Jean Kang

Path to PM

"Jean isn’t a program manager coach solely because she’s done the role. She’s a coach because she’s done both the role AND gone the extra mile to document what she’s researched and learned masterfully. 

“Jean’s the real deal, and I couldn’t recommend her more to someone questioning how to take the next step in their career."

Founder & CEO

LinkedIn

Instructor profile: https://www.linkedin.com/learning/instructors/jean-kang

LinkedIn Learning Instructor 

Business Insider

Contributing Writer

Figma

Focus on leadership strategy and helping Product Support operate with even greater agility, clarity and cohesion

Strategic Program Manager

First Program Manager on Product Support, leading some of our most strategic organizational and company initiatives in partnership with cross-functional leaders across Legal, Product and Eng, Marketing, Comm, and Security

Senior Program Manager

CX GTM program manager responsible for how CS goes to market with Product through scaled enablement such as training, communication, and playbooks for 200+ CSMs globally across 11 offices.

Global GTM Enablement Program Manager

Chief of Staff, Women at Linkedin

UN Women

Board Member

Pinterest

Advertiser Ops & Strategy

Facebook

Client Solutions Manager

Intuit

SMB Sales

✨ PM Career Coach, x7 pivoter, helping other pivoters land amazing Program Manager roles and 🔥 thrive on the job | Founder of 🚀 Path to PM | Senior Program Manager @ Figma • Ex-Linkedin, Meta, Pinterest, Intuit

Over the last decade, I led impactful programs at companies like LinkedIn, Pinterest, & Figma.

But here’s the part that surprises people:

- I didn’t have a PMP certification.
- I’m a proud career pivoter. 
- I didn’t check every box.

What I did have was strategy, storytelling, and a clear sense of how to articulate my value.

That’s how I landed multiple 6-figure Program Manager roles at top tech companies not by following the “traditional” path, but by leaning into my superpowers. 

Eventually, I had a spark to do something different..

What if I used the same skills that helped me thrive in Big Tech… to build something of my own?

So I left to bet on myself (again). 

And what served me well in my career also helped me as a solopreneur.

I owned my story, built with intention and shared learnings in public.

I started creating content in 2023 and in 2 years, built a community of 350K+ across LinkedIn, Instagram, and my newsletter.

Today, I’m the founder of the PM Accelerator, a career transformation program where I help senior professionals land high-paying PM roles without another certification or starting over. 

My mission is to democratize access to tech careers + empower folks to design a career, business & life they love especially in this era of AI.

The Results:

→ Partnered with Google, Hubspot, NVIDIA, Adobe, Kajabi, Notion, & more
→ LinkedIn Learning Instructor with 200K+ learners
→ 100M+ impressions over the last year
→ 230K+ follow my journey on LinkedIn
→ Built a $200K+ business in 1 year 
→ 32K+ read my newsletter 
→ (soon TEDx speaker 😱)

If you want to learn the exact framework I used to land dream PM roles + help others do the same… 

📌 APPLY TO THE PM ACCELERATOR (link in bio)

In this 5-week career acceleration program, I teach you how to get interviews, land dream offers and literally thrive on the job.  

I helped 100+ students land PM roles at Microsoft, SoFi, Scale.AI, Adidas, Workday and more (many in under 4–7 weeks)

→ GO HERE: pm-accelerator.com 

📧 jean@jean-kang.com for partnerships, collaborations, and speaking opportunities

📌 Media kit: jean-kang.com

Imposter syndrome is a silent killer.

5 tips to beat it (and change your life 🔥)

—
☝🏼 Step 1: Recognize Your Fixed Mindset

Negative self-talk sounds like:

↳ “I’m not good enough.”
↳ “I always mess up.”
↳ “I’m too quiet.”

These aren’t facts—they are negative thoughts. Recognizing them is the first step.

—
✌🏼 Step 2: Get Comfortable Being Uncomfortable

Growth lives outside your comfort zone.

↳ Want to improve public speaking? Say yes to that presentation.
↳ Want to become a program manager? Raise your hand to lead that project.
↳ Want to create content? Start posting 3x a week.

The more you stretch, the more you grow.

—
🤟🏼 Step 3: Seek Meaningful Feedback

Feedback starts with you.

↳ Do a weekly retro: What worked? What didn’t? What’s next?
↳ Ask colleagues or friends: What should I do more of? Less of?

Feedback is a gift for growth.

—
🖖🏼 Step 4: Detach Your Self-Worth From Work

You are more than your job.

Grow in areas that align with your values:

↳ Nurture relationships.
↳ Pursue passion projects.
↳ Volunteer or give back.
↳ Prioritize hobbies that bring joy.

