Deal Desk Analyst II

Castlight Health

Castlight Health

IT
United States · Remote
USD 67,349-84,816 / year
Posted on Dec 6, 2025

Job Description Summary

The Deal Desk Analyst II serves as a key partner to Sales, Finance, Legal, and Revenue Operations teams by supporting the structuring, pricing, and approval of complex deals. This role ensures deals are commercially sound, compliant with internal policies, and aligned with company revenue goals.

How will you make an impact & Requirements

Position Qualifications/Essential Functions:

  • Build infrastructure in support of an evolving sales space, thrive in a fast-paced, cross-functional environment, and have a mix of analytic and interpersonal skills.

  • Guide Sales team on deal quality and proper deal structure, fallback positions, and executive approval during contract negotiations

  • Coordinate closely with executives from Sales, Channels, Customer Success, Legal and Finance teams and provide deal analysis and visibility into contract complexity

  • Collaborate with Legal and Finance to structure our deals

  • Take on cross-functional projects targeted at getting dollars in the door faster by improving the organization's deal flow process.

  • Rethink legacy processes to optimize deal flow and identify deal patterns for business improvemen

  • Monitor quarter-end deal progress and close all bookings transactions

Education/Experience:

  • Bachelor’s degree

  • 3-5 years of work experience in Accounting, Finance or Sales Operations experience required

  • Strong written and verbal communication skills, proven project management experience, and the ability to own and maintain end-to-end projects

  • Good under pressure.

  • Great relationships around the business/experience working cross-functionally.

  • Passion for driving top-line growth.

Additional/Preferred Qualifications:-

  • 3+ year experience in high-tech SaaS environment is highly desirable

  • Healthcare industry

  • Salesforce

Demonstrated Attributes:

  • Highly organized and has the ability to handle multiple projects simultaneously

  • Team player with strong interpersonal skills and ability to build effective working relationships throughout all levels of the organization

  • Excellent verbal and written communication

  • Solution-focused with a strong client presence

  • Independent, self-motivated and a strong communicator.

  • Ability to be creative and innovative in a fast-paced environment with a lot of ambiguity and constant change

  • Proficiency with MS Office products, including Word, Excel, PowerPoint

Compensation: $67,349K - $84,816K annual salary