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About the Role

This role is a highly experienced, hands-on leadership position within Highwire's People function, focusing on payroll and payroll tax, benefits and retirement programs, and people analytics. It bridges People, Finance, and business operations, translating data into insights, strengthening controls, and designing understandable benefits programs. The ideal candidate combines technical expertise with business judgment, attention to detail, and the ability to execute strategy.

Responsibilities

Own the end-to-end administration of accurate, timely and compliant semi-monthly payroll for a multistate workforce.
Serve as Highwire’s internal payroll subject-matter expert and primary administrator for Rippling.
Manage the relationship with Rippling, monitor service performance and coordinate issue resolution.
Lead federal, state and local payroll tax administration.
Maintain rigorous payroll controls, review protocols, documentation and audit trails.
Research and resolve complex payroll, tax, timekeeping and pay-related matters.
Partner closely with Finance on payroll funding, general ledger mapping, reconciliations, accruals, invoices, workforce cost reporting, audits and forecasting.
Monitor regulatory developments and translate changes into compliant payroll practices.
Lead the strategy, design, financial evaluation and administration of Highwire’s health, welfare and related benefit programs.
Partner with brokers, carriers and Finance on renewals, plan modeling, employee contribution strategy, vendor selection, implementation and ongoing performance management.
Analyze claims, utilization, enrollment, benchmarking and employee feedback to evaluate plan performance and recommend program enhancements.
Develop and execute a year-round benefits communication and education strategy.
Translate complex benefit information into clear, accessible and engaging communications.
Own benefit administration and compliance, including eligibility, deductions, reconciliations, required notices and applicable ACA, COBRA, ERISA, HIPAA and Section 125 requirements.
Manage broker, carrier and vendor relationships, service levels, contracts and issue escalation.
Serve as the primary administrator for Highwire’s 401(k) plan.
Partner with the plan recordkeeper, third-party administrator, Finance and payroll to ensure accurate data, timely contribution remittance and strong plan controls.
Lead annual compliance testing, census preparation, required notices and other plan governance activities.
Own the execution of the annual 401(k) audit.
Support Form 5500 preparation and filing and ensure audit or compliance findings are resolved promptly.
Monitor regulatory and plan developments and recommend improvements.
Oversee end-to-end leave-of-absence administration for Highwire’s multistate workforce.
Provide clear, compassionate and consistent guidance to employees and managers throughout the leave process.
Coordinate documentation, required notices, payroll, benefit deductions, disability payments, job protection and return-to-work requirements.
Partner with employees, managers, payroll, benefit carriers and external administrators to ensure leaves are handled accurately, promptly and compliantly.
Maintain confidential leave records, monitor timelines and identify issues requiring escalation.
Track leave trends and use insights to improve employee communication, administration and program effectiveness.
Build and advance Highwire’s people analytics capability, including dashboards, reporting and insights.
Define and monitor key measures across headcount, labor cost, turnover, retention, engagement, promotions, performance, workforce composition, recruiting, benefits and leave.
Analyze complex datasets to identify patterns, risks and opportunities.
Partner with People and Finance leaders on headcount planning, labor forecasting, compensation analysis, workforce cost modeling and scenario planning.
Create clear and compelling data narratives and visualizations for senior leaders.
Establish consistent metric definitions, reporting standards and data governance practices.
Protect the confidentiality and integrity of employee data.
Own payroll-related configuration, reporting, workflows and integrations within Rippling.
Partner with internal system owners and external vendors to maintain data integrity across Highwire’s broader People technology ecosystem.
Optimize workflows, permissions, reporting and automation across payroll, benefits, leave administration and the employee lifecycle.
Establish data standards, standard operating procedures and quality controls across People systems and processes.
Conduct regular audits and resolve discrepancies across People, payroll, benefits, vendor and Finance records.
Evaluate technology and process opportunities and lead implementations.
Equip People team members, managers and employees to use systems and processes effectively.
Lead complex, cross-functional initiatives with strong project management, stakeholder alignment and change communication.

Requirements

At least seven years of progressive experience across multistate payroll, payroll tax, benefits, leave administration, HR systems, people analytics and People–Finance operations.
Direct, hands-on experience processing and administering multistate payroll through Rippling is required.
Experience managing a payroll-provider relationship.
Deep knowledge of multistate payroll and payroll tax requirements.
Demonstrated experience leading benefits plan design, renewals, financial analysis, administration, compliance and employee communication.
Hands-on experience administering a 401(k) or other qualified retirement plan and executing annual plan audits, compliance testing and Form 5500 support.
Experience overseeing multistate leave administration and coordinating statutory, company, disability, payroll and benefits requirements.
Advanced people analytics capability.
Strong financial acumen and experience partnering with Finance or Accounting on reconciliations, general ledger activity, audits, forecasting and workforce cost analysis.
Advanced proficiency in Excel or Google Sheets.
Strong HR systems expertise.
Excellent written and verbal communication skills.
Exceptional judgment, organization and attention to detail.
Certified Payroll Professional (CPP) certification is preferred.
Experience working in a professional services, agency, private equity-backed or similarly fast-paced, distributed organization is preferred.
Experience supporting mergers and acquisitions is preferred.
Experience evaluating or administering self-funded or level-funded health plans is preferred.
Experience leading payroll, benefits, HRIS or vendor implementations is preferred.

Skills

Payroll processing
Payroll tax administration
Benefits administration
401(k) administration
Leave-of-absence administration
People analytics
HR systems management
Rippling
Excel
Google Sheets
Project management
Communication

Location

Remote
New York, NY (Hybrid)
San Francisco, CA (Hybrid)

Work Type

Remote
Hybrid

Experience Level

Senior Manager
At least seven years of experience

Education Level

Bachelor’s degree in human resources, business, finance, accounting, analytics or a related field, or equivalent professional experience.

Salary/Compensations

$100,000 to $125,000

Benefits

Medical coverage
Dental coverage
Vision coverage
401(k) matching
Generous paid time off
Flexible hybrid work model
Extended summer and winter breaks
Early log-off on Fridays
Commuter benefits
Annual Growth Mindset stipend
Monthly technology reimbursement
Wellness benefit program
501c3 donation matching program
Mentorship opportunities
Professional development opportunities
Monthly recognition and team celebrations
Employee referral bonuses
New business referral bonuses
Quarterly Highwire events and team gatherings
Dog-friendly office environment

About the Company

Highwire is a strategic marketing communications agency at the intersection of innovation and industry.
We partner with ambitious companies and established brands to navigate complexity, lead markets, and grow with purpose.
Our integrated expertise spans strategic marketing and communications, corporate reputation, creative, and insights.
We deliver bold ideas and measurable impact across B2B technology, healthcare, cybersecurity, energy, professional and financial services.
Highwire believes that storytelling fuels transformation and that impactful stories represent all voices and perspectives.
We foster an inclusive environment where everyone can feel safe, celebrated and worthy.
Our people-first culture is driven by four core values: Team Empowerment, Growth Mindset, Inclusion Always, and Fierce Distinction.
We’re looking for individuals with big ideas, strong opinions, and the energy to bring them to life.
We offer an award-winning culture and an exciting, growing business where you can make a real impact.

Equal Opportunity

We ensure that every Highwire Walker has the requisite support to soar in their careers.
Our commitment to diversity, inclusion and belonging is foundational and embedded in our business and culture.
We aspire to change our industry and build a better future for all.
A supportive, inclusive, and collaborative workplace where you can grow and do your best work.