Director of Human Resources

Company Overview

Who We Are

At Heirloom, we're leading the way in group travel through luxury and innovation. Heirloom offers custom, spacious rental homes to the short-term rental market, providing guests with an unmatched travel accommodation experience. Combining meticulous design, cutting-edge technology, and a data-driven approach, we guarantee our properties set the standard in luxury hospitality.

Join Our Team

When you join Heirloom, you become part of a hard-working, forward-thinking team dedicated to pushing the boundaries of luxury hospitality. We believe in the power of collaboration and continuous improvement, ensuring our employees thrive both personally and professionally. We’re committed to investing in our people and are always excited for new talent to join our team.

Apply today if you’re ready to grow with us.

Position Summary

Our team is seeking a detail-oriented and conscientious leader to take on the hybrid Director of Human Resources role. This is an incredible opportunity to shape our people operations and foster a work culture aligned with our mission and values.

Strategic HR Leadership

Whether you work from home or on-site, you'll lead our HR department, encouraging employee engagement, development, and retention. Working closely with senior leadership, you will drive company-wide strategies related to recruitment, DEI, and corporate social responsibility. You’ll manage feedback, benefits, and policy to uphold Heirloom’s commitment to excellence and compliance.

Operational Precision

As a key leader, you’ll maintain high standards of accuracy and quality in all aspects of HR. From administering payroll and benefits to guiding employee relations and engagement initiatives, you’ll ensure smooth operations. Your expertise in HR systems will be essential to delivering high-quality results in a fast-paced environment.

Are You the Right Fit?

We’re looking for someone diligent, thorough, and disciplined with a strong understanding of HR regulations and best practices. If you excel in structured settings where quality and precision matter and can efficiently manage multiple priorities - we look forward to hearing from you.

Apply today.

Responsibilities

• Foster a work environment aligned with Heirloom’s mission, communicating policies and updates effectively.
• Lead recruitment, DEI, and employee development strategies in collaboration with senior leadership.
• Oversee performance feedback cycles, employee retention, and engagement initiatives.
• Plan and implement comprehensive company-wide programs, including onboarding, engagement events, leadership retreats, and special programs like the internship initiative.
• Manage HR technology systems, ensure legal compliance, and design employee-centric policies.
• Administer employee benefits, including medical and 401(k), and oversee government reporting requirements.
• Ensure accurate payroll processing, collaborating with finance and external teams while addressing payroll inquiries and resolving discrepancies.
  
  

Qualifications

Experience & Education:

• 3-5+ years of leadership experience in Human Resources/People Operations.
• Bachelor’s degree in human resources, labor relations, organizational development, business, or related fields (preferred).
• Professional HR certification (SHRM-CP, SHRM-SCP, or PHR) is a plus.
  
  

Technical Expertise

• Proficient in benefits selection and administration (401k, medical, dental, etc.).
• Experience with cloud-based payroll systems such as Paylocity (preferred), ADP, Paycore, etc.
• High tech literacy, familiar with cloud-based tools for managing workflows, digital filing, and communication.
• Proficiency in MS Office and G Suite, and moderate proficiency in Microsoft Excel for report creation.
  
  

Skills & Competencies

• Strong recruiting, training, and management experience with remote and international staff.
• Exceptional planning, multi-tasking, and time-management skills.
• High level of professionalism, judgment, and ability to handle confidential matters.
• Polished written and verbal communication skills, with memo writing and policy drafting expertise.
  
  

Compensation & Benefits

Annual Salary: $110,000 - $155,000 based on experience and achievement

Benefits

• Paid time off, such as PTO, sick days, and vacation days
• Health insurance
• Life insurance
• Dental insurance
• Vision insurance
• Retirement benefits or accounts
• Healthcare spending or reimbursement accounts, such as HSAs, FSAs, and HRAs
• Long-term disability insurance
• Short-term disability insurance
• Preferential employee stays at Heirloom properties,
• Paid parental leave
• Relocation assistance
• Workplace perks such as recreation activities, food and coffee, and flexible work schedules
  
  

Schedule

• Heirloom's Boston office is located in the Boston Seaport. After an initial 90-day onboarding and training period, this position is eligible for a hybrid work schedule (3 days in office/2 days remote each week).
• Some domestic travel will be required, especially during the initial training and onboarding period, to visit Heirloom's different markets and work locations.