—
🖐🏼 Step 5: Add “…Yet” to Reframe

Turn self-doubt into self-belief with one word: “Yet.”

↳ “I’m not a great leader…yet.”
↳ “I’m not in my dream job…yet.”
↳ “I’m not a skilled writer…yet.”

If you can’t beat fear, just do it scared. If not you, then who?

What’s ONE step you can take today? 👇🏼

📌 P.S. And if you're into actionable tips, try out my newsletter.

I talk about leveling up your 9-to-5, building a fulfilling side hustle, and designing a life on your terms.

https://lnkd.in/gc2mu4yK

Repost to inspire someone who needs to hear it & follow Jean Kang for more 🙏🏼

Tech Creator (400k+) with 8M+ monthly views | Ex-LinkedIn, Meta, Figma | Solopreneur, TEDx Speaker & Angel Investor helping you thrive at work using AI

Stop telling yourself you’re not qualified, good enough, or worthy.

Growth happens when you start 
doing the things you’re not qualified 
to do.

Remote work changed my life.

More rest. Less stress.

And it works for most people:

Individuals, parents, caretakers, pet owners 🐶, or anyone in between.

WFH doesn’t just stand for:

Work. From. Home.

It also means:

- Work 💻
- Family 🙏🏼
- Health 🧘🏻‍♀️

It’s about flexibility and choice.

And with tools like Tango I’ve never been more productive.

Love how easy they made it to learn new processes and train employees efficiently (without being in the office).

Don’t believe me?

I made this quick tutorial on how to find 6-figure REMOTE jobs on LinkedIn

(it took 2 minutes)

The goal is to teach it once and never explain again 😱

👀 Find 6-Figure Remote Jobs on LinkedIn: https://lnkd.in/e7SxhFdX

What’s your favorite part about remote work?

Repost if you love remote work 🙌🏼

I can’t stop thinking about this…

Never underestimate the quiet ones.

The ones who are quietly studying after work / on weekends.

Sending DMs to people they admire.

Choosing podcasts / books > Netflix.

Focused on being just 1% better every single day.

Self-education is what separates the goods from the GREATS.

Because when you choose to learn in your free time...

You’re building something no one can take away

That’s exactly how my “little” side hustle of posting on LinkedIn turned into a 6-fig business.

Allowing me to quit my dream tech job and replace my income in < 1 year.

Here’s how I approach learning something new:

1/ Get ridiculously clear on your learning goal

↳ What exactly am I trying to learn, and why does it matter right now?
↳ Write it down down: “I’m learning [X] so I can [Y] by [Z date].”

2/ Do a brutally honest skill audit

↳ Where am I truly starting from? Beginner? Intermediate?
↳ I rate myself on a 1–5 scale, then identify 1–2 focus areas for the week.

3/ Source high-quality content (not just what's trending)

↳ I follow 2–3 trusted experts who are 5 steps ahead (not 10).
↳ I choose one main format to learn from (podcast, YouTube, course, etc.).

4/ Build a non-negotiable learning routine

↳ I block 10–30 minutes daily on my calendar like it’s a real meeting.
↳ Write down key learnings every time + 1 action you can commit to.

5/ Create social accountability

↳ I tell a friend (or post publicly) what I’m working on.
↳ I set a tiny consequence if I fall off (like buying them lunch or sending $20).

If you’re not learning, you’re not growing.

What’s 1 thing you’re learning in 2025?

Drop it in the comments - I’d love to cheer you on!

PS. If you've been quietly putting in the work and you're ready for the next big leap…

I launched a 5-week program to help you land your next Program Manager role so you can be richer, happier, and thrive on the job (no PMP required)

✅ Apply now & chat with my team!
https://lnkd.in/eN_pc9rX

♻️ Repost to help more people stop waiting and start learning.

Never underestimate a person who practices self education in their free time.

What I learned about life.

It’s not meant to be easy.

It’s hard, uncomfortable, even painful at times.

Here’s what I mean:

↳ I was bullied growing up.
↳ I was fired from a job I loved.
↳ I lost my mom to cancer when I was 25.

I could’ve stayed angry but I chose to start over.

And by giving myself another ‘do over’:

✔️ I have amazing friends & mentors
✔️ I landed dream jobs at dream companies
✔️ I built a 6-figure business doing what I love
✔️ I found the love of my life (I made the first move)

It’s never too late to rewrite your story.

And know what else?

Your environment matters more than you know.

People thrive when things are clear.

Teams thrive when systems replace chaos.

Companies thrive when employees have tools to do their best work.

