Senior Manager, People Operations (Payroll, Benefits & Analytics) at Highwire – Connecticut | Jobyssey

The Senior Manager, People Operations is a highly experienced, hands-on leader responsible for three critical areas of Highwire’s People function: payroll and payroll tax; benefits and retirement programs; and people analytics.

This role sits at the intersection of People, Finance and business operations. It translates complex workforce and financial data into actionable insights, strengthens the controls connecting People and Finance, and designs benefits programs and communication strategies that employees can understand and value.

The ideal candidate combines deep technical expertise with strong business judgment, exceptional attention to detail and the ability to move fluidly between strategy and execution. This person will serve as a trusted partner to People leadership, Finance, senior leaders, brokers, vendors and employees while continuously improving the systems and processes that support our growing, multistate workforce.

Key Responsibilities

Payroll, Tax and Financial Operations

Own the end-to-end administration of accurate, timely and compliant semi-monthly payroll for a multistate workforce, including regular and off-cycle payrolls, variable compensation, deductions, garnishments and employee changes.
Serve as Highwire’s internal payroll subject-matter expert and primary administrator for Rippling, our payroll provider, including payroll configuration, employee and tax setup, reporting, integrations and issue resolution.
Manage the relationship with Rippling, monitor service performance and coordinate the timely resolution of payroll, tax, system and integration issues.
Lead federal, state and local payroll tax administration, including registrations, filings, notices, amendments, quarter-end and year-end processing, W-2s and jurisdictional requirements.
Maintain rigorous payroll controls, review protocols, documentation and audit trails that reduce risk and ensure data accuracy.
Research and resolve complex payroll, tax, timekeeping and pay-related matters with urgency, discretion and clear employee communication.
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, system configurations and employee communications.

Benefits Strategy, Plan Design and Communication

Lead the strategy, design, financial evaluation and administration of Highwire’s health, welfare and related benefit programs, balancing employee value, market competitiveness, cost and organizational priorities.
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 thoughtful program enhancements.
Develop and execute a year-round benefits communication and education strategy, including open enrollment, plan changes, decision-support resources and targeted campaigns.
Translate complex benefit information into clear, accessible and engaging communications that help employees understand and use their programs effectively.
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 while holding partners accountable for performance.

401(k) Administration and Audit Execution

Serve as the primary administrator for Highwire’s 401(k) plan, managing eligibility, enrollment, contributions, loans, distributions, corrections and employee inquiries.
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, including auditor coordination, requested documentation, census and transaction data, reconciliations and issue resolution.
Support Form 5500 preparation and filing and ensure audit or compliance findings are resolved promptly and sustainably.
Monitor regulatory and plan developments and recommend improvements to plan design, administration and employee education.

Leave-of-Absence Administration

Oversee end-to-end leave-of-absence administration for Highwire’s multistate workforce, including federal, state and company-sponsored leaves and disability programs.
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 or additional support.
Track leave trends and use insights to improve employee communication, administration and program effectiveness.

People Analytics and Workforce Insights

Build and advance Highwire’s people analytics capability, including reliable dashboards, recurring reporting and executive-ready insights that connect workforce trends to business performance.
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, moving beyond reporting what happened to explaining why it matters and recommending action.
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 and other stakeholders.
Establish consistent metric definitions, reporting standards and data governance practices that improve confidence in workforce information.
Protect the confidentiality and integrity of employee data in all reporting and analysis.

People Systems and Operational Excellence

Own payroll-related configuration, reporting, workflows and integrations within Rippling, ensuring accurate data, appropriate access and reliable connections with Finance and other People systems.
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 broader 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 that reduce manual work, strengthen controls and improve scalability.
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.

Qualifications

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, including payroll processing, employee and tax setup, deductions, reporting, configuration, integrations and complex issue resolution.
Experience managing a payroll-provider relationship, including vendor performance, service delivery and issue escalation.
Deep knowledge of multistate payroll and payroll tax requirements, including quarter-end and year-end processing.
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, including experience building dashboards, interpreting complex datasets, developing workforce models and presenting actionable recommendations.
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, including complex formulas, pivot tables, lookups, data validation and financial or workforce modeling.
Strong HR systems expertise, including configuration, workflows, integrations, automation, reporting and data governance.
Excellent written and verbal communication skills, including the ability to make technical payroll, benefits and data concepts understandable to employees and senior leaders.
Exceptional judgment, organization and attention to detail, with the ability to manage competing priorities and highly confidential information.
Bachelor’s degree in human resources, business, finance, accounting, analytics or a related field, or equivalent professional experience.

