Client Success Agent Jobs in Chicago, IL (NOW HIRING)

Remote Eastern Time Zone Full-time 9am-6pm ET

Read this part first.

This is not a check-in-with-clients-once-a-week seat. We're not looking for someone to send a monthly report and call it account management.

We're looking for one person who owns the client relationship completely - from day one onboarding through retention, escalation, and everything in between. You anticipate problems before clients feel them. You keep expectations accurate. You make clients feel like the smartest decision they made was joining us.

If you've been reactive your whole career, this isn't your seat. If you've been the one holding accounts together when things get hard - and making clients stay because of how you showed up - keep reading.

ABOUT THE FIRM

We are a high-ticket coaching, consulting, and implementation firm working exclusively with $1M-$10M+ agency owners. We help them transform from talent-heavy, owner-dependent businesses into high-margin, scalable operations through high-level masterminds, implementation intensive programs, and advanced AI-agent integration. We are a systems-first company. We don't just teach the standard - we build it.

We are the #1 fastest-growing coaching program for marketing agencies, with 225+ agencies joining us in the last 12 months. We were built by two founders who've lived it - one scaled his agency from zero to $500K a month and exited in a multi-million dollar deal in three and a half years. The other has run his agency for seven years, been at multi-seven-figures for over five years steady, and his business is fully run by his team. Two founders, two paths, same destination.

WHAT'S HAPPENING RIGHT NOW

This is the moment you join. The company is in motion across four major fronts:

• Flagship Event: Hosting roughly 200 agency owners across four days in Las Vegas (June 11-14)
• Geographic Expansion: Scaling into the United Kingdom market
• AI Integration: Deploying a full AI agent infrastructure across the business
• HQ Buildout: Establishing a flagship destination headquarters for the agency industry

The person who joins now is not joining a finished company. They are joining a company being built.

This is not a standard CSM position. You are the face of the company to every client you own. You onboard them, guide them, report to them, and retain them. You work alongside our marketing and fulfillment teams to make sure what we're delivering is matching what we promised - and when it isn't, you're the first to know and the first to fix it.

You will also help build the function itself. That means writing SOPs, creating process where none exists, and eventually mentoring the next layer of CSMs as the team grows.

The person who joins now is not stepping into a finished machine. They are helping build one.

Client relationships

You are the main point of contact from the moment a client signs. You onboard them, run their weekly or monthly check-ins depending on service type, manage expectations clearly, and make sure they always know where things stand. Response time during working hours is within one hour - no exceptions.

Retention

You don't wait for clients to raise concerns. You see the signals early and you move on them. When things get hard - and they will - you handle it with confidence and professionalism. You don't escalate because it's uncomfortable. You escalate because it's the right call.

Reporting & performance

You track what matters, communicate it clearly, and tie it back to client goals. You work with internal teams to make sure the data reflects reality - and you explain it to clients in plain language, not jargon.

Process & team

You build the documentation. You write the SOPs. As the team grows, you become the person new CSMs learn from. This is a leadership track, not a static seat.

• You own the relationship fully. Not just the happy parts.
• You have real agency experience managing clients in digital marketing - SEO, paid social, or both.
• You communicate clearly under pressure. Clients trust you because you're straight with them.
• You are high-detail and proactive. You don't wait to be asked - you already did it.
• You know GoHighLevel, Asana, Slack, and can pick up new tools fast.
• You're interested in building - process, team, and your own career.

Requirements

• 3+ years in a CSM, account management, or client success role - preferably inside a marketing agency
• Managed clients across SEO and/or Facebook Ads with measurable retention outcomes
• Navigated difficult client conversations without losing the account or your professionalism
• Built or contributed to SOPs, processes, or team infrastructure
• Worked independently in a fully remote environment without needing hand-holding

Bonus, not required: experience managing contractor relationships or working with service-based clients at scale.

You can walk us through a client you retained when things were going sideways - what happened, what you did, and what the outcome was. People who've actually done this work answer that in their sleep.

You think in systems, not tasks. And you can explain what you'd do in month one before anyone asks.

• Complete the Culture Index survey
• Initial screen with recruiting team
• Interview with our internal operations lead
• Final interview with the founders

Benefits

• Competitive base 
• Fully remote, Eastern Time hours
• Paid time off
• A real path to leading your own team
• A company that documents everything and keeps building - you won't be operating in chaos

Send your resume and answer the application questions

This team is building something. The only question is whether you're in it.