IT Manager

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.

Key Responsibilities

Application Lifecycle & Systems Ownership

• 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

Process Standardization & Operational Excellence

• 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

Vendor, Inventory & Cost Management

• 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

Security & Compliance

• 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

Team Leadership & Cross-Functional Collaboration

• 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

Required Skills & Qualifications

• 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 Have

• PSA or ERP implementation experience

• Experience operating in distributed, international organizations

• Exposure to SaaS rationalization and cost optimization initiatives

Personal Competencies

• Outcome-Oriented – Focuses on operational impact, reliability, and measurable improvements.

• Systems Thinker – Standardizes processes without creating unnecessary friction.

• Service-Minded – Prioritizes user experience for internal teams.

• Operationally Disciplined – Drives clarity, structure, and accountability.

• Adaptable – Balances competing priorities calmly and effectively.

• Ownership-Driven – Follows through and ensures systems perform as intended.

Why This Role Matters

At Robots & Pencils, we build smart systems for the human world. When our internal technology is strong, our teams move faster, collaborate better, and spend more time delivering meaningful outcomes for clients. This role turns IT into a true enabler of creativity, security, and scale across borders and time zones.

You will strengthen the foundation that allows every product team to operate at a higher level. This is operational leadership with measurable organizational impact.

Why Join Robots & Pencils?

We don’t just maintain systems; we build environments where teams can do their best work.

You’ll help modernize internal infrastructure, lead high-impact system implementations, and influence how a distributed digital product company operates at scale.

You’ll work at the intersection of operations, security, and systems architecture, driving durable improvements that power the entire organization.