Preferred Qualifications

Certified Payroll Professional (CPP) certification.
Experience working in a professional services, agency, private equity-backed or similarly fast-paced, distributed organization.
Experience supporting mergers and acquisitions, including due diligence and the integration of payroll, benefits, retirement plans, People systems, workforce data and employee communications.
Experience evaluating or administering self-funded or level-funded health plans.
Experience leading payroll, benefits, HRIS or vendor implementations.

What Success Looks Like

Payroll is consistently accurate, timely, well-controlled and compliant.
Payroll tax requirements and filings are managed proactively across all applicable jurisdictions.
Benefits and retirement programs are strategically designed, financially grounded and clearly understood by employees.
Leave cases are managed with accuracy, compliance, consistency and care.
The annual 401(k) audit and other operational audits are completed efficiently, with issues resolved promptly.
Leaders have reliable, decision-ready workforce insights rather than disconnected reports.
People and Finance operate from aligned data, reconciliations and workforce cost assumptions.
People systems and processes scale efficiently while delivering a responsive, high-quality employee experience.

The salary range for this position is $90,000 to $110,000, with the final offer based on a combination of factors, including education, relevant experience, skills, prior training, internal equity, and local geographic market data. This role also includes a competitive benefits package with medical, dental, and vision coverage, 401(k) matching, generous paid time off, and additional perks designed to support your overall well-being and growth. #LI-Remote

About Highwire

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. With integrated expertise in strategic marketing and communications, corporate reputation, creative, and insights, we cut through the noise to deliver bold ideas and measurable impact across B2B technology, healthcare, cybersecurity, energy, professional and financial services, and more.

At Highwire, we believe that storytelling fuels transformation. We know that the most impactful stories represent all voices and perspectives. As a values-driven agency, we foster an inclusive environment where everyone—regardless of age, race/ethnicity, size, shape, gender identity, sexual orientation, religion and different abilities–can feel safe, celebrated and worthy.

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.

Our people-first culture is driven by four core values:

Team Empowerment
Growth Mindset
Inclusion Always
Fierce Distinction

We’re looking for individuals with big ideas, strong opinions, and the energy to bring them to life. If you thrive in an environment that values personal accountability, high standards, and boundless motivation, this is the opportunity for you. Be part of our award-winning culture and contribute to an exciting and growing business where you can make a real impact.

Highwire. Above all.

Our people-first culture is reflected in the meaningful benefits, flexibility, and support we offer:

Competitive salary with merit-based opportunities for growth
Flexible hybrid work model tailored to your schedule and lifestyle
Generous vacation policy, including extended summer and winter breaks
Early log-off on Fridays through our Empower Hours program
401(k) plan with employer matching
Comprehensive medical, dental, and vision coverage, plus FSA options
Paid parental leave benefits
Commuter benefits
Annual Growth Mindset stipend for books, events, or learning experiences
Monthly technology reimbursement
Wellness benefit program for mental and physical health
501c3 donation matching program
Mentorship and ongoing professional development opportunities
Monthly recognition and team celebrations
Employee referral and new business referral bonuses
Quarterly Highwire events and team gatherings
Dog-friendly office environment
A supportive, inclusive, and collaborative workplace where you can grow and do your best work

Location & Work Environment

Highwire offers both remote and hybrid work options, depending on where you live.

Hybrid: Candidates located within commuting distance of our New York, NY or San Francisco, CA offices follow a hybrid schedule, with three in-office days per week.

Remote: We hire for fully remote roles in the following states: California, Colorado, Connecticut, Florida, Georgia, Illinois, Iowa, Kansas, Maryland, Massachusetts, Michigan, New Hampshire, New Jersey, New York, North Carolina, Ohio, Oregon, Pennsylvania, Rhode Island, South Carolina, Tennessee, Texas, Utah, Virginia, Washington, and Washington, D.C..

Please note: We are only able to consider candidates who reside in one of the locations listed above at the time of hire.

Join the Highwire team

If you’re inspired by the opportunity to shape meaningful stories and grow alongside a team that values innovation, accountability, and inclusion, apply below to start the conversation.

Please note: This posting may be used to build our talent pipeline, connect with top professionals in the industry, or extend reach across multiple locations. We welcome all interested candidates to apply and explore opportunities at Highwire!

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