IT Support Career Ladder 2025: From $40K Help Desk to $150K+ Cloud Engineer

You’re working help desk, making $42,000 a year, resetting passwords and troubleshooting printer issues. You see job postings for “Senior Systems Engineer - $125K” and wonder: How do people get from here to there? What’s the actual career ladder in IT support?

Here’s the truth: I’ve spent 12 years in IT infrastructure, started at a help desk making $38,000, and now pull $168,000 as a senior cloud architect. More importantly, I’ve managed IT support teams and hired 47 people across every level of this ladder.

The IT support career ladder has seven clear levels. Most people take 8-12 years to go from help desk to senior engineer ($40K to $130K+). But I’ve also seen people do it in 5-6 years by skipping levels strategically.

Let me show you the complete ladder, what you actually do at each level, how much you make, and how to move up faster than your peers.

The Complete IT Support Career Ladder (7 Levels)

Here’s the full progression with realistic salary ranges and timelines:

Level 1: Help Desk / Service Desk Technician

• Salary: $35K-$50K
• Timeline: 0-2 years in IT
• Primary role: First-line support, password resets, basic troubleshooting

Level 2: Desktop Support Specialist

• Salary: $45K-$65K
• Timeline: 1-3 years experience
• Primary role: Hands-on PC/laptop support, software installation, user training

Level 3: IT Technician / Systems Support

• Salary: $55K-$75K
• Timeline: 2-4 years experience
• Primary role: Multi-device support, server basics, network troubleshooting

Level 4: Junior System Administrator

• Salary: $65K-$85K
• Timeline: 3-5 years experience
• Primary role: Server management, Active Directory, backup systems

Level 5: System Administrator / Network Administrator

• Salary: $80K-$105K
• Timeline: 5-8 years experience
• Primary role: Full infrastructure management, virtualization, automation

Level 6: Senior Systems Engineer / Cloud Engineer

• Salary: $100K-$140K
• Timeline: 7-12 years experience
• Primary role: Architecture design, cloud infrastructure, enterprise solutions

Level 7: Principal Engineer / IT Manager / Director

• Salary: $130K-$200K+
• Timeline: 10-15+ years experience
• Primary role: Strategic planning, team leadership, technology decisions

Let me break down each level in detail, including what you’ll actually do on a Tuesday, what skills you need, and how to get promoted to the next level.

Level 1: Help Desk / Service Desk Technician ($35K-$50K)

What You Actually Do

This is where 90% of IT careers start. You’re the first person users contact when something breaks.

Your Tuesday morning:

• 8:00 AM: Check ticket queue - 12 tickets waiting
• 8:15 AM: Password reset for Sarah in Accounting (3 minutes)
• 8:20 AM: “My email won’t send” - walk user through Outlook settings (8 minutes)
• 8:45 AM: VPN access issue - reset authentication, test connection (12 minutes)
• 9:10 AM: Printer jam in Building B - escalate to desktop support
• 9:15 AM: Software installation request - verify licensing, remote install (15 minutes)
• 9:45 AM: Conference room display not working - troubleshoot HDMI/wireless connection

You’re handling 25-40 tickets per day. Average resolution time: 10-15 minutes per ticket. Most problems are repetitive: passwords, email issues, software access, basic network connectivity.

Skills Required

Technical skills you’ll use daily:

• Windows 10/11 basics (user accounts, permissions, settings)
• Active Directory fundamentals (password resets, account unlocks)
• Basic networking (IP addresses, Wi-Fi troubleshooting, VPN)
• Ticketing systems (ServiceNow, Zendesk, Freshdesk)
• Remote support tools (TeamViewer, AnyDesk, Windows Remote Assistance)
• Office 365 / Google Workspace support
• Basic printer troubleshooting

Soft skills that matter just as much:

• Patience (you’ll explain the same thing 10 times a day)
• Clear communication (translate tech jargon to normal language)
• Customer service (users are frustrated when they contact you)
• Time management (juggling multiple tickets)
• Documentation (writing clear ticket notes)

Certifications That Help

CompTIA A+ ($320 exam cost, 2-3 months study) This is the industry standard entry certification. It covers hardware, software, networking basics, and troubleshooting methodology.

Do you NEED it? No. Will it get you more interviews? Yes. I’ve hired help desk technicians both with and without A+. But candidates with A+ get callbacks 2x more often.

Alternative: Microsoft 365 Certified: Fundamentals (Free exam, 2-4 weeks study) If your company uses Microsoft 365 heavily, this shows you understand the admin portal, user management, and basic troubleshooting.

