About Us

Whip Around is an award-winning, easy-to-use fleet maintenance software company

that connects drivers, mechanics, and fleet managers to improve the uptime of vehicles

and equipment. Founded in 2016 and headquartered in San Diego, CA, we’re on a

mission to keep the world’s fleets moving.

We’re a team of roughly 70 people across the United States and New Zealand, and our

culture runs on our core values — Be the Best You, Be the Driver, Always Bring Value,

and Manaakitanga. We’ve reached the point where HR needs a dedicated owner rather

than a patchwork of contractors, and we’re looking for our next Whip Arounder to build

it.

About the Role

Reporting to the CFO, you’ll own our HR infrastructure end to end: HR systems, payroll

administration and oversight, policies and procedures, compliance, the full employee

lifecycle, benefits, and HR controls.

This is a player-coach role - strategic when it matters, hands-on every day. You’ll

inherit an HR environment currently supported by contracted resources in both

countries, and your job is to bring it in-house and build a scalable, well-controlled

operating model that grows with us.

What You’ll Do

HR Leadership & Strategy

• Serve as the primary internal HR leader and trusted advisor to the CFO, executive team, and managers.
• Develop an HR strategy aligned with business objectives and a scalable operating model suited to a 70-person international organization.
• Advise leadership on organizational structure, workforce planning, compensation, performance management, employee relations, and HR risk - balancing employee experience with controls, compliance, and cost.
• Establish HR metrics and report regularly to the CFO and executive team.

HR Operations & Infrastructure

• Assume day-to-day U.S. HR operations from the existing U.S. contractor and coordinate with the New Zealand consultant on employee support and local compliance.
• Define HR processes, responsibilities, approval authorities, and documentation standards.
• Establish consistent employee lifecycle processes from hiring and onboarding through compensation changes, performance, leave, benefits, and offboarding.
• Maintain accurate employee records and automate or simplify HR administration where possible.

HR Systems & Payroll

• Assess the current HR technology environment, recommend a scalable future state, and lead HRIS selection and implementation as appropriate.
• Evaluate payroll processes and platforms and lead future payroll implementations or migrations.
• Oversee U.S. payroll (currently processed through Deel), including inputs, employee changes, deductions, approvals, and reconciliations.
• Partner with Finance on payroll review, approval, reconciliation, and reporting; keep HR system data accurate; and control access to confidential employee and payroll information.

Policies, Procedures & Controls

• Building a strong HR control environment is a core part of this role.
• Review existing policies for gaps and risk, then develop, document, and maintain HR policies and standard operating procedures.
• Establish HR controls: approval requirements, segregation of duties, documentation standards, system access controls, and periodic reviews.
• Document core processes - hiring and onboarding; compensation, salary, and promotion changes; payroll approvals; benefits; leave; performance reviews; complaints and investigations; terminations; and system access and record changes.
• Monitor and periodically audit compliance with those policies, ensure exceptions are documented and approved, and partner with Finance so HR and payroll controls support the broader financial control environment.

Compliance & Risk Management

• Maintain compliance with U.S. federal, state, and local employment law, and coordinate with the New Zealand consultant and external advisors on New Zealand requirements.
• Monitor regulatory developments, manage employment documentation and record retention, and recommend policy changes as needed.
• Engage external employment counsel when needed, support documentation of employee relations matters, investigations, and terminations, and identify and mitigate HR risk.

Employee Relations & Manager Support

• Serve as a resource for employees and managers on HR policies, employee relations, performance, and workplace concerns.
• Coach managers on people management, feedback, and documentation, and establish consistent handling of performance and conduct issues.
• Manage sensitive matters with discretion and judgment, reinforcing a culture of accountability and consistent application of policy.

Performance, Compensation & Benefits

• Improve the performance management process and partner with leadership on clear expectations and consistent reviews.
• Support compensation planning, benchmarking, salary reviews, promotions, and incentives, including annual planning with Finance.
• Oversee benefit programs and broker relationships, evaluating offerings for competitiveness and cost effectiveness.

Talent Acquisition & Onboarding

• Establish consistent recruiting and hiring processes, partnering with hiring managers on roles, compensation ranges, interviews, and evaluation criteria, and managing external recruiters as needed.
• Deliver a consistent onboarding experience, ensuring approvals, employment documentation, background checks, payroll setup, benefits enrollment, and system provisioning are completed.

In your first 6–12 months, you’ll:

1. Assess the current HR environment - systems, policies, processes, vendors, and compliance.

2. Execute a transition plan to assume the U.S. contractor’s responsibilities and establish a working model with the New Zealand consultant.

3. Strengthen HR and payroll policies, approvals, and internal controls, and document core processes with clear ownership.

4. Evaluate HRIS requirements and lead platform selection and implementation.

5. Evaluate the U.S. payroll environment, including Deel, and recommend improvements or alternatives.

6. Establish ongoing monitoring, reconciliations, and compliance reviews; improve employee data integrity and reporting; and build a scalable HR foundation for growth.

Reports to: Chief Financial Officer

HR Support Structure:

• New Zealand HR consultant - a continuing external partner you’ll work with closely.
• U.S. HR contractor - responsibilities transition to you after an initial ramp and knowledge-transfer period.
• External employment counsel, benefits brokers, payroll providers, recruiters, and other HR vendors as needed.

Location: Remote, with preference in US Central or Eastern time zones

Hours: Full-time. Occasional early or late calls to overlap with New Zealand colleagues

Travel: Minimal

Requirements

• 5+ years of progressive HR experience, including as the primary or senior HR resource in a small or mid-sized organization.

• Bachelor’s degree, or equivalent practical HR experience.

• Strong knowledge of U.S. employment practices and compliance requirements.
• Experience developing and implementing HR policies, procedures, and internal controls.

• Experience managing payroll processes and providers.

• Experience evaluating, implementing, or administering HRIS platforms.

• Command of the full employee lifecycle, including employee relations and sensitive personnel matters.

• Strong organizational, project management, documentation, and communication skills.

• Ability to operate independently with limited administrative support and work effectively with senior executives.

Preferred

• SaaS, software, technology, or private-equity-backed company experience, ideally supporting a distributed or remote workforce.
• International HR experience, particularly in New Zealand.
• Experience with Deel or similar platforms, and with implementing a new HRIS or payroll system.
• Experience building or scaling an HR function, including developing HR controls with Finance.
• SHRM-CP, SHRM-SCP, PHR, SPHR, or similar certification.

Benefits

• Base salary: $110,000 – $130,000, depending on experience and location.

• Annual performance bonus: 10% of base salary

• Medical, dental, and vision coverage

• 401(k) with company match

• Open time off policy, plus company holidays and paid parental leave

• Professional development support, including HR certification and continuing education

Equal Employment Opportunity

Whip Around 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, or any other characteristic protected by law.