Director, M&A People Strategy & Integration

Okta · Chicago, Illinois

  • Senior
  • Full-time
  • $219,000 – $301,000
  • Posted 2026-10-12
  • Confirmed live on 13 October 2026

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Job description

Secure Every Identity, from AI to Human

Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence.

This is an opportunity to do career-defining work. We're all in on this mission. If you are too, let's talk.

We are looking for a strategic, hands-on Director, M&A People Strategy & Integration to lead the human capital lifecycle for our deal pipeline. In this high-impact individual contributor role, you will design and execute due diligence and post-merger integration strategies centered on talent, organizational design, compensation, and cultural alignment.

You will serve as the primary human resources quarterback during transactions, partnering closely with internal People team functional leads (Talent Acquisition, Total Rewards, People Operations) and collaborating with Corporate Development, Legal, Finance, and IT to ensure seamless operational continuity, compliance, and employee experience from announcement through post-close integration.

Key Responsibilities

People Due Diligence & Risk Assessment

• Diligence Execution: Lead HR and talent due diligence across target organizations, analyzing organizational structures, total rewards programs, workforce demographics, employment contracts, and labor compliance risks.

• Talent & Cultural Assessment: Evaluate key talent retention risks, leadership team capabilities, organizational design, critical skills gaps, and cultural alignment to inform valuation, deal terms, and integration strategies.

• Cost & Synergy Modeling: Partner with Finance to analyze workforce cost structures, including compensation, benefits, harmonization costs, retention packages, severance exposure, and synergy targets.

Cross-Functional Integration Planning & Execution

• Integration Playbook & Strategy: Build and maintain scalable People M&A playbooks, defining key deliverables across HR, Legal, Finance, and IT for Day 1 readiness and First 100 Days goals.

• Legal & Compliance Alignment: Partner with Legal to manage employment contract transfers, equity roll-overs, restrictive covenants, immigration/visa transfers, works council/labor relations requirements, and employment law compliance.

• People Ops & Systems Transition (with TD&I & Finance): Collaborate with TD&I and People Ops to manage HR Information System (HRIS) migrations, identity/access management transitions, payroll cutovers, and benefit vendor consolidations.

• Total Rewards Harmonization: Partner with Total Rewards to design side-by-side benefit maps, compensation alignment structures, equity conversions, and stay/retention bonus programs for acquired employees.

Employee Experience & Change Management

• Change & Communications: Partner with Internal Comms and Legal to design Day 1 announcement communications, offer letter rollouts, onboarding experiences, and executive town halls.

• Retention Strategy: Track, monitor, and support key talent post-close, driving initiatives that preserve company culture and minimize unwanted attrition.

Stretch Opportunities & Total Rewards Impact: M&A activity naturally ebbs and flows. During lower deal volume periods, you will drive and project-manage strategic, high-visibility initiatives across the broader Total Rewards organization.

Qualifications & Requirements

• Experience: 7–10+ years in M&A HR and Talent strategy, People Integration, or M&A Human Capital consulting (Big 4 / strategic advisory), with end-to-end deal lifecycle management.

• Cross-Functional Expertise: Proven ability to drive joint workstreams with Legal, Finance/Payroll, IT, and HR functional leads without direct line management authority.

• Technical HR Acumen: Strong fluency in global/domestic employment law fundamentals, compensation/benefits harmonization, equity compensation, and HRIS systems migrations.

• Data-Driven Analysis: Solid skills in workforce data modeling, salary/benefit side-by-side mapping, and workforce financial synthesis.

• Education: Bachelor’s degree in Human Resources, Business Administration, Organizational Development, or related field; Master's or SPHR/SHRM-SCP certification preferred.

Key Competencies

• Cross-Functional Leadership: Adept at aligning disparate stakeholder priorities across Legal, Finance, IT, and HR teams toward tight deal deadlines.

• Proactive "Driver" Skillset: High-agency operator with a strong bias for action; proven ability to take full ownership of deal outcomes, push cross-functional workstreams forward, hold partners accountable to tight deal timelines, and solve complex roadblocks with urgency.

• Structured Problem-Solving: Ability to bring structure, playbooks, and clarity to ambiguous, rapidly moving transaction environments.

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