Sr. Director, Deal Operations & Enablement

OSG is a global provider of leading customer engagement and payment solutions. We help clients integrate critical customer interactions to optimize working capital and drive profitable business growth. Our solutions connect the entire customer experience by aligning transactional, payment, and marketing touchpoints for simplified operations and smarter engagement. Powered by innovative technology and data-driven insights, we build tailored, digital-first strategies for a range of industries. Our clients benefit from a partnership that values simplicity, security, and connectivity, for today and for tomorrow's innovation. We are looking for a Sr. Director, Deal Operations & Enablement to own the full path from "we want this deal" to a signed contract. Reporting to the VP, Revenue Operations & Enablement, you will bring OSG's Deal Desk, Pricing, and RFP teams together into one function and build it into something OSG has not had before. This is a builder's role. The charter is written and the executive sponsorship is in place. The operating model, team structure, tooling, and talent development are yours to design as OSG focuses on revenue growth. Pricing sign-off rests with Finance and the CFO, and contract approval rests with the Contracts team and the Chief Legal Officer. You will hold a dotted line to both and own the analysis, recommendation, speed, and quality, not the final decision. Turnaround commitments with both partners will keep approval time bounded, and you will report cycle time across every stage. Job Details

• 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.

Year-One Success Measures

• Deal cycle time: Measured stage by stage for the first time, and materially reduced.
• First-pass approval rate: Pricing packages approved by Finance without rework.
• Desk coverage: In-scope deals reliably routed through the desk, with published, understood scope.
• Proposal performance: On-time submission near 100%, win rate trending up, and reusable content growing.
• Team and standing: Three teams operating as one, with Finance and Legal describing the desk as making their work easier.

Required 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.

Preferred Qualifications

• 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. The team is six months into using AI to transform the revenue organization.

Location This is an onsite 4-days a week in office position based at OSG's Carol Stream, IL facility.

Benefits

• Paid time off (PTO)
• Medical, dental, and vision plans
• Employee assistance program
• Life insurance and long-term disability (LTD) plans
• Supplemental life insurance
• Voluntary accident and critical illness insurance
• Flexible Spending Account
• 401(k) plan

OSG offers equal employment opportunity and will not discriminate on the bases of race, religion, color, sex (including pregnancy, gender identity, and sexual orientation), parental status, national origin, age, disability, family medical history or genetic information, political affiliation, military service, or other non-merit based factors.