Greenhouse ·
contractDirector, M&A People Strategy & Integration
Okta · Chicago, Illinois
Okta, a provider of identity and access management solutions, is seeking a Director of M&A People Strategy & Integration to lead the human‑capital side of its merger and acquisition activity. In this individual‑contractor role you will own the end‑to‑end people due‑diligence process for target companies, analysing organisational structures, compensation packages, workforce demographics and compliance risks to inform valuation and deal terms. You will design and maintain scalable integration playbooks that outline Day 1 readiness and first‑100‑day goals, coordinating with Legal, Finance, IT and the broader People team on HRIS migrations, payroll cut‑overs, benefit vendor consolidations and equity harmonisation. Post‑close you will drive change‑management communications, retention initiatives and talent‑risk monitoring to preserve culture and minimise attrition. During quieter periods you will also manage strategic Total Rewards projects. The position suits candidates with seven to ten years of M&A‑focused HR or people‑integration experience, preferably from consulting or corporate environments, who are fluent in global employment law, compensation and benefits design, and comfortable driving cross‑functional workstreams without direct line‑management authority.
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. Empathy & Discretion: High emotional intelligence, discretion, and t
| Role | Director, M&A People Strategy & Integration |
|---|---|
| Company | Okta |
| Location | Chicago, Illinois |
| Type | contract |
| Compensation | Not disclosed |
| Posted | 2026-10-12 |
| Deadline | Rolling |
Typical process for this type of role
A general guide — the exact steps for this specific listing may vary; check the original posting for details.
- 1ApplicationSubmit your resume through the apply link.
- 2ScreeningRecruiter reviews your background against the role.
- 3AssessmentA technical test, assignment, or coding round, depending on the role.
- 4Interview(s)One or more rounds with the hiring team.
- 5OfferOffer letter with compensation and start date.
Before you apply
0/4About Okta
Okta, Inc. is an Identity-as-a-Service (IDaaS) company founded in 2009 and based in San Francisco. The company provides identity and access management solutions for workforces, customers, and AI agents. Its offerings include the Okta Platform for governance and the Auth0 Platform for authentication. Okta’s services are designed to secure human and machine identities, helping organizations manage access across their digital ecosystems. The company serves a diverse client base, including major government agencies and two-thirds of the Fortune 100, supporting thousands of organizations globally in securing their business operations and digital infrastructure.
More at Okta
Other jobs at Okta
- Senior Product Designer - Identity Threat Protection/essential Security · Toronto, Ontario, Canada
- Staff SRE- (python, K8s, AWS, Terraform) · Bengaluru
- Staff Product Designer - UI Platform · Bellevue, Washington; Chicago, Illinois; New York, New York; Toronto, Ontario, Canada; Washington, DC
- Design Operations Specialist, Auth0 · Chicago, Illinois
- Software Architect, AI Systems And Platform · San Francisco, California
Explore Related Placements
// similar opportunities
You might also like
Senior Director, R&D Planning & Operations
Okta
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 th...
Program Manager, Accounting Operations & Strategy
Anthropic
About Anthropic Anthropic’s mission is to create reliable, interpretable, and steerable AI systems. We want AI to be safe and beneficial for our users and for s...
Manager, People Systems (workday)
Justworks
Who We Are At Justworks, you’ll enjoy a welcoming and casual environment, great benefits, wellness program offerings, company retreats, and the ability to inter...
Data Center Strategy - Edge
Cloudflare
About Us At Cloudflare, we are on a mission to help build a better Internet. Today the company runs one of the world’s largest networks that powers millions of ...
Rack Integration Operations Engineer
Cloudflare
About Us At Cloudflare, we are on a mission to help build a better Internet. Today the company runs one of the world’s largest networks that powers millions of ...
Strategic Deals Lead, Compute & Infrastructure
Anthropic
About Anthropic Anthropic’s mission is to create reliable, interpretable, and steerable AI systems. We want AI to be safe and beneficial for our users and for s...