Director of Deal Desk

As a senior leader within the Solutions function, the Director of Deal Desk is the operational and commercial engine behind Superside's pricing, scoping, and project structuring for enterprise customers during the sales process. As part of the Solutions team, this role owns the end-to-end Deal Desk function, with a major focus on pricing and scoping support within a fully structured and commercially sound proposal. The Director of Deal Desk leads a team of 3 Deal Desk Associates and is responsible for their day-to-day operations of the team, output, development, and prioritization. This is a player-coach role: hands-on enough to shape the most complex or high-value deals directly, and structured enough to build the systems and standards that make the whole team fast and consistent. Success in this role looks like sales teams feeling unblocked and well-supported on commercial questions; proposals and pricing that are accurate, competitive, and aligned to delivery reality; a Deal Desk team that operates with speed and precision; and commercial workflows that are continuously improved through AI-powered tooling and process automation, in close collaboration with the Head of Solutions Operations and Enablement. This person raises the bar on how Superside prices and scopes — with discipline, data, and creativity. What you'll do: Deal Pricing & Scoping Own end-to-end pricing and scoping support for the largest enterprise deals, ensuring commercial accuracy and alignment with Superside's service offerings and delivery capacity. Review and validate your team's scopes, pricing structures, and deal configurations across the opportunity pipeline. Partner closely with Account Executives and the broader Solutions team to translate discovery findings and customer requirements into commercially viable proposals. Partner with internal subject matter experts to strengthen scoping and solution quality on complex, high-stakes deals. AI & Process Innovation Champion the use of AI tools to accelerate Deal Desk operations — from automating scope generation and pricing lookups to surfacing insights from historical deal data; in close collaboration with the Head of Solutions Operations and Enablement. Identify where AI can reduce manual effort and increase speed and accuracy across the pricing & scoping workflow, and lead the implementation of the improvements. Stay current on AI developments relevant to commercial operations, sales enablement, and proposal automation. Model AI-forward ways of working for the Deal Desk team and the broader Solutions function. Team Leadership & Operations Manage and develop a team of Deal Desk Associates, setting clear priorities, quality standards, and turnaround expectations. Act as the escalation point for the team on complex, ambiguous, or high-stakes deals requiring senior judgment. Drive continuous improvement across Deal Desk workflows, tooling, and documentation — building a function that scales with deal volume without sacrificing quality. Define and track team performance metrics, including deal velocity, pricing accuracy, and SLA adherence. Reporting & Governance Own Deal Desk reporting — including pricing patterns, deal velocity, win/loss trends, and scope accuracy — and surface insights to the Head of Solutions. Maintain and enforce pricing governance frameworks, ensuring deals are structured within approved parameters and exceptions are handled with appropriate visibility. Build and maintain playbooks, pricing guides, and reference documentation that empower the team and sales partners. What you'll need to succeed: Significant experience in Deal Desk, sales operations/strategy, or a pricing/scoping role within a creative, marketing, or professional services environment. Proven track record managing or leading a team, with the ability to develop talent and maintain high-quality output in a fast-paced environment. Strong commercial acumen — able to structure deals that are both competitive for customers and margin-sound for the business. Analytical and data-driven, with the ability to track performance, identify patterns, and make evidence-based recommendations. Genuine curiosity about and fluency with AI tools — particularly as they apply to commercial operations, proposal generation, and workflow automation. Highly organized, with the ability to manage multiple concurrent deals and priorities without losing accuracy or responsiveness. Strong communication skills — clear, concise, and credible with both internal stakeholders and, when needed, customers.