How Long You’ll Be Here

Average timeline: 12-24 months

Fast track (6-12 months) if you:

• Take on projects beyond ticket queue (documentation, process improvement)
• Learn Active Directory, networking, and server basics on your own time
• Ask to shadow desktop support or sysadmin teams
• Get CompTIA A+ within first 6 months
• Demonstrate you can handle escalated issues

Stuck here 3+ years if you:

• Only do ticket queue work, never learn beyond basics
• Don’t pursue certifications or self-learning
• Avoid complex tickets instead of learning from them
• Don’t communicate your career goals to your manager

Real example: Michael’s path Michael started help desk at $42K. First 6 months: focused on mastering ticket resolution and being reliable. Months 7-9: studied for CompTIA A+ at night, passed on first attempt. Months 10-12: volunteered to help with PC deployments and learned Windows 10 imaging. Month 13: promoted to desktop support at $54K.

Timeline: 13 months. Key: He didn’t wait to “feel ready” before taking on more responsibility.

Level 2: Desktop Support Specialist ($45K-$65K)

What You Actually Do

You’ve graduated from remote-only support. Now you’re hands-on, touching hardware, deploying systems, and solving problems that require physical presence.

Your Tuesday morning:

• 8:00 AM: New hire setup - unbox laptop, join to domain, install software suite (45 minutes)
• 9:00 AM: Hardware troubleshooting - laptop won’t boot, diagnose bad RAM, replace (30 minutes)
• 9:45 AM: Office move - relocate 5 workstations, reconnect to network (1 hour)
• 11:00 AM: Conference room setup - install new display, configure wireless presentation system (45 minutes)
• 12:00 PM: Break
• 1:00 PM: Software deployment - push updates to 20 machines, verify installations (1.5 hours)
• 2:45 PM: Escalated ticket from help desk - complex Outlook profile corruption, rebuild (30 minutes)

You’re handling 8-15 tickets per day. But tickets are more complex and hands-on. Less phone support, more field work.

Skills You Need to Develop

Beyond help desk skills, you now need:

• PC hardware (replacing RAM, hard drives, power supplies)
• Windows imaging and deployment (MDT, SCCM basics)
• Software installation and troubleshooting (beyond just “click next”)
• Mobile device management (MDM tools, iOS/Android support)
• Basic server interaction (connecting to file shares, understanding DNS)
• Asset management (tracking hardware, inventory systems)
• Project work (PC refresh projects, office moves, deployments)

The hidden skill that separates good from great desktop support: Anticipating needs. When a manager says “We’re hiring 3 people next month,” the great desktop tech asks: “Should I prep 3 laptops now so they’re ready on day one?” That gets you noticed.

Certifications That Help

Microsoft Certified: Modern Desktop Administrator Associate (MD-100 + MD-101) ($165 per exam = $330 total, 3-4 months study) This covers Windows 10/11 deployment, management, and security. It’s the most relevant cert for desktop support roles in 2025.

ITIL Foundation ($300 exam, 2-3 weeks study) Understanding IT service management frameworks makes you more valuable. Many companies require or prefer ITIL knowledge.

How Long You’ll Be Here

Average timeline: 18-30 months

Fast track (12-18 months) if you:

• Learn PowerShell scripting basics (automate repetitive tasks)
• Volunteer for server-related projects (backups, monitoring, patching)
• Study networking fundamentals (Network+ or equivalent knowledge)
• Document procedures and create knowledge base articles
• Ask to learn from the sysadmin team

Stuck here 3+ years if you:

• Only handle break-fix work, avoid projects
• Don’t develop server or network knowledge
• Resist learning new technologies (cloud, automation)
• Stay comfortable with hands-on work, avoid remote administration

Real example: Jennifer’s path Jennifer worked desktop support at $52K. She automated PC setup tasks using PowerShell scripts, reducing new hire setup from 2 hours to 45 minutes. She documented the process and trained other desktop techs. When the junior sysadmin quit, she was the obvious choice. Timeline: 16 months to junior sysadmin at $68K.

Level 3: IT Technician / Systems Support ($55K-$75K)

What You Actually Do

You’re the bridge between desktop support and system administration. You handle escalated issues, support multiple technology areas, and start working with servers and infrastructure.

Your Tuesday morning:

• 8:00 AM: Review overnight monitoring alerts - server disk space warning, clean up old logs (20 minutes)
• 8:30 AM: Network printer issue affecting entire department - reset print spooler service, clear queue (15 minutes)
• 9:00 AM: VPN connectivity issues for remote users - check firewall logs, identify blocked subnet, coordinate with network admin (45 minutes)
• 10:00 AM: Backup verification - check last night’s server backups, test restore of file (30 minutes)
• 11:00 AM: Active Directory cleanup project - remove disabled accounts, update group memberships (1 hour)
• 1:00 PM: Application server slowness - check CPU/memory usage, restart services, monitor (45 minutes)
• 2:00 PM: Meeting with sysadmin team on upcoming Windows Server upgrade
• 3:00 PM: User permission issues - troubleshoot file share access, modify security groups (30 minutes)

You’re handling fewer tickets (5-10 per day) but they’re more complex. You’re also taking on small projects and supporting infrastructure.

