Enrique Montana
GTM Strategy & Operations, Chief of Staff, Commercial, Public Sector, Defense Industrial Base --- Microsoft, ex-Stripe
ex-StripeGlobal business leader with 20+ years of demonstrated success building and leading GTM strategy, planning, and operations teams for businesses and companies at all growth stages.
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Successful track record designing and operationalizing transformational initiatives to accelerate revenue and market share at scale. Excels at breaking down complex problems to identify the highest value opportunities and GTM mechanisms to drive results. Passionate about designing, testing, and scaling new operating models to deliver value to customers and the business. Skilled relationship builder, collaborator and communicator with C-level executives, colleagues, partners, and customers. Accomplished at building high performing teams and a positive culture. During my tenure at Microsoft, I led and contributed to 3 major transformations in the Global Enterprise Commercial business: the buildout of Enterprise GTM, the transition from on-prem software to Cloud services, and the evolution of Product/Geo GTM to include Industry GTM. At Stripe, I led a global team responsible for enabling the GTM organization to deliver key business objectives and revenue results. We provide strategic and operational partnership to sales teams and cross-functional business partners across the pillars of strategy and planning, sales operations, and analytics & insights.
GTM Index
- MICROSOFTJOB
- Head of GTM Strategy and O…2Y 2M
Head of GTM Strategy and Operations, Global Enterprise Sales
Microsoft
Office of the Global Chief Revenue Officer Microsoft, Enterprise • Designed and launched the US Defense Industrial Base (DIB) Operating Unit •Led strategic market identification initiatives and conducted ROI analyses to guide regional investment decisions •Designed and implemented segment-specific operating units to optimize customer engagement and partner alignment •Developed and refined organizational blueprints to enhance operational efficiency and scalability •Directed internal M&A activities, including due diligence, integration planning, and strategic alignment •Focused on high-impact sectors: Commercial Enterprise, Defense Industrial Base, Digital Native businesses, Federal Agencies
- Chief Of Staff and Global…2Y 11M
Chief Of Staff and Global Operations, Industry Solutions
Microsoft
Led the Executive Office as CoS reporting to the President of Industry Solutions and 10,000+ FTE organization driving $108B annual revenue contribution to MSFT •Led ROB, organization strategy, OKRs, and operating model design. Owned OPEX budget, headcount planning, budget allocation, and spend forecasting. •Led merger of 8 organizations and partnered with 30+ executives (VP and CVP peers reporting to President) to determine core priorities, performance metrics, OKRs, and budgets. •Owned Executive events (e.g., Executive Center Briefings and World Economic Forum, Tier 1 Industry) and prioritized Executive Sponsorship mappings and customer meetings for President. •Ensured clarity and prep…
- Senior Dir, Business Strat…3Y 11M
Senior Director, Business Strategy, Planning, & Operations, Enterprise Commercial & Industry
Microsoft
Led strategy and implementation of Enterprise Commercial shift toward an Industry-based GTM—focusing on Automotive, Energy, FSI, Health, Manufacturing, Telco & Media, and Retail & Consumer Goods. •Defined a standard operating blueprint for Industry organization. Redefined the Sales roles’ profiles by domain expertise versus geography, core responsibilities, performance goals, and compensation design. •Designed, secured investment, and implemented the first-ever “Account P&L” structure for the 5 largest commercial (multi-year, multi-billion strategic partnerships) customer accounts to fund programs and headcount—contributing to 100%+ revenue growth. •Led strategy, requirements criteria, a…
