Access Control, Alliance/Partner Marketing, Amazon Web Services (AWS), Auditing, Automation, Business Support, Cloud Computing, Coaching, Computer Science, Computer Security, Continuous Deployment/Delivery, Continuous Improvement, Continuous Integration, Cross-Functional, Customer Relations, Dental Insurance, DevOps, Disaster Recovery, Establish Priorities, Financial Compliance, Financial Services, Healthcare, ISO (International Organization for Standardization), Incident Management, Incident Response, Information Technology & Information Systems, Information/Data Security (InfoSec), Internet Security, Investment Strategy, Leadership, Life Insurance, Machine Tool, Maintain Compliance, Metrics, Microsoft Windows Azure, Operational Improvement, Operational Strategy, Operations Management, Operations Planning, Operations Processes, Operations Security (OPSEC), Organizational Development/Management, PCI-DSS, Performance Management, Performance Metrics, Process Improvement, Product Development, Regulatory Compliance, Reliability Engineering, Risk, Risk Management, Scorecarding, Security Monitoring, Service Delivery, Service Level Agreement (SLA), Small Business, Software as a Service (SaaS), Staff Development, Strategic Planning, Succession Planning, System Operations, Systems Reliability, Team Lead/Manager, Technical Leadership, Technical Operations, Technical Support, Vendor/Supplier Management, Vision Plan, Workforce Planning
About the Role
The Director of Technology Operations is responsible for leading Clicklease’s Technology Operations function, including IT Operations, DevOps, Infrastructure & Cloud Operations, Platform Reliability, and Information Security operations.
This role owns the operational strategy, governance, reliability, scalability, and security of the company’s technology environment while ensuring operational excellence across internal systems and customer-facing infrastructure.
The Director of Technology Operations partners closely with Engineering, Product, Compliance, and Executive leadership to ensure Clicklease’s technology platforms remain secure, scalable, compliant, and operationally resilient in a fast-paced fintech environment.
This role is ideal for a technology leader who enjoys building operational maturity, improving system reliability, strengthening security posture, scaling technical organizations, and developing high-performing teams.
The Team
You’ll lead a cross-functional Technology Operations organization responsible for:
- Internal IT systems and support operations
- Cloud infrastructure and platform operations
- DevOps and infrastructure automation
- Platform reliability and observability
- Security operations and operational risk management
- Incident response and operational governance
This organization partners closely with Engineering, Product, Compliance, Risk, and business stakeholders to support secure, scalable, and reliable technology operations across Clicklease.
What You’ll Do
- Lead and scale the company’s Technology Operations function across IT Operations, DevOps, Platform Reliability, Infrastructure Operations, and Information Security
- Define and execute the operational strategy for infrastructure reliability, scalability, availability, operational maturity, and security posture
- Establish operational governance standards, service management processes, incident response frameworks, and operational accountability models aligned with fintech and compliance requirements
- Own operational performance metrics, including infrastructure reliability, incident response effectiveness, platform uptime, operational scalability, and service delivery performance
- Partner closely with Engineering leadership to improve infrastructure automation, CI/CD maturity, observability, operational tooling, and platform performance
- Oversee cybersecurity operational initiatives, including access controls, vulnerability management, operational risk mitigation, security monitoring, and security incident response
- Drive operational excellence initiatives focused on process improvement, resiliency, automation, and long-term operational scalability
- Own vendor management, operational tooling strategy, infrastructure investments, and third-party operational partnerships
- Lead organizational planning for the Technology Operations function, including team structure, hiring, coaching, performance management, succession planning, and employee development
- Build and develop high-performing technical leaders and teams while establishing clear accountability, ownership, and operational expectations
- Collaborate cross-functionally with Engineering, Product, Compliance, Finance, and Executive leadership to align operational priorities with company objectives and growth plans
- Support business continuity, disaster recovery readiness, operational risk management, and audit/compliance initiatives
Decision-Making & Ownership
This role has responsibility for:
- Operational governance and standards across Technology Operations
- Infrastructure and operational tooling decisions
- Incident management and escalation frameworks
- Operational readiness and reliability strategy
- Security operations coordination and remediation prioritization
- Technology Operations workforce planning and organizational design
- Vendor and infrastructure operational partnerships
- Operational KPI and SLA/SLO management
What You Have
- 8+ years of experience leading technology operations, infrastructure, DevOps, IT, Site Reliability Engineering (SRE), or Information Security teams
- 5+ years of experience leading technical teams with direct people leadership responsibilities
- Experience leading multi-functional operational technology organizations in cloud-based environments
- Experience managing cloud infrastructure and operational environments in AWS, Azure, or similar cloud platforms
- Experience implementing operational governance processes related to incident management, reliability engineering, infrastructure operations, security operations, and operational risk management
- Experience working within regulated or compliance-focused environments such as fintech, financial services, SaaS, or healthcare
- Experience developing operational scorecards, service performance metrics, reliability targets, and operational roadmaps
- Experience partnering cross-functionally with Engineering, Compliance, Product, and Executive stakeholders
- Strong leadership, coaching, organizational development, and performance management capabilities
- Ability to balance strategic operational planning with executional excellence
- Bachelor’s degree in Information Technology, Computer Science, Cybersecurity, Engineering, or equivalent practical experience
What Will Make You Stand Out
- Experience leading Technology Operations within a high-growth fintech or SaaS environment
- Experience supporting SOC 2, PCI-DSS, ISO 27001, or similar security/compliance frameworks
- Experience implementing Infrastructure-as-Code and modern DevOps automation practices
- Experience leading operational maturity transformations or cloud modernization initiatives
- Experience scaling technical operations teams during periods of rapid organizational growth
- Experience building reliability engineering, observability, or incident management programs
What Success Looks Like in the First 6 Months
- Establish clear operational ownership, governance standards, and accountability models across Technology Operations
- Improve operational visibility through standardized monitoring, observability, incident management, and operational reporting
- Deliver measurable improvements in infrastructure reliability, operational response times, platform stability, and security posture
- Strengthen operational partnership models between Technology Operations, Engineering, Product, and Compliance teams
- Implement scalable operational processes that improve resiliency, operational maturity, and long-term maintainability
- Build organizational clarity across the Technology Operations function, including role accountability, operational metrics, and leadership expectations
Why Join Clicklease
Clicklease is transforming how small businesses access the equipment they need to grow. Our technology platform uses data and automation to make equipment financing faster, simpler, and more accessible for business owners across the United States.
At Clicklease, you’ll work on meaningful problems that directly impact small businesses while collaborating with a team that values ownership, accountability, and continuous improvement.
We look for people who take initiative, work collaboratively, and care deeply about delivering great outcomes for customers and partners.
In return, you’ll have the opportunity to grow your career, contribute to a rapidly scaling fintech platform, and work alongside talented colleagues who are passionate about building great products and services.
What We Offer
Clicklease offers a competitive compensation and benefits package designed to support employees and their families.
Benefits may include:
- Medical, dental, and vision insurance
- Health Savings Account (HSA) and Flexible Spending Account (FSA) options
- 401(k) with company match
- Employer-paid short-term disability (STD), long-term disability (LTD), and life insurance
- Paid time off and company holidays
- Professional development and learning opportunities
Benefits eligibility and details may vary based on role and employment status.