Compensation & Benefits Specialist

Proper is a quickly growing startup that values your skills, voice, and happiness.   We’re a team of developers, designers, engineers, accountants, CPAs, project managers, and creatives from all over the world. But we’re also surfers, hikers, Sichuan-eaters, photographers, artists, world travelers, meme lovers, and life-havers. Together, we provide the most technologically advanced property accounting services in the world - and we think that’s pretty epic. We’re proud to be creating something new that improves people’s lives while working together in a culture of collaboration, respect, communication, joy, and personal growth. Read more about what we do at Proper.ai We’re proud to create something new that improves people’s lives while working together in a culture of collaboration, respect, communication, joy, and personal growth. We’re seeking a Compensation and Benefits Specialist to join our team. Proper is seeking an Compensation and Benefits Specialist who thrives in a dynamic, fast-paced, and evolving environment. The ideal candidate ensures accurate payroll execution across geographies, administers sales commissions and organizational bonuses, and oversees employee benefits, including U.S. and LATAM insurance programs. This role bridges compliance, equity, and strategic compensation planning across Proper’s diverse workforce. If that sounds like you and you’re excited about joining a world-class team passionate about growing together, we look forward to hearing from you!  Proper is a San Francisco-based tech startup. This full-time position would be based remotely in Colombia or Mexico.  Role Description

The Compensation and Benefits Specialist will be responsible for: Managing payroll and benefits operations across the U.S. and LATAM regions. This role administers biweekly/monthly payroll, processes variable compensation such as bonuses and commissions, and oversees health and insurance benefits programs. They ensure compliance with labor laws and internal policies, resolve employee benefit issues, maintain accurate HRIS data, and support compensation reviews, audits, and benchmarking. Collaborating closely with HRBPs, this specialist also advises employees on compensation and benefits while researching new offerings to enhance total rewards.

Required skills

Administer biweekly/monthly payroll for U.S. FTEs and LATAM contractors (e.g., Mexico, Colombia).

Calculate and process variable compensation (sales commissions, performance bonuses) across orgs.

Manage benefits programs, including U.S. health, dental, vision insurance, and LATAM health coverage.

Provide timely resolution to benefits issues, including claims, eligibility, and reimbursements.

Partner with HRBPs to advise employees on benefits and compensation inquiries.

Maintain and audit payroll and benefits data in HRIS and ensure timely updates.

Ensure compliance with labor laws, benefit regulations, and internal controls.

Support annual compensation cycles, audits, and benchmarking efforts.

Help analyze pay bands and market data for role budgeting

Research and identify additional benefits for team members

Qualifications:

Direct experience processing LATAM contractor payroll and U.S. FTE payroll.

Experience with commission structures and bonus schemes.

Familiarity with tools such as Deel.

Strong understanding of LATAM health insurance and labor practices.

Fluency in English and Spanish preferred.

Type of Degree

Bachelor’s degree in Accounting, Business administration or a related field.

Years of experience in the field

3–5 years experience in payroll and benefits administration.

Proper is proud to be an equal opportunity employer committed to creating a diverse environment to work by offering the same opportunities to all applicants regardless of gender, sexual orientation, race, color, religion, disability, national origins, marital status, or other characteristics. We base our talent search exclusively on competencies, abilities and potential. Apply To This Job