- Sr. Dir, Microsoft 365 GTM…3Y 11M
Sr. Director, Microsoft 365 GTM Operations and Sales Programs
Microsoft
Led large-scale initiatives and operations working closely with Sales, Product Marketing, Engineering, Field teams. • Spearheaded merger and management of 13+ investment programs ($150M+ budget) distributed across Windows, Security, Office, EDU, and Surface organizations—streamlining operations and driving efficiency. • Led “New Customer Add” initiative (Office Dark-to-Cloud). Implemented programs to accelerate and secure new cloud customers across all segments. Optimized for various sales models: direct, inside sales, partner co-sell/led, and channel. Operationalized Field Sales incentives to boost adds, including compensation accelerators, sales contests, and customer offers. • Receive…
- Dir, Microsoft 365 Strateg…3Y 11M
Director, Microsoft 365 Strategy and Operations
Microsoft
Led H2 Investment Program designed to convert opportunity upside to incremental revenue commitment for CFO forecast. Transacted 62+ investments totaling $5.5M+ and generating a ROI of 12X+ incremental revenue. • Shipped Office Enterprise Agreement Renewal and Recapture Dashboard to measure renewal and recapture rates at the geo and account level. Provided 360-degree view of actuals, pipeline, and forecast coverage. • Built Office 365 Sales Operations team accountable for sales force automation, sales process optimization and adoption, ROB performance, quota, pipeline, forecasting, scorecard, competitive opportunity executive escalations (including Google Compete Win Room), Office 365 syst…
- Microsoft 365 Sales and Bu…2Y 11M
Microsoft 365 Sales and Business Architecture
Microsoft
Recruited by CVP of Office Sales to define strategy, business model, and operations plan for Microsoft’s entry into Cloud Services sales (Office 365).
- Microsoft Additional Exper…9Y 11M
Microsoft Additional Experience
Microsoft
Director, Worldwide Enterprise & Partner Group | Enterprise 365 Sales Director, Communications and Media Sector | Finance and Sales Operations (Circle of Excellence Platinum Award) Communications and Media Sector, Sales | Customer and Partner Channel Various roles in US Enterprise Sales organization including Field Sales, Sales Strategy & Operations, Sales Programs
- STRIPEJOB
- GTM Head of Strategy & Ope…1Y 4M
GTM Head of Strategy & Operations
Stripe
Served as the primary strategy and operations business partner to the CRO Office. •Led a global team of business partners (COOs) to their aligned field sales leaders supporting and enabling Stripe sellers •Led the Global rhythm of business, including forecasting, pipeline analysis, OKRs (WBR, MBR, QBR). Work across cross-functional teams (Finance, Data Science, Systems, People) to define, operationalize, and adopt Standard Operating Metrics (Gross and Net) •Led annual planning outcomes such as headcount budgeting, segmentation, territory carving, target setting and landing across sales leadership and sellers •Evolved GTM processes and systems of the future to support scaled growth •Led…
- VARIOUS COMPANIESJOB
- Additional Experience4Y 11M
Additional Experience
Various Companies
FILM AXIS Founder, CTO DIMENSION DATA Professional Services Sales and Consultant - Financial Services concentration DELUXE CORPORATION Software Development Engineer
- Job: Microsoft — Microsoft 365 Sales and Business Architecture · 2010 – 2012 — Recruited by CVP of Office Sales to define strategy, business model, and operations plan for Microsoft’s entry into Cloud Services sales (Office 365).
