CONFIDENTIAL – Deal Desk Lead

W2 only, no C2C, must be authorized to work in the US (both now and in the future).

CONFIDENTIAL - Deal Desk Lead (Direct Hire) - Hybrid in Milwaukee, Wisconsin. Apply now for this opportunity at Carex!

Carex is partnering with a tech start-up to identify a highly organized, analytical, and solutions-oriented Sales Ops & Deal Desk Lead. This individual will play a key role in supporting commercial growth by strengthening deal execution, improving sales processes, and providing actionable insights that drive business performance. This hands-on position combines deal desk management with broader sales operations responsibilities, including contract administration, pricing support, CRM optimization, reporting, forecasting, and sales enablement. The ideal candidate brings a strong understanding of complex B2B sales environments, commercial agreements, and operational best practices, along with the ability to balance strategic initiatives with day-to-day execution. Must be able to navigate the fast-paced nature and ambiguity of a startup environment.

Duration: Direct Hire

Location: Milwaukee, WI requiring 2 days/week in-office

Salary: $95,000-115,000

What You'll Do

• Manage the end-to-end deal desk process for new business, renewals, and account expansions, ensuring accurate documentation, efficient execution, and alignment with internal policies.
• Partner with commercial teams to structure deals, develop pricing proposals, evaluate contract terms, and navigate non-standard requests and approval requirements.
• Coordinate contract preparation, negotiations, legal reviews, and execution while maintaining standardized templates, approval workflows, and accurate records.
• Oversee RFPs, RFIs, and other procurement-related activities, coordinating cross-functional input, managing deadlines, and ensuring complete and compliant submissions.
• Develop and maintain Salesforce dashboards, reports, and performance metrics to provide visibility into pipeline health, sales activity, conversion rates, renewals, and revenue trends.
• Support sales forecasting and business planning through pipeline analysis, KPI tracking, performance reporting, and actionable recommendations to leadership.
• Maintain Salesforce data integrity, establish CRM best practices, and partner with internal teams to improve system functionality, automation, and reporting capabilities.
• Develop and deliver sales enablement resources, training materials, and process documentation to support consistent execution across Sales and Customer Success teams.
• Collaborate with Marketing and other stakeholders to strengthen lead management, improve sales funnel visibility, and ensure alignment across commercial operations.
• Identify operational inefficiencies and implement scalable processes, tools, and workflows that improve deal turnaround times, contract management, and overall sales productivity.
• Lead cross-functional projects and continuous improvement initiatives that enhance commercial effectiveness, strengthen internal collaboration, and support organizational growth.
  
  
  

What You'll Bring

• 5 years of experience in Sales Operations, Revenue Operations, Deal Desk, Commercial Operations, Contract Management, or a related function supporting complex B2B transactions.
• Demonstrated experience managing commercial deal execution and sales operations responsibilities, including contract processes, reporting, KPIs, and sales enablement.
• Strong understanding of commercial contracts, pricing structures, discounting, approval processes, and negotiation practices.
• Experience coordinating contract reviews, managing redlines, and collaborating with legal and financial stakeholders.
• Hands-on Salesforce experience, including building reports and dashboards, maintaining data quality, and supporting pipeline management.
• Advanced Excel skills and strong analytical capabilities, with the ability to translate complex data into meaningful business insights.
• Experience supporting sales forecasting, performance reporting, and operational planning.
• Familiarity with formal procurement processes, proposal development, and RFP coordination.
• Experience developing process documentation, delivering training, and supporting adoption of sales tools and operational best practices.
• Excellent organizational and project management skills, with strong attention to detail and the ability to manage competing priorities.
• Strong written and verbal communication skills, including the ability to work effectively with senior leadership, cross-functional teams, and external stakeholders.
• A proactive, solutions-oriented mindset with the ability to independently build processes while remaining hands-on with execution.
• Comfort leveraging technology, automation, and AI tools to improve reporting, analysis, and operational efficiency.
• Experience with electronic signature platforms, CPQ solutions, contract lifecycle management systems, business intelligence tools, or SQL is preferred.
• Experience supporting complex procurement environments, regulated industries, or growing organizations with evolving processes and systems is a plus.
  
  
  

Carex Consulting Group is an equal opportunity employer. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, marital status, disability, gender identity or Veteran status.