S

Shakudo

Data stack operating system for AI

General Manager - OS Platform Business Unit

Full-Time
No salary listed
Senior, Expert
MBA
Toronto, ON, Canada
In PersonOn-site in Toronto, Ontario. Immigration and relocation support available.
Business & Strategy

About the job

Requirements
  • 8+ years of experience in enterprise data platforms, infrastructure software, or operating systems
  • Proven track record of building and scaling platform businesses with $10M+ ARR
  • Deep understanding of data and AI infrastructure, modern data stacks, and enterprise requirements
  • Experience with enterprise software sales cycles, customer success, and platform adoption
  • Strong technical background with ability to engage with engineering and customer technical teams
  • Understanding of Kubernetes, container orchestration, and cloud-native architectures
  • Experience with data platforms, data lakes, data warehouses, and modern data stack technologies
  • Knowledge of AI/ML infrastructure, MLOps, and production AI deployment requirements
  • Familiarity with enterprise security, compliance, and on-premises deployment models
  • Experience with platform APIs, extensibility, and ecosystem development
  • Demonstrated ability to operate independently with full P&L responsibility for $10M+ business units
  • Experience managing complex enterprise customer relationships and deployments
  • Strong communication skills for C-level executives and technical decision makers
  • Proven ability to build and manage cross-functional teams including engineering, sales, and customer success
  • Track record of scaling platform businesses in competitive enterprise markets
  • Previous experience at major data platform companies (Databricks, Snowflake, Palantir, etc.)
  • Background in enterprise infrastructure software or developer platform companies
  • Experience with air-gapped and on-premises enterprise deployments
  • MBA or equivalent business strategy experience in technology platforms
  • International market expansion experience with enterprise software
  • Background in open-source platform development and ecosystem building
  • Financial services, healthcare, aerospace, or other highly regulated industries
  • Understanding of data governance, privacy, and compliance in enterprise environments
  • Experience with digital transformation initiatives and enterprise technology adoption
  • Background in DevOps, SRE, or infrastructure operations
Responsibilities
  • Own complete P&L responsibility for the core OS Platform business unit
  • Drive the majority of company revenue through platform licensing and infrastructure
  • Manage enterprise customer relationships for $100K-$300K annual contract values
  • Report directly to CEO with full autonomy over platform business decisions
  • Define and execute product strategy for the core Shakudo Data & AI Operating System
  • Drive platform roadmap decisions based on enterprise customer requirements
  • Ensure platform capabilities support and enable other business unit offerings
  • Balance innovation with enterprise stability and reliability requirements
  • Own relationships with enterprise customers requiring full platform capabilities
  • Ensure successful deployments in on-premises and air-gapped environments
  • Drive platform adoption metrics: active users, stack component utilization, production use cases
  • Establish customer success frameworks measuring time-to-value improvements
  • Collaborate closely Principal Engineers on platform architecture
  • Ensure platform scalability, security, and performance for enterprise deployments
  • Drive integration capabilities that support Stack and Professional Services units
  • Maintain competitive positioning against major cloud providers and data platforms
  • Position Shakudo as the leading Data & AI Operating System in the enterprise market
  • Develop competitive strategies against Databricks, Snowflake, and major cloud platforms
  • Build thought leadership in data and AI platform modernization
  • Drive enterprise market expansion and strategic customer acquisition
  • Collaborate with other GMs to ensure platform supports their service offerings
  • Provide platform capabilities that enable Applications and Professional Services success
  • Maintain platform integrity while allowing business unit customization and extension
  • Balance resource allocation between core platform and enabling other units
Desired Qualifications
  • Ex-Founder Preferred: Raised $1M+ in venture funding, OR Generated $500K+ in revenue for their company
  • Previous experience at major data platform companies (Databricks, Snowflake, Palantir, etc.)
  • Background in enterprise infrastructure software or developer platform companies
  • Experience with air-gapped and on-premises enterprise deployments
  • MBA or equivalent business strategy experience in technology platforms
  • International market expansion experience with enterprise software
  • Background in open-source platform development and ecosystem building
  • NVIDIA-Inspired Organization: Fully autonomous, platform-first, remote-friendly culture experience not required but desirable
  • Industry Experience in Financial services, healthcare, aerospace or regulated industries
  • Understanding of data governance, privacy, and compliance in enterprise environments

