Troy Siiter
Chicago,United States
Summary
Senior Manager, Deal Design with 14+ years of experience structuring and governing complex, high-value commercial agreements across healthcare and diagnostics environments. Proven track record of partnering with Sales, Finance, and Legal to drive disciplined deal execution, margin-aligned pricing strategies, and scalable governance frameworks. Experienced in CPQ systems, cross-functional stakeholder influence, and IDN and multi-site commercial agreements. Delivered multi-million-dollar deal structuring while optimizing commercial risk for Fortune 100 clients. Skilled in Salesforce, margin analysis, stakeholder engagement, and cross-functional collaboration. Proven ability to influence senior leaders, establish governance frameworks, and drive scalable growth through disciplined deal strategy and process optimization.
Overview
19
19
years of professional experience
Work History
Team Lead, Deal Desk
Merative US L.P. (formerly IBM Watson Health)
Chicago, IL
01.2022 - 01.2026
- Served as a trusted advisor across a 10-person cross-functional team including Sales, Finance, and Legal partners on deal strategy, risk mitigation, and commercial structuring to enabling $15M in recurring revenue, reinforcing governance and decision discipline across deal execution.
- Led contract management development for large-scale payers, pharma/biotech, and consulting firms by gathering detailed business requirements to shape complex, high-value contracts for data analytics services (SOW) and SaaS offerings.
- Leveraged Salesforce CPQ systems architecture, including object relationships and approval workflow configurations, to improve data integrity, reporting accuracy, and quote-to-cash efficiency.
- Championed a data-centric culture by embedding continuous improvement practices into deal desk workflows, achieving a 99% compliance rate with internal Service Level Agreements (SLAs), driving measurable efficiency gains across contract execution cycles.
- Coached a cross-functional Sales team on deal structuring best practices, accurate quoting within CPQ systems, and adherence to pricing governance and approval frameworks.
- Applied SaaS pricing principles and revenue recognition frameworks to evaluate deal structures, contracting policies, and recommend optimal commercial terms.
Senior Manager, Proposal Operations
IBM Watson Health (formerly Truven Health Analytics)
Chicago, IL
01.2017 - 01.2022
- Orchestrated 150+ annual provider client contract agreements accelerating growth for $10M portfolio; enabled data product development and delivery services supporting international enterprises and industry-leading healthcare systems; frequently led client sales calls to ensure alignment and address stakeholder concerns.
- Monitored and evaluated deal metrics across active pipeline to identify optimization opportunities and surface actionable business insights for leadership review.
- Engineered request for proposal (RFP) responses, collaborating cross functionally with key stakeholders to gather and analyze business needs and requirements for multi-year contracts.
- Developed detailed contract specifications aligning service delivery with client expectations, revenue recognition, and ensuring compliance and mitigating commercial risks.
Manager, Data Operations
Truven Health Analytics
Chicago, IL
01.2007 - 01.2017
- Enabled Provider (hospital, system, IDN) sales teams with targeted support and account management, driving direct sales beyond corporate goals and increasing enterprise profit margins.
- Promoted to senior management after Thomson Reuters divestiture; partnered with executive leadership to expand business segment, achieving 230% revenue growth surpassing $10M.
- Collaborated cross-functionally to optimize proposal and commercial operations processes, enhancing deal execution efficiency and supporting scalable growth.
- Became a subject-matter expert (SME) in key data offerings to support customized, client-driven deliverables.
- Established excellent relationships with sellers and cultivated similar connections with pharma and academic sellers.
- Maintained clear, regular communication and prevented crises and adverse outcomes in contracting.
- Received multiple instances of positive feedback from the sales team demonstrating strong support and collaboration skills.
Education
Bachelor of Individualized Study (BIS) - Healthcare Database Analytics
George Mason University
Fairfax, VA, United States01-2019
Skills
- MS Office Suite
- CRM Platforms: Salesforce/CPQ
- Tableau, SQL
- DocuSign CRM
- Relational Databases
Websites
Core Competencies
Deal Design & Governance | Complex Commercial Structuring | CPQ Systems | Financial Analysis | Margin Optimization| Cross-Functional Influence | Pricing Strategy | Healthcare & IDN Environments | Stakeholder Engagement
Timeline
Team Lead, Deal Desk
Merative US L.P. (formerly IBM Watson Health)
01.2022 - 01.2026
Senior Manager, Proposal Operations
IBM Watson Health (formerly Truven Health Analytics)
01.2017 - 01.2022
Manager, Data Operations
Truven Health Analytics
01.2007 - 01.2017
Bachelor of Individualized Study (BIS) - Healthcare Database Analytics
George Mason University