IT Manager

Robots and Pencils

14h

About The Position

Robots & Pencils is seeking an experienced, outcome-oriented IT Manager to lead and evolve our internal technology environment across a distributed, international team. You will own the lifecycle, performance, and reliability of internal systems supporting team members across four countries, with offices in Cleveland, Calgary, Lviv (Ukraine), and Bogota You will implement scalable systems, standardize core processes, and strengthen internal technology foundations so our teams can move faster, collaborate better, and focus on meaningful client outcomes.

Requirements

8+ years of relevant corporate IT experience
Experience analyzing, implementing, and evaluating enterprise IT systems
Strong background in SaaS management and cloud infrastructure (AWS)
Demonstrated success with security frameworks, audits, and compliance programs, including SOC 2
Fluency with Microsoft 365 (certification is a plus) and comfort working with tools such as GitHub and AWS
Project management experience with successful rollouts of new systems and documented risk mitigation strategies
English fluency (written and spoken)

Nice To Haves

PSA or ERP implementation experience
Experience operating in distributed, international organizations
Exposure to SaaS rationalization and cost optimization initiatives

Responsibilities

Own application lifecycle management end-to-end, including evaluation, acquisition, rollout, support, maintenance, optimization, and retirement
Rationalize underused or redundant tools to reduce platform sprawl
Lead critical systems implementations, including HRIS and PSA platforms
Build structured implementation plans with clear milestones, adoption targets, and risk mitigation strategies
Ensure internal systems scale with company growth across offices and time zones
Standardize onboarding and offboarding processes across countries and offices
Improve helpdesk and service workflows for speed, clarity, and accountability
Create repeatable, documented processes that balance consistency with flexibility
Strengthen internal operational visibility without introducing unnecessary bureaucracy
Continuously refine systems based on usage patterns and team feedback
Own vendor relationships and service-level agreements
Manage hardware and software procurement, inventory tracking, and cost allocation
Strengthen oversight of SaaS subscriptions and AI-related spend
Optimize licensing and subscription usage for efficiency and scalability
Ensure vendor performance meets reliability and support expectations
Support security awareness training and internal risk assessments
Contribute to annual SOC 2 compliance certification efforts
Strengthen documentation and audit readiness, including maintaining a structured Vanta repository
Ensure internal systems meet security, governance, and compliance standards
Proactively identify and mitigate operational and compliance risks
Lead the team responsible for helpdesk support and systems maintenance
Partner closely with HR, Operations, and Engineering to translate business needs into durable IT solutions
Communicate clearly with both technical and non-technical stakeholders
Balance competing priorities with sound judgment and a service-oriented mindset
Drive accountability and clarity across distributed teams