project44

Director, Pricing & Commercialization

project44 • $130K — $180K *
Chicago, IL 60629In-Person
Enterprise Technology
8 - 10 years of experience
Today
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Job Overview by Ladders

Qualifications

  • 8+ years in pricing or monetization strategy for enterprise B2B SaaS
  • Deep knowledge of various enterprise SaaS pricing models
  • Experience in pricing for complex, multi-product platforms
  • Proven track record influencing senior revenue leaders
  • Strong quantitative and financial modeling skills
  • Excellent communication skills for explaining pricing strategies
  • Iterative approach to testing and refining pricing models

Responsibilities

  • Own pricing architecture across the product portfolio and model designs
  • Lead packaging and bundling decisions in collaboration with Product
  • Develop AI-driven custom bundling tools for the Sales team
  • Drive co-development initiatives through partnerships and funding
  • Run structured pricing experiments to enhance decision-making
  • Partner with Product for monetization strategies in new launches
  • Build clear internal processes for pricing approvals and escalation

Benefits

  • Flexible work environment and remote work options
  • Access to cutting-edge tools and AI technologies
  • Opportunities for career growth and advancement
  • Collaborative culture with cross-functional teamwork
  • Support for professional development and continuous learning
Full Job Description
What You'll Do:

Pricing Strategy & Model Design
  • Own pricing architecture across the project44 product portfolio, including usage-based, subscription, and outcome-linked models for large enterprise and mid-market segments.
  • Lead packaging and bundling decisions: work with Product to define what goes in which tier, how add-ons are structured, and how we evolve pricing as the platform expands.
  • Bring a passion for using AI to create custom bundling and offer-management toolkits for the Sales organization, fostering a customer-focused orientation to solution selling.
  • Understand levers for solution expansion, including partnerships and customer-funded initiatives to drive co-development and new capabilities.
  • Ensure guardrails and guidance provided to Sales allow for consistency and reportability of offerings while maintaining flexibility for customer and deal variability.
  • Run structured pricing experiments: define hypotheses, instrument the funnel, and synthesize results into actionable recommendations.

Commercialization & GTM Execution
  • Partner with Product on new feature and product launch pricing, from initial monetization strategy through rollout, enablement, and iteration.
  • Partner with the deal desk on commercial guardrails: bundling proposals, discounting frameworks, approval thresholds, and exception handling that let Sales move fast while responding to deal-specific requirements.
  • Build internal pricing governance with clear processes for approvals, exceptions, and escalations so the field operates with confidence and consistency.
  • Align with Finance on revenue modeling, ARR impact analysis, and pricing-related forecasting inputs.
  • Maintain competitive pricing intelligence: track competitor models, pricing moves, and win/loss pricing dynamics, and feed that back into packaging and deal strategy.

Cross-Functional Influence & Executive Communication
  • Operate as the internal pricing authority - a credible, decisive voice that Product, Sales, Finance, and Executive leadership can rely on.
  • Present pricing strategy and business cases to senior leadership with clarity and commercial conviction.
  • Navigate competing stakeholder priorities with structured thinking and a bias toward action.
  • Build credibility with senior sales leadership and ensure they are fully brought along for alignment and clarity.
What You'll Need

Required:
  • 8+ years in pricing, monetization strategy, or commercial strategy in enterprise B2B SaaS, with demonstrated ownership of pricing model design.
  • Deep fluency in enterprise SaaS pricing mechanics: usage-based, seat-based, module-based, outcome-linked. You know the tradeoffs and when to apply them.
  • Experience building pricing for complex, multi-product platforms sold into enterprise accounts with long sales cycles and multi-stakeholder buying.
  • Track record of working directly with CROs, VP Sales, or senior revenue leaders and influencing their thinking on commercial strategy.
  • Strong quantitative and financial modeling skills; comfortable building and stress-testing pricing models from scratch.
  • Excellent communicator who can make a complex pricing argument land cleanly with a senior executive audience.
  • Bias toward iteration: you move fast, test assumptions, and refine based on data rather than waiting for the perfect framework.

Preferred:
  • Background in supply chain, logistics, or adjacent enterprise software verticals.
  • Experience in a high-growth SaaS environment through a scale or transformation phase.
  • Exposure to channel and partner commercial models (resellers, SIs, marketplace).
  • MBA or equivalent analytical training (not required if your work speaks for itself).

About project44

project44 is a logistics technology company that provides cloud-based transportation management solutions. The company's platform provides real-time visibility into the transportation supply chain, enabling shippers, carriers, and logistics service providers to improve operational efficiency, reduce costs, and enhance customer satisfaction. project44's solutions include carrier onboarding, real-time tracking, predictive analytics, and automated freight invoice auditing. The company serves customers in various industries, including retail, manufacturing, and healthcare.
Learn more about project44
Size
500 employees
Industry
Information Technology
Founded
2014
* Ladders Estimates

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