- Job: Stripe — GTM Head of Strategy & Operations · 2023 – 2024-05 — Served as the primary strategy and operations business partner to the CRO Office. •Led a global team of business partners (COOs) to their aligned field sales leaders supporting and enabling Stripe sellers •Led the Global rhythm of business, including forecasting, pipeline analysis, OKRs (WBR, MBR, QBR). Work across cross-functional teams (Finance, Data Science, Systems, People) to define, operationalize, and adopt Standard Operating Metrics (Gross and Net) •Led annual planning outcomes such as headcount budgeting, segmentation, territory carving, target setting and landing across sales leadership and sellers •Evolved GTM processes and systems of the future to support scaled growth •Led…
- Job: Microsoft — Head of GTM Strategy and Operations, Global Enterprise Sales · 2024-06 – present — Office of the Global Chief Revenue Officer Microsoft, Enterprise • Designed and launched the US Defense Industrial Base (DIB) Operating Unit •Led strategic market identification initiatives and conducted ROI analyses to guide regional investment decisions •Designed and implemented segment-specific operating units to optimize customer engagement and partner alignment •Developed and refined organizational blueprints to enhance operational efficiency and scalability •Directed internal M&A activities, including due diligence, integration planning, and strategic alignment •Focused on high-impact sectors: Commercial Enterprise, Defense Industrial Base, Digital Native businesses, Federal Agencies
- Job: Microsoft — Chief Of Staff and Global Operations, Industry Solutions · 2021 – 2023 — Led the Executive Office as CoS reporting to the President of Industry Solutions and 10,000+ FTE organization driving $108B annual revenue contribution to MSFT •Led ROB, organization strategy, OKRs, and operating model design. Owned OPEX budget, headcount planning, budget allocation, and spend forecasting. •Led merger of 8 organizations and partnered with 30+ executives (VP and CVP peers reporting to President) to determine core priorities, performance metrics, OKRs, and budgets. •Owned Executive events (e.g., Executive Center Briefings and World Economic Forum, Tier 1 Industry) and prioritized Executive Sponsorship mappings and customer meetings for President. •Ensured clarity and prep…
- Job: Various Companies — Additional Experience · 1997 – 2001 — FILM AXIS Founder, CTO DIMENSION DATA Professional Services Sales and Consultant - Financial Services concentration DELUXE CORPORATION Software Development Engineer
- Job: Microsoft — Sr. Director, Microsoft 365 GTM Operations and Sales Programs · 2015 – 2018 — Led large-scale initiatives and operations working closely with Sales, Product Marketing, Engineering, Field teams. • Spearheaded merger and management of 13+ investment programs ($150M+ budget) distributed across Windows, Security, Office, EDU, and Surface organizations—streamlining operations and driving efficiency. • Led “New Customer Add” initiative (Office Dark-to-Cloud). Implemented programs to accelerate and secure new cloud customers across all segments. Optimized for various sales models: direct, inside sales, partner co-sell/led, and channel. Operationalized Field Sales incentives to boost adds, including compensation accelerators, sales contests, and customer offers. • Receive…
- Job: Microsoft — Director, Microsoft 365 Strategy and Operations · 2012 – 2015 — Led H2 Investment Program designed to convert opportunity upside to incremental revenue commitment for CFO forecast. Transacted 62+ investments totaling $5.5M+ and generating a ROI of 12X+ incremental revenue. • Shipped Office Enterprise Agreement Renewal and Recapture Dashboard to measure renewal and recapture rates at the geo and account level. Provided 360-degree view of actuals, pipeline, and forecast coverage. • Built Office 365 Sales Operations team accountable for sales force automation, sales process optimization and adoption, ROB performance, quota, pipeline, forecasting, scorecard, competitive opportunity executive escalations (including Google Compete Win Room), Office 365 syst…
- Job: Microsoft — Senior Director, Business Strategy, Planning, & Operations, Enterprise Commercial & Industry · 2018 – 2021 — Led strategy and implementation of Enterprise Commercial shift toward an Industry-based GTM—focusing on Automotive, Energy, FSI, Health, Manufacturing, Telco & Media, and Retail & Consumer Goods. •Defined a standard operating blueprint for Industry organization. Redefined the Sales roles’ profiles by domain expertise versus geography, core responsibilities, performance goals, and compensation design. •Designed, secured investment, and implemented the first-ever “Account P&L” structure for the 5 largest commercial (multi-year, multi-billion strategic partnerships) customer accounts to fund programs and headcount—contributing to 100%+ revenue growth. •Led strategy, requirements criteria, a…
- Job: Microsoft — Microsoft Additional Experience · 2001 – 2010 — Director, Worldwide Enterprise & Partner Group | Enterprise 365 Sales Director, Communications and Media Sector | Finance and Sales Operations (Circle of Excellence Platinum Award) Communications and Media Sector, Sales | Customer and Partner Channel Various roles in US Enterprise Sales organization including Field Sales, Sales Strategy & Operations, Sales Programs
- School: University of Michigan — Bachelor of Science - BS, Biology
Skills
Playbooks
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