Matthew Sibley

“A bad system will beat a good person every time.”

New York1.8k followers
Moderneex-MITex-GTM.build

Career through-line: helping enterprises ship and operate software at massive scale, and the start-ups that get them there.Currently: Moderne.

Career Timeline

JobSchool

GTM Index

  1. MODERNEJOB
    1. Dir, GTM
      3M
  2. PLATFORMATICJOB
    1. Lead, GTM and User Success
      1Y 8M
  3. GTM.BUILDJOB
    1. GTM Advisor
      11M
  4. ARTIUMJOB
    1. VP, Strategy and Innovation
      9M
  5. NEARFORMJOB
    1. Client Principal
      1Y 5M
  6. PIVOTAL SOFTWARE, INC. (NOW VMWARE)JOB
    1. Senior Enterprise Account…
      3Y
  7. LIGHTCRESTJOB
    1. Dir of Enterprise Sales
      2Y 2M
    2. Senior Enterprise Sales Ex…
      8M
    3. Enterprise Sales Executive
      1Y 6M
    4. Enterprise Sales Associate
      8M
  8. BUILT IN COLORADOJOB
    1. Contributing Writer (Start…
      6M
  9. MITJOB
    1. Audio Visual Lab Technicia…
      5M

Time in market 15Y 9MOpen 6Closed 10Stints 16

gtmindex.io/p/matthew-sibley

  1. Job: Moderne — Director, GTM · 2026-07 – present · 1 mo — I help large engineering organizations change code at estate scale: hundreds or thousands of repositories at once, deterministically, with an audit trail. Moderne is the company behind OpenRewrite, the open-source refactoring standard, and the platform that runs it as infrastructure: framework migrations, CVE remediation, and tech-debt pay-down that used to consume years of headcount, delivered as reviewable PRs in hours. The same substrate now powers deterministic tools for coding agents, so AI-written change becomes something enterprises can actually review and trust.
  2. Job: MIT — Audio Visual Lab Technician (Co-Op) · 2011-01 – 2011-06 · 5 mo — Served as key support staff for presentation technology and services. Wide-ranging activities include technical support for alumni events, conferences, class lectures, and concerts. Responsible for an audio-visual MIT inventory management system that services over 11,000 events per year. Interacted with diverse clientele ranging from diplomatic corps, undergraduate students, and event planners.
  3. Job: GTM.build — GTM Advisor · 2024-03 – 2025-02 · 11 mo — Applying AI to GTM to help teams at seed-stage start-ups and services orgs scale their revenue.
  4. Job: Platformatic — Lead, GTM and User Success · 2025-02 – present · 1y 6mo — Making sure we ship the right bits while helping developers adopt and drive outcomes from Platformatic’s Open Source ecosystem.
  5. Job: Lightcrest — Senior Enterprise Sales Executive · 2016-08 – 2017-04 · 8 mo
  6. Job: Lightcrest — Enterprise Sales Associate · 2014-05 – 2015-01 · 8 mo
  7. Job: Artium — VP, Strategy and Innovation · 2023-03 – 2023-12 · 9 mo
  8. Job: Built In Colorado — Contributing Writer (Start-up Community) · 2013-11 – 2014-05 · 6 mo — Covering the start-up scene in the Denver/Boulder metro area for BuiltInColorado, an online community that covers and connects the members of Colorado’s thriving startup community. These interviews gave me a rare opportunity to learn directly from the perspective of founders and CEOs about what it takes to build a winning culture.
  9. Job: Lightcrest — Director of Enterprise Sales · 2016-08 – 2018-10 · 2y 2mo — Our goal is to help you focus on your business while our open source and cyber security experts optimize and manage every aspect of your cloud infrastructure - either on the public cloud or on top of our home-grown private cloud platform.
  10. Job: NearForm — Client Principal · 2021-10 – 2023-03 · 1y 5mo — NearForm is a remote-first global consultancy that teaches clients how to leverage Open Source as a catalyst for their business objectives. Together, we design and build mission-critical digital products at speed and scale for enterprise and public sector clients. During my time at NearForm, I engaged with the Open Source community to help source, manage, and grow some of NearForm's most strategic clients. This ranged from leveraging Open Source at incredible scale with one of the planet's largest retailers to improve their developer experience and drive improvement across key metrics such as time-to-recover for critical services, and helping a web3 start-up and research accelerator re-ar…
  11. Job: Pivotal Software, Inc. (now VMware) — Senior Enterprise Account Executive · 2018-10 – 2021-10 · 3y — *Acquired by VMware* I partnered with leading companies to help them not just adopt new technologies, but new ways of working in order to transform how their organizations delivered software.
  12. Job: Lightcrest — Enterprise Sales Executive · 2015-01 – 2016-07 · 1y 6mo
  13. School: Northeastern University — Bachelor of Arts (B.A.), Communication and Media Studies
  14. School: General Assembly — Certificate, Product Management
  15. School: Universitat Autònoma de Barcelona
  16. School: Colorado Academy

Skills

Sales ProspectingDirect SalesOutbound SalesSales ProcessesDeveloper ProductivityOpen Source PlatformsConsultingGo-to-Market StrategyAgile MethodologiesTest-Driven DevelopmentExtreme ProgrammingUser-centered DesignContract NegotiationDigital TransformationServerless ComputingDevOpsOpen-Source SoftwareCommunity EngagementMarketing CommunicationsAccount Management

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