Director, Deal Desk

About Showpad

Showpad is the leader in revenue effectiveness, helping organizations in complex, field-driven industries turn strategy into execution and execution into measurable growth. Purpose-built for industrial organizations such as those in manufacturing, consumer packaged goods, and medical device companies, Showpad’s AI-native platform unifies content management, sales readiness, buyer engagement, and revenue intelligence into a single system of execution.

Powered by GenieAI and grounded in trusted first-party data, Showpad enables revenue teams to automate workflows, scale winning behaviors, and reclaim lost revenue across every customer interaction. More than 2,000 global organizations rely on Showpad to drive consistent, high-impact performance in the field.

Built for effectiveness and recognized for excellence, Showpad is consistently named a Leader by Gartner, Forrester, IDC, and Aragon, and backed by 2,500+ five-star reviews on G2 and Gartner Peer Insights.

Job & Department Summary

Showpad’s Revenue Operations team owns the systems, data, and operating processes that allow the go-to-market organization to sell, service, and grow revenue. The team spans GTM Systems, Deal Desk, Insights and Innovation, GTM Strategy, and Sales and Customer Operations, across North America, EMEA, and India.

The Director, Deal Desk is the senior commercial leader within that team and the executive owner of how Showpad prices, structures, governs, and books its business. This leader sets the strategy and standards for the global Deal Desk function, builds and leads the team that delivers it, and is accountable for the integrity of every deal from first quote through signed contract, booking, and handoff to billing and revenue recognition.

This is an executive partnering role. The Director serves as a trusted commercial advisor to the Chief Revenue Officer, Chief Financial Officer, SVP of North America Sales, VP of EMEA Sales, and VP of Revenue Operations, shaping the company’s most strategic, complex, and high-value deals, framing difficult trade-offs for executive decision, and representing the Deal Desk point of view in forecast, pricing, and planning conversations. They are expected to unlock revenue through creative, defensible deal structures while holding a firm, principled line on pricing discipline, margin, and policy, particularly under quarter- and year-end pressure.

The team and how the role operates

The role reports to the Vice President, Revenue Operations and leads a global Deal Desk team, currently three Deal Desk Analysts, supporting North America, EMEA, and APAC, with the majority of volume in North America and EMEA. The Director owns the function’s operating model, organizational design, coverage across time zones, hiring, and talent development, and is expected to scale the team and its capabilities as the business grows. The Director leads largely through influence across the executive team and cross-functional partners: Finance and Accounting on revenue recognition, billing, and collections; Legal on contract terms and risk; GTM Systems on CPQ and quote-to-cash infrastructure; Product Marketing on pricing and packaging; and Sales and Customer Operations on bookings and forecast integrity.

Why this role exists now

Following the Bigtincan merger, Showpad has two heritage customer bases, a recently unified systems landscape, and pricing, packaging, and approval practices that have not yet been fully rebuilt for the combined business. Discounting, deal structures, and quote-to-cash handoffs currently rely heavily on manual effort and individual judgment. Showpad needs a senior leader who can design and implement a scalable, well-governed commercial framework for the combined company, chair the Value Pricing Board, resolve the complex commercial problems that come with integration (heritage contract migrations, conflicting price books, legacy terms, and renewal risk), and give executive leadership a single, trusted partner on deal strategy, commercial terms, and pricing.

Key Responsibilities

Deal Desk Leadership

- Set the vision and strategy for Showpad’s global Deal Desk function, aligned to the company’s revenue, margin, and value-creation objectives.

- Lead, coach, and develop the Deal Desk team, setting a high bar for commercial judgment, responsiveness, quality, and executive-ready communication.

- Own the function’s operating model: regional coverage across North America, EMEA, and APAC, capacity planning, and the case for future headcount as the business scales.

- Establish and publish service levels for quote turnaround, approval cycle time, and order processing, and hold the function accountable to them, especially through month-, quarter-, and year-end.

- Design a tiered engagement and prioritization model so that strategic, high-value, and time-sensitive deals receive senior attention while standard deals move through with minimal friction.

Executive Partnership and Commercial Advisory

- Serve as the primary commercial advisor to the CRO, CFO, SVP of North America Sales, VP of EMEA Sales, and VP of Revenue Operations on deal strategy, pricing, and commercial risk.

- Partner with the SVP of North America Sales and VP of EMEA Sales and their leadership teams to shape the regional deal pipeline, prepare for quarter-end, and align on approach for the largest and most complex opportunities.

- Partner with the CFO and Finance leadership to ensure commercial decisions balance growth with margin, cash, and revenue quality, and that the financial consequences of every non-standard term are understood before signature.

- Frame contested or high-stakes commercial decisions for executive resolution, with the options, economics, risks, and a clear recommendation, rather than escalating open questions.

