Senior Director, People Operations

The Opportunity

This is a builder role at a company that is running at full speed. Pindrop has the people, the product, and the market momentum. What we need now is the operational backbone that matches that ambition- an HR Operations function that is not just keeping the lights on, but actively enabling the business to scale with precision, compliance, and speed.

The Senior Director, People Operations will own the full scope of people operations infrastructure: our HRIS, payroll, domestic and international benefits, immigration, compliance, audits, and the standard operating procedures that make all of it repeatable and scalable. This person will be the operational engine of the People team; the person who makes sure that accuracy and urgency are not in conflict, and that the People function shows up as a genuine business partner to Finance, Legal, IT, and the broader organization.

What You’ll Do

Standard Operating Procedures & Process Infrastructure

• Lead the team that will design, document, and maintain comprehensive SOPs for every HR Operations process from onboarding and offboarding to payroll changes, benefits enrollment, and immigration filings
• Build a process infrastructure that can survive personnel changes, scale with headcount growth, and be audited by external parties at any time
• Identify workflow inefficiencies and lead continuous improvement initiatives, the goal is always to reduce manual work, eliminate error risk, and create repeatable operational excellence
• Automate where possible, and own the intersection between HR technology and HR process

Cross-Functional Partnership

• Be a genuine business partner to Finance, ensuring payroll data, headcount reporting, and benefits costs are accurate, timely, and presented in a format that supports financial planning and decision-making
• Partner with Legal on employment matters, immigration filings, compliance questions, and any HR-related risk exposure
• Collaborate with IT and Security on system access, data governance, and any HR systems that intersect with the company's security posture
• Work closely with the HRBP team to ensure that operational processes support, not slow down, the employee experience and people programs
• Serve as the internal subject matter expert when customer or investor due diligence requires HR and people operations documentation

HRIS Ownership — UKG Ready Implementation and Optimization

UKG Ready is our system of record for headcount, compensation, onboarding, and reporting. It is currently under-optimized, causing downstream data quality issues that affect data accuracy, finance reporting, and compliance. You will own changing that.

• Lead the ongoing optimization of UKG Ready- including module configuration, workflow builds, system integrations, and self-service functionality
• Serve as the internal SME and escalation point for all UKG-related questions, issues, and enhancements
• Build and maintain system integrations between UKG and downstream tools including payroll, benefits carriers, and finance systems
• Own data integrity- audits, error correction, quality controls, and reporting accuracy
• Design and deliver manager and employee training on HRIS self-service functionality so the system works for the whole organization, not just HR
• Partner with AI Leaders to build AI-enabled self-service agents and automations where they reduce friction and improve the employee experience
• Develop and maintain a comprehensive dashboard and system reporting suite that gives Finance, ELT, and functional leaders real-time visibility into people data

Payroll

• Oversee the Payroll and Benefits Manager and end-to-end payroll process — domestic and international — with zero tolerance for errors and an obsessive attention to accuracy
• Ensure payroll is fully integrated with HRIS, benefits, and Finance reporting so there is a single source of truth for compensation data
• Build and maintain payroll SOPs that can survive personnel changes and scale with headcount growth
• Merit & Incentive Cycles: Managing the operational execution of annual merit cycles, bonus calculations, and market benchmarking data

Domestic & International Benefits

• Own the full benefits program- medical, dental, vision, 401k, life, disability, and ancillary benefits- from vendor selection and renewal through employee communication and ongoing administration
• Manage international benefits programs across all Pindrop employee populations globally, ensuring compliance with local requirements and competitive positioning in each market
• Lead the annual benefits renewal process including benchmarking, carrier negotiations, and cost modeling in partnership with Finance
• Own 401k plan administration and the annual 401k audit, ensuring the plan is compliant, well-documented, and employees have visibility into their options
• Build a total rewards communication strategy so employees understand the full value of their compensation and benefits, not just their base salary

Compliance, Audits & Immigration

• Own all state and federal HR compliance oversight, including multi-state employment law, annual filings, EEO-1, VETS-4212, ACA reporting, and any jurisdiction-specific requirements as Pindrop grows
• Oversee immigration- H-1B, L-1, green card sponsorships, and all related filings- in partnership with immigration counsel, ensuring employees and their families are supported through every step of the process
• Own customer compliance audits, preparing all required people and HR documentation in response to enterprise customer security and compliance audit requests
• Manage benefit audits including the annual 401k audit end-to-end- coordination with auditors, documentation preparation, and remediation of any findings
• Oversee the design and deploy company-wide compliance training,  including harassment prevention, data privacy, security awareness, and any regulatory requirements, and maintain completion records
• Build and maintain an HR compliance calendar so nothing falls through the cracks as the organization scales
• Pre-Employment Operations & Onboarding Governance: Direct the strategy, compliance, and SLA performance of pre-employment operations (background checks, pre-hire screening, and onboarding workflows), guiding the People Systems Specialist who executes day-to-day delivery.

