Director of Customer Success (Well-Oiled Operations)

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.

The Role

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!

Who You Are

• A systems driven leader who believes client experience is the growth engine of the business.

• You’ve scaled teams, built processes, and turned busy departments into predictable machines.

• You bring strong executive presence, clear judgment, and the ability to lead calmly under pressure.

• You thrive leading a younger, collaborative team, coaching through energy, adaptability, and direct communication.

• You don’t wait for direction, you create clarity, drive accountability, and build structures that last.

What You’ll Do

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.

What You Bring

Core Experience

• 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.

Leadership and Cultural Fit

• 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.

Location and Time Zone

• Must be able to work CST hours.

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

Technical and Operational Skills

• 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.

What Success Looks Like

• Retention and upsell targets are consistently met or exceeded.

• Clients are progressing, implementing, and achieving measurable results.

• Engagement rates stay above 85% weekly.

• The team runs with clarity, communication, and accountability.

• Clients describe the experience as premium, proactive, and world class.

Compensation and Culture

• Base salary: $160K to $180Ks base salary.

• A culture that values systems, excellence, and ownership.

• Join a mission driven team where Well-Oiled isn’t a slogan, it’s how we run.

We’re looking for a builder, someone who sees the friction before anyone else does and removes it. If that’s you, we can’t wait to meet you!

Acquisition.com Core Values

Our core values are the heart and soul of this incredible company. The right person for this role will appreciate each of these values, personally subscribe to them, and understand why each is critical to having a great business.

Competitive Greatness

Be at your best when your best is needed. Enjoyment of a hard challenge. Those who have the drive to constantly improve, the superior intellect and long term commitment to see incremental improvements become compounding returns.

Sincere Candor

Have the self awareness to accurately perceive and communicate hard truths that improve others and self, the courage to do so, and the humility to accept them, even when it hurts. Nothing great can be built without feedback: internally or externally.

Unimpeachable Character

Be the type of person with whom people are always proud to associate, personally and professionally. We look for true alignment of thoughts, words, and actions towards a goal worth pursuing.