TTKE Enterprises is the financial and legal backbone for a family of operating companies spanning retail, manufacturing and transportation operations, real estate development, construction management, software development and additional consulting and professional services across multiple U.S. states and Puerto Rico.

About the Role

TTKE Enterprises is a Puerto Rico export services company under Act 60. It provides finance, legal, analytics, marketing, HR, and technology services to a family of operating businesses in cannabis retail, cultivation, manufacturing, real estate, construction, and software. The Vice President of Human Resources and Talent Acquisition reports to the CEO, sits on the executive leadership team, and sets and executes HR and recruiting strategy across the United States, Puerto Rico, and Colombia. The workforce supported by this role is projected to grow to more than 500 employees as the operators we serve open more than 40 new retail locations over the next 18 months. This is a hands-on executive role for someone who builds systems and processes directly and works comfortably in both English and Spanish.

What You'll Do

Leadership and Team

Lead the HR and Talent Acquisition functions, starting with three direct reports: two Talent Acquisition employees and a Human Resources Manager
Recruit, hire, develop, and evaluate HR and recruiting staff as the corporate function grows in San Juan and Medellín
Set priorities, performance standards, and development plans for the team
Own the annual HR and recruiting budget

Strategy

Develop and execute a people strategy that supports the growth plan, including organizational design, workforce planning, and succession planning for critical roles
Advise the CEO and executive team on all people-related matters
Establish and maintain HR policies, procedures, and standards across all entities and jurisdictions

Talent Acquisition

Lead corporate and professional recruiting in the United States, Puerto Rico, and Colombia, including executive and management searches
Oversee high-volume retail recruiting across all markets, including staffing plans for new retail openings
Build and maintain a 12-month hiring forecast aligned with the expansion calendar, in partnership with Finance and Retail Operations
Own the applicant tracking system, employer branding, and recruiting metrics

Total Rewards

Design and administer compensation structures, salary bands, and annual review cycles across the United States, Puerto Rico, and Colombia
Oversee benefits strategy, renewals, and administration
Support the administration of incentive and long-term reward programs for leaders

Employee Relations and Compliance

Oversee employee relations, investigations, and separations, ensuring consistency and legal compliance across all locations
Ensure compliance with federal, state, Puerto Rico, and Colombian employment law, working with legal counsel as needed
Keep the handbook, policies, required postings, and personnel records audit-ready

HR Operations and Technology

Own the HR technology stack, including Greenhouse (ATS), Wurk (HRIS), and AI-enabled screening and scheduling tools
Lead the evaluation and implementation of new platforms
Automate recurring HR and recruiting processes and document all core processes to a high standard

Performance, Development, and Culture

Design and administer performance management, including scorecards, review cycles, and calibration
Build leadership development and promotion pathways across retail and corporate roles
Champion company values and support internal communications, including employee town halls
Lead retention initiatives in partnership with operating leadership

What You Bring

Required

Bachelor's degree in Human Resources, Business Administration, or a related field
8+ years of progressive HR experience, including 5+ years leading HR managers, recruiters, or both at the Director level or above
Experience leading the people function for an hourly, multi-site workforce or for employees across multiple countries
Demonstrated experience building or substantially rebuilding an HR function
Full professional fluency in English and Spanish, written and verbal
Thorough knowledge of U.S. multi-state employment law and Puerto Rico employment law
Demonstrated experience designing and implementing compensation structures, performance systems, and workforce plans
Administrator-level experience with an ATS and an HRIS, and experience selecting and implementing HR software
Daily use of AI tools for drafting, analysis, and process design
Strong analytical skills with workforce and compensation data
Sound judgment and discretion, and the ability to advise executives candidly

Preferred

Advanced degree, or SHRM-SCP or SPHR certification
People leadership experience in retail, restaurant, hospitality, or multi-site healthcare
Familiarity with Colombian employment practices
Experience leading remote team members

Work Environment

Based in the San Juan, Puerto Rico area; 100% on-site, Monday through Friday, 9:00 a.m. to 6:00 p.m.
Occasional travel, primarily to Washington State, Minnesota, and Medellin, Colombia.

Compensation & Benefits

Compensation is commensurate with experience. Benefits are provided in accordance with company policy.

Any offer of employment is contingent on the successful completion of our pre-employment process, which includes your written consent to a background check conducted by a third-party consumer reporting agency.

TTKE Enterprises is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, genetic information, or any other characteristic protected by applicable federal, state, or local law.

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