Y Combinator Director of Deal Desk
Superside is hiring a Director of Deal Desk to lead the commercial engine behind enterprise pricing, scoping, and proposal structuring. Sitting within the Solutions function, you’ll oversee the end-to-end Deal Desk operation, ensuring deals are commercially sound, operationally realistic, and built to scale.
This is a player-coach role leading a team of Deal Desk Associates while directly supporting high-value and complex opportunities. You’ll partner closely with Sales, Solutions, Finance, and Operations to improve deal quality, speed, and consistency through strong processes and AI-powered automation.
What you'll do:
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Own pricing and scoping support for complex enterprise deals, ensuring commercial accuracy and delivery alignment.
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Review and approve deal structures, pricing models, and scopes across the pipeline.
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Partner with Account Executives and Solutions teams to turn customer requirements into scalable proposals.
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Collaborate with subject matter experts to strengthen solution quality on strategic deals.
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Lead and develop the Deal Desk team, setting clear priorities, standards, and turnaround expectations.
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Act as the escalation point for complex or high-risk commercial situations.
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Improve Deal Desk workflows, documentation, and tooling to increase speed and consistency.
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Define and track operational metrics such as deal velocity, pricing accuracy, and SLA performance.
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Drive AI adoption across pricing and scoping workflows, identifying opportunities for automation and efficiency.
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Maintain pricing governance frameworks and ensure exception handling follows clear approval processes.
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Build and maintain pricing guides, playbooks, and reference materials for internal teams.
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Deliver reporting and insights on pricing trends, deal performance, and commercial operations.
What you'll need to succeed:
- Significant experience in Deal Desk, pricing, sales operations, or commercial strategy roles.
- Experience leading and developing high-performing operational or commercial teams.
- Strong commercial acumen with experience structuring profitable, scalable deals.
- Ability to balance customer needs, delivery realities, and business margins.
- Analytical mindset with experience using data to improve workflows and decision-making.
- Experience working in creative, marketing, SaaS, or professional services environments.
- Strong interest in AI tools and workflow automation within commercial operations.
- Excellent organizational skills with the ability to manage multiple complex deals simultaneously.
- Clear and confident communication skills with senior cross-functional stakeholders.
- Ability to operate effectively in fast-paced, high-growth environments.
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