Managing Director, Human Resources

Cabrera Capital; Chicago (IL); On-site; USD 170,000 - 260,000; Full time

Benefits offered by this job

Medical, Dental & Vision Coverage

PTO & Holidays

401(k) with Employer Match

Profit Sharing Program

FSA/HSA

Commuter Benefits

Disability Insurance

Life & AD&D Insurance

Job summary

Cabrera Capital is seeking a Managing Director of Human Resources to lead the HR function and the Chicago office facilities. You will partner with the CEO and executives to shape compensation, talent acquisition, development, performance, and engagement strategies across the firm’s employee lifecycle.

The role requires a strong track record in strategic HR leadership within a knowledge-intensive environment, the ability to implement scalable processes, and a readiness to evolve foundational

Qualifications

• Bachelor's degree required; MBA or equivalent graduate degree preferred.
• 10–15 years of progressive HR leadership, with at least 5 years in a senior HR leadership role.
• Experience in financial services, professional services, or another knowledge-intensive environment.
• Fluency with compensation constructs, workflows, and cultural dynamics of producer-driven or client-facing businesses.

Responsibilities

• Lead Compensation, Total Rewards, Workforce Planning, and People Budgeting with strategic architecture.
• Oversee Talent Acquisition, Campus Recruiting, onboarding, and employer branding across the firm.
• Build Learning & Development, leadership development, and career progression pathways.

Skills

Executive presence

Judgment

Strategic leadership

Hands-on execution

Coaching

Strong communication

Systems thinking

Values alignment

Education

Bachelor's degree

MBA or equivalent

Job description

Position Summary & Purpose

The Managing Director of Human Resources leads the human resources function at Cabrera Capital Markets. Reporting to the President and partnering closely with the Chief Executive Officer and the firm’s Managing Directors, this leader is responsible for the strategy and execution of the firm’s people function across every dimension of the employee lifecycle. The role also includes oversight of the firm’s Chicago office facilities function. The successful candidate joins the firm at a point of intentional evolution. Foundational elements of the HR function are in place — documented process flows across the core employee lifecycle, an HR Generalist, and vendor relationships that support the day-to-day operation of the function. Other elements remain in various states of development, and the Managing Director will build, assess, refine, and progress each in partnership with the President, the Chief Executive Officer, and the Managing Director group.

Essential Duties and Responsibilities

• Compensation, Total Rewards, Workforce Planning, and People Budgeting — Own the strategic architecture of how the firm invests in its people.
• Today: Benefits administration runs day to day, while compensation strategy, workforce planning, and people-related budgeting are not yet fully formalized.
• You'll: Build the compensation philosophy, band structure, and rewards architecture; run the annual compensation cycle with the CEO, President, and Finance; lead workforce planning and headcount planning with business heads; support people-related budgeting and investment decisions; and own retention structures, deferred compensation, and benefits.

• Talent Acquisition, Employer Brand, Campus Recruiting, and Onboarding — Own the shape, pace, and quality of the firm's hiring engine.
• Today: Recruiting practices vary by business line, and Cabrera has an important internship program that should be leveraged as a broader talent pipeline.
• You'll: Run full-cycle recruiting across all business lines; develop a campus recruiting strategy that strengthens the internship program and early-career pipeline; set the retained-versus-contingent framework and external search partnerships; own employer brand, recruiting marketing, and candidate experience; and build a consistent firm-wide onboarding experience.

• Learning and Professional Development — Build capability across the firm, from Managing Directors to the HR team itself.
• Today: Learning and development is not yet organized through a formal firm-wide program.
• You'll: Design leadership development, functional and technical skill-building tied to Cabrera's business lines, and career progression pathways that retain talent.

• Performance Management, Talent Review, and Succession Planning — Own how the firm evaluates, calibrates, and progresses its people.
• Today: Cabrera has an established mid-year annual performance review and compensation cycle. The current process is more administrative and cycle-driven than feedback-driven, with an opportunity to strengthen the quality, consistency, and timeliness of performance feedback, manager capability, calibration, and ongoing development conversations.
• You'll: Strengthen the performance management cycle so it supports meaningful feedback, manager accountability, calibration, progressive discipline, annual talent review, and succession planning for critical roles.

• Employee Experience, Engagement, and Relations — Own the day-to-day experience of working at Cabrera.
• Today: Employee relations matters are managed through close partnership between HR and business leaders as situations arise. There is an opportunity to strengthen consistency, documentation standards, manager guidance, proactive listening, and the mechanisms for acting on employee feedback.
• You'll: Build the annual engagement cycle and practical mechanisms for listening to and acting on employee feedback; serve as the senior point of contact for employee relations, escalation, and resolution; support managers with thoughtful guidance; and own offboarding with the same care as other lifecycle moments.

