Vice President, Strategy & Business Operations

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. Few roles at Five9 cover that whole range. This one is accountable for it.

The right candidate is not a strategist whose work ends at the recommendation, and not a planning administrator who inherits someone else's strategy and maintains the calendar around it. They are an operator who can set direction and then live with the consequences — someone comfortable presenting a position 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 the organizations they lead.

This is a small and deliberately senior team, and we expect its leader to run it as an AI-native operation. Capacity comes from agentic workflows and from principals rotating in from across the business, rather than from headcount. Five9's Business Technology organization is forward-leaning on internal AI and actively supports citizen-builder-native teams with sanctioned platforms, data access, and connectors, so the tooling you build will have real infrastructure behind it.

Key Responsibilities

Strategy setting and financial ambition

• Set the company strategy and the financial ambition behind it — including the intended balance of growth and profitability, carried with the executive team and the Board.
• Own the long-range plan in partnership with FP&A — the multi-year view of where the business is going, built on a shared financial model and refreshed on a defined cycle rather than rebuilt each time it is asked for.
• Enable the strategy across the company so functional leaders can act on it without re-interpreting it.

Integrated planning and functional interlock

• Maintain one integrated plan, reconciled with FP&A — a single view that reflects the chosen balance of growth and profitability rather than a stack of functional plans assembled after the fact.
• Drive shared interlock on topline targets and OKRs so functional plans commit to the same numbers.
• Own the company OKR architecture — definition, cascade, and the discipline that keeps the set small enough to mean something.

Investment and efficiency portfolio

• Build the costed, return-ranked view of the portfolio in partnership with FP&A, so investment allocation follows the strategy.
• Bring the efficiency portfolio into the same frame as the growth portfolio, so trade-offs between the two are made deliberately.
• Set the yardstick for build, buy, and partner decisions that Corporate Development applies, so organic and inorganic options are measured consistently.
• Build the commercial and economic thinking behind our AI portfolio and make sure it is reflected in how the company plans.

Bookings targets and market view

• Translate geography and product mix into bookings targets that Go-to-Market, Product, and Finance have all committed to.
• Maintain a current view of the market — competitor capability, agentic positioning, and where the industry is moving — built as a standing AI-enabled pipeline rather than a periodic project.
• Bring an outside-in perspective into planning so the plan is tested against the market and not only against last year.

Operating cadence and decision forums

• Define and standardize the QBR and MBR cadence — one structure, run consistently, with material that supports decision making.
• Stand up the cross-functional interlocks across Go-to-Market, Product, and Engineering that convert disagreement into committed trade-offs.
• Build the recurring mechanisms to course-correct when the plan and reality diverge, early enough for the correction to matter.

Running the function AI-natively

• Run Strategy & Business Operations as an AI-native function — deciding how the work gets done, where agentic workflows replace manual effort, and what the team therefore does not need to focus on.
• Build the function's recurring analysis as durable pipelines — market intelligence, variance analysis, and executive reporting — with named owners and a clear standard for when output is trustworthy enough to use.
• Raise the analytical throughput of a small senior team so capacity comes from tooling and rotating secondees rather than headcount.
• Develop the team to run teams of agents — building the skill to scope, supervise, and quality-check agentic work, so throughput scales with how well a principal directs agents rather than with hours worked.

Candidate Requirements and Experience

• 10+ years of combined experience across top-tier management consulting and corporate strategy or business operations at a technology company, including time spent owning outcomes rather than advising on them.
• Experience leading a strategy, business operations, or corporate development function is required, with 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 how they apply to strategy and business operations work — including how large language models behave in production, where agentic systems fail, and what evaluation discipline costs to sustain.
• Demonstrated ability to translate high-level corporate ambition into scalable AI and agentic automation frameworks. 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.
• Comfort operating on imperfect data, with the judgment to know when an answer is defensible enough for an executive audience and when the underlying systems have to be fixed first.
• Excellent executive communication. Board and executive-staff material, authored by you, on compressed timelines.
• Enterprise SaaS background, with 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.
• MBA or equivalent advanced degree is highly recommended.

About You

• You take a position. You would rather bring a recommendation with the reasoning exposed than a menu of options with the decision left open.
• You have already woven AI into how you and your teams work — not as a talking point, but as a tool that changes what is possible. You have a view on where it does not yet belong.
• You are comfortable being the person who tells the executive team the plan does not add up, and you do it early rather than at the end of the quarter.
• You work well without complete information and are precise about the difference between what you know, what you estimate, and what you are guessing.
• You build small teams of strong people and give them room, rather than scaling through headcount.
• You are drawn to a company mid-pivot rather than one running a settled playbook, and you understand that the work is unfinished by design.