Senior Director, R&D Planning & Operations

Okta•Chicago, IL

1d•$258,000 - $355,000•Hybrid

About The Position

Okta is seeking a seasoned operations leader to run the financial and workforce operating engine for its Product & Technology organization, a 2,000+ person R&D function spanning the Okta Platform (ORD) and Auth0. The role owns the budget and workforce strategy components of the R&D Operating Plan, program-spend and budget governance, financial compliance, vendor operations, headcount governance, annual goal-setting, and the operating cadence used to track R&D performance. It combines deep engineering finance operations experience with the organizational judgment to translate executive strategy into a defensible budget and credible hiring plan. The role sits within Okta's R&D organization and reports to the Head of Strategy & Operations and Chief of Staff to the President of Okta R&D. It is hub-based in San Francisco, Seattle, or Chicago; candidates must live within commuting distance of one of those offices and are expected to work in the office multiple days each week. The role leads a team with five direct reports and includes hiring and developing Director-level leaders. The leader will own the R&D budget and workforce strategy; direct budget governance and executive reviews; evolve the R&D P&L framework; model and optimize AI token spend; lead engineering cost modeling and margin analysis; oversee R&D financial compliance; build a Snowflake-based expense data platform; manage headcount, contingent workers, and vendors; and partner with Product and Engineering leadership on annual goals and OKRs. The role is also expected to apply AI to financial analysis, dashboards, and workflow automation and establish AI fluency as a core team capability.

Requirements

12+ years of work experience, including 6+ years leading business operations, R&D/engineering operations, or FP&A functions within a technology company.
Demonstrated ownership of an engineering or R&D budget at scale, including annual planning, in-year governance, variance management, and executive budget review.
Proven ownership of workforce planning and headcount governance in close partnership with Recruiting and Finance.
Experience managing a vendor portfolio, including contract negotiation and renewal, SLA management, and capacity planning.
Hands-on experience with Capitalized Software accounting and R&D tax credit programs in the US and/or Canada.
Strong understanding of B2B SaaS business models and engineering cost structures.
Track record of building and developing high-performing operations teams, including hiring and developing Director-level leaders.
Extensive experience navigating complex data sets and operating amid ambiguity when clean data is unavailable.
Demonstrated use of AI in finance and operations work, including analysis, reporting, dashboard generation, and workflow automation, with a clear point of view on future applications.
Must live within commuting distance of Okta's San Francisco, Seattle, or Chicago office and work from the office multiple days each week.
Must be on US soil, defined as the 50 states, the District of Columbia, or outlying areas of the United States under FAR 2.101; there is no citizenship requirement.

Nice To Haves

Experience operating across multiple product units or post-acquisition entities with distinct financial and operational systems.
Familiarity with Snowflake or comparable experience building financial data platforms and self-service reporting.
Experience modeling or governing consumption-based spend, such as cloud infrastructure or AI/LLM token usage.
Experience with global workforce and location strategy, including India-based engineering centers.
Understanding of the B2B enterprise technology space, specifically Enterprise Security.
Experience running an annual goal-setting or OKR process for a technology organization, including the review cadence that tracks progress.
Prior experience in FP&A, management consulting, or a central strategy and operations function.
MBA, or an undergraduate degree with a concentration in Finance, Economics, Statistics, or Engineering.

Responsibilities

Own the budget and workforce strategy components of the R&D Operating Plan, translating corporate strategy and the long-range plan into an annual plan across ORD and Auth0.
Direct R&D budget governance, including program-spend oversight, variance reporting, fiscal discipline, and executive-level budget reviews with the President of Okta R&D and Finance leadership.
Own and evolve the P&L framework for R&D lines of business, providing executive leadership with cost and investment data for portfolio decisions.
Model, govern, and optimize AI token spend across Product & Technology; establish cost baselines and forecasting, develop a return-measurement framework, and partner with engineering leaders on efficiency.
Lead engineering cost modeling and partner with FP&A and Deal Desk on account-specific margin analysis supporting pricing, packaging, and large-deal decisions.
Own R&D financial compliance, including Capitalized Software entries and US/Canada R&D tax credit capture.
Build and own the Product & Technology expense data platform on Snowflake to support line-of-business cost distribution and self-service cost visibility for engineering leaders.
Set fiscal-year workforce strategy with Recruiting leadership, including headcount governance, real-time allocation tracking, backfills, organizational growth mapping, and location strategy.
Own the contingent workforce program, including contractor and agency lifecycle, capacity, and spend.
Own R&D vendor operations, including third-party relationships, capacity management, contract renewals, and performance SLAs.
Refine financial and workforce operating processes to reduce friction and support efficient organizational growth.
Partner with Product and Engineering leadership to develop fiscal-year R&D goals and OKRs, and run monthly and quarterly reviews to gauge performance.
Apply AI to financial analysis, dashboard generation, and workflow automation, and make AI fluency core to how the team works.
Build, mentor, and develop the operations team, including hiring and developing Director-level leaders.