Senior Director, Revenue Deal Operations & Enablement

OSG; Carol Stream (IL); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Paid time off (PTO)

Medical, dental, and vision plans

Employee assistance program

Life insurance and long-term disablity

Supplemental life insurance

Voluntary accident and critical Illess

Flexible Spending Account

401(k) plan

Job summary

OSG is seeking a Sr. Director, Deal Operations & Enablement to own the full path from initial interest to signed contract.

Reporting to the VP, Revenue Operations & Enablement, you will unify Deal Desk, Pricing, and RFP teams into one high-impact function, shaping the operating model, tooling, and talent development to drive revenue growth. This builder’s role emphasizes speed, quality, and measurable outcomes.

Qualifications

• 7+ years in revenue or sales operations, deal desk, pricing, or commercial finance, including time owning a commercial function directly.
• Experience leading more than one discipline and developing team members rather than running everything yourself.
• Hands-on experience building pricing models and deal structures for complex business, with the judgment to discuss the tradeoffs.
• Strong working knowledge of Salesforce as the system of record for deal and approval workflow.
• A track record of winning through influence with Finance, Legal, and senior sales leaders.
• Experience measuring your own function, with clear views on which metrics matter.

Responsibilities

• Deal desk: Own intake, triage, and structuring for complex deals. Build a desk sellers use by choice, and expand coverage deliberately to where it makes deals better.
• Pricing leadership: Lead the analysts who model and structure non-standard pricing. Own the quality of every recommendation that reaches Finance, and make exceptions visible early.
• Proposal and RFP: Lead the RFP team and close the gap between what OSG proposes and what it can profitably deliver. Build the content library and response rhythm that make each submission faster and stronger.
• Enablement: Create playbooks, training, and tooling so the deal path runs on documented practice. Build processes that scale with revenue growth.
• Team integration: Unite three teams into one function with shared measures and clear handoffs. Retain and develop talent, including future successors.
• Cross-functional influence: Partner with Finance, Legal, Contracts, and senior Sales leadership to agree turnaround commitments and move deals forward.
• Measurement and reporting: Measure deal cycle time stage by stage, first-pass approval rate, desk coverage, and proposal performance, and report results to leadership.

Skills

Leadership

Cross-functional collaboration

Influence with Finance/Legal

Tools

Salesforce

Claude AI

Job description

OSG is seeking a Sr. Director, Deal Operations & Enablement to own the full path from initial interest to signed contract.

Reporting to the VP, Revenue Operations & Enablement, you will unify Deal Desk, Pricing, and RFP teams into one high-impact function, shaping the operating model, tooling, and talent development to drive revenue growth. This builder’s role emphasizes speed, quality, and measurable outcomes.