Vice President, Strategy & Business Operations

Five9•San Ramon, CA

4d•Hybrid

About The Position

The Vice President, Strategy & Business Operations owns Five9's integrated corporate plan and the investment decisions that flow from it. The role reports to the EVP, Transformation & Strategy and leads one of three functions in the organization, alongside the Transformation Office and Corporate Development & Integration. The mandate spans the full arc from strategy setting to execution: defining where the company plays and how it wins, setting the financial ambition behind that direction, translating it into an integrated plan and a ranked set of investments, and holding the operating cadence that keeps execution honest against it. This role is accountable for the entire range from strategy setting to execution. The ideal candidate is an operator who can set direction and live with the consequences, comfortable presenting to a board one week and reconciling it against a functional plan the next. You will partner with the CEO, the CFO, the Chief Product Officer, the Chief Sales Officer, and their teams. This is a small, senior team, expected to operate as an AI-native function. Capacity will be derived from agentic workflows and rotating principals, rather than headcount. Five9's Business Technology organization supports internal AI initiatives with sanctioned platforms, data access, and connectors.

Requirements

10+ years of combined experience across top-tier management consulting and corporate strategy or business operations at a technology company, including owning outcomes.
Experience leading a strategy, business operations, or corporate development function.
Direct exposure to CEO, CFO, and Board audiences.
Strong financial fluency: long-range planning, return-based investment allocation, unit economics, Rule-of-40 mechanics, and scenario and sensitivity modeling.
Practical proficiency with AI tools and a developed point of view on their application to strategy and business operations.
Demonstrated ability to translate high-level corporate ambition into scalable AI and agentic automation frameworks.
Comfort operating on imperfect data, with the judgment to know when an answer is defensible for an executive audience.
Excellent executive communication skills, including creating board and executive-staff materials on compressed timelines.
Enterprise SaaS background.
MBA or equivalent advanced degree is highly recommended.

Nice To Haves

Hands-on experience designing agentic workflows (orchestration, retrieval over unstructured internal content, tool use, human-in-the-loop review) is highly recommended.
Track record of building or redesigning a planning or investment-allocation process jointly with an FP&A organization is highly recommended.
Contact center, customer experience, unified communications, or adjacent cloud infrastructure experience highly recommended.
Exposure to M&A strategy, diligence, or post-merger integration is a plus.

Responsibilities

Strategy setting and financial ambition: Set the company strategy and financial ambition, including the balance of growth and profitability, for executive team and Board approval. Own the long-range plan in partnership with FP&A, providing a multi-year business outlook based on a shared financial model, refreshed cyclically. Enable the strategy across the company so functional leaders can execute it without re-interpretation.
Integrated planning and functional interlock: Maintain a single integrated plan, reconciled with FP&A, reflecting the chosen balance of growth and profitability. Drive shared interlock on topline targets and OKRs to ensure functional plans align. Own the company OKR architecture, including definition, cascade, and discipline to maintain a concise set.
Investment and efficiency portfolio: Build a costed, return-ranked investment portfolio in partnership with FP&A, aligning allocation with strategy. Integrate the efficiency portfolio with the growth portfolio for deliberate trade-offs. Set criteria for build, buy, and partner decisions for Corporate Development, ensuring consistent measurement of organic and inorganic options. Develop the commercial and economic rationale for the AI portfolio and integrate it into company planning.
Bookings targets and market view: Translate geography and product mix into committed bookings targets for Go-to-Market, Product, and Finance. Maintain a current market view, including competitor capabilities, agentic positioning, and industry trends, using an AI-enabled pipeline. Incorporate an outside-in perspective to test the plan against the market.
Operating cadence and decision forums: Define and standardize QBR and MBR cadences with a consistent structure and decision-support materials. Establish cross-functional interlocks across Go-to-Market, Product, and Engineering to convert disagreements into committed trade-offs. Build recurring mechanisms for early course correction when the plan diverges from reality.
Running the function AI-natively: Operate Strategy & Business Operations as an AI-native function, determining how work is done, where agentic workflows replace manual effort, and what the team focuses on. Build recurring analysis as durable pipelines (market intelligence, variance analysis, executive reporting) with clear ownership and quality standards. Increase analytical throughput of a small senior team through tooling and rotating secondees. Develop the team to manage agents, focusing on scoping, supervising, and quality-checking agentic work for scalable throughput.

Benefits

Health, dental, and vision coverage, beginning on the first day of employment.
Five9 covers 100% of the employee portion of the health, dental and vision coverage and shares a high portion of the dependent cost.
Short & Long-Term Disability
Basic Life Insurance
401k saving plan with employer matching.
Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching and self-guided mindfulness exercises for all covered employees and their covered dependents.
Generous employee stock purchase plan.
Paid Time Off
Company paid holidays
Paid volunteer hours
12 weeks paid parental leave.
Annual performance bonus
Stock
Other applicable incentive compensation plans.