectives
• You’re happy carrying a book yourself for the first 60 days and then giving it away
• You’ve fixed a churn problem with product and automation, not just by adding people
• You’d rather hire two excellent people than five adequate ones
• You think of expansion as evidence the product worked, not as a target you hit
• You’re comfortable being 80% right and moving
• A creative problem solver with strong listening, logic, and critical thinking skills
• Team player with a passion for helping others succeed and a commitment to doing the right thing
• Bonus: Mortgage or fintech experience. Experience standing up an AI‑first support motion.
• How we operate
• 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.

What we offer

• $180,000–$200,000 base salary. National band, no geo‑adjustment. Performance bonus on top, which we will walk through together
• 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%
• Generous 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.
• A quota dressed up as customer success. This is not a sales job with a softer title.
• Bureaucracy. We’re small and we like it that way.
• Layers between you and the work. You report to our COO. That’s the org.
• Equal opportunity employer

We welcome candidates of all backgrounds, experiences, abilities, and perspectives. We do not discriminate on the basis of race, re

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