• Culture, Values, and Internal Communications — Steward the firm's five core values across eight business lines.
• Today: Cultural cohesion across business lines is an active focus area for firm leadership.
• You'll: Own the internal HR voice on people, policy, and culture matters; partner with the CEO and President on firm-wide people communications.

• HR Operations, Systems, Analytics, Policy, and HR Technology Strategy — Own and evolve the firm's HR operating infrastructure.
• Today: An HR Operations Playbook exists, and Paycom and Monday.com are in place.
• You'll: Maintain and evolve the playbook; own the firm's HR technology strategy and roadmap; strengthen data integrity, workflows, reporting, and system governance; build practical workforce analytics; and oversee the employee handbook, PTO, work-from-home policy, leave, and regulatory HR compliance.

• Facilities and Office Operations — Oversee the Chicago office facilities function
• Today: Facilities and reception are handled effectively at the operational level.
• You'll: Provide oversight and strategic direction through direct management of the Receptionist / Facilities role; own vendor relationships tied to the office environment.

Management & Decision-Making Responsibilities

• Directly manage a two-person team: the HR Generalist and the Receptionist / Facilities role.
• Today: An HR Generalist and Receptionist / Facilities role are in place.
• You'll: Coach and develop the HR Generalist; build cross-training so HR operations continue when team members are out; provide direction to the Receptionist / Facilities role; and run both the strategic and day-to-day sides of the function.

Qualifications

Knowledge, Skills & Abilities Requirements

• Executive presence — the ability to hold one's own with senior leaders and owner-operators, and to deliver difficult messages with care.
• Judgment — the ability to make sound decisions on incomplete information and to navigate ambiguity.
• Comfort with both strategic leadership and hands-on execution.
• Demonstrated ability to develop and coach members of the HR team.
• Strong written and verbal communication.
• Systems thinker — able to see connections across people, process, technology, data, compensation, performance, talent, and business operations; designs scalable solutions rather than isolated fixes.
• Demonstrated commitment to the values that anchor Cabrera Capital: Excellence, Inclusion, Integrity, Client-centered, and Innovation.

Education & Work Experience

• Bachelor's degree required. MBA or equivalent graduate degree preferred. 10-15 years of progressive HR leadership, with a minimum of five years in a senior HR leadership role.
• Experience in financial services, professional services, or another knowledge-intensive environment.
• Demonstrated experience leading HR at a firm of comparable scale — approximately eighty to five hundred professionals.
• Fluency with the compensation constructs, workflows, and cultural dynamics of producer-driven or client-facing businesses.
• Experience in founder-led or family-run business environments preferred.

Required Licenses & Certificates

• N/A

Physical Demands & Work Environment

• While performing the duties of this position, the employee is regularly required to sit, talk, and hear to express oneself and exchange information with others. The employee is frequently required to use a desktop computer or laptop and regularly use a desk phone and/or cell phone. The employee may occasionally be required to stand, walk, reach with hands and arms, and lift or move up to 15 pounds.

• The employee generally will work in an office environment with a typical office setting. If seated on the trading floor, the noise level is usually moderate with elevated voices and sounds from the televisions. The position may involve extended periods of working at a desk or using a computer or other office equipment. The employee may be required to occasionally travel within the city or surrounding areas of their job, domestically, and/or internationally, for meetings or other job-related activities.

• The above job description is intended to describe the general nature and level of work performed by individuals assigned to this position. It is not intended to be an exhaustive list of all duties, responsibilities, and qualifications required of employees in this role. Management reserves the right to modify, add, or remove duties and assign other responsibilities. This job description is not an employment contract, and employment with Cabrera Capital Markets is at-will, meaning that either the employee or the company may terminate the employment relationship at any time, with or without notice, and for any reason, in accordance with applicable law.

• The employee must be able to perform the essential functions of the position satisfactorily and, if requested, reasonable accommodation may be made to enable employees with known disabilities to perform the essential functions of the position, unless such accommodation would cause an undue hardship.

Work Authorization Requirement: Applicants must be currently authorized to work in the United States on a permanent basis. This position does not offer employment visa sponsorship now or in the future. Candidates requiring sponsorship, including F-1 OPT, CPT, H-1B, TN, E-3, or any other employment-based visa sponsorship, are not eligible for consideration.

We offer a competitive and well-rounded benefits package designed to support your health, well-being, and financial future:

• Medical, Dental & Vision Coverage
• Paid Time Off & Holidays
• 401(k) with Employer Match
• Profit Sharing Program
• Flexible Spending & Health Savings Accounts (FSA/HSA)
• Commuter Benefits (Pre-tax transit & parking)
• Short- & Long-Term Disability Coverage
• Life & AD&D Insurance Options
• Employee Assistance Program (EAP)
• Pet Care Discount Program