Principal Deal Desk Strategist

LeanData helps the world’s fastest-growing companies automate, simplify, and accelerate revenue.

We’re seeking a Principal Deal Desk Strategist to drive strategic initiatives across the commercial engine, owning complex enterprise deals while designing scalable processes, governance, and systems that enable revenue growth. Reporting directly to the CFO, you will be a trusted advisor to Sales leadership, shaping deal strategy, optimizing commercial outcomes, and influencing enterprise-wide revenue decisions.

Hybrid : This role is based in our Santa Clara office, with in-office days on Monday, Wednesday, and Thursday.

What You’ll Do

Strategic Deal Leadership

• Lead the strategy and execution of complex, high-value deals, ensuring alignment with business priorities and revenue goals.

• Serve as a trusted advisor to senior AEs and Sales leadership, influencing deal structure, pricing, and risk mitigation across the enterprise.

• Act as the final approver on exceptions to pricing, terms, and discounting policy, balancing deal velocity with commercial integrity.

• Partner with Legal and Finance to remove blockers, manage risk, and ensure revenue recognition compliance, shaping enterprise-wide deal practices.

Process, Systems & Strategic Initiatives

• Drive strategic automation and process improvements that reduce friction, accelerate cycle times, and scale across the organization.

• Own the CPQ system architecture, pricing rules, and approval workflows, leading initiatives that expand capability and adoption.

• Develop playbooks, templates, and SOPs that empower the sales team while maintaining oversight on strategic deals.

Cross-Functional Collaboration & Enablement

• Collaborate with Sales Operations, RevOps, and Finance to align strategy, standardize operations, and share insights across teams.

• Lead enablement initiatives for Sales on pricing, product packaging, and commercial best practices.

• Drive actionable recommendations to optimize revenue strategy and deal outcomes, influencing enterprise decision-making.

Governance, Policy & Analytics

• Own pricing models, discounting guidelines, and approval matrices, proactively identifying policy gaps and driving updates as the business scales.

• Track and analyze deal desk metrics—cycle time, discount rates, win/loss trends, and approvals—to provide insights that inform executive decisions.

• Partner with leadership to translate deal insights into strategic recommendations that enhance revenue performance and commercial effectiveness.

What We’re Looking For

• 8–10+ years of experience in Deal Desk, Sales Operations, or closely related commercial roles at high-growth SaaS or technology companies.

• Proven ability to structure, advise on, and influence complex enterprise deals with multiple stakeholders, custom terms, and non-standard pricing.

• Hands-on experience with CPQ and CRM systems (Salesforce required) and a track record of leading automation and process initiatives.

• Deep understanding of SaaS revenue recognition principles (ASC 606) and financial/commercial implications of deal strategy.

• Exceptional analytical skills, including modeling, risk assessment, and presenting strategic insights to executives.

• High executive presence with the ability to influence, challenge, and drive alignment across senior stakeholders.

• Strategic mindset with a bias for scalable processes, automation, and driving enterprise-wide initiatives.

Why LeanData

• Comprehensive benefits: covers employee insurance premiums up to 90%

• Stock options for all full-time employees

• Flexible PTO

• 401K plan