Sr. Director, Pricing & Packaging

Own end-to-end pricing & packaging for Smartsheet’s global product portfolio, leading a major commercial transformation from traditional seat-based licensing to modern consumption‑ and value‑based monetization, with AI as a core value driver. This is a highly visible, hands‑on operator role that turns strategy into execution and builds a scalable, data‑driven pricing engine.

You will report to the VP of Product Management located in our Bellevue, WA office, or you may work remotely from anywhere in the US where Smartsheet is a registered employer.

You Will:

Strategy & leadership

• Own global pricing & packaging strategy across products, segments, and geographies, tightly linked to revenue growth, NRR, and competitive positioning.
• Translate current pricing strategy work into an executable monetization roadmap, including sequencing of changes and risk management.
• Lead cross‑functional alignment across Product, Sales, Finance, RevOps, Customer Success, and Marketing; run a regular pricing governance forum with executive stakeholders.
• Act as the senior “voice of pricing” with the executive team, providing clear recommendations and trade‑off frameworks.

Pricing model innovation (consumption & AI)

• Design and implement consumption and value‑based pricing models for the core platform and new AI‑driven capabilities (e.g., metered usage, credits, feature entitlements).
• Define value metrics and units of consumption that align to customer outcomes and usage patterns, while keeping constructs simple and understandable.
• Build hybrid models that balance PLG / self‑serve and enterprise sales motions (tiers plus usage add‑ons, overage models, expansion paths).
• Continuously evolve packaging (tiers, bundles, add‑ons) to drive adoption of AI features and expansion into new segments and use cases.

Customer‑centric design

• Ensure all pricing and packaging changes are designed with customer experience at the centre: transparency, predictability, and administrative simplicity.
• Collaborate with Customer Success and Support to capture field feedback, understand edge cases, and refine policies based on real‑world usage.
• Partner with Product Marketing to create clear external narratives and collateral that explain value, pricing, and upgrade paths in simple, customer‑friendly language.

Execution & governance

• Convert strategy into executable pricing changes: detailed designs, policies, playbooks, rollout plans, and internal tooling requirements.
• Establish and run a robust pricing governance process: decision rights, approval thresholds, exception handling, and global consistency.
• Partner with Product & Engineering to embed pricing and packaging into product design (entitlements, limits, metering, upgrade triggers) and ensure customers have robust tools to manage licenses and usage.
• Work with RevOps and Sales to operationalize discounting frameworks, deal guidelines, and renewals / expansion motions; ensure strong field enablement and change management.
• Coordinate with Legal and Finance on contract structures, terms, and revenue recognition implications of new models.

Analytics, research & experimentation

• Build an analytics capability around pricing: define and track key metrics (ARR, NRR, ARPU, attach rates, churn, price realization, discount levels, migration performance).
• Lead structured customer and market research, including willingness‑to‑pay studies, segmentation analyses, and competitive benchmarking.
• Design and run experiments and pilots (A/B tests, regional rollouts, cohort migrations) to validate price levels, packaging structures, and value metrics before global deployment.
• Partner with Data Science / BI to model revenue and margin impact of proposed changes; stress‑test scenarios and downside risks, and establish clear “go / no‑go” criteria.

Team leadership & collaboration

• Lead and coordinate a small, high performing team (currently ~3 FTE) without direct reports initially, while upgrading capabilities in analytics, operations, and experimentation.
• Coach and develop team members, including managing transition and knowledge transfer from current resources; ensure continuity while raising the bar.
• Foster a high‑trust, low‑ego, highly collaborative culture, consistent with Smartsheet’s flat organizational model.

You Have:

• 10–15+ years in B2B SaaS / cloud, with at least 5+ years in a dedicated pricing, monetization, or commercial strategy leadership role (e.g., Senior Director / VP Pricing & Packaging, Monetization, Commercial Strategy).
• Proven end‑to‑end ownership of at least one major pricing transformation at scale (preferably $500M+ ARR), including a shift toward consumption or usage‑based models (experience in high‑usage platform environments ideal).
• Deep experience in multi‑product, multi‑segment SaaS environments where packaging, bundling, and upgrade paths are core growth levers.
• Demonstrated ability to go beyond strategy: has personally driven implementation through Product/Engineering, Sales, Finance, and RevOps – including tooling, metering, policies, and change management.
• Strong pricing analytics toolkit: able to lead WTP research, build and challenge financial models, and run experiments tied to clear revenue and margin hypotheses.
• Excellent executive communication skills; comfortable working with C‑level stakeholders and operating with high visibility.

Nice‑to‑have

• Experience in work management, collaboration, productivity, analytics, or adjacent SaaS categories, ideally with AI‑enhanced products.
• Exposure to private‑equity‑backed environments and value‑creation programs.
• Prior responsibility for both pricing and packaging in PLG + enterprise “hybrid GTM” contexts.
• Global experience (US + EMEA / APAC) with an understanding of regional pricing nuances.