Technical Project Manager at Entara

We invite you to collaborate with Entara and further your professional journey as a member of our Professional Services (PS) department. As a top-tier provider of technical service delivery, Entara maintains partnerships that require our team to flex into immediate, high-priority security remediation projects.  Our projects are essentially a rescue operation: taking environments in the aftermath of a security breach and restoring them to full operations remotely from dusk till dawn.

The incident response (IR) work we perform requires extreme care and precision to ensure we cross every t and dot every i, getting our clients back to work. Our engineers are tasked with an outline of project deliverables, running through requirement checklists, and working collectively on issues that arise mid-completion. These range from server reimagining, and restoring backups, to rebuilding or redesigning a VMWare environment. Our team accomplishes more than only, “turning the lights on”— we are also tasked with improving our client environment's resiliency to attacks, executing deployment projects of leading security toolsets, and implementing strategic security solutions in client environments.

We are searching for a technically seasoned project manager who is skilled in engineering and adept in leading multiple concurrent projects. If you are excited by the challenge of meeting high-stakes deadlines with an extreme focus on the details, you may be the creative ringleader we've been searching for! 

(Otherwise known as the fine print, the list of job tasks and responsibilities.)

Entara’s Professional Services: Technical Project Manager (TPM) is primarily dedicated to external, client-facing projects within our Incident Response team. Our TPM is the driving force behind successful, thorough, and robust project deliverables that result in progressive change and secure enhancements to our client’s technical environments. As the primary face of the team on client calls, our TPM fields questions, establishes trust, and sets precedent as the go-to person for all incident-related matters. Our TPM is tasked with understanding the current state of an incident, establishing ownership of the overall direction of containment and recovery, and ensuring all parties are aligned with the verticals defined. Our TPM is constantly in sync with the primary lead engineer leading containment and recovery strategies and delivering agreed-upon strategic initiatives to all parties. Our TPM works as part of a dynamic, flexing team – ready to respond at a moment’s notice mapping into their team's on-call rotation. This position will report directly to our Director of PMO.

Project Management

• Coordinates multiple, external technical projects from inception to completion:
  • Follows established core processes, project templates, and methodologies
  • Takes a lead in Professional Services Stand-ups & meetings
  • Collaborates on project planning, project design, preparation of deliverables, timelining, and contingency planning
  • Understands SOW requirements and converts them into realistic, executable project plans
  • Manages project resources to effectively execute on-time deliverables
  • Tracks and manages the project budget from the outset through successful completion
  • Tracks and oversees T&M project scope and related time entries, confirming their validity
  • Employs creative measures to keep project scope contained
  • Ensures QA standards are being met before project delivery
• Outlines goals, strategy, and execution with Entara’s engineers:
  • Assists in the initial triage and establishment of access for project kick-off
  • Drives team’s development of project proposals and scope documentation
  • Leverages conflict management techniques to address disagreements
  • Assigns and aligns necessary resources, understanding resource requirements and capacity (perm or contracted) on projects, maximizing available resources and leveraging each engineer’s skill set effectively
  • Follows up with engineers on a weekly, daily, or (when necessary) hourly basis to understand the progress of their assigned work and to identify potential roadblocks
• Monitors and summarizes progress of project(s) to stakeholders:
  • Entara Leadership
  • Finance
  • Client Contacts and IR Partners
• Sets and conducts status meetings with client contacts, keeping them informed of progress and setting proper expectations 
  • Leads the creation of PowerPoint presentations and project reports as required for large projects
• Participates in incident response on-call rotation for incoming IR projects
• Identifies and understands when it is necessary to escalate issues to higher-level resources
• Addresses billing disputes, overruns, and customer service issues with meaningful resolutions, looping in additional Entara resources as necessary
• Conducts post-mortems to outline lessons learned and improve internal processes
• Treats each project as if you are the end-all be-all, you are the final straw, if you ignore an issue, then the issue will blow up--you are the last line of defense on your project