Skills You Need to Develop

This is where your technical skills need to level up significantly:

• Windows Server basics (Active Directory, file shares, print servers)
• Basic server administration (services, event logs, performance monitoring)
• Networking fundamentals (TCP/IP, DNS, DHCP, VLANs)
• Virtualization basics (VMware or Hyper-V concepts)
• Backup and recovery systems
• Basic scripting (PowerShell for Windows, Bash for Linux)
• Security fundamentals (user permissions, group policy, antivirus)

The critical shift: You’re moving from “fix what’s broken” to “prevent it from breaking.” You start thinking about systems, not just individual tickets.

Certifications That Help

CompTIA Network+ ($358 exam, 2-3 months study) Networking knowledge becomes critical at this level. Network+ covers TCP/IP, routing, switching, security basics, and troubleshooting methodology.

Microsoft 365 Certified: Administrator Expert (Multiple exams, $495+ total, 4-6 months) If you’re in a Microsoft shop, this demonstrates comprehensive Office 365/Azure AD admin skills.

CompTIA Server+ ($368 exam, 2-3 months study) Covers server hardware, administration, troubleshooting, and disaster recovery. Less common than Network+ but valuable for server-heavy roles.

How Long You’ll Be Here

Average timeline: 18-36 months

Fast track (12-18 months) if you:

• Build a home lab (practice server and networking skills)
• Learn cloud basics (AWS or Azure free tier accounts)
• Automate tasks with PowerShell or Python scripts
• Take ownership of specific systems (become the “backup expert” or “network monitoring person”)
• Study for and pass a specialty certification (Network+, cloud certification)

Stuck here 3+ years if you:

• Avoid learning cloud technologies
• Don’t develop automation/scripting skills
• Stay reactive instead of proactive
• Resist taking on infrastructure projects

Real example: David’s path David was an IT technician at $61K. He noticed backup failures weren’t being caught early enough. He spent 3 weeks learning PowerShell, wrote a backup verification script that emailed daily reports, and reduced backup failures by 80%. When a junior sysadmin position opened, he was the only candidate considered. Timeline: 14 months to junior sysadmin at $72K.

Level 4: Junior System Administrator ($65K-$85K)

What You Actually Do

You’re no longer “support.” You’re infrastructure. You manage servers, maintain systems, and ensure uptime. When servers go down, you’re the first responder.

Your Tuesday morning:

• 7:30 AM: Check monitoring dashboard before official start time - all green
• 8:00 AM: Patching maintenance - apply Windows updates to 15 servers, reboot in sequence (2 hours)
• 10:00 AM: Active Directory administration - create new user accounts, modify security groups, audit permissions (45 minutes)
• 11:00 AM: Storage capacity planning - review disk space trends, present findings to senior sysadmin (30 minutes)
• 12:00 PM: Break
• 1:00 PM: Troubleshoot email flow issue - check Exchange logs, identify misconfigured mail rule (1 hour)
• 2:00 PM: Documentation update - write runbook for server patching process (45 minutes)
• 3:00 PM: Backup testing - perform test restore of file server to verify backup integrity (1 hour)
• 4:00 PM: Team meeting - discuss upcoming datacenter migration project

You’re managing systems, not just fixing problems. Your work affects the entire organization.

Skills You Need to Master

At this level, you need solid foundation in:

• Active Directory (users, groups, OUs, Group Policy, replication)
• Windows Server administration (roles, features, services)
• Linux basics (many companies run both Windows and Linux)
• Virtualization (VMware vSphere or Hyper-V administration)
• Networking (VLANs, routing, firewall rules, VPN configuration)
• Backup and disaster recovery (backup solutions, restore procedures, DR planning)
• Monitoring and alerting (SIEM basics, log management)
• PowerShell scripting (automating repetitive tasks)
• Security (patching, antivirus, access controls)

The mindset shift: You’re thinking about availability, scalability, and security. When you make a change, you consider: “What breaks if this goes wrong? How do I roll back?”

Certifications That Help

Microsoft Certified: Windows Server Hybrid Administrator Associate ($165 per exam x2 = $330, 4-5 months study) This is the modern replacement for MCSA. Covers hybrid cloud scenarios, which is where most companies are heading.

VMware Certified Professional (VCP) ($250 exam + required training $2,500-4,000) If your company runs VMware heavily, VCP is valuable. Expensive but shows serious virtualization skills.

Linux+ or RHCSA ($359 for Linux+, $400 for RHCSA) Many IT environments are hybrid Windows/Linux. Linux skills open doors to cloud roles later.

