Founder of “Change is Possible” Community & Accelerator where corporate professionals build influential brands & portfolio careers I Change Advisor to Leaders I Ex-Citi COO I Follow for modern leadership, career & change

Over the past 25 years, I have built a successful international banking career.
Most recently, I was the Regional COO for Citibank’s $2Bn business across 16 countries in Asia - leading large-scale transformations in digitisation and culture.

But in 2021, I walked away from my high-paying executive role.

Why?

Because I wanted more space.
More time with family.
More alignment between who I am and how I work.

But I didn’t want to start from scratch.
So I asked myself a question:
What if I could build a career around everything I already know - and love?

That’s how my portfolio career began.
And it changed everything.

Now, I help other professionals do the same.

What I’ve built since 2021:
→ A 6-figure portfolio business with 3 income streams
→ Founder of Change is Possible - a business community for professionals redesigning their next chapter
→ 100K+ LinkedIn followers (grew from 17K in under a year)
→ Coached 100+ professionals through successful career transitions
→ Host of a Top 20 global podcast on career change, Change is Possible
→ TEDx speaker, Forbes columnist, and Bloomberg TV guest

Want to build your own portfolio career?
🚀 THE PORTFOLIO CAREER ACCELERATOR (Launching January 2026) 
Apply here: https://docs.google.com/forms/d/1thkmph_EwRxLGfuL9muCsRir1uKDdF2nXYeI7X_1oSA/edit

This is an 8-week program designed to help you:
→ Turn your expertise into income
→ Build a personal brand that opens doors
→ Create your first income stream - even before you leave your job

Only 20 spots. 12 already claimed.

Other ways we can work together:
✔️ Join my business community — Change is Possible https://changeispossible.co.uk/ - doors open for new members on Sept.10, 2025
✔️ Book me to speak — I deliver keynotes on leadership, change, career reinvention, and the future of work - send a DM.
✔️ Hire me as an advisor — I support companies navigating complex transformation - send a DM to meet and explore.
✔️ Book 1:1 coaching — For senior execs ready to design their next chapter - send a DM.
✔️ Book my LinkedIn Growth Bundle — A 2-session intensive where I teach you the exact system I used to grow to 100K+ followers. Apply here: https://docs.google.com/forms/d/1bLp7wmK8xhIpfFu8beImvD5JZQHYsbraTBx5Orjx0zs/edit

P.S. Still wondering if change is really possible?
🎧 Tune in to my podcast Change is Possible — where 100+ professionals share how they redesigned their careers and lives. Watch here - https://www.youtube.com/@ChangeIsPossiblePodcast

Ani Filipova

The first time someone told me the truth about my leadership, I wanted to fire them.

I did not, obviously.
But I wanted to.
"Who are they to tell me...." 🤯 

Most leaders say they want honesty.
Then someone actually gives it.
And they get defensive.

Start explaining why that person is wrong.
Or worse - they punish honesty.
Withdraw.
Get cold.
"Manage out" the truth-teller.

Do it enough times and people learn.
They stop telling you the truth.
They tell you what you want to hear.

Look around.
Scandals at every level.
Boards blindsided.
Leaders shocked by what "nobody told them."

Nobody told them because they made it unsafe to speak.

The first time someone tells you a hard truth, you will want to fight it.
Your ego will scream.
You will feel attacked.
Misunderstood.
Betrayed.

This is normal.
This is human.
This does not make you a bad leader.

Leadership is not being okay with hard feedback.
Leadership is what you do in the 10 seconds after hearing it.

How to train yourself to receive truth better:

→ Leadership is not being okay with hard feedback.
→ Leadership is what you do in the 10 seconds after hearing something that makes you want to defend yourself.
→ It is saying "tell me more" when every cell in your body wants to say "you are wrong."
→ It is thanking someone for their honesty even when their delivery was clumsy and it stung.
→ It is sleeping on feedback that feels unfair. Then waking up and finding that some of it is true and deciding to take it on.

You do not have to be perfect at this.
You just have to be 5% better than last month.

The more truth people tell you, the less scary it becomes.
Not because feedback gets easier.
But because you prove to yourself that honesty does not destroy you.

It builds you.

Follow me, Ani Filipova, for more on leadership and building a career on your terms.
♻️ Repost if a leader in your network needs to hear this.

-----
📌 Check my free webinars this month:
Future of work: https://lnkd.in/gT5S8Sbs
Portfolio career: https://lnkd.in/gf-ifWqj

Some people did everything right and still didn’t make it.

I think about them a lot.