And I’m so grateful to partner with Jotform, an incredibly powerful and intuitive form builder to help teams operate faster and smarter (all driven by data).

With their updated Enterprise version (2.0), they're giving companies a clearer & more thoughtful way to organize/understand their data, and build systems that run quietly in the background.

I love their new admin console that centralizes literally everything (think assets and analytics), access to a curated help center + actionable guides, and ability to create visual dashboards to see what actually works (and doesn’t).

While it’s never too late to start over,
it can be too late to stay stuck.

A toxic partner costs your peace.
A bad process can cost thousands.
A role with no growth drains your potential.

If you’re looking for a solution that is truly tailored for your custom needs: better data, cleaner workflows, and a centralized source-of-truth,

I highly recommend you try out Jotform: https://lnkd.in/eQepb6wn

What’s 1 hard thing you can do today that your future self with thank you for?

Don’t be afraid to start over again. 
You may like your new story better.


Introverts love remote work.

I noticed I’m way more productive WFH.

No more dealing with:

- Office distractions
- Endless meetings
- Commuting

I’ve traded it for:

- Flexibility
- A quiet mind
- A healthier body

The truth is: people operate at their best in an environment that works for them.

It can be hybrid, in-office, or entirely remote.

For many introverts like me, it’s a dream lifestyle 🥹.

And with tools like Jotform, an incredibly powerful and intuitive form builder, I’ve never been more productive. 

I love how ridiculously simple they make online data and payment collection that enable me to build strong systems that operate in the background.

It’s no surprise that it’s literally trusted by 34M users worldwide including nonprofits, SMBs and enterprises that may need bespoke tools for gathering better data. 

Remote work isn’t just a new way of working.

It’s a new way of living. 

Did you know Jotform has AI-powered template creation that lets users generate server-wide forms from a single prompt and makes them available to everyone at work?

🔗 Check it out here: https://lnkd.in/eNy3fNFP

Repost if you love remote work 🙌🏼

Leadership is not a title.

And not all bosses are leaders.

I’ve worked at some of the best companies in the world.

But you know what?

Great companies don’t = quality bosses.

If I were to go back to corporate, I would choose my boss over any paycheck.

Because no paycheck is worth your mental health 💙

__

7 Qualities of a Great Leader:

✅ Lead by example

✅ Values & respects you

✅ Have your best interests

✅ Be kind and constructive

✅ Care about you as a person

✅ Help you grow in your career

✅ Advocate for you in rooms you’re not in

A good boss is better than a good company.

Repost if you agree 🙏🏼 and follow Jean Kang for more.

a toxic boss will cost you more than any paycheck

What I used to care about (before accepting a job)

↳ Perks (Free food, swag, etc)
↳ Company name
↳ Location
↳ Title

What I care about now (after I got all the above)

★ Flexible time off (without the guilt)

★ A manager who has my back

★ Growth opportunities

★ Psychological safety

★ Exciting challenges

★ Supportive team

★ Remote-friendly

The superficial things are temporary bliss.

Prioritize your non-negotiables.

And assess your list regularly.

If you’re looking for a job, I hope you find the right role, culture and boss for you 💙.

What’s your non-negotiable? 👇🏼

Things employees don't care about
- title
- perks
- benefits
- company name
- nice office

What employees actually care about
- Flexible time off (without the guilt)
- A manager who has my back
- Growth opportunities
- Psychological safety
- Exciting challenges
- Supportive team
- Remote-friendly

Rule for life: Don’t get stuck in the wrong place

9 questions to ask to get UNSTUCK (and break free 🦋):

1. Am I learning and growing?

→ Do I feel challenged and stimulated in my current role?

2. Do I feel like I can make an impact?

→ Am I contributing meaningfully to the team and organization?

3. Do I align with the values of the company?

→ Do our shared beliefs and goals resonate?

4. Am I being valued and recognized for my work?

→ Do I feel appreciated and rewarded for my contributions?

5. Do I enjoy working with my team and my boss?

→ Are there positive relationships and support at work?

6. Am I being underutilized or overextended?

→ Is my workload balanced and fulfilling?

7. Am I feeling burnt out or stressed?

→ Is my mental and emotional health being affected?

8. Am I aligned with the company's direction and goals?

→ Do I see a clear path for my career growth within the organization?

9. Am I considering alternative career paths or opportunities?

→ Do I feel hopeful about exploring new possibilities?

It's better to admit you walked through the wrong door than to spend your life in the wrong room. Repost if you agree 🙏🏼

P.S. Grab my worksheet for finding a job you love and the best-curated big tech interview guide from places like Meta, Pinterest & Apple

🎁 Just add your email and get it for free https://lnkd.in/ef2GJX5P

Better to admit you walked in the wrong
door than spend your life in the wrong room. 