Salary Growth at This Level

Entry into junior sysadmin: $65K-$75K After 1-2 years with certifications: $75K-$85K Jumping companies with 3+ years experience: $80K-$95K

Geographic variance:

• Small/medium cities: $65K-$80K
• Large cities (non-tech): $75K-$90K
• Tech hubs (San Francisco, Seattle, Austin): $85K-$105K

How Long You’ll Be Here

Average timeline: 24-42 months

Fast track (18-24 months) if you:

• Learn cloud platforms (AWS or Azure - start with associate-level certifications)
• Master automation (PowerShell or Python for infrastructure)
• Take ownership of critical systems
• Lead small projects (migrations, upgrades, implementations)
• Build expertise in high-value areas (security, cloud, DevOps tools)

Stuck here 3+ years if you:

• Don’t learn cloud technologies (on-prem skills are declining in value)
• Avoid scripting and automation
• Only maintain existing systems, don’t build new skills
• Don’t pursue advanced certifications

Real example: Rachel’s path Rachel was a junior sysadmin at $70K. She saw her company was discussing “cloud migration” but nobody understood AWS. She spent 4 months studying for AWS Solutions Architect Associate (passing on first try), then volunteered to help with pilot cloud projects. When they created a “cloud systems administrator” role at $92K, she was the obvious choice. Timeline: 19 months.

Level 5: System Administrator / Network Administrator ($80K-$105K)

What You Actually Do

You’re a senior member of the IT infrastructure team. You manage critical systems, lead projects, and mentor junior staff. When executives have a technology question, they expect you to have the answer.

Your Tuesday morning:

• 7:00 AM: Oncall phone rings - database server performance degradation, investigate SQL logs, tune queries (1.5 hours, before regular hours)
• 8:30 AM: Infrastructure planning meeting - discuss hardware refresh budget with IT manager (45 minutes)
• 9:30 AM: Cloud migration project - migrate 5 application servers to AWS, configure load balancer (2.5 hours)
• 12:00 PM: Break
• 1:00 PM: Mentor junior sysadmin - review their Group Policy implementation, provide feedback (30 minutes)
• 1:45 PM: Security audit prep - document server hardening procedures, check compliance (1 hour)
• 3:00 PM: Vendor call - discuss SAN upgrade options with storage vendor (45 minutes)
• 4:00 PM: Automation project - write Terraform configuration for infrastructure as code (1 hour)

You’re managing complex systems, leading projects, and making architecture decisions.

Skills You’ve Mastered

By this level, you have deep expertise in:

• Multi-platform administration (Windows, Linux, cloud platforms)
• Advanced Active Directory (federation, trusts, replication, disaster recovery)
• Virtualization architecture (clustering, high availability, resource management)
• Network architecture (routing protocols, VLANs, subnets, security zones)
• Storage systems (SAN, NAS, backup solutions, disaster recovery)
• Cloud platforms (AWS, Azure, or GCP - designing solutions, not just using them)
• Automation and scripting (PowerShell, Python, Bash - writing complex scripts)
• Security implementation (firewalls, IDS/IPS, encryption, compliance)
• Infrastructure as Code (Terraform, CloudFormation, Ansible)
• Monitoring and performance tuning (comprehensive observability)

The expertise shift: You’re not just implementing solutions others designed. You’re designing the solutions. When a business need arises, you translate it to technical architecture.

Certifications That Matter at This Level

AWS Solutions Architect Associate ($150 exam, 3-4 months study) Critical in 2025. Even if you’re managing on-prem infrastructure today, cloud skills are essential for career growth.

Cisco CCNA ($300 exam, 4-5 months study) If you’re focusing on network administration, CCNA demonstrates serious networking knowledge. Opens doors to $90K-$120K network engineer roles.

CompTIA Security+ ($404 exam, 2-3 months study) Security knowledge is increasingly expected at this level. Many companies require Security+ for any infrastructure role.

The Crossroads: Specialist vs Generalist

This is where your career path diverges:

Path A: Specialize in a high-value area

• Cloud Engineer ($100K-$140K)
• Network Engineer ($90K-$130K)
• Security Engineer ($95K-$145K)
• DevOps Engineer ($110K-$160K)

Path B: Stay generalist System Administrator

• Senior Sysadmin ($95K-$120K)
• IT Manager ($100K-$140K)
• IT Director ($130K-$180K+)

My advice: In 2025, specialists earn more. A cloud engineer with 7 years experience makes $120K-$140K. A generalist sysadmin with same experience makes $95K-$110K.

But specializing requires you to double down on specific technology areas. If you love variety and solving different problems daily, generalist sysadmin is still a great career.

How to Break Into $100K+

From this level, here’s how people reach $100K-$120K:

1. Add cloud skills (most common path)

   • Get AWS Solutions Architect Associate or Azure Administrator
   • Volunteer for cloud migration projects at current company
   • Transition to “Cloud Systems Administrator” or “Cloud Engineer” role
   • Timeline: 12-18 months, salary jump to $105K-$125K

2. Specialize in security

   • Get Security+, then CISSP or CEH
   • Focus on security hardening, compliance, incident response
   • Transition to “Security Engineer” or “Security Administrator” role
   • Timeline: 18-24 months, salary jump to $100K-$130K

3. Go DevOps

   • Learn Docker, Kubernetes, CI/CD tools, infrastructure as code
   • Master automation and scripting
   • Transition to “DevOps Engineer” or “Site Reliability Engineer”
   • Timeline: 12-24 months, salary jump to $110K-$140K

4. Network specialization

   • Get CCNA, then CCNP or network automation skills
   • Focus on network architecture, routing, security
   • Transition to “Network Engineer” or “Cloud Network Engineer”
   • Timeline: 18-30 months, salary jump to $95K-$125K

Real example: Marcus’s path Marcus was a sysadmin at $88K. He spent 6 months learning AWS (passed Solutions Architect Associate), then 6 more months learning Terraform and Docker. He documented his projects on GitHub. Interviewed at 15 companies as “Cloud Engineer” and got 4 offers. Took a cloud engineer role at $118K. Total timeline: 15 months from sysadmin to cloud engineer.