They made smart decisions.
Built the right skills.
Were genuinely good at what they did.

And the break never came.

Meanwhile, I know people (myself included) who caught a moment of luck so precise, so accidental, that if you shifted timing by six months, or moved geography by one country, the whole story collapses.

Here are two of mine:

1) A colleague in London mentioned, almost in passing, that there was a COO role available. I applied. I got it. That one conversation shaped the next chapter of my career.

2) Years later, I got invited to an event where entrepreneurs pitched to magazine editors. I saw what people were building. The energy in the room. The possibilities. That night is a direct line to me leaving my job.

Neither moment was “earned”.
Both changed everything.

And I know plenty of successful people have these moments too, but they rarely mention them because it complicates their success story.

We are sooo binary:

- Success is merit: work hard, decide well, win.
- Success is luck: hard work doesn't matter anyway.

The real version sits in the middle.

Decisions create the conditions.
Luck pulls the trigger.

Sometimes luck pulls the trigger for someone who didn’t deserve it.
Sometimes it never shows up for someone who did.

If you are navigating this, here is what I know:

1️⃣  Your decisions still matter a great deal.
They don’t guarantee the outcome.
But they are how you stack the odds in your favour.

2️⃣  Luck is real.
You don’t get to choose when it shows up. Acknowledging it keeps you hungry without making you bitter, and grateful without making you passive.

3️⃣  Make peace with the unfairness.
This is the hardest part.
Sometimes you do everything right and still don’t make it. The only move left is to accept and move on

The truth is: most success stories are part skill, part luck, and a lot of editing.

---
You can’t control luck, but you can control your odds.
That’s what we build inside the Portfolio Career Accelerator. Apply here: https://lnkd.in/gpEqqqFs

or DM me

I used to think I handled feedback well.

Then I watched myself get defensive almost immediately.

I nodded. Said, “Thank you for sharing.”

Then spent the next three days arguing with it in my head.
And thinking, “Who does he think he is?”

Here is what most people get wrong about criticism:

They do not hear, “Here is how to improve.”
They hear, “You are not as good as you thought.”

That is why people:

▶️ Get defensive.
▶️ Justify themselves.
▶️ Go quiet.
▶️ Blame the delivery.

It feels like a threat.

The top 1% leaders do not hear feedback and think, “That is unfair.”

They think, “What is useful here?”

That shift changes everything.

Here is what that looks like:

▶️ Pause.
▶️ Let them finish.
▶️ Write it down.
▶️ Ask for an example.

Then leave the room and decide what is signal and what is noise.

Not all feedback is right.
But almost all feedback reveals something.

If you want to grow fast:

Stop protecting your ego.
Start mining for signal.

Feedback is uncomfortable.
But staying the same is worse.

Follow me, Ani Filipova, for leadership truths most people avoid.
♻️ Repost if someone in your network needs to hear this.

How to learn so fast it feels unfair.

Here is why this matters now more than ever:

- The half-life of skills is shrinking.
- What you learned 5 years ago may already be outdated.
- AI is changing industries faster than most people can adapt.

Learning how to learn is no longer a nice-to-have.
It is the skill that makes all other skills possible.

Leaving corporate was one of the biggest learning curve of my life.

- Suddenly, no team.
- No structure.
- No playbook.

If I did not learn fast, I did not earn.

So I devoured information.
And still felt behind.
Because volume is not the same as mastery.

When I interviewed Dr. Justin Sung on my podcast, he explained why.
The best learners do 3 things differently:

1️⃣ They pause.
Your brain needs time to organise what it just received.

2️⃣ They synthesise.
They teach it, apply it, turn it into something useful.
This is where real understanding happens.
And where you discover what you actually do not know yet.

3️⃣ They compare.
They connect new ideas to what they already know.
This anchors new knowledge into your existing mental frameworks.
It makes learning stick.

🎥 Watch the full podcast episode with Dr.Sung here: https://lnkd.in/g32j73jq

♻️ Repost if someone in your network needs to learn faster.

I built my first income stream with a Calendly link and 5,000 followers.

My only regret? Waiting until I left my COO job to start.

While you are at your job, you have the credibility.
You do not need the testimonials.
You have the big title as a crown, and you are sought after.

Who would not choose to be coached by a COO?

But I convinced myself I needed to leave first.
I thought it would look strange.

So I waited.
I left.
And then I started from almost zero.

It still worked.
But it took longer than it needed to.

Because once you no longer have the crown to vouch for you, you need something else - you need proof that you are doing a good job.

