Sr. Director, Pricing & Packaging at Smartsheet

United States

$263.75k - $306.25k

For over 20 years, Smartsheet has helped people and teams achieve–well, anything. From seamless work management to smart, scalable solutions, we’ve always worked with flow. We’re building tools that empower teams to automate the manual, uncover insights, and scale smarter. But more than that, we’re creating space– space to think big, take action, and unlock the kind of work that truly matters. Because when challenge meets purpose, and passion turns into progress, that’s magic at work, and it’s what we show up for everyday. 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. Current US Perks & Benefits: Employer subsidized medical/vision and dental coverage for full-time employees 401k Match to help you save for your future (50% of your contribution up to the first 6% of your eligible pay) Monthly stipend to support your work and productivity Flexible Time Away Program, plus Sick Time Off US employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plans US employees receive 12 paid holidays per year Up to 24 weeks of Parental Leave Personal paid Volunteer Day to support our community Opportunities for professional growth and development including access to Udemy online courses Company Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet account Teleworking options from any registered location in the U.S. (role specific) Smartsheet provides a competitive base salary range for roles that may be hired in different geographic areas we are licensed to operate our business from. Actual compensation is determined by several factors including, but not limited to, level of professional, educational experience, skills, and specific candidate location. In addition, this role will be eligible for a market competitive incentive opportunity. US Base Salary Pay Range $263,750—$306,250 USD Get to Know Us: At Smartsheet, your ideas are heard, your potential is supported, and your contributions have real impact. You’ll have the freedom to explore, push boundaries, and grow beyond your role. We welcome diverse perspectives and nontraditional paths—because we know that impact comes from individuals who care deeply and challenge thoughtfully. When you’re doing work that stretches you, excites you, and connects you to something bigger, that’s magic at work. Let’s build what’s next, together. Equal Opportunity Employer: Smartsheet is an Equal Opportunity (EEO) employer committed to fostering an inclusive environment with the best employees. It is our policy to provide equal employment opportunities to all qualified applicants in accordance with applicable laws in the US, UK, Australia, Germany, Costa Rica, Japan, Bulgaria, and India. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information. If there are preparations we can make to help ensure you have a comfortable and positive interview experience, please let us know. #LI-Remote