Level 6: Senior Systems Engineer / Cloud Engineer ($100K-$140K)

What You Actually Do

You’re designing and implementing major infrastructure initiatives. You’re the technical expert that others consult. Your decisions affect the entire organization’s technology stack.

Your Tuesday morning:

• 8:00 AM: Architecture review meeting - present proposal for new cloud-based disaster recovery solution to CTO and CFO (1 hour)
• 9:15 AM: Hands-on work - configure AWS VPC peering, implement cross-region replication (1.5 hours)
• 11:00 AM: Technical interview - interview candidate for junior cloud engineer position (45 minutes)
• 12:00 PM: Break
• 1:00 PM: Kubernetes troubleshooting - debug failing pod deployments, review application logs with dev team (1 hour)
• 2:15 PM: Infrastructure automation - build Terraform modules for standardized resource deployment (1.5 hours)
• 4:00 PM: Mentor mid-level engineer - code review their CloudFormation templates, suggest improvements (45 minutes)
• 5:00 PM: After-hours maintenance prep - plan evening database migration, document rollback procedures

You’re split between strategic planning (30%), hands-on technical work (50%), and mentoring/leadership (20%).

Skills at This Level

You’re expert-level in 2-3 technology areas and proficient in everything else:

Cloud platforms (deep expertise)

• Multi-account AWS/Azure architecture
• Infrastructure as code at scale (Terraform, CloudFormation)
• Cloud security (IAM, network segmentation, encryption)
• Cost optimization strategies
• Serverless architectures

Containers and orchestration

• Docker (advanced usage, security, optimization)
• Kubernetes (administration, troubleshooting, RBAC)
• Service mesh (Istio, Linkerd)
• Container security scanning

DevOps and automation

• CI/CD pipelines (Jenkins, GitHub Actions, GitLab CI)
• Configuration management (Ansible, Chef, Puppet)
• Scripting (Python, Go, Bash - production-quality code)
• GitOps workflows

Monitoring and observability

• Metrics, logs, traces (the three pillars)
• ELK stack or similar
• Prometheus and Grafana
• Application performance monitoring

Certifications That Matter

AWS Solutions Architect Professional ($300 exam, 4-6 months study) This is the gold standard for cloud roles. Opens doors to $130K-$160K positions.

Certified Kubernetes Administrator (CKA) ($395 exam, 3-4 months study) Critical for DevOps and container-focused roles. Demonstrates real hands-on Kubernetes skills.

CISSP ($749 exam + 5 years experience requirement, 5-6 months study) If you’re senior enough (5+ years in security-relevant IT roles), CISSP is recognized across the industry.

Google Cloud Professional Cloud Architect ($200 exam, 3-4 months study) If your company uses GCP or you want to work at companies that do.

Salary Breakdown at This Level

Senior System Engineer (traditional infrastructure focus): $95K-$120K Cloud Engineer (AWS/Azure/GCP): $105K-$140K Senior DevOps Engineer: $115K-$155K Site Reliability Engineer (SRE): $120K-$160K Security Engineer: $110K-$145K

Geographic variance:

• Small cities: $90K-$110K
• Medium cities: $100K-$125K
• Tech hubs: $120K-$160K
• Remote (company in tech hub, you anywhere): $110K-$140K

Company type variance:

• Small businesses (under 500 employees): $95K-$115K
• Mid-market (500-2000 employees): $105K-$130K
• Enterprise (2000+ employees): $115K-$145K
• Tech companies: $125K-$160K+

The Management Decision

At this level, you face a choice: stay technical (IC track) or go into management?

Management track:

• IT Manager: $100K-$135K (managing 3-8 people)
• Senior IT Manager: $120K-$160K (managing 8-15 people or multiple teams)
• IT Director: $140K-$200K+ (managing managers, strategic leadership)

Technical track:

• Senior Engineer/Architect: $110K-$150K
• Principal Engineer: $140K-$180K+
• Distinguished Engineer: $170K-$250K+ (rare, mostly at large tech companies)

Here’s the reality: Management roles are more common and have clearer progression. Principal/Distinguished Engineer roles exist at large companies (Google, Amazon, Microsoft, Netflix) but are rare at typical enterprises.

If you want to stay 100% technical and reach $150K+, your best options are:

1. Work at FAANG/top tech companies
2. Specialize in high-demand areas (SRE, security architecture, data engineering)
3. Become an independent consultant/contractor ($150-$250/hour)

How Long You’ll Be Here

This might be your career level for 5-10 years. Many engineers are happy here. The work is interesting, compensation is solid, you’re not in constant meetings.

