Deal Desk Analyst - OpenSesame

About OpenSesame

OpenSesame is the trusted partner for Workforce Reinvention in the age of AI. OpenSesame delivers integrated software, curated and customizable content, and expert services – embedded into existing learning, HR, and work systems – to help organizations expand their human+AI potential and thrive through change.

Learn more at www.opensesame.com/about.

About the Revenue Operations Team

The Revenue Operations team is the operational backbone and growth catalyst of OpenSesame. We focus on creating the clarity, discipline, and systems that allow revenue to scale responsibly and predictably.

We design, operate, and automate processes, systems, and insights that connect strategy to execution — from first customer conversation through renewal. We partner closely with Sales, Marketing, Customer Success, Partner, Finance, Legal, Enablement, and Business Systems to remove friction, enforce smart standards, and help teams move faster without cutting corners.

About the Role

The Deal Desk Analyst is a critical partner to Sales and Go-To-Market teams, responsible for accelerating deal velocity while protecting margin, ensuring policy compliance, and improving forecast accuracy.

You will support deals across the quote-to-cash lifecycle, helping sellers close complex opportunities faster while maintaining pricing discipline and clean execution. Success in this role is defined by faster approvals, cleaner deals, fewer escalations, and higher seller confidence.

Performance Objectives

Establish Strong Deal Execution (First 30 Days)

• Become fully operational and independently support standard new business, expansion, and renewal deals.
• Validate pricing, discounts, approvals, and required documentation within defined SLAs.
• Route and track approvals accurately, maintaining complete and audit-ready CRM and CPQ records.
• Build strong working relationships with Sales, Partners, Finance, and Customer Success.

Sustain Speed and Discipline (60 Days)

• Handle increased deal volume independently without becoming a bottleneck.
• Enforce pricing and approval guardrails consistently across deal types.
• Identify deal risks earlier to reduce last-minute escalations.
• Track deal cycle times, exceptions, and execution bottlenecks.
• Partner cross-functionally to structure deals that protect margin and accelerate close.
• Proactively identify top issues causing friction in the sales process and present proposed solutions that drive efficiency and speed to close.

Scale Predictability and Efficiency (90+ Days)

• Maintain consistent deal turnaround times with minimal oversight.
• Reduce manual effort through standardization, automation, and AI-assisted validation.
• Provide clean exception and bottleneck data to inform process and system improvements.
• Support adoption of new workflows, tools, and AI automation enhancements.
• Maintain high data accuracy to support billing, forecasting, and audits.
• Build process documentation outlining existing processes and train sellers on best practices, including enablement on policy changes, tools, or automation enhancements.

What Success Looks Like

• Deals move through approval quickly and predictably, even during peak periods.
• Sellers trust Deal Desk as a partner that helps them win — not a blocker.
• Pricing, discounting, and approvals are consistently enforced with minimal escalation.
• Deal data is clean, complete, and audit-ready, reducing post-booking corrections.
• Manual effort decreases over time as automation and standard workflows are adopted.
• Leadership has clear visibility into deal health, approval friction, and margin risk.

Location & Travel

• Location: Anywhere in the U.S. (Remote)
• Travel: Up to 15 days per year for company-wide events (typically January, May, September)

Compensation & Benefits

• On-Target Earnings (OTE): $80,000 – $90,000 per year (includes base salary + variable performance incentive compensation)
• Benefits: Incentive Stock Options (ISOs), health insurance, 401(k) matching, and paid time off (PTO)