- Represent Deal Desk in executive forecast calls, QBRs, and annual planning, bringing a credible, data-backed view of deal quality, discounting, and commercial risk.

Complex Deal Strategy and Problem Solving

- Personally lead the structuring of Showpad’s most strategic, complex, and non-standard deals across new logo, expansion, renewal, and multi-year agreements.

- Solve the hardest commercial problems in the business: heritage customer migrations and consolidations, conflicting legacy terms and price books, at-risk renewals, competitive displacements, multi-entity and multi-currency agreements, and channel or partner structures.

- Design creative, defensible deal structures (ramped pricing, multi-year commitments, co-terming, bundling, upgrades, and enterprise agreements) that win while protecting margin, revenue quality, and long-term customer value.

- Partner with Legal on non-standard commercial terms (payment terms, termination rights, price caps, renewal uplifts, liability, and SLAs) and set the commercial position the business is willing to accept.

- Act as the final escalation point for deal-level disputes between Sales, Finance, and Legal, resolving issues quickly and consistently with policy and precedent.

Value Pricing Board and Commercial Governance

- Chair the Value Pricing Board, Showpad’s executive forum for approving deal discounts, non-standard structures, and commercial exceptions.

- Own the Board’s charter, membership, cadence, and decision rights in alignment with the CRO and CFO, ensuring decisions are fast, consistent, and well documented.

- Ensure every deal brought to the Board is executive-ready, with deal economics, discount rationale, competitive context, risk assessment, and a clear Deal Desk recommendation.

- Own and evolve the global discount approval matrix and delegation of authority, ensuring thresholds are clear, consistently applied, and reviewed as the business changes.

- Use Board decisions and outcomes to refine policy, strengthen guardrails, and steadily reduce the volume of deals that require executive escalation.

Quote-to-Cash Strategy and Transformation

- Own the end-to-end quote-to-cash process strategy, from quote creation and approval through contract execution, booking, provisioning, invoicing, and renewal.

- Lead the redesign of quote-to-cash for the combined Showpad and Bigtincan business, identifying bottlenecks, manual effort, and control gaps, and driving a prioritized transformation roadmap.

- Act as the executive business owner for CPQ, approval workflows, contract management, and billing integrations, partnering with GTM Systems on requirements, prioritization, and adoption.

- Ensure bookings are accurate, complete, and audit-ready, partnering with Finance and Accounting on ASC 606 / IFRS 15 considerations and revenue recognition outcomes.

- Drive clean, accountable handoffs between Sales, Deal Desk, Finance, Legal, and Customer Success so that what is sold is what is provisioned, billed, and recognized.

- Deliver measurable reductions in quote-to-cash cycle time and booking errors, and report progress to the VP, Revenue Operations and executive leadership.

Pricing Strategy and Commercial Policy

- Partner with the CRO, CFO, and VP, Revenue Operations to shape Showpad’s pricing strategy, including list pricing, packaging, discount guardrails, and renewal uplift policy.

- Bring deal-level evidence to pricing decisions: discount trends, win/loss by price point, deal size and mix, price realization, and regional and segment variation.

- Partner with Product Marketing and Finance on new product and packaging launches, ensuring they are quotable, approvable, and bookable from day one.

- Own the global commercial policy framework (discounting policy, approval matrix, payment terms, and standard deal structures) and ensure it is understood and followed across the field.

- Identify sources of pricing leakage and commercial friction, and bring executive leadership clear, quantified recommendations for change.

- If a global pricing change requires Finance, Legal and GTM Systems to reprioritize work, the Director Deal Desk must own the rollout decision, commit capacity, and be accountable for the result.

Deal Intelligence and Executive Reporting

- Deliver executive-level reporting on discounting, deal velocity, approval cycle time, non-standard terms, and price realization across regions and segments.

- Partner with Sales and Customer Operations to ensure bookings data supports an accurate forecast, and with Finance to reconcile bookings each period.

- Provide the CRO, CFO, and regional sales leaders with quarterly insight into deal quality and commercial trends, with a clear point of view on what should change.

Leadership Standards

- Bring recommendations, not open questions. When a deal or policy decision is contested, propose a path forward and make the trade-offs explicit.

- Build a function that is consistent, auditable, and scalable, with documented processes, policies, and approval logic.

- Champion automation and simplification, working with Revenue Operations colleagues to eliminate manual and spreadsheet-driven steps in the deal and quote-to-cash process.

- Lead change management for pricing, policy, and process updates, communicating clearly and early to executives, sales leaders, and everyone affected.

Key Performance Outcomes

Deal Desk Performance

- Quote turnaround and approval cycle times consistently meet published service levels across all regions, including at quarter- and year-end.