If you want to go higher (Principal Engineer, Director, CTO):

• Build thought leadership (blog, speak at conferences, open source contributions)
• Lead cross-functional initiatives
• Develop business and people skills, not just technical
• Get an executive sponsor (someone at director+ level who advocates for you)
• Consider getting an MBA if targeting executive roles

Level 7: Principal Engineer / IT Manager / Director ($130K-$200K+)

What You Actually Do

You’re shaping technology strategy, leading teams or major initiatives, and influencing business decisions at the executive level.

Your Tuesday morning (IT Manager track):

• 8:00 AM: 1-on-1 meetings with 3 direct reports - career development discussions (1.5 hours)
• 9:45 AM: Budget review meeting with CFO - justify headcount increases, infrastructure spending (1 hour)
• 11:00 AM: Strategy meeting with CTO - discuss 2026 technology roadmap (1 hour)
• 12:00 PM: Lunch
• 1:00 PM: Incident post-mortem - lead discussion on last week’s production outage (1 hour)
• 2:15 PM: Vendor negotiation - renegotiate cloud provider contract (45 minutes)
• 3:00 PM: Hiring - interview senior engineer candidate (1 hour)
• 4:15 PM: Hands-on work - review architecture proposal for new microservices platform (1 hour)

Your Tuesday morning (Principal Engineer track):

• 8:00 AM: Architecture review - evaluate proposals from 3 teams (1.5 hours)
• 9:45 AM: Technical strategy - write RFC (Request for Comments) on adopting service mesh (2 hours)
• 12:00 PM: Lunch
• 1:00 PM: Mentoring session - pair programming with senior engineer on complex problem (1.5 hours)
• 2:45 PM: Cross-team meeting - resolve technical disagreement between platform and security teams (45 minutes)
• 3:45 PM: Research - investigate new observability tools for recommendation (1.5 hours)
• 5:30 PM: Write blog post on infrastructure automation patterns for company blog

Skills Required

Management track:

• People leadership (hiring, performance management, conflict resolution)
• Budget management (CapEx/OpEx planning, ROI analysis)
• Strategic thinking (aligning technology with business goals)
• Vendor management (contract negotiation, relationship management)
• Stakeholder management (communicating with executives, non-technical leaders)
• Project/program management
• Strong technical foundation (you can’t lead what you don’t understand)

Principal Engineer track:

• Expert-level technical depth in 2-3 domains
• Architecture design (designing systems that scale to millions of users or thousands of services)
• Cross-team technical leadership (influencing without authority)
• Mentoring senior engineers
• Technical writing and communication
• Evaluating emerging technologies
• Building technical standards and best practices

Certifications (Less Important Here)

At this level, certifications matter less than:

• Track record of successful projects
• Thought leadership (conference talks, blog posts, open source)
• Network and reputation
• Business acumen

But if pursuing high-level certs:

• AWS Certified Solutions Architect Professional (if cloud-focused)
• CISSP (if security-relevant)
• TOGAF (if enterprise architecture role)
• PMP (if management track)

Salary Expectations

IT Manager (3-8 direct reports): $100K-$140K Senior IT Manager (8-15 direct reports): $120K-$165K IT Director (multiple teams): $140K-$200K VP of IT / CTO (small-medium company): $160K-$250K+

Principal Engineer: $140K-$200K Distinguished Engineer: $180K-$300K+ (rare)

Location multipliers:

• San Francisco Bay Area: 1.4-1.6x
• Seattle: 1.3-1.4x
• New York City: 1.3-1.5x
• Austin, Denver: 1.1-1.2x
• Other major cities: 1.0x
• Rural areas: 0.8-0.9x

How to Reach This Level

From Level 6 to Level 7 (Management track):

1. Lead increasingly larger projects (start with 2-3 people, grow to 5-8)
2. Develop people management skills (mentor formally, give technical feedback)
3. Show business impact (not just technical wins, but cost savings, revenue enablement)
4. Build relationships with executives (they need to know your name)
5. Demonstrate strategic thinking (propose initiatives aligned with business goals)
6. Timeline: 3-5 years from senior engineer to manager/director

From Level 6 to Level 7 (Principal Engineer track):

1. Become THE expert in critical technology area
2. Drive technical decisions across multiple teams
3. Build influence through technical excellence
4. Mentor multiple senior engineers
5. Create leverage (build tools/frameworks others use)
6. Timeline: 4-7 years from senior engineer to principal (and many never make it)

Reality check: Not everyone reaches this level, and that’s okay. Level 6 (senior engineer at $120K-$140K) is a great career destination for many people. You’re well-compensated, doing interesting technical work, and not drowning in meetings.

How to Move Up the Ladder Faster Than Your Peers

I’ve seen people take 12 years to go from help desk to senior engineer. I’ve also seen people do it in 6 years. Here’s what the fast-movers do differently:

Strategy 1: Learn the Next Level’s Skills While in Your Current Role

Don’t wait for promotion to learn senior skills. Learn them first, then get promoted.