I think I get the Formula 1 hype now ✨

F1 is one of the rare sports that brings together the human and the machine ⚙️🏎️

I spent all week in Vegas with Atlassian and Williams Racing and saw up close how world class collaboration really works.

They invest in people, hardware and software to keep thousands of team members operating at their best.

Everything moves in sync so parts get to the track faster, and the car gets faster too 💨

It was surreal to watch a high performance team move in true harmony.

Who else cheered for Atlassian Williams Racing? 🙌🏼🏎️

#ad #atlassianpartner #f1

Brand partnership • Tech Creator (400k+) with 8M+ monthly views | Ex-LinkedIn, Meta, Figma | Solopreneur, TEDx Speaker & Angel Investor helping you thrive at work using AI

Lester Chng

Cyber CEOs Brand Strategist. I build your brand as you build your business. | Senior Cybersecurity Advisor | Author | Naval Officer | CISSP | 🇨🇦🇸🇬 |

You head a leading cybersecurity firm.
But your online presence doesn't reflect it.

In fact, being invisible is damaging. 

You understand the power of thought leadership.
You know LinkedIn shapes deal flow and adds credibility in the industry.
You just don’t have the cycles (or the copy) to share your expertise and experience.

You have stories worth telling.

The insights from being in the trenches.
The deep conversations with your ace teams.
The hard discussions with your clients. 

Don’t let this wisdom go to waste.

That’s where I come in.

--------------------------------------------------------------------------------------------

How we work together.

Profile & Positioning
=> Rebuild your LinkedIn profile so visitors see industry authority, not “another vendor.”

Content engine
=> Ghostwritten posts that leverage your insights and expertise into engaging LinkedIn posts. 

Outreach campaign
=> Targeted DM campaigns and audience-building strategies that build your authority and land you on podcasts and conference stages.

--------------------------------------------------------------------------------------------

You focus on growing your firm and protecting your clients.
And we will ensure the industry, clients, prospects, and investors can’t ignore it.

Let’s build the personal brand that commands the cybersecurity conversation and drives business.


Worked with global client portfolio 
- MSPs
- MSSPs
- Agentic AI SOC
- AI-powered GRC 
- Operational Resilience 

Senior Advisor, Financial Crimes Unit Exercises. BMO Fusion Centre

Execution of Financial Crimes Unit Exercise and Drill Program
• Design and execution of exercises and drills to operationalize the Financial Crimes Unit Fusion Centre
• Scenario creation and exercise execution for Information Security, Enterprise Fraud Management, Physical Security, and Global Crisis and Continuity Management teams 
• Providing effective challenge of incident response readiness through exercise observation
• Execution of enterprise-wide Purple Team Exercise


Cybersecurity Exercises: Purple Team, Ransomware, DDoS, Malware, Data Corruption, Data Breach, 3rd Party Incidents
Fraud Exercises: ATOs, Attack on Payment systems, Business Email Compromise, PII Breach
Physical Security Exercise: Active Assailant, Civil Unrest, Bomb Threats
Crisis Exercises: Disaster Recovery, Business Continuity, Operational Resilience, Fire Incidents, Natural Disasters, Utilities Disruption

We landed in Canada 8 years ago. 
Today I still get this question. 
Why did you move from Singapore?

I always answer with this as if one of the reason. 

“We were very comfortable and had stable jobs. In fact, I know almost exactly how many career will pan out”

And we wanted to try something diff. 

This is what it wld have looked like:
- stayed on in the Navy
- promotions to LTC or SLTC
- 300k salary (don’t quote me)
- waiting on a ~500k bonus in 2026
- complete command of 2-3 warships

This is the last 8 years instead:
- ~50% pay cut for first role
- took 3 role changes to gain parity 
- only to be laid off after a few years
- and living through a dead economy

If we take a snapshot view here, it is a disastrous decision. 

But of course it’s never that linear. 

Here are other things that I gained:
- explored 2 career paths. PM + cyber
- grew professional network from 0
- gained experience in enterprises
- sold digital products & services
- found mission driven role + team
- resilience and independence
 
The questions will always be asked. 

And the journey is still being written. 

P.S what questions do u always get when you tell your story?
How do u answer them?

Sales Navigator

li_at

JSESSIONID

Talks about #linkedin, #resilience, #cybersecurity, #crisismanagement, and #personalbranding

The Brand Strategist for Cyber CEOs. I build your brand as you build your business. | Senior Cybersecurity Advisor | Author | Naval Officer | CISSP | 🇨🇦🇸🇬 |

You are all busy. I don't expect you to read my history, so here is a little about me.

