Cortlandt Armstrong
GTM Leader @ Sierra
- Role
- Regional Vice President, Enterprise Sales at Sierra
- Location
- Chicago, IL, US
- LinkedIn followers
- 500 followers
About Cortlandt Armstrong
Dynamic and results-driven business leader with extensive experience in digital transformation, go-to-market strategy development, and new business integration. Proven success in driving enterprise-wide collaboration and intrapreneurship to create significant value within Fortune 100 organizations. Known for building and growing high-performing teams, fostering innovation, and delivering exceptional results in complex, high-stakes environments. Strong expertise in sales leadership, digital marketing, and economic inclusion initiatives.
Experience
Regional Vice President, Enterprise Sales
Aug 2025 — Present · Chicago, IL, US
Education
United States Military Academy Prep School
General, General
2003 — 2004
Basic Officer Leadership Course
Entry level management and leadership training
2008 — 2008
United States Military Academy at West Point
Bachelor of Science, Sociology, Minor in Environmental Engineering
2004 — 2008
Skills
- Customer Relationship Management (Crm)
- Strategy
- Cross-Functional Team Leadership
- Military
- Competitive Analysis
- Contract Negotiation
- Product Management
- Sales Operations
- Logistics
- Training
- New Business Development
- Key Account Management
- Process Improvement
- Operations Management
- Forecasting
- Continuous Improvement
- Program Management
- Supply Chain Management
- Variant Configuration
- Six Sigma
- Sales
- Retail
- Military Experience
- Software Configuration Management
- Account Management
- Change Management
- Business Development
- Business Strategy
- Risk Management
- Leadership
- Budgets
- Negotiation
- Strategic Planning
- Business Process Improvement
- Configuration Management
- Product Development
- Analysis
- Product Marketing
- Project Planning
- Supply Chain
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