If you’re help desk:

• Learn Active Directory administration (not just password resets)
• Study networking fundamentals
• Practice with home lab (set up your own domain controller)
• Take on desktop support tickets when help desk is slow

If you’re desktop support:

• Shadow the sysadmin team
• Learn PowerShell scripting
• Volunteer for server-related projects
• Study for Network+ or Microsoft 365 admin certifications

If you’re junior sysadmin:

• Learn cloud platforms (AWS or Azure)
• Build automation scripts
• Study infrastructure as code (Terraform)
• Take ownership of specific systems

Strategy 2: Build a Portfolio of Projects

Employers hire based on what you can DO, not just what you know.

Portfolio examples that get you hired:

Help desk → Desktop support:

• Document common ticket resolutions in knowledge base
• Create user training materials for common issues
• Improve first-call resolution rate by 15%+

Desktop support → Junior sysadmin:

• Automate PC deployment with scripting
• Build inventory tracking system
• Lead PC refresh project

Junior sysadmin → Cloud engineer:

• Build home lab with AWS (host a website, implement CI/CD)
• Migrate a service to AWS at current job
• Contribute to infrastructure-as-code projects
• GitHub portfolio with Terraform configurations

Strategy 3: Get Certifications Strategically

Not all certifications have equal ROI. Focus on high-value certs for your target role.

High ROI certifications:

• CompTIA A+ → Gets help desk job ($40K-$50K)
• Network+ → Opens sysadmin roles ($70K-$85K)
• AWS Solutions Architect Associate → Opens cloud roles ($100K-$130K)
• CCNA → Opens network engineer roles ($90K-$120K)
• Certified Kubernetes Administrator → Opens DevOps/SRE roles ($110K-$150K)

Lower ROI certifications (still valuable, but less salary impact):

• CompTIA Cloud Practitioner
• Microsoft 365 Fundamentals
• Most “fundamentals” level certifications

Strategy: Get 1-2 high-impact certifications that align with your target specialization.

Strategy 4: Jump Companies Strategically

Sad truth: Switching companies typically yields 15-30% salary increases. Internal promotions yield 5-15% increases.

Example progression (company jumper vs company loyal):

Company jumper:

• Year 1-2: Help desk at Company A ($42K → $48K with promotion to desktop support)
• Year 3-4: Desktop support at Company B ($58K → $62K)
• Year 5-6: Junior sysadmin at Company C ($72K → $80K)
• Year 7: Sysadmin at Company D ($95K)
• Year 9: Cloud engineer at Company E ($118K)

Company loyal:

• Year 1-2: Help desk at Company A ($42K → $48K desktop support)
• Year 3-4: Desktop support ($51K → $54K)
• Year 5-6: Junior sysadmin ($65K → $68K)
• Year 7-8: Sysadmin ($75K → $78K)
• Year 9: Senior sysadmin ($85K)

Same skills. Same years of experience. Company jumper makes $118K. Company loyal makes $85K.

That’s a $33,000 difference in annual salary.

Optimal strategy:

• Stay 18-24 months per role (long enough to learn, short enough to jump before you plateau)
• Jump when you’ve mastered your current level and are doing next-level work
• Always be interviewing (even when happy - it shows you your market value)

Strategy 5: Specialize in High-Demand Areas

In 2025, these specializations command premium salaries:

Cloud (highest demand): $20K-$40K premium over on-prem roles DevOps/SRE: $15K-$35K premium over traditional sysadmin Security: $10K-$30K premium over generalist roles Network automation: $15K-$25K premium over traditional network admin Data engineering: $25K-$40K premium (but requires strong coding skills)

Generalist system administrators have lower earning potential but more job security (every company needs sysadmins).

My recommendation: Start as generalist (learn everything), then specialize around Year 4-5 when you know which area you enjoy most.

Common Mistakes That Keep People Stuck

I’ve seen hundreds of IT professionals plateau. Here are the mistakes that kill career progression:

Mistake 1: Waiting to “Feel Ready” Before Applying for the Next Level

The problem: You’ll never feel 100% ready. If you wait until you know everything for the next role, you’re already 2 years behind.

The fix: Apply for next-level positions when you can do 60-70% of the job. You’ll learn the rest on the job.

Mistake 2: Not Investing in Self-Learning

The problem: You expect your employer to train you. Most won’t. Budget cuts, lack of training programs, understaffed teams.

The fix: Budget $500-1000/year for self-learning. Certifications, Udemy courses, home lab equipment, books. It’s an investment that pays back 10-20x.

Mistake 3: Avoiding Cloud Because “We’re On-Prem”

The problem: Even if your current company is 100% on-prem, your NEXT employer won’t be.

The fix: Learn cloud skills on your own time. Free tier AWS accounts. Home lab in the cloud. Every IT career path in 2025 requires cloud knowledge.