𝗕𝗼𝗿𝗻 𝗮𝗻𝗱 𝗿𝗮𝗶𝘀𝗲𝗱 𝗶𝗻 𝗦𝗶𝗻𝗴𝗮𝗽𝗼𝗿𝗲.

Never the model student.
Made a career choice at 19.
To serve in the Navy and see the world.

𝗖𝗮𝗿𝗲𝗲𝗿 𝗶𝗻 𝘁𝗵𝗲 𝗡𝗮𝘃𝘆

Daily lessons of leadership, critical thinking.
Ran the wargaming and simulation centre.
Left in 2017 after rejecting a promotion and the opportunity to command a ship.

𝗢'𝗖𝗮𝗻𝗮𝗱𝗮

Moved to Canada w no corporate exp
Struggled for years to climb a ladder
Fortunate to move into cybersecurity

𝗖𝘆𝗯𝗲𝗿𝘀𝗲𝗰𝘂𝗿𝗶𝘁𝘆

Currently in my 3rd role in cyber.
1. Project Management
2. Senior advisor - security exercises
3. Senior advisor - security exercises

𝗖𝘂𝗿𝗿𝗲𝗻𝘁 𝗲𝗻𝗱𝗲𝗮𝘃𝗼𝗿𝘀

Full-time at Rogers Cybersecure Catalyst, Toronto Metropolitan University. 
Best place I have worked in Canada.

Need cybersecurity tabletop exercises, cyber range training, cyber advisory services?

Give me a shout.

𝗖𝗼𝗻𝗰𝘂𝗿𝗿𝗲𝗻𝘁 𝗮𝗰𝘁𝗶𝘃𝗶𝘁𝗶𝗲𝘀

Book author
The Essential Cybersecurity Ex Playbook.
I still refer to it when I design exercises. 
Get it if you are tasked to run exercises.

Ghostwriter for Cyber CEOs and Founders
Your LinkedIn Account is a goldmine.
Build your thought leadership and authority.
I write your LinkedIn posts for you.

P.S What did you not know abt me?

No alternative text description for this image

How to create a content calendar in 10 mins and never worry abt what to post. 
 
Follow this process and save time. 
 
I never worry about what to post about. 
Not because I have a constant stream of inspiration and the words flow naturally. 
 
Writing and posting on LinkedIn has become part of my professional portfolio and I constructed a simple system. 
 
1. Decide what your objectives are 
- to establish thought leadership 
- to build stronger professional relations 
- to bring awareness to brand and product 
 
=> The clearer this is, the easier it gets. 
 
2. Decide how frequent you post 
- minimum twice a week 
- thrice is good 
- seven if able 
 
=> Schedule your time to write. 
 
3. Decide what are your content pillars 
- keep it no more than 2-3 
- for me it is ghostwriting 
- and cyber exercises 
 
=> What you want to be known for? 
 
4. Decide the various themes 
- posts that builds awareness 
- posts that builds authority 
- posts that builds trust 
 
=> How do u get ppl to like, trust, know u? 
 
5. Decide the theme for the day 
- Mon = Awareness 
- Wed = Authority 
- Fri = Trust 
 
=> Saves your time thinking of the theme 
 
6. Mind-map and research abt topics 
- Content should be planned 
- Mind-map your experience 
- Answer yr client qns 
 
=> If it is not planned, u will struggle  
 
7. Keep it simple and you will follow 
- create a simple system 
- don't complicate it 
 
=> It takes some prep but well worth it 
 
I planned out my content calendar and stick to it for at least 6 months. 
 
Struggling with posting consistently? 
Chances are you are winging it. 
 
Do you also leave yr business to chance? 
Didn't think so. 
 
It's time to take action. 
Get in touch. Start being intentional.

Cyber CEOs are missing one of the biggest opportunities on LinkedIn.

Your founder story.

Not the pitch.
Not the product.
The reason you started.

Here is why it matters.

1. It builds trust faster than yr website.

People want to know the conviction behind your company. Your story answers the core question every buyer has: why should I trust you.

2. It humanizes your brand.

Cybersecurity is technical and crowded. Your story cuts through the noise and shows the person behind the mission.

3. It creates instant differentiation.

Competitors can copy language, pricing, and positioning. They cannot copy your journey.

4. It strengthens every future conversation.

When people understand your why, your product demonstrations, sales calls, and partnerships become warmer and easier.

Your founder story is not optional.
It is a strategic asset.

If you do not tell it, your audience will never hear it. And don’t wait for permission to share too. 

No one is gonna give you that.

“I’ll take a break from writing/posting”. 

