Customer Success Manager (Pittsburgh)

Location: Remote, United States (Eastern or Central hours)

Employment Type: Full time

Location Type: Remote, with quarterly travel to Pennsylvania

Department: Landman Education

Compensation: On Target Earnings $95K to $135K • $65K to $80K base • Uncapped bonus on member results

The short version

Most people who buy a real estate course never close a deal. This job exists to make sure ours do. You own one number: every Deal Engine member under contract with funding approved within 120 days. When they win, you get paid. When they stall, you find out why and fix it.

About Landman

Landman has closed 200+ land deals in 25+ states. We teach people to do the same through Deal Engine, and when a member gets a good property under contract, we fund it. Members stay because they get funded deals. Member results aren't a support function here. They are the business.

Role

As the Customer Success Manager, you'll take every new member from signup to their first funded deal and keep them funding deals and in our community after that. You'll set up their business, track their numbers every week, call the ones who fall behind, and remove whatever is blocking them. You'll also run the front door: our free Skool community, where future members come from.

This is not a help desk. You'll know every Monday morning exactly which members hit their numbers and which didn't, and you'll call the ones who didn't.

Responsibilities

Set members up fast: run the setup call within 24 hours of a member's first call. Bank, data, texting, partner tools, first list built, first send date set.

Run the weekly scoreboard: every member rated green, yellow or red by Monday at 8am Eastern. Call every yellow and red member that week.

Diagnose the constraint: when a member stalls, name the one thing blocking them (marketing not going out, wrong market, bad data, not tracking, slow follow-up) and fix it with a date.

Own member communication: weekly check-ins, the Day 30 call, the six-month continuity conversation, and the call when someone wants to quit.

Keep the funding desk honest: every deal a member submits gets an answer inside 48 hours. No member waits without a date.

Connect members to the right partners: marketing tools, transaction coordination, our mobile home dealership, realtors. Track every one.

Grow the free community: answer every new member within an hour and every question within a day. Become the person on our team who knows Skool best.

Report what's broken: every Friday, in writing, tell the founder where members are stuck and what in our system needs to change.

Automate your own job: build AI tools for the reports, the reminders and the roll-up.

Requirements

Has managed a book of clients or accounts and hit numbers without someone checking in daily. You can show us the numbers.

Comfortable telling someone they missed their numbers, twice if needed, and comfortable being told you got something wrong.

Detail-obsessed. You notice when numbers don't match, and it bothers you.

Has built something with AI on your own: a workflow, a dashboard, a Claude or GPT system. Bring it.

Self-directed and all in. No side business competing for your attention.

Who this is not for

People who want the same paycheck whether members win or not.

People who avoid hard conversations.

People who want to sell. You never pitch, quote prices or upsell. You get members results. You will have consultive based conversations which end up resulting in yor commission.

Results

97% of members go under contract with funding approved by day 120.

95% of members stay on after month six. 93% stay to month 12.

Every member's marketing goes live, verified, by day 14.

The scoreboard lands every Monday by 8am. No exceptions.

Every member is set up on our partner tools, and every referral is tracked and paid.

The founder knows every Friday exactly where members are getting stuck.

Schedule

Full time, Monday through Friday, Eastern or Central hours. Monday mornings are fixed: the scoreboard is due at 8am Eastern.

Location

Remote, anywhere in the United States. Your first week is in person with the founder in Ligonier, Pennsylvania, then one trip a quarter, timed to our live events. Travel paid.

Compensation

$60,000 to $80,000 base, plus three uncapped bonuses:

• A bonus when a member's first funded deal sells
• $200 when a member's first marketing campaign goes live on our partner tools
• $100 when a member runs a deal through our transaction coordination partner

On target earnings of $95,000 to $135,000 depending on how many members succeed.

Benefits

Health Insurance via ICHR within 6 months.

Landman Core Values

Unquestionable Standards. We do the right thing, every time. How we do one thing is how we do everything.

Total Ownership. The results are up to me. No blame, complain or defend. Honest, open candor, and we welcome feedback.

Radical Adaptability. We innovate, welcome change, and lean into discomfort. Speed bumps are something to adapt to, not stop at.

Competitive Greatness. Do your best work when no one is watching, and thrive under pressure.

How to apply

Send a resume, a link or screenshot of something you built with AI, and two sentences on what you want to be doing in three years. No cover letter. Finalists complete an initial call with our team, short behavioral assessment, a second interview, and a 20-minute role-play/test task.