Director of Customer Success (Well-Oiled Operations)

Acquisition.com

86d • $160,000 - $180,000

About The Position

At Acquisition.com, we don’t just hire for open roles—we hire for impact. If you’re exceptional at what you do and align with our core values: competitive greatness, sincere candor, and unimpeachable character, we want to know you. Our portfolio company Well-Oiled Operations builds systems that scale for teams, clients, and leaders who want to grow. We're hiring a Director of Customer Success who can take our client journey from great to effortless. This is not just a leadership role, it’s a chance to design a high-performing client engine that delivers retention, referrals, and revenue on repeat. You’ll lead a talented team, refine the systems behind every client touchpoint, and ensure our brand feels premium, proactive, and personal. If you love people, live in systems, and know how to turn outcomes into processes, please read on!

Requirements

• 5+ years in Customer Experience, Client Success, or Fulfillment at the Director level.
• Direct experience leading teams of 40+, including middle management, CSMs, and support staff.
• Proven track record of driving retention, upsells, and client satisfaction targets.
• Executive presence and steady judgment, especially in high stakes client situations.
• Leadership style that meshes with a vibrant, collaborative, high energy team.
• Thrives in a fast paced, dynamic environment bringing clarity, adaptability, and confident communication to every challenge.
• Must be able to work CST hours.
• Advanced proficiency with CRM systems, project management tools, and engagement tracking software.
• Excellent written and verbal communication.
• Proven ability to design SOPs, track KPIs, and optimize client lifecycle processes for scale.

Nice To Haves

• Based in the Milwaukee or Chicago area, our HQ is in Chicago and we host two live events per month.

Responsibilities

• Architect the Client Journey
• Own the full post sale lifecycle: onboarding, engagement, renewal, expansion.
• Create a world class experience that feels intentional, seamless, and results focused.
• Implement systems that keep every client seen, supported, and progressing toward measurable outcomes.
• Partner cross functionally to ensure client feedback drives program improvements and product decisions.
• Lead and Develop the Team
• Manage and mentor a 40+ person department, including middle management, CSMs, and support staff.
• Build SOPs, SLAs, and team rhythms that create consistency and confidence.
• Lead weekly 1:1s, coach for ownership, and maintain a culture of excellence.
• Handle escalations with professionalism, empathy, and sound judgment.
• Drive Retention and Growth
• Hit and exceed quarterly retention, upsell, and satisfaction targets.
• Identify churn risks early, implement solutions fast, and turn client wins into referrals.
• Analyze engagement data to guide strategic decisions that increase lifetime value.
• Operational Excellence and Reporting
• Establish and track KPIs that make performance visible and actionable.
• Build dashboards, reports, and feedback loops for executive insight.
• Continuously refine systems to scale client management without sacrificing quality.

Benefits

• Base salary: $160K to $180Ks base salary.
• A culture that values systems, excellence, and ownership.

What This Job Offers

• Job Type: Full-time
• Career Level: Director