Pat Calhoun

CEO

San Francisco, California, United States28 yrs experience
Highly Stable

Contact

About

I’ve spent my career building and scaling category-defining enterprise platforms—from early product-market fit to global adoption and exit. At Cisco (via acquisition of Airespace), we built the #2 wireless market share position globally in under 18 months from zero—helping define the modern enterprise Wi-Fi architecture. As Founder & CEO of Espressive, we became a three-time leader in the Forrester Wave for Conversational AI for Employee Services, achieving 85%+ adoption, 65%+ ticket reduction, and millions of enterprise interactions annually. Across prior roles at Cisco, McAfee, and ServiceNow, I’ve led and scaled multiple category-leading products—including IPS, firewall, NAC, and ITSM platforms—each reaching market leadership positions. In addition to building from zero, I’ve repeatedly stepped into situations where growth stalled—diagnosing and correcting go-to-market, positioning, and operating issues to get companies back on trajectory. Today, I work directly with CEOs and boards at critical inflection points—typically when growth stalls, positioning breaks down, or execution no longer matches ambition. I step in to diagnose what’s actually driving the gap and, where there’s a clear path, take ownership of correcting it—across go-to-market, product positioning, and operating model.

Experience

28 yrs
Total Experience
3 yrs 4 mos
Average Tenure
3 mos
Current Experience

Inflection point partners

Founder / CEO

Feb 2026Present · 3 mos · Santa Clara, CA · On-site

  • Founder of Inflection Point Operating, working with CEOs and investors at critical moments of growth, scale, and transformation.
  • I focus on identifying the underlying constraints impacting performance — across product-market fit, positioning, go-to-market execution, and operating model — and driving the changes required to improve trajectory.
  • This is not advisory. I work alongside leadership teams with ownership for execution and outcomes, typically in a small number of high-impact engagements.
  • I’ve spent my career building and scaling category-defining enterprise platforms.
  • At Airespace, we built the #2 global market share position in enterprise Wi-Fi within 18 months from zero, leading to the acquisition by Cisco and helping define the modern wireless architecture.
  • As Founder and CEO of Espressive, we built a category-leading AI platform, achieving 85%+ adoption and recognition as a three-time leader in the Forrester Wave for Conversational AI for Employee Services.
  • Across Cisco, McAfee, and ServiceNow, I’ve led and scaled multiple market-leading products spanning security, networking, and enterprise service platforms.

Resolve

Chief Strategy Officer – Resolve (Following Acquisition of Espressive)

Sep 2025Feb 2026 · 5 mos · San Francisco Bay Area · On-site

  • Led post-acquisition enterprise growth execution following Espressive’s sale to Resolve, with responsibility spanning product direction, partner motion, and go-to-market delivery.
  • Accountable for revenue impact and ecosystem expansion, building and operationalizing a repeatable MSP-led growth model to support enterprise-scale deployments.
  • Worked cross-functionally across product and engineering to translate agentic AI architecture into deployable, high-volume enterprise automation at commercial scale.

Forbes technology council

Forbes Councils Influencer, Focus on AI, ML and Employee Experiences

Sep 2020Present · 5 yrs 8 mos

  • Member of the Forbes Technology Council, contributing perspectives on AI, automation, and employee experience informed by building and operating enterprise platforms at scale.
  • Write on enterprise platform strategy, ecosystem leverage, and the future of work, with a focus on how AI-driven automation changes how large organizations operate.

Espressive

Founder & Chief Executive Officer

Sep 2016Sep 2025 · 9 yrs · San Francisco Bay Area

  • Founded and scaled Espressive, creator of the industry’s first agentic, intent-less AI platform for enterprise service.
  • Owned product, revenue, and go-to-market execution end to end, leading the company through growth, scale, and a transition to operational discipline and profitability.
  • Built a differentiated enterprise platform designed to eliminate customization debt and upgrade friction common in traditional ITSM and chatbot models.
  • Led Espressive to become a three-time Forrester Wave Leader, supporting millions of employee interactions annually across IT, HR, Facilities, and more, and delivering industry-leading outcomes: 85%+ employee adoption, 65%+ ticket reduction, and 90%+ accuracy without intent modeling.
  • Designed and scaled an MSP-led go-to-market and partner ecosystem, positioning the platform as the enterprise front end for digital workplace and managed service providers and enabling structurally lower cost of sale at scale.
  • Built and sustained a high-performance, employee-endorsed culture that scaled with the business.