That’s what I told myself as I returned from my vacation. 

“It will be easy to get back into it”. 

Just like my exercise routine, my writing and networking rhythm were severly derailed. 

Even though my systems and tools were in place, I need to reconvince myself of the intend of being active on this platform. 

And it really does fall back to the why. 

Once that is reaffirmed, then the other pieces of the how kicks back in. 

Here’s back to sharing:
- how organizations should use cyber exercises to improve their readiness and resilience 
- how cyber CEOs should use LinkedIn to drive brand awareness 

P.S who thinks the LinkedIn feed is darn boring these days. Let’s start sharpening our storytelling skills.

Cybersecurity professionals struggle in OT organizations.

Especially if they don’t take the time to understand operations.

I interviewed my friend Osman Saleem, the Managing Director of Actimeta, who helps his clients secure their OT and IoT infrastructure.

What Makes OT/IoT Security Complex

Q3: What makes protecting operational environments fundamentally different from traditional IT cybersecurity?

OT environments have physical processes, so organizations prioritize safety, reliability, and availability of OT systems. Confidentiality of data takes a back seat. Additionally, OT systems have a much longer life cycle. As a result, these systems operate 24/7 on legacy equipment and networks making patching and rebooting a challenge. Security changes can directly impact physical processes, which means risk management must balance cyber controls with operational continuity.

Q4: Can you share an example of how operational and security priorities sometimes conflict — and how organizations can bridge that gap?

Security teams may recommend immediate patching or network changes, while operations teams push back due to downtime risks or safety concerns. Capital upgrades of legacy equipment are also cited as reasons for avoiding immediate patches. Bridging that gap comes from joint risk assessments, staged mitigation plans, or designing controls that reduce risk without disrupting critical operations
_____________________________

If you enjoyed this interview series, please follow Osman. He is a security infrastructure expert and has helped organizations build IoT and OT security programs.


P.S. What’s the biggest challenge in OT security?

It seems like privacy is a premium these days.

And it can be sidelined if we don’t preserve it.

AI models feed on data. And yet so many organizations have headed straight for the AI gravy train without due consideration for the impact on data management and privacy. 

I interviewed my friend Patrick Lo, the CEO of Privacy Horizon, who helps his clients make sense of the ever-changing landscape of privacy and the impact of AI.

The Future of Privacy Leadership

Q7: What qualities will define the next generation of privacy leaders in healthcare?

Future privacy leaders will combine a strong understanding of technology, turning intricate risks related to AI, data, and cybersecurity into transparent, human-focused governance approaches that build trust among stakeholders.

Q8: If you could change one thing about how organizations approach privacy today, what would it be and why?

I would change the perspective from viewing “privacy as compliance” to seeing “privacy as strategy.” Privacy doesn’t have to be a boat anchor. Privacy is about common sense. Privacy is nothing more than good information management and good customer service. When organizations integrate privacy with trust, innovation, and brand value, compliance occurs naturally and a culture of accountability becomes self-sustaining.

_____________________________

If you enjoyed this interview series, please follow Patrick. He is a healthcare privacy expert and has helped organizations build privacy and security programs.


P.S Is privacy a top concern when implementing AI?

Have you tried asking ChatGPT abt yourself?

Try it. I hope you don’t find sensitive information.

AI models feed on data. And yet so many organizations have headed straight for the AI gravy train without due consideration for the impact on data management and privacy. 

I interviewed my friend Patrick Lo, the CEO of Privacy Horizon, who helps his clients make sense of the ever-changing landscape of privacy and the impact of AI.

The Intersection of Privacy and AI

Q5: As AI becomes more embedded in diagnostics and digital health tools, where do you see the biggest privacy blind spots emerging?

Many organizations that adopt AI often overlook the importance of a solid AI Governance Framework. This oversight can lead to unsupervised AI being used within the organization, allowing users to leverage AI solutions without proper guidance. Such a lack of direction often leads to unintended disclosures of sensitive information. Additionally, a significant blind spot exists where many organizations are unaware of what personal or health data their AI models are accessing, retaining, or inferring. 


Q6: How is Privacy Horizon adapting its services — for instance, with AI-PIAs or automated privacy assessments — to address these new challenges?

We’ve expanded our service model to include AI Privacy Impact Assessments, AI Governance Frameworks, AI Training, and readiness tools aligned with the EU AI Act and ISO 42001. These help healthcare organizations assess AI systems’ risks, ensure transparency, and demonstrate trustworthy AI adoption.
_____________________________

If you enjoyed this interview series, please follow Patrick. He is a healthcare privacy expert and has helped organizations build privacy and security programs.


