Director, Sales Planning

Why We Need You

We are seeking a Director of Sales Planning, Compensation & Analytics who will serve as a strategic partner to our Senior Sales Leaders. This role is integral to our commitment to revenue growth, with responsibilities encompassing sales planning, forecasting, compensation design, headcount investments and quota coverage. As our Director of Sales Planning, Compensation & Analytics, you will be reporting to the VP, Field Operations, leading the charge in the development, implementation, and ongoing refinement of sales strategies, programs, and initiatives.

The perfect candidate has experience working in fast-paced, high-growth environments and possesses a comprehensive understanding of diverse sales metrics, processes, and tools. Proficiency in enterprise selling processes, SaaS, and digital sales metrics is highly desirable. We are looking for a leader who can identify and implement improvements in all aspects of sales operations, with a particular emphasis on sales planning.

This role demands a combination of strong operational skills, deep analytical abilities, and the capacity to provide strategic support to our sales leadership teams. Your focus will be managing functions crucial to our go-to-market strategy and sales-related initiatives aimed at driving enablement and productivity.

How You Contribute to Our Vision: Key Responsibilities

GTM & Sales Planning

• Own the annual and in-year planning calendar with Sales, Finance, and People. Deliver territories, quotas, and comp plans that are ready on day one of the fiscal year.
• Build capacity and coverage models that turn bookings/ARR targets into headcount, ramp, and productivity assumptions across field, inside/digital, product-led, and partner motions.
• Lead account segmentation, territory design, and account assignment rules. Find where we're over- or under-covered and recommend fixes.
• Set and allocate quotas across segments, geographies, and roles, balancing top-down targets against bottom-up opportunity. Own quota-relief and adjustment governance.
• Build scenario models that show leaders the tradeoffs among headcount, coverage, quota, productivity, cost of sales, and revenue before they decide.

Sales Compensation Design & Governance

• Design role-based incentive plans (pay mix, measures and weights, thresholds, accelerators, caps, SPIFs) that reward the behaviors our strategy depends on, such as new logo, expansion, multi-product, and retention.
• Partner with Finance, Total Rewards, and Legal on plan cost modeling, market benchmarking, and approvals. Run the compensation governance committee.
• Maintain clear, consistent policies for crediting, splits, territory transfers, windfalls, clawbacks, and exceptions. Resolve disputes fairly and quickly.
• Own plan documents, rollout, and field enablement so every seller understands how they're measured and paid.

Compensation Operations

• Oversee the full monthly and quarterly commission cycle (crediting, calculation, validation, approval, payout) with high accuracy and on-time delivery.
• Own the incentive compensation management (ICM) platform and the data flows among Salesforce, billing, HRIS, and payroll.
• Design and maintain controls, documentation, and audit readiness, including SOX compliance and support to Accounting on ASC 340-40 commission capitalization.
• Set service levels for seller inquiries and track operational KPIs such as payout accuracy, cycle time, exception volume, and dispute resolution time.

Sales Analytics & Insights

• Measure plan and program effectiveness: attainment distribution, pay-for-performance alignment, cost of sales, productivity, ramp time, and seller retention. Turn findings into changes for the next cycle.
• Partner with Sales Operations and Finance on forecasting methodology, pipeline coverage, and bookings and capacity inputs to the forecast.
• Define and govern core GTM metrics as a single source of truth, and deliver executive reporting for QBRs, board materials, and operating reviews.
• Answer ad hoc strategic questions from the CRO and sales leaders with clear, decision-ready analysis.

Systems, Automation & AI

• Work with GTM Systems/Business Technology to improve our planning, analytics, and ICM stack (Salesforce, Anaplan, Clari, Tableau, and ICM tooling).
• Use automation and AI to speed up territory and quota modeling, catch commission anomalies, and give sellers self-serve visibility into attainment and earnings.

Leadership

• Build, lead, and develop a high-performing team of managers and analysts. Set clear goals, operating rhythms, and career paths.
• Build alignment across Sales, Finance, People, Marketing, Customer Success, and Product on GTM strategy and process improvements.

What Success Looks Like in Year One

• The next fiscal year's territories, quotas, and comp plans are designed, modeled, approved, and communicated before the year starts.
• Commission payouts run on a predictable calendar with measurably lower errors, disputes, and manual work.
• Leadership has a trusted, regular view of plan effectiveness, capacity, and productivity that it uses to make investment decisions.
• A documented governance model (planning calendar, policies, exception process, controls) holds up in audit and scales as we grow.

Minimum Requirements

• 10+ years of progressive experience in Sales/Revenue Operations, GTM planning, sales compensation, or business strategy and analytics.
• 5+ years in a B2B SaaS environment, ideally with multiple sales motions (enterprise, commercial, digital/PLG, partner).
• Hands-on ownership of territory design, quota setting, and sales compensation plan design; experience running or overseeing commission operations.
• 4+ years leading and developing teams, including managers or senior individual contributors.
• Track record of presenting recommendations and modeling tradeoffs to executive leadership and earning their trust.
• Advanced financial modeling and analytical skills; fluency with Salesforce data and comfort with SQL or similar tools.

Preferred Qualifications

• Salesforce power user; experience with Anaplan (or similar planning platform), Clari, and Tableau.
• Experience administering or implementing an ICM platform (e.g., Xactly, CaptivateIQ, Varicent, Spiff, Anaplan ICM, Pigment).
• Working knowledge of SOX controls and ASC 606 / ASC 340-40 as they relate to commissions.
• Experience with usage- or consumption-based, multi-product, or hybrid PLG and sales-led models.
• Practical experience applying AI and automation to planning, analytics, or compensation workflows.
• WorldatWork Certified Sales Compensation Professional (CSCP) or similar credential.

Skills & Attributes

• Strategic thinker who is still willing to dig into the details.
• Clear, concise communicator in writing and in the room, with the credibility to push back on senior leaders and say no when needed.
• Builds a high-performing, metrics-driven, and inclusive team culture.
• Strong judgment on fairness and consistency, balancing policy against practical business needs.
• Handles ambiguity well and brings structure and repeatable process to complex, cross-functional work.

The base salary range for this position is 147,000 - 246,400 USD. This role may also be eligible for bonus, commission, equity, and/or benefits.