About the company

Shakudo provides an operating system for data and artificial intelligence stacks that helps teams build, deploy, and manage AI products. The platform works by automating DevOps tasks and integrating over 170 different open-source and commercial tools into a single environment that can be self-hosted for better data security. It distinguishes itself from competitors by creating compatibility between many different software tools, which prevents companies from being locked into a single vendor's ecosystem. The company's goal is to reduce engineering overhead and complexity so that data science teams can focus on developing AI solutions more quickly.

Company Size

11-50

Company Stage

Series A

Total Funding

$17M

Headquarters

Toronto, Canada

Founded

2021

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Simplify Jobs

Simplify's Take

What believers are saying

  • Wittington Ventures led Shakudo's $7 million February 17, 2026 strategic round.
  • Loblaw said Shakudo cut AI deployment from six months to same-day delivery.
  • Whitecap's June 2026 case study shows Shakudo expanding from analytics into advanced AI.

What critics are saying

  • Shakudo depends on regulated-enterprise wins; losing Loblaw damages credibility by 2027.
  • AWS, Databricks, and Snowflake compress Shakudo's differentiation through bundled platforms.
  • One serious governance failure turns Shakudo into an existential compliance liability.

What makes Shakudo unique

  • Shakudo runs inside customer VPCs, keeping models and data under enterprise control.
  • Its February 17, 2026 launch bundled Kaji, AI Gateway, and Compass governance.
  • Loblaw and Whitecap adopted Shakudo in 2026 for standardized in-house AI operations.

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Benefits

  • Professional Development Budget

Growth & Insights and Company News

Headcount

6 month growth

12%

1 year growth

9%

2 year growth

0%
BetaKit
Feb 17th, 2026
Toronto's Shakudo converts customers into investors with $7M Series A2 raise

Toronto-based Shakudo has raised $7 million USD in a Series A2 round led by Wittington Ventures, the venture arm of the Weston family's holding company that controls Loblaw and Shoppers Drug Mart. The round attracted investment from existing customers, including CentralReach executives who personally backed the company. Founded in 2021, Shakudo provides AI infrastructure software that helps enterprises deploy AI tools securely within their existing systems. Loblaw reportedly reduced its AI development cycles from six months to same-day delivery using Shakudo's platform. The round included participation from Golden Ventures, GreatPoint Ventures, and RTP Global, bringing total funding to approximately $18 million USD. The company has grown sevenfold since its $7.2-million USD Series A in early 2023 and plans to raise a larger Series B within two years.

Shakudo
Feb 17th, 2026
Shakudo raises $7M to power sovereign enterprise AI with new autonomous agents

Shakudo, a platform providing operating systems for enterprise AI, has raised $7 million in a strategic funding round led by Wittington Ventures, a venture capital firm affiliated with Loblaw Companies Limited. The round included participation from existing investors Golden Ventures, GreatPoint Ventures and RTP Global, as well as personal investments from enterprise customers. The San Francisco and Toronto-based company will use the funding to expand its US operations and launch two new products: Kaji, an autonomous AI agent running within customers' Virtual Private Clouds, and Shakudo AI Gateway, a control plane for managing models and agents across organisations. Shakudo's platform deploys natively within customers' infrastructure, ensuring intellectual property remains within the organisation whilst targeting regulated industries including nuclear energy, healthcare and financial services.

BetaKit
Jul 5th, 2023
Shakudo closes $9.5M Series A to help companies adopt generative AI

Toronto-based Shakudo has secured $9.5 million CAD in Series A funding to help companies launch artificial intelligence products more quickly and cost-effectively.

BetaKit
Nov 3rd, 2021
Rebranded Shakudo raises $4.2 million to expand reach of AI platform

Toronto-based software startup Shakudo has rebranded from DevSentient, raising $4.2 million CAD in seed funding to expand the reach of its AI platform for data science and ML teams.