P.S What worries you about AI and privacy?

Take a second to count your personal connected devices.

Now, estimate that number for an enterprise set-up.

Enterprises struggle to keep up with the inventory, tracking, management, and governance of their IT systems. Industries and companies that rely heavily on physical systems, such as monitoring devices, automated systems, and highly integrated systems, add layers of complexity and associated risks to maintaining operational efficiency and security.

I interviewed my friend Osman Saleem, the Managing Director of Actimeta, who helps his clients secure their OT and IoT infrastructure.

The OT/IoT Security Landscape 

Q1: How has the growing interconnection between physical systems and digital networks changed the way organizations think about cybersecurity?

Organizations that run physical systems and OT are more aware now of the risks that come with connecting them to digital networks. Asset owners are increasingly focused on securing these environments—marketing hype can amplify the fear, but the concern is justified. More connectivity expands the attack surface and links cyber incidents to real-world impacts on safety, reliability, and finances. As a result, there is a shift to treat cybersecurity as an operational responsibility, not just an IT issue.

Q2: From your experience, what are the biggest misconceptions business leaders still have about securing operational or connected environments?

Many business leaders place more emphasis on tooling and technology. Their main focus should be prioritized towards embedding cybersecurity practices and controls in their business workflows, organizational processes and ensuring their governance is not just documented, but functional. 
_____________________________

If you enjoyed this interview series, please follow Osman. He is a security infrastructure expert and has helped organizations build IoT and OT security programs.


P.S. What are some IoT/OT security assumptions that many have?

If growing your LinkedIn presence as a cyber CEO is not part of your 2026 plan, it is a huge marketing miss. 

The others parts are shaping up:
- website copy
- marketing swag
- cold email blasts
- conference booth
- CISO wine and dine 😃

All that is important and probably takes up the bulk of your budget. 

And then when your prospects land on your LinkedIn page, it blands (yes bland) in with the rest of the corporate copy. 

“We are on brand.”
“Our product speaks for itself.”

What could have been a differentiator from your competitors and a vibrant platform to build a community and awareness for your company. 

Instead, it just fades to the background. Like many of the other passive accounts. 

Is your LinkedIn account working your you, your company, and your vision?

Or will 2026 be another missed opportunity? 

Your platform. 
Your choice.

Cyber CEOs have endless stories. 

Here are some ideas if u r stuck.

1. The moment you realized the cybersecurity problem you’re solving was real (A client incident, a failure you witnessed, or a blind spot in the market.)

2. Why you decided to start the company instead of joining another one (Your conviction, frustration, or spark.)

3. The first obstacle you faced as a founder and what it taught you
 (Funding, product clarity, hiring, credibility.)

4. The early version of your solution and how different it was from today
 (Show evolution and persistence.)

5. A hard lesson you learned that shaped how you lead now
 (Trust, communication, resilience, decision speed.)

6. The turning point when you knew the company would work
 (First client, first renewal, first big validation.)

7. A belief you hold about cybersecurity that most people overlook
 (Your “why” behind your mission.)

8. How your background shaped the way you approach security problems
 (Past industries, roles, failures, or personal experiences.)

9. The sacrifice most people don’t see
 (Time, stability, opportunity cost, personal growth.)

10. Your vision for the industry and why you’re committed to it
(Where things are going and why you care.)

P.S Expand on each point in a few different angles and your content is set for months. 

Any other story ideas?

I consult with many Cyber CEOs. 

These 4 questions come up in every strategy call I run with founders.

⸻

1/ What should I post without oversharing or sounding salesy

They worry about balancing:
- Oversharing insights 
- Being authoritative vs promotional

But the real issue?

This isn’t a writing problem.
It’s a positioning + content strategy problem.

Once you define your POV and boundaries, posting becomes easy.

⸻

2/ Will this really generate business, or is it just vanity?

They’re skeptical because:
- Impressions ≠ pipeline
- “Likes” don’t close deals
- Decision-makers feel invisible on LI

Behind this question is a deeper fear:

“Will my effort pay off?”

LinkedIn is a trust engine, not a slot machine. It compounds if you show up consistently.

⸻

3/ How do I stand out when every cyber CEO sounds the same?

Their feed is full of:
- News reposts
- Corporate announcements 
- Zero Trust / AI buzzwords

Their real question is:

“What is MY unique point of view?”

The answer is always the same. 
Stand out by being specific, not louder.

Your niche, your observations, your client stories, your lessons.

Those are the differentiators.

⸻

4/ How much time does this take each week?

They assume LinkedIn is:
- Daily posting
- Daily commenting
- Constant DMing
- Full time social media diva

But what they actually want is simple:
A strategy that is intentional. 
A plan that drives results. 

