Director of Annual Planning and Sales Model Design

Location: US Nationwide/Remote

The Opportunity

Oracle is seeking a Director of Annual Planning and Sales Model Design to fundamentally redesign annual go-to-market planning and lead the design of our global sales model. You will determine how we segment customers, allocate sales coverage, and align roles and selling motions to the needs and growth potential of each segment.

You will connect Global Field Organization’s long-term growth strategy to an executable annual plan, bringing customer opportunity, sales capacity, productivity, investment, and field readiness into one coherent process. Your mandate spans diagnosis, design, executive alignment, implementation, and ongoing improvement across regions and the businesses within your remit.

We are looking for a leader who has built and implemented major GTM changes in a complex technology business. You will challenge established assumptions, make clear recommendations on difficult trade-offs, and remain accountable for whether the resulting model improves customer coverage, seller effectiveness, and growth. Redesign annual GTM planning end to end.

• Rebuild the planning process from strategic choices through fiscal-year launch in alignment with President, Global Field Organization. Diagnose current weaknesses, define the future approach, and lead a sequenced transformation with clear ownership and measurable outcomes.
• Integrate market opportunity, segmentation, coverage, role design, capacity, territories, quota methodology, and investment decisions. Align Marketing, Partners, Customer Success, Finance, HR, Sales Compensation, and regional Sales Operations around shared assumptions and dependencies.
• Connect annual decisions to a multiyear view of growth. Reconcile leadership targets with customer potential and achievable field capacity; quantify gaps, test alternatives, and recommend where to invest, redeploy resources, or change the model.
• Own the global planning calendar, decision rights, executive reviews, approval milestones, and exception process. Establish common data definitions and planning standards, with explicit criteria for justified regional variation.
• Lead deployment with the teams responsible for execution. Ensure account assignments, territories, roles, targets, systems, and field communications are reconciled and ready for the fiscal year; use post-launch reviews to improve subsequent cycles.

Own global customer segmentation

• Build a segmentation framework grounded in addressable opportunity, customer needs, buying behavior, industry, growth potential, and product adoption. Define account hierarchies, segment assignment rules, and criteria for movement between segments.
• Validate segment choices against customer and seller evidence, commercial potential, and economics. Establish a repeatable refresh process that keeps the model relevant while preserving continuity for customers and account teams.

Design coverage roles and selling motions

• Define the coverage model for each customer segment for each region globally, including the appropriate use of dedicated account teams, pooled coverage, digital sales, specialists, partners, and self-service. Balance customer experience and growth potential with capacity and cost to serve.
• Design role charters, account ownership, specialist engagement, and team responsibilities across the customer lifecycle. Clarify how sellers, technical teams, customer success, renewal teams, and partners work together, with practical rules of engagement and handoffs.
• Define differentiated motions for acquiring customers, expanding relationships, cross-selling, driving adoption and consumption, and retaining business. Specify the target customer, buying stakeholders, lead role, supporting resources, and success measures for each motion.
• Model territory potential, account workloads, seller capacity, ramp time, attrition, specialist ratios, and management spans. Assess the implications for productivity, customer reach, quota capacity, and cost of sales before recommending structural changes.
• Partner with Finance, HR, and Sales Compensation to align targets, job design, performance expectations, and incentives with the intended model and seller behaviors.

Lead transformation and measure results

• Translate analysis into clear executive recommendations that explain options, assumptions, financial implications, risks, and the decisions required. Resolve conflicting priorities across global and regional leaders and drive agreement on implementation.
• Pilot material changes where practical, define comparison groups or other credible evaluation methods, and use results to refine the model before broader deployment. Distinguish the effect of design changes from market conditions and differences in customer opportunity.
• Establish a performance framework covering planning speed and quality, field readiness, coverage effectiveness, seller productivity, customer outcomes, and commercial return. Use evidence to recommend in-year adjustments and future investments.
• Set business requirements for planning data, analytics, and systems. Partner with technology teams to automate repeatable work, improve scenario modeling, and apply AI where it demonstrably improves speed or decision quality, with appropriate validation.
• Lead adoption through regional implementation plans, manager and seller enablement, and structured field feedback. Anticipate transition risks, including account disruption and unclear ownership, and hold workstream leaders accountable for resolving them.

Build and develop a team with strong capabilities in GTM strategy, quantitative analysis, planning, and sales model design. Set high standards for analytical rigor, commercial judgment, concise communication, and delivery.

RESPONSIBILITIES

Experience and capabilities

• 12+ years of relevant experience in GTM strategy, sales planning, sales strategy and operations, or a related discipline, including substantial experience in enterprise software, cloud, or another complex technology business.
• 5+ years leading and developing global teams, with a record of delivering major initiatives across global functions and regions in a matrixed organization.
• Demonstrated personal ownership of at least one major GTM planning or sales model redesign, from diagnosis and executive approval through implementation and measurement. Ability to explain the decisions made, trade-offs accepted, and business results achieved.
• Deep experience designing customer segmentation, coverage models, sales roles, and selling motions, with evidence of translating those decisions into territory, capacity, and annual planning processes.
• Strong commercial and financial judgment. Ability to build and challenge opportunity, capacity, productivity, and investment models; test assumptions; and distinguish achievable growth from unsupported targets.
• Experience working across enterprise, commercial, or smaller-customer segments and multiple routes to market. Understanding of how subscription and consumption models affect acquisition, adoption, expansion, and retention.
• Proven ability to influence senior sales and functional executives, challenge established practices constructively, resolve disagreements, and secure decisions without relying solely on reporting authority.
• Strong analytical fluency and the ability to interrogate underlying data, assess model quality, and direct advanced analysis. Experience translating business requirements into scalable planning processes and systems.
• Exceptional written and verbal communication, including concise executive proposals that make the recommendation, supporting evidence, and required decisions clear.
• Bachelor’s degree in business, economics, finance, engineering, a quantitative discipline, or equivalent practical experience.

PREFERRED EXPERIENCE

• Experience in a large global technology company with multiple product portfolios, regional sales organizations, and an established partner ecosystem.
• Experience building a planning or sales design capability, modernizing planning platforms, or applying AI and automation to improve planning quality and speed.
• Strategy consulting experience combined with direct accountability for implementation in an operating business; MBA or relevant advanced degree.

WHAT SUCCESS LOOKS LIKE

Success means an adopted global sales model with clear segment definitions, coverage choices, role responsibilities, and selling motions; an integrated annual planning cycle that delivers an executable plan on time; and measurable improvement against agreed baselines for planning quality, coverage, productivity, and commercial outcomes. You will establish those baselines early, agree targets with business leaders, and demonstrate progress through implementation and results.

QUALIFICATIONS

Assists in the development of short, medium, and long term plans to achieve strategic objectives. Regularly interacts across functional areas with senior management or executives to ensure unit objectives are met. Ability to influence thinking or gain acceptance of others in sensitive situations. Strong analytical and problem solving skills. Serves as process owner; ability to identify cross-functional issues. Demonstrated leadership skills. 10 years relevant experience and BA/BS degree in Accounting or Finance preferred. CPA/MBA desired.

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