Ricardo I. Cruz, MBA

I lead the enterprise client portfolios, platform migrations, and cross-functional delivery that revenue depends on.

Client services, customer success, and transformation executive with 15+ years in financial services. Already operating at vice president scope: $6M ARR owned, 275,000 employees migrated, 50 to 75 professionals directed across two continents without a single direct report.

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$6MARR portfolio owned across four strategic enterprise clients
275,000Employees served across 10 enterprise migrations and implementations
90%Average reduction in client escalations
95%Reduction in recurring operational defects
+5NPS improvement from a single systems change

The executive case

Enterprise revenue is protected in the hardest quarter, not the easiest one

I take the accounts where the revenue is concentrated, the regulatory exposure is real, and the delivery organization does not report to me.

01

Retention held at the highest-risk moment

Migration and implementation are when enterprise clients decide whether to stay. I run migration risk across data integrity, operational readiness, and adoption, and convert those events from cost centers into expansion.

02

Authority earned, not assigned

A 50 to 75 person matrixed organization across eight functions in the United States and India has delivered to my standard for a decade with no direct reporting line. Influence at that scale is the VP job.

03

Structural fixes, not training plans

Recurring failure is an operating model defect. Redesign produced a 95% cut in recurring defects and a 90% average cut in escalations.

04

Credible in the boardroom

Executive advisor to C-suite client and vendor stakeholders, arbitrating tradeoffs across regulatory exposure, platform capability, and experience.

05

Recognized and repeatable

President’s Circle recipient, and multiple mentees have won the same award under my development.

Capability pillars

Three mandates I own end to end

Pillar I

Enterprise Revenue Leadership

Full ownership of retention, satisfaction, and growth on a $6M ARR book of four strategic clients at $1–2M each, serving 16,000+ end users.

  • Retention and expansion strategy tied to client business outcomes
  • Account strategy balancing service margin against expansion investment
  • Portfolio analytics that surface service risk before the client sees it
  • Executive client advisory and voice of the customer
Pillar II

Transformation & Platform Leadership

5 strategic migrations covering 100,000+ eligible employees and 5 implementations totaling 175,000 employees.

  • Multi-year migration strategy from discovery through execution
  • 3–5 year capability adoption roadmaps
  • Migration risk modeling and operational readiness
  • Platform governance and standardization
Pillar III

Global Matrix Leadership

Delivery directed across eight functions in the United States and India, majority offshore, entirely through influence.

  • Cross-functional alignment across Product, Engineering, Compliance, Operations, Delivery
  • SLA performance and service governance
  • Operating model redesign and standardization
  • Leadership development and succession

Selected impact

Executive briefs, not narratives

Brief 01

Moved a high-risk election out of the call and into the system

Fortune 500 financial services / Severance and benefits transition / Operating model redesign

Challenge
A single severance election drove three downstream outcomes and was captured verbally, mid-call. Missed capture surfaced weeks later as lapsed coverage.
Action
Stopped the training-and-performance remediation, reframed the failure as an operating model defect, and relocated the election to a guided digital flow at step one, identical for employee and representative.
Business impact
Retention risk removed at the most sensitive point in the employee lifecycle, with every choice recorded at the moment it was made.
93%Reduction in escalations tied to this decision
Brief 02

Made an eligibility engine show its work

Fortune 500 financial services / Retiree healthcare eligibility / Systems visibility and auditability

Challenge
Service, age, and hire date produced roughly 15 eligibility outcomes. The rules engine ran invisibly, so answers were assembled by hand and still came back wrong.
Action
Directed the work at surfacing the existing engine's output as one eligibility indicator across internal and client-facing tools, with every outcome traceable to the rule that produced it.
Business impact
Calls shifted from searching for an answer to confirming one, and the same logic became the backbone of employee self-service modeling.
+5NPS points gained on this single change
Brief 03

Turned standardization into commercial capacity

Enterprise health and welfare book of business / Platform governance and client advisory

Challenge
Enterprise clients expected bespoke build. Refusal costs the relationship; unlimited customization costs the business.
Action
Negotiated every client onto Fidelity standards without a single refusal, and treated the 8% of declined standards as product intelligence directing enterprise investment.
Business impact
Migrations became repeatable rather than bespoke, letting the business pursue larger migration clients it previously could not support.
100%Client adoption of standards, achieved through influence

Track record

Fifteen years inside one regulated institution, with scope expanded every time

Long tenure in financial services is not a narrow career. It is repeated promotion of trust: deeper enterprise exposure, larger revenue accountability, and a leadership pattern proven where compliance failure is not survivable. The operating discipline transfers; the enterprise judgment is hard to hire.

  • Deep enterprise experience in a regulated environment
  • Repeated expansion of scope, from portfolio ownership to platform strategy
  • Trust held at C-suite client and vendor level
  • A transferable executive leadership pattern, not a single-role résumé
2022 – Present

Director, Platform Migrations, Enterprise Health & Welfare

Fidelity Investments. 10 enterprise engagements, 275,000 employees, 100% client adoption of standards with 92% of proposed standards accepted.

2015 – 2022

Director, Client Services Manager

Fidelity Investments. $6M ARR portfolio, 16,000+ end users, 50-person matrixed organization approximately 75% India-based. 20% reduction in management reporting effort.

Recognition

President’s Circle Award

Fidelity Investments, for exceptional client delivery. Voice of the Customer Ambassador and Health Savings Account (HSA) Ambassador.

Education

MBA, Southern New Hampshire University

Conferred May 2026. BS, Accounting, University of Phoenix, 2008.

Leadership and talent

The credential I am proudest of is other people’s promotions

A continuous mentoring practice since 2015: four concurrent mentees across client management, operations, and specialty functions.

Development

Built for the role they actually wanted

Mentorship is focused on in-role growth and on moving people into their target roles anywhere in the enterprise, not only within my own function.

Outcome

Multiple mentees have won President’s Circle

The same award I received for client delivery. Developing people to the standard you were recognized against is how a leadership bench gets built.

Contact

Let’s talk about what your client services organization needs to become over the next three years.

ricardo@workwithricardocruz.com317.674.3338linkedin.com/in/ricardoicruzDownload resume (PDF)Remote, United States