All coaching

Start in Cybersecurity

6 sessions45 min per session

For people who want a cybersecurity job but don't know where to begin

We will take you by the hand for the next 3 months to launch your cybersecurity career with

  • The exact roles to target and why,

  • Exams to write and how to prepare

  • Projects to implement and how to document it

  • A polished LinkedIn profile and a refined resume

  • A strategy for volunteering to get your first cybersecurity experience

Who this is for:

  • Students, new graduates, and self-taught learners with 0–1 years in tech

  • People lost in free courses, YouTube videos, and "Which certificate first?” advice

  • Anyone who can name three certificates but not one job they want

Not for: people already working in security who want a promotion. That is Move Up in Cybersecurity.

What happens in each session:

  1. Review your route and score your strengths. The real jobs on your RouteFinder route, what each does day to day, and which ones hire beginners. We score your strengths and shortlist two target roles for you.

  2. Decode the market, and name your destination. Review 10 live job postings, 5 for each role, sorted into real requirements and noise. We help you narrow down to one job and one backup, and your plan is refined to that role at six months.

  3. Put a target date on your milestone, select the exam to book, and select the lab to start. We refine your certification list, pick the most significant one to book immediately, and date every core item of your roadmap.

  4. Scope your projects with target dates attached. The three most impactful projects selected from your own milestone.

  5. Publish your project artifacts on GitHub and build your real resume and LinkedIn profile. Your project goes online with a README, your LinkedIn is rebuilt, and your anticipated resume is cut down to what is true today.

  6. Mock recruiter screening, technical interview, and strategy for getting your first volunteer job. Both scored, with a fix list.

What you take home

  • A one-page Target Plan: the job, the backup, why

  • Your six-month roadmap, every core item dated

  • Three selected projects, with a template to report them on your resume and as Markdown on GitHub

  • A security resume and a rebuilt LinkedIn profile

  • 25 target companies and a referral message template

  • 10 review questions about your project and 10 role questions a hiring manager would ask

  • Volunteer job strategy

6 sessions of 45 minutes over 3 months · 4 to 6 hours of practice per week

How this program works

  • Complete the RouteFinder before your first call. Your plan is where we start.

  • One-to-one video calls, 45 minutes each, recorded and transcribed.

  • Your coaching dashboard holds the plan and your progress.

  • Your coach pushes action points and assignments to you. Assignments are due before the next session and you get a notification.

  • You can message your coach between calls. Replies within two working days.

  • Homework is required.

Meet your coach

Abel Olumide

Founder at SailingCyber | CISSP | AWS-Sec | PMP | Msc | MBA

I have been enabling security operations, managing technical teams and building security tools for over a decade now, covering Africa, Asia, Europe and North America. I currently serve as Security Engineering Lead at Bloomberg Industry Group and have held senior roles at TikTok and Visa, where I learned that great security is never just about technology. It's about people, process, and earning trust at scale. I've also made it my mission to open the door for others. I've designed cybersecurity learning programs reaching over 60,000 learners across 105 countries. That is exactly why I built SailingCyber to give people the direction I wish I'd had when I was starting out. From your very first step into security to your next big move, I'm looking forward to being a part of your journey on SailingCyber!

What's included

  • 6 one-to-one video sessions
  • 45 minutes per session
  • Action points tracked between sessions
  • Direct messaging with your coach

Enrol on this programme

Sessions are booked from your dashboard once you're enrolled.

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