You don’t need to post daily.
You need clarity, consistency, and relevance.

⸻

If you’ve have all these questions too, the good news is they’re all solvable.

Cyber CEOs don’t need more content.
They need a clearer strategy, stronger positioning, and a repeatable system.

P.S what other qns do u have?

Here’s one signal to know yr cyber exercise is highly effective. 
And most TTXs never trigger this. 

We recently executed a cyber range simulation exercise that put an IT team through a stressful scenario. 

The team was actively analyzing the IOCs and raise many relevant points for decision making. The leadership team weighed the risks and make a decision for containment. 

This decision was communicated to the technical teams and it spark a behavior which I didn’t expect but was glad it happened. 

The IT team responded to seek clarification on the decision. The instructions from the leadership team was clear on intent but the IT teams wanted to ensure that the leadership team understood the risks and nuances of the decision. 

And the discussion got pretty heated. 

This is termed as “Challenge and Response” and is something that we used while we manage the navigation team to ensure the safety of the ship. 

Team members would challenge the instructions (not the authority) if they were unclear or they had information that may impact the decision. The officer of the watch will have to respond to confirm or clarify the order. 

The purpose of this mechanism was to ensure that there was an avenue for clarification of an order without the risk of insubordination. 


So to my surprise, I saw this playing out as we ran our exercise. 

This is a healthy sign that the team had the right culture and understood the intent of the team’s actions. 

How did the heated discussion end?

I had to intervene, acknowledge the perspectives of both parties, and park the issue aside to continue w the exercise. 

This learning point would not occur in a benign tabletop exercise. It took a realistic high pressure scenario to tease out the practical considerations of incident response. 

P.S can u guess what the discussion was about? 
I’ll give a prize if anyone guessed it!

10 planning considerations for a live red team exercise.

A live Red Team exercise can transform your organization’s cyber readiness.

Or it can blow up in your face.

Most companies underestimate the planning required. 
Live exercises introduce operational risk, reputational exposure, and real technical consequences if poorly scoped.

Here are 10 planning considerations. 

⸻

1. Define crystal-clear objectives before touching the scenario.

A Red Team exercise easily derails without a defined purpose.
•	Are you testing detection?
•	Decision-making?
•	Business response?

Knowing the objective helps guide the red team and enables alignment.  

⸻

2. Assess organizational maturity honestly before selecting tactics.

Live exercises should match capability.
Teams still struggling with escalation protocols shouldn’t jump straight to advanced APT emulation.
Ensure your IRP, SOC workflows, and communication playbooks are mature enough to withstand live pressure.

⸻

3. Secure executive sponsorship and socialization early.

Leadership must know what they’re approving. This includes scope, risks, expected disruptions, and reporting cadence.

⸻

4. Establish strict scope, boundaries, and rules of engagement.

A Red Team must know exactly what is allowed.
Examples:
•	No production data exfiltration.
•	No destructive actions.
•	Limited hours for intrusion.
•	Clear ‘stop game’ conditions.

Defined ROE protects your systems, your people, and your reputation.

⸻

5. Map out all critical systems, dependencies, and crown jewels.

You can’t test everything.
Choose what matters most:
•	Mission-critical applications
•	Identity systems
•	Cloud environments
•	OT/ICS (very rare)

Have a clear reason why this is the target. 

⸻

6. Involve key third-party vendors before game day.

Many Red Team exercises collapse due to vendor bottlenecks.

Notify them early. 

Their tools, logging, and escalation capabilities determine how realistic and valuable the exercise becomes.

⸻

7. Prepare the SOC and security teams without revealing the scenario.

Let them know the exercise window and who to clarify with if there are doubts. 

A Red Team exercise shouldn’t overly hamper operations. Yes there will be increased load for short periods of time. 

⸻

8. Decide the battle rhythm for decision-making and communication.

Synchronisation avoids chaos and ensures realism in response flow.

Also include exercise control meetings to keep teams updated. 

⸻

9. Create a safety plan.

Live operations = live risk.

A safety plan ensures the Red Team can push boundaries without endangering the business.

⸻

10. Design a mature debrief, learning review, and AAR process.

The biggest ROI comes after the exercise.

A rigorous debrief is where transformation happens.

⸻

Conclusion

A live Red Team exercise is a meticulously planned, high-stakes enterprise learning event.

Plan it properly, and you elevate your team’s resilience.
Rush it, and you erode trust in security

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The Battle

Jean Kang

Lester Chng

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taplio

The Battle

Jean Kang

Lester Chng

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Engagements

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Jean Kang's LinkedIn Performance

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