Head of Deal Strategy

The Opportunity

Okta is seeking a Head of Deal Strategy to lead a high-impact global function at the center of our commercial engine. This leader will shape how Okta structures, evaluates, and executes strategic and complex transactions, while building the operating model, governance, and team required to scale with the business.

This role is equal parts strategist, operator, and trusted business partner. You will work closely with Sales leadership and cross-functional partners across Finance, Legal, Revenue, Product, and Operations to improve deal quality, accelerate velocity, and ensure commercial decisions align with Okta’s growth, profitability, and risk objectives.

What You’ll Do

Strategic Deal Leadership

• Lead Okta's Deal Strategy team for global upmarket accounts. 
• Serve as a trusted advisor to Sales leadership on strategic, competitive, and non-standard deals.
• Act as a senior escalation point on high-value, high-risk, and business-critical transactions, balancing growth, customer outcomes, profitability, and risk.

Commercial Governance & Deal Structuring

• Establish and evolve global guardrails for pricing, discounting, approvals, exception handling, and non-standard commercial structures.
• Partner with Finance, Legal, Revenue, Product, and Operations to ensure deal structures are commercially sound, operationally executable, and aligned to company policy.
• Drive consistency and rigor in commercial decision-making while preserving flexibility for strategic deals.

Cross-Functional Execution & Business Insights

• Lead cross-functional alignment on deal execution, including clear decision rights, escalation paths, and rules of engagement.
• Build metrics, dashboards, and inspection mechanisms that improve visibility into cycle time, exception trends, commercial quality, and risk.
• Translate field feedback, market dynamics, and deal trends into actionable recommendations on policy, pricing, packaging, and process improvements.

Team Leadership & Enablement

• Build, lead, and develop a high-performing global team with strong commercial judgment and executive credibility.
• Coach the team to operate as strategic advisors to the field, not just transaction managers.
• Create playbooks, training, and enablement that improve seller effectiveness and reinforce best practices in deal formation.

AI-Enabled Deal Strategy

• Define and scale AI-enabled workflows that improve seller productivity, deal quality, approval consistency, and speed across the deal lifecycle.
• Partner with Systems, Operations, and Analytics teams to embed AI into areas such as pricing guidance, approval routing, risk flagging, and deal summarization, with clear guardrails for accuracy, auditability, and policy compliance.
• Establish a tiered service model that uses automation for high-volume standardized deals and expert human judgment for complex, high-value, or non-standard transactions.

What We’re Looking For

• 12+ years of experience in Deal Strategy, Deal Desk, Commercial Operations, Revenue Operations, Finance, Pricing, or related functions in a global SaaS or enterprise software environment.
• Proven experience leading and scaling high-performing global teams.
• Deep expertise in SaaS deal structuring, pricing strategy, discount governance, approval frameworks, and complex commercial negotiations.
• Strong understanding of quote-to-cash processes, including revenue recognition implications.
• Demonstrated ability to influence senior Sales leaders and cross-functional executives (Finance, Legal, Revenue, Product, Operations) in fast-paced, matrixed environments.
• Strong business and financial acumen, with the ability to evaluate tradeoffs and make sound commercial recommendations.
• Track record of building scalable operating models, governance frameworks, and process improvements that enable growth.
• Experience with Salesforce, CPQ, CLM, and related commercial systems preferred; Bachelor’s degree or equivalent relevant experience required; (MBA, CPA, or equivalent a plus).

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