Servicenow – the enterprise cloud company

Senior Vice President Product, Applications

May 2015Aug 2016 · 1 yr 3 mos · Santa, Clara, CA

  • Led product, go-to-market, and pricing execution for ServiceNow’s emerging application portfolio, spanning HR, ITOM, ITBM, Security Operations, CSM, and Analytics.
  • Owned GTM and pricing strategy for new enterprise applications, driving 48% YoY growth in $1M+ ACV deals and a 51% increase in backlog to $2.8B.
  • Played a key role in expanding ServiceNow beyond ITSM into a multi-workflow enterprise platform, reinforcing Gartner-recognized market leadership and establishing the foundation for enterprise service management at scale.

Mcafee / intel security

SVP/GM Network Security Business Unit

Feb 2012Apr 2015 · 3 yrs 2 mos · Santa Clara, CA

  • Owned full P&L and business strategy for a $550M global network security business spanning next-generation firewall, IPS, proxy firewall, and network-based malware detection.
  • Led a global organization of 800+ across 10 locations and three continents, with responsibility for product, engineering, sales, and go-to-market execution.
  • Executed three strategic acquisitions to complete the portfolio, including McAfee’s second-largest acquisition (Next Generation Firewall).
  • Established market leadership across the portfolio, with McAfee’s IPS recognized as best performance by NSS and most innovative by Gartner.
  • Transformed the go-to-market model to accelerate growth and materially improve operating leverage.

Cisco systems

2 roles

VP/General Manager, Secure Network Services Business Unit

Sep 2009Feb 2012 · 2 yrs 5 mos

  • Served as General Manager of Cisco’s Access Control and Identity business, with responsibility for product strategy, execution, and enterprise adoption.
  • Drove enterprise-wide adoption of TrustSec, integrating access control policy across Cisco’s enterprise portfolio and establishing Cisco’s leadership position in network-wide access control.

Chief Technology Officer, Wireless Networking Business Unit

Mar 2005Sep 2009 · 4 yrs 6 mos

  • Appointed CTO for Cisco’s Wireless Networking Business Unit following the Airespace acquisition, with responsibility for system architecture, product direction, standards leadership, and patent strategy.
  • In 2007, assumed CTO responsibility for the Network Access & Services Business Group, a $12B organization spanning switching, routing, wireless, and security.
  • Served as Cisco’s executive spokesperson for next-generation access and wireless technologies, representing the company at industry, standards, and customer forums.

Canarie inc.

Board Member

Jun 2009May 2012 · 2 yrs 11 mos · Canada

  • Served on the board of CANARIE, Canada’s national advanced research and innovation network, supporting next-generation digital infrastructure for researchers and public institutions.

Airespace (acquired by cisco)

Chief Technology Officer & Founder

Jan 2001Jan 2005 · 4 yrs

  • Founded Airespace and invented the centralized Wi-Fi architecture, fundamentally reshaping enterprise wireless networking.
  • Led product architecture and system design for the Airespace WLAN platform, achieving #2 market share within 18 months and a $50M run rate in a highly competitive market.
  • Drove industry adoption through customer, analyst, and standards engagement, establishing Airespace as the foundation for next-generation enterprise WLAN.
  • Acquired by Cisco for $450M, forming the core of Cisco’s enterprise WLAN strategy.

Sun microsystems, inc

Sr. Staff Engineer, Next Generation Mobility Technology

Jan 1998Jan 2001 · 3 yrs

  • Early career role at Sun Microsystems, where I led work in Sun Labs on next-generation mobility and large-scale networking architectures, and contributed to foundational standards and protocols—including Mobile IP and DIAMETER—now embedded in global LTE deployments.

Education

Algonquin College of Applied Arts and Technology