Deal Desk Manager

Obsidian Security•Palo Alto, CA

54d•$115,000 - $170,000

About The Position

As a Deal Desk Manager at Obsidian Security, you will play a pivotal role in driving operational excellence across the quote-to-cash (QTC) process. You'll partner closely with Sales, Legal, Finance, and Revenue Operations to structure strategic, compliant, and scalable deals that balance customer needs with company objectives. This role is ideal for a strategic operator and analytical problem-solver who thrives in a fast-moving SaaS environment. You will influence how Obsidian structures deals, prices offerings, and automates revenue workflows as we scale globally.

Requirements

Bachelor's degree in Business, Finance, Economics, or related relevant areas and/or experience
5 years of related experience, in deal desk, pricing/finance, contracts or sales operations within a SaaS or high-tech company
Be well-versed in deal economics, commercial agreements, revenue accounting, and ASC 606, along with experience using Salesforce and CPQ (or similar quoting tools)
Previous experience with complex contract negotiations and long sales cycles
Ability to break down complex ideas and issues and communicate in simple terms to different levels of the organization with excellent communication and presentation skills (written and verbal)
Proven ability to operate autonomously in a high-growth, fast-paced environment.

Nice To Haves

Hands-on experience with CPQ and billing systems; prior implementation or optimization experience preferred

Responsibilities

Partner with the Sales and Customer Success teams to structure strategic, multi-year, and enterprise SaaS agreements.
Advise on pricing, packaging, and discounting strategies that align with business goals and margin targets.
Serve as the primary contact for non-standard deal terms, facilitating cross-functional approvals and negotiations.
Drive excellence across the end-to-end QTC process - from pre-sales quoting to post-sale billing and collections.
Partner with Revenue Accounting to ensure clean order ingestion, invoicing accuracy, and compliance with ASC 606 and internal controls.
Identify and resolve deal and billing escalations in collaboration with internal stakeholders.
Champion automation and scalability across CPQ, ERP, and billing systems (e.g., Salesforce, Nue, NetSuite, or similar).
Define and implement policies and internal controls to support global scale and audit readiness.
Continuously evaluate and refine approval workflows, pricing guardrails, and documentation standards to increase efficiency and compliance.
Partner with Legal, Finance, GTM Ops, and Engineering to operationalize new pricing, monetization, and packaging models.
Provide decision support and deal analysis to senior leadership, articulating risk/reward tradeoffs and compliance implications.
Act as a trusted advisor to Sales leadership, guiding teams through deal structuring, pricing, and contract execution.
Train and empower the Sales organization on deal desk policies, pricing frameworks, and QTC processes.
Build strong internal relationships to foster collaboration and alignment across all deal stakeholders.