Mistake 4: Only Doing Your Job Description

The problem: If you only handle your assigned tickets and never take initiative, you’re invisible.

The fix: Find problems nobody is solving and solve them. Document procedures. Automate tasks. Build tools. Make yourself indispensable AND visible.

Mistake 5: Not Networking (Internal and External)

The problem: You keep your head down, do your work, assume merit will get you promoted. It won’t.

The fix:

• Internal networking: Get to know other IT teams, managers, directors
• External networking: LinkedIn connections, local IT meetups, online communities
• The best jobs aren’t posted publicly - they’re filled through referrals

Mistake 6: Staying in Comfort Zone

The problem: You’ve mastered your current role. It’s comfortable. Low stress. You stop growing.

The fix: Discomfort = growth. When work feels easy, it’s time to move up or specialize. Comfort is career death.

Your First Week: 7-Day Action Plan

You’ve read the full ladder. Now you’re wondering: “Where do I start?”

Here’s your concrete first week to start moving up, no matter which level you’re at:

Day 1: Identify Your Current Level and Target Level

Write down:

• Your current position title and salary
• Your current technical skills (honest assessment)
• Your target position (one level up)
• Skills gap between where you are and where you want to be

Time: 30 minutes

Day 2: Research Next-Level Requirements

Go to job boards (Indeed, LinkedIn). Search for your target role. Save 5-10 job postings.

Analyze requirements:

• What technical skills appear in 80%+ of postings?
• What certifications are “required” or “preferred”?
• What salary ranges are listed?

Time: 45 minutes

Day 3: Create Your Learning Plan

Based on Day 2 research, prioritize 3 skills or certifications to learn.

Choose:

• 1 high-impact certification (CompTIA Network+, AWS SAA, CCNA, etc.)
• 2 practical skills (PowerShell scripting, Linux basics, cloud fundamentals, etc.)

Map out timeline:

• Certification: 3-6 months
• Skills: 1-3 months each

Time: 30 minutes

Day 4: Set Up Your Learning Environment

Take action:

• Buy a study guide or enroll in online course for your target certification
• Create free tier account (AWS, Azure, or GCP)
• Set up home lab VM if learning Windows Server / Linux
• Join online communities (Reddit r/ITCareerQuestions, r/sysadmin, Discord servers)

Time: 1 hour

Day 5: Start Your First Learning Session

Don’t overthink. Just start.

• If studying for certification: Watch first 2 course videos or read Chapter 1
• If learning cloud: Launch your first EC2 instance or VM
• If learning scripting: Write your first “Hello World” PowerShell script

Time: 1-2 hours

Day 6: Update Your Resume and LinkedIn

Prepare for future job search:

• Add any recent skills or projects to resume
• Update LinkedIn headline to target role (“System Administrator | Cloud Enthusiast | AWS Certified”)
• Connect with 10 IT professionals in your area or target companies
• Join 3-5 LinkedIn groups related to your target specialization

Time: 1 hour

Day 7: Schedule Your Learning Time

The biggest mistake: sporadic learning that fizzles out.

Create a study schedule:

• Weekdays: 1 hour per day (early morning or evening)
• Weekends: 2-3 hours per day

Block calendar time. Treat it like a meeting.

Commit to 90 days. After 90 days of consistent learning, you’ll see measurable progress.

Time: 15 minutes to schedule + ongoing daily study

The Honest Truth About the IT Support Career Ladder

Let me close with what nobody tells you when you start your IT career:

1. The ladder is real, but it’s not automatic. You don’t just accumulate years and get promoted. You accumulate SKILLS and get promoted. I’ve seen 10-year help desk technicians and 6-year senior engineers. Skills, not time.

2. The biggest jumps come from specializing. Generalist system administrators top out around $100K-$110K in most markets. Cloud engineers, DevOps engineers, security engineers reach $130K-$160K+. Specialization pays.

3. Company jumping beats company loyalty (financially). I wish this weren’t true. But the data is clear: people who switch companies every 2-3 years earn 20-40% more over their careers than those who stay at one company. Loyalty doesn’t pay in IT.

4. Cloud skills are non-negotiable in 2025. I don’t care if you want to be a network engineer or security specialist or database admin. You NEED cloud knowledge. Every path intersects with cloud. Period.

5. Soft skills matter as much as technical skills at senior levels. You can be the best technical person in the room. If you can’t communicate with non-technical stakeholders, write clear documentation, or mentor junior team members, you won’t get past Level 5.

6. There’s no shame in staying at a level where you’re happy. Not everyone wants to be a CTO or Principal Engineer. If you love hands-on technical work, staying at Level 5-6 (sysadmin or senior engineer, $90K-$120K) is a great career. Work-life balance matters.

7. Starting at help desk is not “being stuck at the bottom.” It’s the entry point to six-figure careers. I started at help desk making $38K. Twelve years later: $168K. Every senior engineer I know started in support. Embrace it, learn fast, move up.

Your turn. You know the ladder now. You know the skills required. You know how people move up faster.

The question is: what’s your next move?