Problem Solving

• Becomes an active part of project teams solving technical or business roadblocks until a resolution is reached and the outcome is personally verified
• Perseveres in making sound judgment calls when lacking one or more desired resources or data points
• Challenges technical or business requirements, ensuring that we deliver the right solution, at the right price, at the right time
• Leverages and employs an understanding of intermediate to advanced systems configuration, management, and maintenance in areas including the following (this is a sample but not exhaustive listing of work areas and project tasks assigned to our IR-focused engineers):
  • Microsoft-related technologies: Windows Server, Exchange, SQL Server, SharePoint, Active Directory, GPO, LAPS, SCCM, MDT, etc.
  • Virtualization technologies: VMware and Microsoft Hyper V
    • Restore and reimage virtual servers from images and various backup solutions
    • Restore and rebuild ESX and Hyper-V hosts, domain controller, etc.
  • Mount ISOs to virtual systems
  • Upload virtual templates to any hypervisor
  • Out of Band access to Physical systems
  • Leverage console access such as ILO and iDrac to establish remote connection to offline physical systems
  • Backup and disaster recovery solutions for both desktops and servers
  • Remote access solutions: VPN, Remote Desktop, Citrix, etc.
  • Diagnostic tools; review event logs, Syslogs, monitoring data, and memory dumps to troubleshoot issues.
  • Security-enhancing solutions for systems and applications (including MFA and endpoint protection).

Metrics Measuring Success

• Maintains billable utilization targets
• Ensures all mandatory reports are generated and updated daily
• Meets or exceeds deadlines for all assigned projects
• Keeps projects profitable while not skimping on quality
• Leverages cost variance and schedule variance formulas to measure project success
• Contributes to the team’s attainment of high customer satisfaction scores on project delivery
• Records complete change details, time worked entries, and work notes in ServiceNow in real-time
• Identifies opportunities for process improvement

Following Process

• Follows Entara’s project process to execute project deliverables: configure, test, implement, refine, document, monitor, and transition to appropriate stakeholders.
• Follows Entara’s Change Management Process to perform approved changes in client environments
• Communicates internally and (as directed) externally to provide timely information regarding project status, promised follow-ups, and requested feedback on a detailed and professional basis. 

• You’re a knowledge seeker. Regardless of method, you have obtained and exposed yourself to knowledge centers that have qualified you to master technical project delivery and the systems engineering required to successfully recover, deploy, and enhance infrastructures. You ideally have a four-year degree in a relevant field and are working towards or have already obtained your PMP certification.

• You’ve managed projects as the assigned “PM” instead of just delivered them as an engineer. You enjoy the dynamic of wearing multiple hats and taking the lead on client-facing communication, expectations, and timelines.

• You’ve owned client-facing projects and have established a consultative rapport resulting in high client satisfaction levels upon project closure.

• You have at least 5 years of experience delivering IT waterfall projects or support working with systems and virtualization with exposure to enterprise infrastructures.

• You keep us true to our word. You have a tried-and-true organizational system to keep yourself (and others) on task while ensuring exceptional quality.

• You wield general productivity tools such as Microsoft Word, PowerPoint, Visio, and Excel to compose tasteful and informative documentation, outlines, and status reports for reference by interested parties.

• Ideally, you’ve mastered at least one tool in the PM arsenal (i.e. Microsoft Project, Microsoft PowerPoint, Microsoft Planner, Excel Gantt Charts, Monday.com, ServiceNow Project Portfolio) and you’re familiar with popular methodologies (Agile, Waterfall, etc.). Your strength lies in picking up new tools and being able to learn on the fly—employing your past tool knowledge while addressing a new learning curve.

• You possess a winning combination of superb writing skills and highly refined verbal communication skills. You convey energy, confidence, and genuine interest over a call just as easily as you convey competence, professionalism, and trustworthiness in person. You translate to a C-Suite audience as seamlessly as you “talk tech” with engineers. Your emails are professionally worded, grammatically pristine, with the right pinch of personality. In any medium, you pride yourself in clear, effective, and persuasive communication.

