Senior Director, R&D Planning & Operations

Okta•Chicago, WA

20h•Onsite

About The Position

Okta is seeking an experienced 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 team owns budget and workforce strategy components of the R&D Operating Plan, program spend and budget governance, financial compliance—including Capitalized Software and R&D tax credit capture—vendor operations, and headcount governance in partnership with Recruiting. It also manages annual goal setting and the operating cadence for tracking R&D performance against goals. The role requires deep engineering finance operations expertise and the organizational judgment to translate executive strategy into a defensible budget and credible hiring plan. It is based in San Francisco, Seattle, or Chicago, and candidates must live within commuting distance of one of those offices. The leader is expected to work from the office multiple days each week and will report to the Head of Strategy & Operations and Chief of Staff to the President of Okta R&D. The position has five direct reports. The role owns the R&D budget and workforce strategy, financial and vendor operations, engineering cost modeling, and the P&T expense data platform on Snowflake. It also leads fiscal-year goals and OKRs, reviews organizational performance, and applies AI to financial analysis, reporting, dashboard generation, and workflow automation. The successful leader will build and develop the operations team, including hiring and developing Director-level leaders. Okta describes this as an opportunity to own the financial and workforce operating infrastructure for a large R&D organization, shape its operating model, and define how the organization budgets for, measures returns on, and optimizes AI spending. The employee must be on US soil, defined in the posting as the 50 states, the District of Columbia, or US outlying areas under FAR 2.101 P7363. The annual base salary range for candidates located in California (excluding the San Francisco Bay Area), Colorado, Illinois, New York, and Washington is $258,000–$355,000. Okta also offers equity where applicable, bonus, and benefits including health, dental and vision insurance, 401(k), flexible spending account, and paid leave, including PTO and parental leave, according to applicable plans and policies.

Requirements

12+ years of work experience, including 6+ years leading business operations, R&D or 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 working 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 perspective on future applications.
Must live within commuting distance of the San Francisco, Seattle, or Chicago office and work from the office multiple days each week.
Must be on US soil, as defined in the posting.

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 spending, such as cloud infrastructure or AI/LLM token usage.
Experience with global workforce and location strategy, including India-based engineering centers.
Understanding of B2B enterprise technology, specifically Enterprise Security.
Experience running an annual goal-setting or OKR process for a technology organization, including progress-review cadence.
Prior experience in FP&A, management consulting, or a central strategy and operations function.
MBA, or an undergraduate degree concentrated 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 for a 2,000+ person organization, including program spend oversight, variance reporting, fiscal discipline, and executive budget reviews.
Own and evolve the P&L framework for R&D lines of business and provide cost and investment data for portfolio decisions.
Model, govern, and optimize AI token spending across Product & Technology; establish cost baselines and forecasting, create 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 for 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 P&T expense data platform on Snowflake to support line-of-business cost distribution and self-service cost visibility.
Set fiscal-year workforce strategy with Recruiting leadership, including headcount governance, 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 performance reviews.
Apply AI to financial analysis, dashboard generation, and workflow automation, and establish AI fluency as a core team practice.
Build, mentor, and develop the operations team, including hiring and developing Director-level leaders.