Principal Systems Engineer

Taxwell helps everyday Americans get every tax advantage they deserve by finding credits and deductions they never even knew existed. Our tax preparation software offers easy guidance and ensures your maximum tax refund. We strive to build a team of like-minded experts in both tax and technology who align with our brand purpose, are advocates for our customers and have a fresh, non-traditional approach to the tax industry.

Drake Software is a leading digital tax filing platform which offers customers professional digital and downloadable products that are easy-to-use, best-in-class technology, and provide unparalleled customer support. We are a trusted solution for all users including those with complex tax returns. We strive to attract and retain candidates who exemplify our values: performance, perseverance, progress and partnership. Drake Software is a member of the Taxwell family of products. We are an organization of forward thinkers looking to add industry experts to our growing team. 

This role will primarily support Drake Software as we provide the tools and support tax professionals need to build their businesses and attract new clients. We are an organization of problem solvers continually looking for solutions to support our customers. Our customers know they can rely on Drake Software for comprehensive product excellence and value. 

The Principal Systems Engineer is a senior technical leader responsible for the architecture, modernization, and reliability of enterprise infrastructure across colocation, on-premises, and cloud-connected environments. This role sets technical direction, leads complex initiatives, mentors engineers, and serves as a trusted escalation point while remaining hands-on in implementation and troubleshooting.

ESSENTIAL DUTIES AND RESPONSIBILITIES:

• Own architecture, technical standards, lifecycle strategy, and multi-year roadmaps for enterprise systems infrastructure, with emphasis on colocation and hybrid environments.

• Design and optimize highly available compute, virtualization, storage, backup, and recovery solutions for performance, scalability, security, supportability, and cost.

• Provide deep technical leadership for virtualization, server and blade infrastructure, storage, data protection, and related data center technologies.

• Lead platform refreshes, migrations, consolidations, disaster recovery improvements, data center transitions, and cloud integration through operational handoff.

• Partner across cloud, security, network, application, database, and operations teams to deliver resilient end-toned solutions.

• Establish engineering standards, reference architectures, build patterns, configuration baselines, capacity models, and lifecycle practices.

• Serve as a senior escalation point for high-impact incidents, leading root-cause analysis, response coordination, and durable corrective actions.

• Apply security-by-design principles and maintain controls supporting policy, regulatory requirements, vulnerability management, and audit readiness.

• Mentor systems engineers, review designs and implementation plans, promote knowledge sharing, and raise engineering capability across the team.

• Influence technical decisions through clear recommendations, tradeoff analysis, risk communication, and stakeholder collaboration.

• Manage technical vendor relationships involving architecture, escalations, product strategy, licensing, lifecycle planning, and service improvement.

• Evaluate and responsibly use GPT, Anthropic Claude, agentic AI, and local LLM solutions to improve automation, troubleshooting, documentation, and engineering efficiency.

• Establish secure patterns and governance for AI-enabled infrastructure, protecting company data, identities, credentials, and intellectual property.

• Promote automation through AI, infrastructure-as-code, scripting, APIs, and repeatable workflows.

• Maintain architecture diagrams, system documentation, operating procedures, recovery plans, standards, and decision records.

• Travel and provide hands-on implementation, maintenance, troubleshooting, and after-hours support when business needs require it.

EDUCATION AND EXPERIENCE:

• Bachelor's degree in Information Technology, Computer Science, Information Systems, or a related field, or equivalent education and relevant experience.

• 8+ years of progressive systems or infrastructure engineering experience, including 3+ years leading technical designs, major initiatives, architecture decisions, or engineering standards.

• Experience supporting production infrastructure requiring high availability, security, recoverability, and disciplined change management.

TECHNICAL SKILLS:

• Expert VMware vSphere/ESXi and vCenter knowledge, including clustering, lifecycle management, performance, and troubleshooting.

• Strong storage, backup, and recovery experience, preferably with Pure Storage and Cohesity.

• Experience with Dell chassis and blade infrastructure, firmware, lifecycle management, and vendor support.

• Advanced Windows Server, Active Directory, Group Policy, DNS, identity, and authentication knowledge; working knowledge of Linux/Unix.

• Experience designing resilient colocation, on-premises, and hybrid cloud infrastructure, including AWS integration.

• Familiarity with Cisco, Ubiquiti, and Palo Alto products; primary focus remains systems, compute, storage, virtualization, backup, and hardware.

• Experience with monitoring, capacity planning, observability, incident response, root-cause analysis, and performance troubleshooting.

• Experience with PowerShell, Python, Ansible, Terraform, CloudFormation, APIs, or similar automation tools, plus secure configuration and compliance practices.

• Ability to evaluate technologies, document architecture decisions, and communicate recommendations to technical and non-technical audiences.

PREFERRED CERTIFICATIONS AND VENDOR EXPERIENCE:

• Relevant certifications or equivalent hands-on expertise are welcomed, including VMware VCP/VCAP, Pure Storage, Cohesity, Dell Technologies, AWS, Cisco, Palo Alto, Ubiquiti, Security+, or Network+.

LEADERSHIP AND PROFESSIONAL SKILLS:

• Lead through technical influence, sound judgment, mentorship, and clear communication; balance strategic architecture with hands-on engineering, prioritization, and effective response during high-pressure incidents.

• Strong prioritization and time-management skills with the ability to lead multiple complex efforts and work independently with limited oversight.

• Commitment to continuous improvement, operational discipline, documentation, and accountable follow-through.

At Taxwell, we believe our work benefits from the diverse perspectives of our employees. As such, Taxwell welcomes and celebrates diversity and inclusion and is committed to equal opportunity employment. At Taxwell, you can expect a supportive, open, and inclusive atmosphere and a team that values your contributions.

Taxwell is committed to providing an environment of mutual respect where equal employment opportunities are available to all applicants without regard to race, color, religion, sex, national origin, age, disability, marital status, sexual orientation, gender identity, veteran status, and any other status protected under applicable law. Taxwell considers information gathered in the hiring process, including information on this application, confidential, and only shares it on a need-to-know basis or as required by law.

If you need assistance or accommodation due to a disability, you may contact us at HR@Taxwell.com  or by calling 828-349-5887 to speak with a member of the HR Talent Acquisition team.