• You have an approach to working hours that is more adaptable than the traditional "9-to-5". As this team responds to business-critical remediation projects, we are looking for an individual who is career-driven and won’t shrink back when work requirements extend into evenings, weekends, and holidays. While travel is minimal, you’re also open to getting on a plane when needed to be present at client sites when a project requires it. On the flip side, your hard work is rewarded with a generous comp plan that grows with the efforts you contribute, a flexible PTO policy, and an equally inspiring team that climbs mountains together.

• You are ready to be an effective remote worker and have a dedicated, private space for a home office with a private internet connection with at least 50MBPS bandwidth. Public WiFi and shared common spaces do not meet these standards.

• A Mythical Character. You aren’t alarmed when someone expects you to be a hero; in fact, you pride yourself on frequently delivering big just when all hope seems lost. Your persistence is notable, and you are a determined soul who insists on turning “we can’t” into “we can”. If you meet a roadblock, you’ll try to scale it, dodge it, or blast through it before ever admitting defeat.
• On Defense. You own each project as if you are the end-all be-all and take personal ownership of the stakes. In other words, you are the final straw--nothing can slip past you. You assume that if you ignore an issue, then the issue may implode. You continually operate with the mindset of being “the last line of defense” on your projects
• The Devil is in the Details. You have an angelic ability to sort through chaos and make order. Your eye and attention for details helps you uncover hidden gems, while your thorough documentation and status updates capture and convey every facet of each stone.
• Corporate Usain Bolt. You’re capable of moving rapidly from task to task without getting rattled. Your desk is clear, your email inbox is empty, your kitchen counters aren’t cluttered, and you never spend 15 minutes tearing around the house in a desperate hunt for your car keys or train pass. You are a lean, mean, well-oiled machine.
• A Combo Meal. Your style is winningly ambidextrous. While you are known to be a loyal teammate and never falter on your commitment to seeing others thrive, you are not a push-over. You will fight back and advocate for the best marriage of client desires and superb delivery-pushing us along the path towards perfection. If Samwise Gamgee and Monica Geller had a child, it would be you.
• Emotionally Mature. Through your years of experience, you’ve learned that occasional hiccups are inevitable and now know enough to just keep moving towards the end goal. You’re calm under pressure, encourage respectful dialog, and understand that communication is the balm that can soothe the sting of conflict.

Founded in 2001, Entara is an eXtended Service Provider (XSP) focused on providing cutting edge technology and cyber security solutions to companies in regulated industries. With our roots in providing service to the electronic trading market, we are known for growing with the pace of technological change and the developing security needs of our clients. We are redefining ourselves - and our industry - and creating a new class of service providers, XSPs, because we recognize that MSPs and MSSPs are no longer what our clients need. Downward pressure from both regulators and insurance providers convinced us that it was time to integrate our IT and cyber security offerings and deliver strategic, future facing solutions for our clients.  

In order to build, maintain, and optimize these types of solutions, we need high-performing, highly-collaborative teammates who are excited to join in this journey with us. There are several reasons why employees love being a part of the Entara team. We’ve been recognized as one of Chicago’s Best and Brightest Companies to Work For since 2017. We are a remote-first workplace. We seek to build a team that’s brought together by more than just skills, but who embrace a personal-alignment to the values that precede the work we deliver: Empathy, Excellence, Execution, and Evolution. If this sounds like you, let’s connect and discover if we have the foundation to build something great together.  

As an employee at Entara, you will have a direct impact on our operations, our clients, and your fellow EntaraCorps members. Because of that impact, you get our respect and gratitude for the role you play in making Entara the best it can be. We consider mentoring and participating in the continual learning of others to be absolutely essential for both you and your co-workers.

To reflect our commitment to our employees, we offer unlimited PTO, remote-first work, 401k matching, paid parental leave, employee outings (virtual and in person), reimbursement for approved seminars, conferences, and certifications, and 100% employee premium coverage for medical, dental, life, and disability insurance….and that’s just the tip of the iceberg.