Thinking about moving into cybersecurity or tech but worried you do not have enough experience? In this episode, Adam Hewitt sits down with Lindsay, CEO of Techwell, to unpack what employers actually look for when hiring career changers into IT, managed services, and security roles. With 35 years in the technology industry and firsthand experience hiring Cyber Revolution graduates, Lindsay shares a practical employer-side view of what helps candidates stand out.

You will hear why certifications matter, but do not guarantee the job, how communication and customer-facing skills can become a major advantage, and why MSPs can be great entry points for people changing careers. Lindsay also explains Techwell's interview process, the balance between technical acumen and cultural fit, how new hires are trained through shadowing and structured development, and why attitude, punctuality, teamwork, and curiosity can influence hiring decisions. Adam and Lindsay also discuss real career pathways, including how Michael progressed through project management, level 1 support, security, and technical pre-sales within just a few years.

Key Takeaways:

• Use your previous career experience as an advantage. Customer service, stakeholder management, teamwork, and communication can make you more attractive to tech employers.

• Treat certifications as the entry ticket, not the finish line. They can help you get an interview, but how you present yourself often determines whether you win the role.

• Research real tech roles before committing. If possible, seek internships, shadowing, or time with an IT team to understand the good, bad, and practical day-to-day realities.

• Show commitment to the career change. Employers notice when candidates have invested time, money, study, and even short-term sacrifices to build a long-term tech career.

• Prepare for interviews beyond technical questions. Eye contact, punctuality, clear articulation, curiosity, and professional presence all influence hiring decisions.

• Look for employers with growth pathways. MSPs and growing tech companies may offer opportunities to move from entry-level support into security, projects, pre-sales, or leadership.

Chapters:

00:00 Introduction and Welcoming Guest Lindsay

02:18 Lindsay's Career Journey to Techwell CEO

06:30 Overview of Techwell Services

09:02 Hiring Career Changers and Soft Skills

18:05 Inside Techwell Interview Process

20:58 Michael and Alex Career Progression

25:44 Advice for Aspiring Career Changers

30:03 Closing Remarks and Key Takeaways

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