- Booking accuracy improves measurably, with order and contract errors reducing quarter over quarter.

- Sales leadership regards Deal Desk as a strategic enabler of revenue rather than a bottleneck.

Pricing Discipline and Value Pricing Board

- Average discount and discount variance trend toward agreed targets, with improved price realization and reduced pricing leakage.

- The Value Pricing Board runs on a predictable cadence, with decisions made quickly and documented consistently.

- The share of deals requiring executive escalation reduces as policy, guardrails, and seller enablement mature.

Quote-to-Cash Transformation

- End-to-end quote-to-cash cycle time reduces against an agreed baseline.

- A unified quote-to-cash process, approval framework, and price book are in place for the combined business.

- Bookings reconcile to Finance each period without material adjustment, and audit findings related to the deal process are closed.

Pricing Strategy

- Pricing and packaging recommendations are grounded in deal data and adopted by executive leadership.

- New pricing and packaging changes launch on schedule and are quotable and bookable from day one.

Team Leadership and Executive Partnership

- The Deal Desk team is fully staffed, engaged, and developing, with clear career paths and no single points of failure across regions.

- The CRO, CFO, SVP of North America Sales, VP of EMEA Sales, and VP of Revenue Operations regard this role as a trusted commercial advisor and rely on it for the company’s most complex deals.

- Complex commercial issues are resolved at the Deal Desk level, with fewer escalations to executive leadership.

Required Skills & Experience

Experience: Must have

- 10+ years in B2B SaaS go-to-market organizations, with significant experience in Deal Desk, Revenue Operations, Sales Finance, or Pricing.

- Proven experience serving as a trusted advisor to C-level and senior sales and finance leaders (CRO, CFO, regional sales executives), including the ability to influence decisions and hold a position constructively under quarter-end pressure.

- Deep experience structuring and negotiating complex enterprise SaaS deals, including multi-year, ramped, co-termed, multi-entity, and non-standard agreements.

- Demonstrated ownership of a quote-to-cash or deal approval process at scale, including leading measurable process and systems transformation.

- Experience chairing or leading an executive deal review or pricing approval forum.

- Experience supporting a global sales organization across multiple regions and time zones, including North America and EMEA.

- Strong working knowledge of revenue recognition principles (ASC 606 / IFRS 15) and how contract terms affect bookings and revenue.

- Strong analytical and financial acumen, with comfort forming and defending a clear view from imperfect data.

Experience: Nice to have

- Experience shaping SaaS pricing and packaging strategy, including list price changes and new packaging launches.

- Experience leading commercial integration in a post-merger environment with multiple heritage customer bases, price books, and systems.

- Exposure to APAC commercial practices and contracting.

- Experience with reseller, partner, or channel deal structures.

- Background in a private-equity-backed business with value-creation accountability.

Technical Skills: Must have

- Salesforce: strong working knowledge of opportunities, quotes, products, and price books.

- CPQ platforms (e.g., Salesforce CPQ / Revenue Cloud, DealHub, or equivalent), including experience owning approval workflow design and business requirements.

- Advanced deal modeling capability: discount analysis, multi-year economics, and margin and cash impact.

- Expert grasp of SaaS commercial metrics: ARR, ACV, TCV, NRR, GRR, discount, and price realization.

Technical Skills: Nice to have

- Contract lifecycle management tools such as DocuSign CLM, Ironclad, or equivalent.

- Billing and subscription management platforms such as NetSuite, Zuora, or equivalent.

- QuickSight, Power BI, Tableau, or equivalent.

- Revenue intelligence platforms such as Gong or Clari.

Competencies

- Executive presence: credibility and composure with C-level leaders, and the confidence to deliver an unwelcome decision without damaging the relationship.

- Strategic commercial judgment: the ability to balance winning the deal with protecting margin, revenue quality, and long-term value.

- Complex problem solving: breaking down ambiguous, high-stakes commercial problems into clear options and a recommended path.

- People leadership: coaching, accountability, and building a team others want to join.

- Influence without authority across Sales, Finance, Legal, Product, and Systems.

- Composure and pace under month-, quarter-, and year-end pressure.

- Transformation mindset, with a drive to simplify, standardize, and automate.

Certifications and/or Licenses

- Bachelor’s degree in business, finance, economics, or equivalent practical experience; MBA or advanced degree a plus.

- Salesforce CPQ or Revenue Cloud certification (nice to have).

- Pricing or finance certification, e.g., CPP, CMA (nice to have).

Location and Working Hours

- Based in the United States, with working overlap sufficient to support EMEA sales leadership and periodic APAC deal activity.

- Occasional international travel for executive offsites, planning cycles, and stakeholder sessions.

- Availability during month, quarter, and year-end close peaks is expected.