Director, Pricing & Commercialization

Segment (Twilio); Chicago (IL); On-site; USD 160,000 - 230,000; Full time

Job summary

project44 is seeking a senior pricing leader to own the pricing strategy and architecture for its mult product SaaS portfolio. You will lead packaging decisions, build AI-driven pricing tools for the Sales team, and collaborate across Product, Finance, and Sales to drive value-based pricing in an enterprise setting.

You will influence executives with data-backed business cases, run pricing experiments, and expand pricing through partnerships and new capabilities.

Qualifications

• 8+ years in pricing or monetization strategy in enterprise B2B SaaS.
• Fluency in pricing mechanics: usage-based, seat-based, module-based.
• Experience pricing multi-product platforms for enterprise accounts.
• Proven track with CROs or senior revenue leaders and influencing strategy.
• Strong quantitative and financial modeling skills.
• Excellent communicator for senior executive audience.
• Bias toward iteration and data-driven decision making.
• Preferred: background in supply chain/logistics or adjacent enterprise software.

Responsibilities

• 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: define tiers, add-ons, and how pricing evolves as the platform expands.
• Develop AI-enabled pricing tools and offer-management kit for Sales, driving customer-focused solutions.
• Identify levers for expansion, including partnerships and customer-funded initiatives for co-development.
• Ensure guardrails and governance for consistent and reportable pricing while remaining flexible for deals.
• Run structured pricing experiments and translate results into actionable recommendations.
• Collaborate with Product on new feature pricing from monetization strategy to rollout.
• Partner with the deal desk on discounts, approvals, and exceptions to accelerate deals.
• Build pricing governance with clear approvals and escalation processes.
• Align with Finance on ARR impact and forecasting inputs.
• Maintain competitive pricing intelligence and feed insights back to packaging and pricing strategy.

Skills

Pricing strategy

Monetization modeling

Enterprise SaaS pricing

Financial modeling

Executive communication

Cross-functional collaboration

Education

MBA or equivalent training

Job description

At project44, we believe in better. We challenge the status quo because we know a better supply chain isn’t just possible—it’s essential. Better for our customers. Better for their business. Better for the world.

With our Decision Intelligence Platform, Movement, we’re redefining how global supply chains operate. By transforming fragmented logistics data into real-time, AI-powered insights, we empower companies to connect instantly, see clearly, act decisively, and automate intelligently. Our Supply Chain AI enhances visibility, drives smarter execution, and unlocks next-gen applications that keep businesses moving forward.
Headquartered in Chicago, IL with a 2nd HQ in Bengaluru, India we are powered by a diverse global team that is tackling the toughest logistics challenges with innovation, urgency, and purpose.

AI at project44

We expect every project44 team member, regardless of role or function, to actively leverage AI in their day-to-day work. Whether you're building product, serving customers, managing people, or running operations, AI is a tool you're expected to use with intent, curiosity, and judgment. We don't expect everyone to be a data scientist. We do expect everyone to be an intelligent user of AI: able to identify where it adds value, direct it effectively, evaluate outputs critically, and govern it responsibly. We invest in our team's AI fluency because we believe it's a competitive advantage for every person at project44, not just our engineers.

If you’re driven to solve meaningful problems, leverage AI to scale rapidly, drive impact daily, and be part of a high-performance team – we should talk.

In-office Commitment: Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for candidates who are enthusiastic and committed to joining our team on-site, in our beautiful headquarters four days a week. Together, we’re building something extraordinarily learn, grow, and thrive in our fast-paced, transformative environment.

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.
• 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).

Diversity & Inclusion

We’re designing the future of how the world moves and is connected through trade and global supply chains. We can only deliver a truly world-class product and experience if our teams are as diverse and unique as the communities we are building for. It’s up to us to create a company where anyone can bring their authentic self to work every day. We’re constantly working to improve, and we accept our responsibility to elevate the voices left in the margins. It’s on every one of us.

Our focus on inclusion manifests in the way we hire, the customers we serve, and the regions we prioritize. We’re building a company that every one of us at project44 is proud to work for: a company that celebrates you for being you.

We pride ourselves on celebrating everyone — project44 is an equal opportunity employer actively working on creating a diverse and inclusive work environment where underrepresented groups can thrive. If you share our values and our passion for helping the way the world moves, we’d love to review your application!

For any accommodations needed during the hiring process, please email [e-mail]. Even if you don’t meet 100% of the above qualifications, you should still seriously consider applying. Studies show that you can still be considered for a role if you meet just 50% of the role’s requirements.

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