Team Leadership

• Lead, develop, and grow the HR Operations team, currently including a Operations Specialist, Sr. Manager, Payroll and Benefits Manager, and any office facilities personnel as the function scales with the business
• Build a team culture where accuracy and urgency are not in conflict,  where the standard is high, the pace is fast, and the team is proud of the work they put out
• Develop team members' skills and career trajectories with the same intentionality you bring to your own work

Your skill-set

You are:

• 7+ years of progressive HR Operations experience, with at least 5 years in a senior leadership role at a scaling technology company
• Deep, hands-on HRIS expertise, UKG Ready experience is strongly preferred. You have implemented, configured, and optimized an HRIS before, not just used one
• Proven ownership of payroll, multi-state compliance, and benefits administration,  including international benefits programs and 401k plan administration
• Direct experience managing immigration programs including H-1B and green card sponsorships in partnership with outside counsel
• Experience managing external audits, including 401k audits, customer compliance audits (SOC 2, ISO, or equivalent), and state/federal regulatory filings
• A track record of building compliance training programs that actually change behavior, not just check a box
• Exceptional cross-functional partnership skills-  you have worked closely with Finance, Legal, and IT and have earned their trust as a subject matter expert, not just a service provider
• Strong SOPs discipline- you build documentation that outlasts the person who built it
• The operational mindset that accuracy and urgency belong together, you do not sacrifice one for the other

Strongly Preferred:

• Experience at a company scaling for growth- you know what breaks at this stage and how to get ahead of it
• Familiarity with AI-enabled HR tools and a genuine curiosity about automation.  You are looking for ways to use technology to reduce manual work, not reasons to avoid it
• Experience designing total rewards communication strategies and building employee-facing compensation and benefits transparency
• PHR, SPHR, SHRM-CP, or SHRM-SCP certification preferred but not required

Who you are

• Runs toward complexity, not away from it. Sees a messy HRIS and a compliance gap and thinks about how to fix it, not how to explain why it is hard.
• Holds an incredibly high bar for accuracy, and does not see that as being in conflict with moving fast. Has figured out how to do both simultaneously.
• Shows up as a business partner, not a process administrator. Understands what Finance needs from payroll data and gives it to them in the format they need, not the format that is easiest to produce.
• Is a builder. Has done this before in an environment where the infrastructure did not yet exist, and is energized by the opportunity to build it right this time.
• Communicates with clarity and confidence at all levels of the organization, equally comfortable presenting to the CEO, running a benefits enrollment meeting, or working through the technical details of a UKG integration with IT.

What’s in it for you

This role will be evaluated against outcomes, not activity:

• UKG Ready fully optimized and integrated within 6 months, with measurable improvement in data quality, payroll accuracy, and finance reporting reliability
• Zero compliance findings in state, federal, or customer audits attributable to HR Operations gaps
• Payroll error rate at or below industry benchmark (measured monthly)
• All SOPs documented and accessible within 120 days; updated on a defined cadence thereafter
• Immigration cases managed on-time with no lapses in employee work authorization
• Company-wide compliance training completion at 95%+ within 60 days of program launch
• Finance, Legal, and HRBP partners rate HR Operations as a strong cross-functional partner in quarterly stakeholder surveys

Why Pindrop, Why Now

• HR Operations is taken seriously here you will have the organizational support, and the CPO backing to build it right
• The scope is real. You will own immigration, international benefits, customer audits, and HRIS implementation simultaneously-  this is not a narrow administrative role
• You will be building something that lasts. The infrastructure you design will support a $300M organization
• The culture values accuracy and urgency in equal measure; you will fit in here if you hold both standards simultaneously
• AI-native environment.  Pindrop's product is built on AI, and we expect the same innovation mindset in how we run our internal operations