Calderwyn Advisory Group

Enduring judgment
for consequential
decisions.

Trusted counsel for organizations navigating their most consequential workplace decisions. Discreet, institutional-grade advisory for executives, boards, and legal leaders.

Experience Judgment Leadership

Every organization eventually faces a decision that cannot be delegated — a sensitive investigation, an executive concern, a governance breakdown, or a people risk with consequences extending far beyond HR. Calderwyn provides experienced, confidential counsel when the path forward must be both principled and practical.

Counsel that stands
the test of scrutiny.

Calderwyn Advisory Group was founded by Kristie Jimenez — a Senior HR Executive with more than 20 years of enterprise-level experience leading HR, Legal, and Compliance functions for large, complex organizations.

We work at the intersection of leadership, governance, and risk — bringing the kind of measured, institutional judgment that consequential decisions demand and that most organizations cannot afford to keep on staff full time.

Calderwyn serves CEOs, founders, boards, general counsel, executive directors, and senior HR leaders across private companies, nonprofits, healthcare organizations, and multi-state employers. The firm does not operate as a staffing agency, recruiting firm, payroll provider, or outsourced HR administration service.

About the Firm
Founder's Career Experience

Enterprise experience brought to every engagement.

7,500+Employees supported
12States of enterprise HR leadership
500+Workplace matters managed
20+Years of HR leadership
Professionally Insured — Professional Liability (E&O) & General Liability

The Calderwyn Standard

Every engagement is guided by four principles: discretion in handling sensitive matters, diligence in assessing the facts, defensibility in the decisions made, and precision in execution.

Discretion

Sensitive matters handled with the confidentiality they require.

Diligence

Thorough, methodical assessment of the facts before any recommendation.

Defensibility

Advice built to withstand legal, regulatory, and public scrutiny.

Precision

Clear, actionable guidance — not vague frameworks.

What We Do

Advisory services for
high-stakes organizations.

Two decades of senior HR executive leadership — now available on a fractional and advisory basis. Calderwyn brings the judgment of a seasoned CHRO to the decisions that define organizations and the leaders who run them.

Fractional CHRO & HR Leadership

Senior HR executive leadership available to your organization without the cost of a full-time hire. We embed into your leadership team and drive HR strategy, compliance, and people operations at the highest level.

  • HR strategy and executive leadership
  • People operations oversight
  • Compliance and risk management
  • Organizational design and workforce planning

Workplace Investigations

Independent, defensible investigations conducted by an AWI-CH certified investigator with experience across hundreds of complex matters. Every report is built to withstand legal and regulatory scrutiny.

  • Harassment & discrimination investigations
  • Executive misconduct & board-level complaints
  • Retaliation & whistleblower matters
  • Ethics, policy, and compliance violations

Board & Governance Advisory

Independent advisory support for boards, audit committees, and directors navigating governance challenges, compliance obligations, and workforce matters requiring credible outside counsel.

  • Board governance and risk reporting
  • Independent investigation oversight
  • Compliance framework design
  • Audit and ethics committee support

Employment Law & HR Compliance

Multi-state employment law compliance and litigation support across ADA, FMLA, Title VII, FLSA, ADEA, PWFA, and state-specific requirements — from initial risk assessment through resolution.

  • Multi-state compliance audits
  • EEOC & DOL response support
  • Policy & employee handbook development
  • Litigation risk assessment and management

People & Organizational Strategy

Strategic advisory for organizations at inflection points — restructuring, rapid growth, cultural transformation, or succession planning. Grounded in enterprise-scale experience.

  • Organizational restructuring & design
  • Succession planning programs
  • Culture transformation
  • Change management leadership

Executive & Leadership Coaching

ICF-credentialed coaching (ACC) for executives, senior leaders, and high-potential managers navigating transitions, leadership development, and performance challenges.

  • Executive leadership coaching
  • Leadership transition support
  • Manager and team development
  • Performance and career coaching

HR Technology & Digital Transformation

HRIS implementation, system migration, and HR technology strategy for organizations modernizing their people operations — including hands-on experience leading Ceridian-to-UKG migrations.

  • HRIS selection & implementation
  • System migration leadership (UKG, Ceridian Dayforce)
  • Workforce analytics & reporting
  • Process redesign & change management

Labor Relations & Union Matters

Strategic counsel for organizations navigating union activity, labor relations challenges, and workforce communications during sensitive labor matters.

  • Union avoidance strategy
  • Decertification counsel
  • Labor relations advisory
  • Workforce communications during labor activity

Not sure which service fits your situation?

Request a Confidential Consultation

How We Engage

Advisory relationships built on trust and discretion.

Every engagement begins with a candid conversation about your situation. We do not offer one-size-fits-all solutions — we bring experienced judgment to the specific facts in front of us.

Request a Confidential Consultation
1

Confidential Inquiry

A confidential conversation to understand your situation, the nature of the matter, and whether Calderwyn is the right fit for your needs.

2

Engagement Design

We propose a clear scope, timeline, and fee structure — project-based, retainer, or session-based, depending on the work.

3

Advisory Work

We engage with the depth and discretion your situation requires — bringing experienced judgment, not templated answers.

4

Defensible Outcomes

Every deliverable — whether a recommendation, report, or ongoing counsel — is built to withstand scrutiny and support sound decisions.

Executive Insights

Perspectives on governance,
risk, and leadership.

Practical perspectives on the workplace and organizational matters that shape how leaders and boards lead. Updated periodically.

Workplace Investigations

Conducting Defensible Workplace Investigations

What separates a legally sound investigation from one that creates more exposure than it resolves.

Governance

When HR Issues Become Board Issues

The threshold at which personnel matters escalate to governance obligations — and what boards need to know.

Read article →

Executive Leadership

Managing High-Risk Employment Matters

How experienced HR leadership changes the outcome of investigations, claims, and workforce crises.

Client relationships are confidential by design. Professional references may be made available upon request for qualified engagements.

When the stakes are high,
judgment matters.

Calderwyn Advisory Group is available for confidential engagements with executives, boards, and legal counsel.

Request a Confidential Consultation