Sr. Director, Deal Operations & Enablement

OSG•Carol Stream, IL

5d•$145,000 - $160,000•Onsite

About The Position

OSG is seeking a Sr. Director, Deal Operations & Enablement to own the process from deal pursuit through signed contract. Reporting to the VP, Revenue Operations & Enablement, this builder role brings the Deal Desk, Pricing, and RFP teams together into a single function. The role will design the operating model, team structure, tooling, and talent-development approach as OSG focuses on revenue growth. Pricing sign-off remains with Finance and the CFO, while contract approval remains with the Contracts team and Chief Legal Officer. The Sr. Director owns the analysis, recommendations, speed, and quality of the work—not the final approval decisions—and will establish turnaround commitments with those partners and report cycle time across each stage.

Requirements

At least 7 years of experience in revenue or sales operations, Deal Desk, pricing, or commercial finance, including direct ownership of a commercial function.
Experience leading more than one discipline and developing team members rather than doing all the work personally.
Hands-on experience building pricing models and deal structures for complex business, with the judgment to discuss tradeoffs.
Strong working knowledge of Salesforce as the system of record for deal and approval workflows.
A track record of influencing Finance, Legal, and senior Sales leaders.
Experience measuring the performance of a function and a clear perspective on relevant metrics.

Nice To Haves

RFP or proposal operations experience.
Experience with technology that supports the quote-to-contract lifecycle.
Experience with Claude or other AI tools for reporting and process automation.

Responsibilities

Own intake, triage, and structuring for complex deals; build a Deal Desk that sellers choose to use and expand its coverage where it improves deals.
Lead analysts who model and structure non-standard pricing; ensure recommendations presented to Finance are high quality and surface exceptions early.
Lead the RFP team and align proposals with what OSG can profitably deliver.
Build a proposal content library and response rhythm to make submissions faster and stronger.
Create playbooks, training, and tooling so the deal process follows documented practices and scales with revenue growth.
Unite the Deal Desk, Pricing, and RFP teams into one function with shared measures and clear handoffs.
Retain and develop talent, including future successors.
Partner with Finance, Legal, Contracts, and senior Sales leadership to agree on turnaround commitments and move deals forward.
Measure and report deal cycle time by stage, first-pass approval rate, Deal Desk coverage, and proposal performance.