Director of Pricing

This is a fully remote position, open to applicants in Florida.

📋 Description

• Take charge of and advance Cendyn's pricing strategy for the entire product lineup, which includes defining suitable pricing models (per-property, per-seat, usage-based, tiered, or hybrid) tailored to each product and market segment.

• Create and uphold a value-driven pricing framework based on customer willingness-to-pay, competitive analysis, and Cendyn's strategic positioning.

• Lead annual and periodic pricing reviews, which encompass list price adjustments, and manage communication and commercial strategies for price hikes across the customer base.

• Collaborate with Product teams to design pricing models for new products, features, and acquisitions, ensuring that monetization strategies are integrated early in the product development process.

• Develop and sustain a packaging and bundling strategy across Cendyn’s offerings, including tier design (e.g., Starter, Professional, Enterprise) and pricing logic for cross-selling and upselling.

• Create pricing models for AI and agentic capabilities embedded in Cendyn products, balancing customer value, infrastructure costs (compute, inference, third-party model usage), and competitive defensibility.

• Establish a clear perspective on monetization strategies for AI features, including usage-based, outcome-based, and consumption-based models, and collaborate with Finance and Product to analyze unit economics at scale.

• Monitor competitor pricing for AI capabilities in the hospitality SaaS sector and translate that intelligence into proactive pricing recommendations.

• Work alongside Operations and Product to ensure that pricing structures for AI features remain commercially viable as model costs and infrastructure economics evolve.

• Collaborate with the Pricing and Contracts Office across Field Sales, Key Account Management, Inside Sales, and Account Directors.

• Partner with senior Sales and Finance leaders to drive deal strategies and pricing for sales teams, ensuring alignment with products, technology, implementation, and more.

• Manage the pricing-related deal governance process and approvals for quotes, ensuring compliance with pricing strategies, discount limits, and exception-handling protocols.

• Guide field teams and PCO colleagues on structuring deals for new business, add-ons, upsells, and renewals, aligning financial outcomes with Cendyn's targets, corporate strategy, and contractual obligations.

• Create a standardized, scalable deal evaluation framework, tools, and approval workflows to reduce sales cycle time and enhance closing velocity.

• Offer confident, evidence-based justifications for deals rejected due to pricing policies or discount violations, acting as a constructive partner rather than a gatekeeper for the field.

• Develop a strategic renewal pricing plan, including uplift objectives, multi-year incentive frameworks, and strategies for contract consolidation among multi-product customers.

• Collaborate with Customer Success to align pricing strategies with churn risk indicators, defining clear guidelines on when to adjust pricing and when to remain firm.

• Create pricing playbooks for expansion scenarios (new properties, seat additions, module upgrades) that enable Customer Success and Account Management to act confidently without needing case-by-case escalation.

• Conduct systematic competitive pricing benchmarking against key players in hospitality SaaS (e.g., Duetto, IDeaS, Amadeus, Revinate), tracking variations in their packaging, pricing, and go-to-market strategies.

• Develop a comprehensive understanding of hotel operator willingness-to-pay by market segment (independent properties, mid-scale chains, enterprise groups) and region to inform pricing differentiation.

• Track macroeconomic factors affecting Cendyn's pricing power, including occupancy trends, technology consolidation, and buyer sophistication; translating these into proactive pricing recommendations.

• Contribute to Cendyn’s broader go-to-market and product strategies through regular pricing intelligence updates for senior leadership.

• Ensure the integrity and reporting of pricing data across CPQ, CRM (Salesforce), and financial systems, providing leadership with accurate visibility into pricing realization, discount rates, and deal economics.

• Develop and maintain pricing analytics dashboards that monitor key metrics: ARR impact, pricing realization (list vs. net), win rates by price point, discount frequency and depth, and renewal uplift.

• Oversee the configuration and governance of pricing rules within the CPQ system, collaborating with RevOps to ensure the system accurately reflects the current pricing strategy.

• Leverage AI-enabled tools and assess and implement pricing methodologies (e.g., Van Westendorp, conjoint analysis, price elasticity modeling) to enhance the rigor of pricing decisions over time.

• Cultivate strong working relationships with Product, Finance, Legal, Sales, Marketing, and Customer Success teams, serving as the authoritative internal voice on pricing.

• Collaborate with Product Marketing to ensure that pricing architecture aligns with product positioning and that packaging messaging is both consistent and compelling externally.

• Develop and deliver ongoing training sessions for field teams on pricing policy, best practices for deal structuring, and any updates to strategy or processes.

• Engage in deal reviews with Sales and Sales Leadership to drive account-level strategies for key opportunities and renewals.

• Provide insights to CLM (Contract Lifecycle Management) processes to ensure that pricing terms are accurately documented and enforceable.

⛳️ Requirements

• Proven experience in a pricing-specific leadership role within a B2B SaaS organization (minimum of 3 years).

• Familiarity with hospitality technology, travel tech, or related sectors; a strong understanding of hotel operator purchasing behavior is a significant advantage.

• Demonstrated capability to build or substantially enhance a pricing function rather than merely maintaining an existing one.

• Extensive subject matter expertise in SaaS deal structuring, commercial terms, and revenue recognition principles.

• Direct experience in designing and defending pricing for software products, including knowledge of AI-enabled, usage-based, consumption-based, and outcome-based monetization models.

• Proficient in value-based pricing methodologies and quantitative pricing frameworks (such as willingness-to-pay research, price elasticity, conjoint analysis, or equivalent).

• Skilled in Salesforce CRM and CPQ systems; familiarity with CLM platforms is a plus.

• Strong analytical abilities and comfort in working with pricing and financial data to derive insights and recommendations.

• Excellent cross-functional collaboration and stakeholder management skills, with the ability to present to and influence C-level executives.

• Results-oriented with strong conflict resolution skills and adaptability in complex, fast-paced commercial environments.

🏝️ Benefits

• Flexible hours are expected during the final two weeks of each fiscal quarter to support the sales team.

• Up to 10% travel may be required, including occasional overnight trips to customer sites, industry conferences, or internal company meetings.