VP 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 Vice President of Customer Success to take our client journey from great to effortless.

This is not just a leadership role. It is an opportunity to design a high-performing client engine that delivers retention, referrals, and revenue on repeat. You will lead a talented team, refine the systems behind every client touchpoint, and ensure our brand feels premium, proactive, and personal at every stage.

If you love people, live in systems, and know how to turn outcomes into repeatable processes, keep reading.

Who You Are

• A systems-driven executive who sees client experience as the growth engine of the business.

• Experienced in scaling teams, building processes, and transforming busy departments into predictable, high-performing machines.

• Confident, composed, and credible with the ability to lead with calm judgment and clear direction under pressure.

• A coach who thrives leading a collaborative, high-energy team through direct communication and genuine connection.

• A builder who creates clarity, drives accountability, and designs structures that last.

What You’ll Do

Architect the Client Journey

• Own the full post-sale lifecycle including onboarding, engagement, renewal, and expansion.

• Create a world-class experience that feels intentional, seamless, and results-focused.

• Implement systems that ensure every client feels seen, supported, and successful.

• Partner cross-functionally to turn client feedback into product and program improvements.

Lead and Develop the Team

• Manage and mentor a 40+ person department including managers, CSMs, and support staff.

• Build SOPs, SLAs, and operating rhythms that drive consistency and confidence.

• Lead weekly one-on-ones and team meetings that foster ownership, alignment, and growth.

• Handle escalations with empathy, precision, and sound judgment.

Drive Retention and Growth

• Meet and exceed quarterly retention, upsell, and satisfaction targets.

• Identify churn risks early and implement solutions quickly.

• Translate client wins into referrals and brand advocacy.

• Analyze engagement data to guide strategic decisions and increase lifetime value.

Operational Excellence and Reporting

• Establish KPIs that make performance visible and actionable.

• Build dashboards and reporting systems that provide real-time insight for executives.

• Continuously refine processes to scale efficiently without sacrificing quality.

What You Bring

Core Experience

• 8+ years in progressive experience in Customer Success, Client Experience, or Fulfillment including 5+ years in a Director or above role.

• Proven success leading large teams (40+ people) including middle management and frontline staff.

• Demonstrated ability to achieve retention, upsell, and satisfaction goals.

Leadership and Cultural Fit

• Executive presence and steady judgment in complex, high-stakes situations.

• A leadership style that inspires collaboration, excellence, and accountability.

• Thrives in a fast-paced, dynamic environment by bringing clarity and confident communication to every challenge.

Technical and Operational Skills

• Advanced proficiency with CRM and project management systems.

• Strong analytical and communication skills.

• Proven ability to design SOPs, define KPIs, and optimize client lifecycle processes for scale.

Location and Time Zone

• Must be able to work CST hours.

• Bonus: Based in the Milwaukee or Chicago area (HQ in Chicago with two live events per month).

• Occasional travel for leadership sessions and client events.

What Success Looks Like

• Retention and upsell targets are consistently exceeded.

• Clients achieve measurable outcomes and report satisfaction above 4.5 out of 5.

• Engagement rates stay above 85 percent weekly.

• The team operates with clarity, consistency, and accountability.

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

Compensation and Culture

• $190K-$235K base salary + variable compensation

• A culture built on systems, excellence, and ownership.

• Join a mission-driven team where “Well-Oiled” is not a slogan. It is how we run.

We are looking for a builder, someone who spots friction before anyone else and removes it. If that is you, we cannot 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.