IT Lead (In-Office)

About Ottimate

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.

About the Role

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.

Responsibilities:

• 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.

Nice to haves:

• 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

We care deeply about making Ottimate an incredible place to work and invest a significant amount of time and energy into creating and maintaining a company culture that provides our team with a generous level of support whilst inspiring them to do their best work. 
The specific benefits/perks we offer are continually evolving, but currently include:

• Compensation: $100,000-110,000 USD /year.
• Competitive salary based on skills & experience.
• Medical, Dental, Vision and other Company-Subsidized Benefits for you and your family.
• Employer sponsored 401(k) with company match.
• Paid Time Off (and the encouragement to use it).
• Promote from within philosophy.

Beyond the tangible benefits though:

• You will be part of a growing team, at a pinnacle moment of scale for the business, and experience the excitement of working in a startup where each action makes a huge difference.
• You will have the agency to solve difficult problems creatively, the freedom to explore work that inspires you, and infrastructure to ensure you're constantly challenged and developing.
• You will work with sharp, passionate teammates solving some of the most unique challenges and positioning our product as a premier finance automation solution. 
• Our commitment to empowering a diverse and inclusive workforce, celebrating differences, and creating a safe space for our employees to bring their whole selves to work is second to note.
• We are transforming entire industries using innovative technology including Artificial Intelligence, Payment Tech, and Neural Networks.
• Our leaders lead with a people-first approach; inspiring excellence, nurturing ideas, and finding creative ways to eliminate obstacles for cultivating growth.
• We truly love what we do and who we do it with - and we think you will too!

Ottimate is an equal opportunity employer that is committed to diversity and inclusion. We do not discriminate based on race, color, national origin, religion, gender, gender expression, sexual orientation, age, veteran status, disability status, or marital status. If you are excited about the role but do not meet 100% of the qualifications listed above, we encourage you to apply. Nothin