Jeff Whitehead

Co-Founder

San Jose, California, United States28 yrs 6 mos experience

Key Highlights

  • Over 25 years in mission-critical service ownership.
  • Expertise in cloud computing and site reliability engineering.
  • Proven track record in digital transformation leadership.
Stackforce AI infers this person is a SaaS and Cloud Computing expert with extensive experience in digital transformation and site reliability engineering.

Contact

Skills

Core Skills

Cloud ComputingCompliance ManagementSite Reliability EngineeringApache KafkaProduct ManagementIt StrategyInformation Security ManagementLinux System AdministrationCross-functional Team Leadership

Other Skills

Large Language Models (LLM)Sales OperationsUnstructured DataInformation SecurityChange ManagementProject ManagementSalesforce.comAnalyticsScalabilityStart-upsSoftware DevelopmentSecuritySaaSData CenterNetworking

About

25+ years of experience in Internet facing mission critical service ownership, across both B2B/Enterprise and consumer facing services. Specific expertise in Product, SRE/DevOps/Cloud, internet scale networking, storage, AWS, security (technical and policy), organizational change, and systems architectures.

Experience

28 yrs 6 mos
Total Experience
3 yrs
Average Tenure
1 yr 1 mo
Current Experience

Meshly

Founding Advisor

Jun 2025Present · 11 mos · Mountain View, California, United States · Hybrid

  • System aware infrastructure and automation that acts as connective tissue across your GTM stack, designed to surface misalignment before it turns into revenue exposure.
Large Language Models (LLM)Cloud ComputingCompliance ManagementSales OperationsUnstructured Data

Confluent

Engineering Director II

Apr 2025Present · 1 yr 1 mo · Mountain View, CA · Hybrid

  • Confluent also offers fully managed, cloud-native data streaming services built for any cloud environment, ensuring scalability and reliability for modern data infrastructure needs. Apache Kafka and Flink allow for unifying the operational and reporting concerns, based on real-time data at global scale.
  • As part of the Cloud Architecture and Reliability team, I work on Confluent Cloud's managed services.
Apache KafkaSite Reliability EngineeringInformation SecurityChange Management

Sterling capital brokers ltd.

CIO

Mar 2023Apr 2025 · 2 yrs 1 mo · Canada · Remote

  • Leading the charge in digital transformation at Sterling, Canada's top independent group benefits provider. My vision is to empower businesses with technology that simplifies benefits administration and enhances the employee experience.
  • Key achievements include developing a cutting-edge benefits management platform, building a data-driven culture, and fostering a collaborative and innovative technology team.
  • As an executive leader, I've spearheaded product management and software development teams resulting in a 60% reduction in customer-facing defects and a decrease in issue resolution time from weeks to days. I've also successfully fostered a remote-first work environment.
  • I have extensive experience leading teams in data science, site reliability engineering (AWS), business applications (Salesforce), and internal IT. I'm passionate about data accessibility and have led company-wide data literacy training programs.
IT StrategyProject ManagementProduct ManagementCompliance ManagementSalesforce.com

Airkit.ai

CIO

Jan 2021Feb 2023 · 2 yrs 1 mo · Palo Alto, California, United States · On-site

  • Airkit's low code customer engagement platform enables businesses to rapidly design and implement personalized customer experiences across mobile, web, and voice.
  • I was responsible for backend engineering, compliance, data governance, technical security and information technology.
Information Security ManagementCompliance ManagementCloud Computing

Nutanix

Sr. Manager, Developer Productivity

Dec 2018Jan 2021 · 2 yrs 1 mo · San Francisco Bay Area

  • Responsible for source code management, infrastructure related to our build/release/test pipeline, incident management, technical security/ compliance, and quality reporting frameworks.
  • Lead a team of DevOps/SRE practitioners, as well as infrastructure (servers, networking) with a focus on providing an internal cloud/infrastructure as code, as well as standardizing our services so they can be run internally or at major cloud providers (AWS, GCP).
  • Agile service owner for multiple services with diverse global internal customer base: Gerrit, JIRA, PagerDuty, DataDog, Artifactory

