IT Lead (In-Office)

Ottimate is an AI-powered AP [Accounts Payable] automation platform that empowers finance teams to reduce costs, prevent overpayments, detect fraud, and enforce policy compliance across the entire invoice-to-payment lifecycle.

We’re looking for an IT Lead to join Ottimate and help us scale our internal systems as we grow. This is an in-person position in our Tampa, Florida office. In this role you’ll own IT end-to-end, leading a small team focused on keeping our people productive, our systems secure, and our day-to-day operations running smoothly. You’ll administer the tools our team relies on, manage our laptop fleet, support our audits, and build the processes that let us scale. You’ll partner closely with engineering, security, people operations, and finance, and you’ll have a direct line to leadership to make recommendations that shape how we work.

• →Google Workspace Administration - Administer Google Workspace, including user accounts, groups, shared drives, calendar resources, and security settings.
• →Identity & Access Management - Manage identity and access across our SaaS stack: SSO, MFA, provisioning, and access reviews — in partnership with our security team.
• →SaaS Application Administration - Administer our SaaS applications. Configure access, track licenses and seats, monitor usage, and surface opportunities to consolidate tools or reduce spend.
• →Asset Management - Own our laptop inventory end-to-end: procurement, shipping to and from remote employees, configuration, repair coordination, and lifecycle tracking.
• →Audit Support - Coordinate and support our internal and external audits — including SOC 2, HIPAA, and PCI DSS — by gathering evidence, maintaining documentation, and partnering directly with auditors.
• →Process Development - Design and document scalable processes for handling incoming IT requests, including intake, triage, escalation, and resolution. Then execute against them consistently.
• →Organization & Documentation - Bring order to our internal systems and records. Maintain accurate, well-structured documentation and trackers (spreadsheets, runbooks, asset registries) that the rest of the team can rely on.
• →IT Strategy & Budget - Own the IT roadmap and budget, including vendor selection and renewals, and make recommendations to leadership on tools, processes, and security improvements as we scale.
• →Employee Support - Provide responsive, friendly support to employees across time zones, and serve as the escalation point for issues the team cannot resolve.
• →Employee Onboarding & Offboarding - Set up and manage seamless onboarding and offboarding of employees, ensuring proper provisioning and deprovisioning of access and equipment.
• →Endpoint Management - Administer Mac, Windows, and Linux laptops and workstations. Deploy and manage antivirus software; when a device is compromised, lead the recovery process to ensure it is safe for use.
• →Network Security & VPN - Configure and maintain VPN access to keep the network and remote connections secure.
• →Device Management (MDM) - Administer a mobile device management platform (e.g., ActZero, Jamf, Kandji, or Intune) to enforce policies, manage configurations, and maintain visibility across the device fleet.
• →Team Leadership - Hire, mentor, and manage IT Specialists. Set priorities, delegate day-to-day requests, and ensure consistent, high-quality support across time zones.

• 5+ years of experience in IT support or systems administration, including 2+ years owning IT for a growing company or leading other IT staff.
• Hands-on experience administering Google Workspace.
• Familiarity with identity providers (e.g., Okta, JumpCloud, Google as IdP) and configuring SSO and MFA.
• Experience administering common SaaS tools (e.g., Slack, Zoom, Atlassian) and managing licenses and access.
• Exceptional organizational skills and strong spreadsheet chops (advanced Google Sheets and/or Excel). You take pride in bringing structure to messy environments.
• Excellent written communication. You can support a fully remote team clearly and patiently over chat, email, and tickets.
• A proactive, solutions-oriented mindset. You spot problems before they escalate and propose fixes rather than waiting for direction.
• A security-first mindset and good judgment around confidentiality and least-privilege access.
• Experience administering Mac, Windows, and Linux endpoints, including deploying antivirus software and recovering compromised devices.
• Familiarity with configuring and supporting VPN access for a remote workforce.
• Experience mentoring or managing IT staff, with the judgment to prioritize competing requests and set clear service expectations.

• Experience supporting SOC 2, HIPAA, or PCI DSS audits.
• Experience with mobile device management (ActZero, Jamf, Kandji, Intune, or similar).
• Familiarity with AWS infrastructure management.
• Familiarity with ticketing systems (Jira Service Management, Zendesk, Freshservice, or similar).
• Basic scripting experience (Python, Bash, or Google Apps Script) for automating repetitive tasks