Deal Desk Analyst

About OpenSesame

OpenSesame is transforming workforce development with an AI-powered marketplace of over 50,000 skill-building courses. We help organizations build skills and stay compliant through a high-quality content catalog, seamless LMS/LXP integrations, and advanced capabilities like skills-based curation and multilingual content creation. More than 2,000 companies, including 150+ of the Global 2000, rely on OpenSesame to develop the world’s most productive and admired workforces.
Learn more: www.opensesame.com/about

About the Revenue Operations Team

The Revenue Operations team is the operational backbone and growth catalyst of OpenSesame. While others may see sales mechanics, we focus on something more fundamental: creating the clarity, discipline, and systems that allow revenue to scale responsibly and predictably.

We design, operate and automate the processes, systems, and insights that connect strategy to execution — from first customer conversation through renewal. Our work ensures revenue flows efficiently, governance is strong, and customer experience remains consistent as the business grows.

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 Deal Desk Analyst

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.

This role exists to remove friction from selling. You’ll 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 — not volume of activity.

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 will 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 to outline existing process and train Sellers on best practices; includes continued enablement regarding policy changes and new 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.

You might notice we don’t have the typical list of requirements and buzzwords here. That’s intentional.

We’re looking for proven examples from your career that show you can do this job — that you’ve built systems, driven alignment, and created impact at scale. When you look back a year from now, you’ll know you’ve made OpenSesame better, faster, and stronger because of your leadership.

Although it should go without saying (but it doesn’t), OpenSesame is an equal opportunity employer and we strive to create a welcoming, inclusive environment that celebrates diversity.

Location: This position can be located anywhere in the U.S. All positions will require up to 15 days of travel per year for company-wide events (typically January, May, September).

Performance Driven: We’re looking for self-starters with a track record of follow-through, curiosity, and results. We don’t hire based on a checklist — we hire for potential, drive, and evidence of performance. If you’re motivated to learn, comfortable with experimentation, and excited about how technology can make sales more human, you’ll fit right in.

Compensation: On-target earnings for this role range between $80,000 and $90,000 per year, depending on experience, which includes base salary and variable incentive compensation based on performance. At OpenSesame, we offer a comprehensive benefits package to employees upon hire, including ISOs, health insurance, 401(k) matching, and paid time off. We carefully consider a wide range of compensation factors, relying on market data to determine compensation and consider your specific job family, background, skills, and experience.

Equal Employment Opportunity: OpenSesame is an Equal Employment Opportunity and Affirmative Action employer that values and welcomes diversity. We do not discriminate on the basis of various legally protected characteristics, including criminal history, and strive to provide reasonable accommodations to qualified individuals with disabilities. We prioritize safety and security and may use your information accordingly, and you can contact us for assistance or accommodations during the job application process.

Pay Transparency: At OpenSesame, we prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals. We provide competitive and fair compensation to our employees based on their skills, experience, and performance.

CPRA (California Candidates): When you submit your application, OpenSesame may collect and use your personal information in accordance with our privacy policy and the CPRA. This may include personal details and employment history, and will only be used for employment-related purposes. We may share this information with third-party service providers, but we will not sell it to third parties. If you have any questions or concerns, please contact us, and for more information on your rights under the CPRA, refer to our privacy policy or the California Attorney General's website.