Zetta, inc. / arcserve

CTO / Co-founder

Feb 2008Feb 2018 · 10 yrs · Sunnyvale, CA

  • Zetta's Disaster Recovery as a Service let customers adopt the cloud for failover (single server or whole site) on their own terms, without extensive re-architecture, incorporating custom networking, firewall, and VPN options, deployed and managed by Zetta.
  • Zetta's technology was implemented as a single image multi-tenant solution which enabled the re-synchronization and verification of petabytes of data across tens of thousands of endpoints (typically servers), overnight, every night -- using the standard internet connection they already had.
  • As a founder, I established and scaled teams and processes from inception, including our award wining Customer Support, Operations/Site Reliability Engineering functions, and later expanding to Technical Pre-Sales and Product Development (Software Engineering).
  • In addition to leadership, I was contributed in large scale storage administration, capacity planning, technical security and compliance, and overall system and service architecture.
  • Zetta was acquired by Marlin Equity in June 2017 and merged into Arcserve, where I served as CTO for the overall company during the integration period.

Shutterfly, inc.

CIO / VP Technical Operations

May 2005Dec 2007 · 2 yrs 7 mos · Redwood City, CA

  • While at Shutterfly I helped scale both the team and the service with the goal of improving reliability, end user performance, and overall business economics. I actively managed the culture, implementing a post-mortem & incident management process, resolving several long standing issues and significantly improving uptime.
  • Responsibilities included customer facing website operations, technical security, business applications, internal IT (including phones, desktops) as well as print lab infrastructure - everything until the customer orders reached the printers on the manufacturing floor. I helped position the overall company for IPO (including Sarbanes-Oxley IT compliance).
  • I was directly involved in the network re-architecture, storage systems, database, load balancing, capacity planning, network and systems security, budgeting, and performance profiling of all aspects of the service.

Memory matrix, inc.

Co-founder / Software Developer

Dec 2004May 2005 · 5 mos · Redwood Shores, California

  • Memory Matrix was PC based photo organization software (similar to Picasa/Lightroom) and was rapidly acquired by Shutterfly in May 2005.
  • At Memory Matrix I was a project manager and hands-on C++ programmer responsible for the database implementation using the SQLite engine, including schema design. I built a query optimizer to improve its native performance, allowing for managing millions of photos with a highly expressive, user extensible metadata query and keyword tagging system on a standard consumer / windows PC.

Shopping.com

Director, Internet Operations

Jun 1999Dec 2004 · 5 yrs 6 mos · San Francisco Bay Area

  • Epinions / Shopping.com helped consumers decide what to buy, and where to buy it. By scraping the web (and data feeds from merchants), we identified products (and their attributes), and created a taxonomy of consumer goods.
  • As the first system administrator/SRE/DevOps, I was responsible for our build/release process, content management, and all aspects of our datacenter environment, including initial network deployment (Layer 2&3, running own BGP AS), network load balancing, monitoring infrastructure, and both network and host security, in addition to managing our internal IT infrastructure (email/DNS/network/desktops). I negotiated vendor contracts (colocation, bandwith, servers) as well as managed the vendor relationships.
  • I scaled responsibilities first as a manager, then director, through Dealtime's acquisiton of Epinions and the companies subsequent rebranding as Shopping.com and IPO.

Knowledge universe

Lead Systems Engineer

Sep 1998Jun 1999 · 9 mos · Emeryville, CA

  • I advised on IT Infrastructure for the KU family of companies (private equity firm with over $1B in holdings).
Linux System AdministrationCross-functional Team Leadership

Netscape

Technical Solutions Engineer

Oct 1996Sep 1998 · 1 yr 11 mos · Mountain View, California

  • Starting at the IT Help Desk, setting up SGI and Sun workstations for developers, and rapidly working my way up, I built substantial components of Netscape's internal IT infrastructure, such as a knowledge management tool (an early wiki), internal user management (YP/NIS & LDAP) and reporting, scale out file storage (NFS & automounter) as well as large scale targeted marketing email delivery systems with automatic bounce processing and unsubscribe capabilities with deliverability reporting.
  • I soon moved to the website team, where my main areas of responsibility were the content management systems, load and capacity management, and the management of external DNS. I worked extensively with Sun Microsystems tuning their TCP/IP stack for large scale web servers and the result of that became the Solaris 2.5.1 "ISS" release. During this time we also hooked DNS into BGP routing, developing an early form of global load balancing, supporting Netscape Japan and other international properties.

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