A career built at the intersection of technology, partnerships, and revenue. From early roles in defense engineering and venture capital to leading billion-dollar incentive programs at Microsoft and negotiating transformative alliances at Sage.
Engineering- and business-trained, with global operational experience and leadership across customer segments ranging from scalable SMB engagement to Fortune 50 global enterprises.
2012 · Microsoft's first F1 entry
In 2012, Brendan O'Connor negotiated Microsoft's first entry into Formula One from his role leading commercial strategy for the $1.4 billion Dynamics division. That deal created the technology sponsorship model that Microsoft now runs at $60 million per year with Mercedes.
Read the case study →Founded The Brushton Group to bring enterprise-grade partnership expertise to technology companies at every stage of growth. Engagements span commercial strategy, channel program design, investor readiness, and commercial execution for mid-market, growth-stage, and AI-native companies. Past and current clients include Microsoft, Intuit, ASG Technologies, and an early-stage AI-native e-commerce search platform.
Led the global strategic alliances function reporting to the Chief Growth Officer, with multimillion-dollar partnerships across hyperscalers (AWS, Microsoft) and professional services firms (PwC, Deloitte). Led channel-first organizational transformation across sales, marketing, product, and customer success.
Recruited to the Offer Monetization Office to convert Cisco's substantial software engineering output (roughly 80% of Cisco engineering effort) from a free hardware bundle into separately monetizable software revenue. Co-developed Cisco's first Enterprise Agreement model and designed the partner-led sales playbook for hardware-focused Global System Integrators (GSIs) to sell enterprise software licensing, creating the GTM foundation for the company's first global GSI EA channel.
VP-scope role leading global incentive strategy, partner ecosystem enablement, and commercial model design for Microsoft's enterprise and SMB businesses across SMB, Enterprise, SLG and Government segments. Oversaw a $1.2B global partner incentive budget covering 400+ resellers across 160 subsidiaries, scaling cloud adoption across Azure, Office 365, and Dynamics. Funded the launch of Microsoft's first Cloud Solution Provider (CSP) incentive model from within the enterprise incentive budget.
Founded Microsoft Dynamics' first Deal Desk for a $1.4B business unit. Led licensing, pricing, and negotiations across ~150 internal Partner Account Managers and ~6,000 external partner sellers. Restructured renewal and discounting practices for a combined $119M annual commercial impact: $78M renewal recovery (rate improved 86% to 94% on $980M base) plus $41M discount reduction (38% to 32% on $420M new-license base). Reported to the Business Unit Global CFO.
Reporting to the Corporate Vice President of Worldwide Licensing and Pricing, led global channel strategy for Microsoft's Enterprise Agreement program: directed the conversion of the enterprise channel from indirect resale to direct billing, designed the Enterprise Software Advisor (ESA) compensation model, and co-created the Licensing 6.0 program. Scope also included SMB channel programs distributed through Tech Data and Ingram Micro. Recognized as Microsoft's worldwide expert on commercial channel strategy. The ESA designation remains in Microsoft's FY2025 10-K, twenty-four years after launch.
Managed a $6M early-stage technology investment portfolio across western Pennsylvania for the regional non-profit venture investor (now operating as Innovation Works). Revamped the review process to evaluate 150+ new business proposals annually using 300 local and national experts. Sourced the early Challenge Grant investment in FreeMarkets Online, which later IPO'd with a 440% first-day gain (one of the largest in Nasdaq history) and grew into a $4.3B acquisition chain with Ariba.
Managed critical-path startup operations as one of six Lead Engineers for a $400M classified national security project at one of the Department of Energy's largest nuclear facilities. Engineering discipline (systems thinking, operational rigor, first-principles problem solving) has shaped every commercial role since.
Operating Scope
Core Domain
Operator Depth
Modern GTM
I'm focused on senior executive roles in commercial strategy, channel leadership, partner ecosystems, and alliance strategy across enterprise software, cloud, and AI-native companies. The work is consistent across titles: building the commercial, partner, incentive, and channel systems that turn enterprise software into repeatable revenue.