Director, M&A People Strategy & Integration

Okta•Chicago, IL

5d•Onsite

About The Position

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.

Requirements

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.
Proven ability to drive joint workstreams with Legal, Finance/Payroll, IT, and HR functional leads without direct line management authority.
Strong fluency in global/domestic employment law fundamentals, compensation/benefits harmonization, equity compensation, and HRIS systems migrations.
Solid skills in workforce data modeling, salary/benefit side-by-side mapping, and workforce financial synthesis.
Bachelor’s degree in Human Resources, Business Administration, Organizational Development, or related field; Master's or SPHR/SHRM-SCP certification preferred.
Adept at aligning disparate stakeholder priorities across Legal, Finance, IT, and HR teams toward tight deal deadlines.
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.
Ability to bring structure, playbooks, and clarity to ambiguous, rapidly moving transaction environments.
High emotional intelligence, discretion, and tact when handling sensitive employee information and high-stress organizational changes.

Responsibilities

Lead HR and talent due diligence across target organizations, analyzing organizational structures, total rewards programs, workforce demographics, employment contracts, and labor compliance risks.
Evaluate key talent retention risks, leadership team capabilities, organizational design, critical skills gaps, and cultural alignment to inform valuation, deal terms, and integration strategies.
Partner with Finance to analyze workforce cost structures, including compensation, benefits, harmonization costs, retention packages, severance exposure, and synergy targets.
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.
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.
Collaborate with TD&I and People Ops to manage HR Information System (HRIS) migrations, identity/access management transitions, payroll cutovers, and benefit vendor consolidations.
Partner with Total Rewards to design side-by-side benefit maps, compensation alignment structures, equity conversions, and stay/retention bonus programs for acquired employees.
Partner with Internal Comms and Legal to design Day 1 announcement communications, offer letter rollouts, onboarding experiences, and executive town halls.
Track, monitor, and support key talent post-close, driving initiatives that preserve company culture and minimize unwanted attrition.
During lower deal volume periods, drive and project-manage strategic, high-visibility initiatives across the broader Total Rewards organization.