So, I started.

Just one offer: I will help you prepare for interviews or figure out your next career move.
No website.
No marketing funnel.

At that time I was posting three times a week on LinkedIn.
I remember refreshing my inbox constantly to see if I had new bookings.

One person booked.
Then another.
Then people started sending me messages saying, “That session changed everything.”

Those messages became my proof.

The testimonials replaced the title.

Imagine having the title AND the testimonials - you will have a much better start in your portfolio career.

You do not need a business plan to start.
You do not need a big audience.
You do not need to quit your job first.

You need one skill.
One person willing to pay for it.
One session.

That is how it starts.

Most people already know what that skill is.
They just haven’t treated it like an offer yet.

I walk through the exact steps to build a portfolio career - including how to start while still employed - inside the Portfolio Career Accelerator. Cohort 1 is underway, and Cohort 2 is starting on April 27, 2026

Apply here: https://lnkd.in/gpEqqqFs

Career Strategist I Change advisor for Leaders | I help successful professionals build freedom, income & impact through portfolio careers | Speaker I Ex-Citi COO | Follow for modern leadership, career and change

I have appeared on Bloomberg from a desk that looks like a crime scene.

Papers everywhere.
Cables tangled.
Notes scribbled on random sheets.
Three pairs of spectacles because I can never find the right ones.

Chaos.

Or so it looks.

Here is the secret: I know exactly where everything is.

That mess is my system.
It works for me.
It has always worked for me.

From this desk I have recorded over 100 podcast interviews.
Run webinars.
Taught in my community and accelerator.
Coached clients.
Appeared on Bloomberg.
Delivered keynotes.

No fancy studio.
Amazing sophisticated office.
Just me, a microphone, and a desk that looks like a crime scene.

We spend so much energy to look "professional."
The clean background.
The perfect setup.
The polished image.

Meanwhile, the real work, the “magic” happens elsewhere.

You do not need a fancy studio to be taken seriously.
You do not need a minimalist setup to be credible.
You do not need to hide your chaos to be professional.

What you need is a system that works for you.
Even if nobody else understands it.

Most people are optimising how they look.
Very few are optimising how they work.

♻️ Repost if your workspace would never make it on camera.
Follow me Ani Filipova for leadership and career stories without the performance layer.
------

📌 Check my free webinars this month:
Future of work: https://lnkd.in/gT5S8Sbs
Portfolio career: https://lnkd.in/gf-ifWqj

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

15 Feb 1942 - The day Singapore surrendered to Japan.
This day was chosen as a solemn commemoration.
"Never Again".

It wasn't until 1984, that the Total Defence concept was launched. The government saw the necessity for a whole-of-society approach that went beyond just the military.

• Civil Defence
• Social Defence
• Military Defence
• Economic Defence
• Psychological Defence

Digital Defence was added as the 6th Pillar, 35 years later in 2019. 

• fake news
• cyberattacks
• disinformation campaigns

There was a need to tackle these new challenges.

Additionally, a fourth Service of the SAF, the Digital and Intelligence Service (DIS), was stood up to underline the importance of this domain.

Would I have crossed over if I were still in active service...

Dear LinkedIn,
Here is what it is like using the app. 

Suggested

Suggested

Suggested

Sponsored

Suggested

Sponsored 

Suggested

Sponsored


What’s up with this feed?

Did you even consider the experience?

Pls bring my connections’ posts. 

Sincerely,
Everyone.

Here are things I avoid on LinkedIn. 

But some of you dive head in. 

- rants
- politics
- religion
- complaints 
- sensitive info
- overly personal info
- every trending or news event 

What else do you see others posting about that should be avoided?

undefined undefined

bootcamp

Sign up here:
https://catalystcorporatetraining.classe365.com/form/view/AutoBootCamp?_gl=1*9rfqtg*_ga*MTQ4NTczNDM0MC4xNjk4MjQxODM1*_ga_YYXBQS6S5Q*MTcwNzgzMzEyNi4xODEuMS4xNzA3ODMzMTYwLjI2LjAuMA

LinkedIn

When I first moved to Canada, I remember reading about their Navy and Air Force capabilities (don’t ask me why I didn’t bother abt the Army). 

12 Halifax frigates. Ageing, 1990s
4 Victoria subs. Second hand. 
6 OPVs. Still coming online. 
12 Patrol crafts. 

F18s - started from 1982….


And to defend coast to coast….
to the True North

Was an impossible task. 

This Defence budget and Strategy is long overdue and may be the silver lining in this rocky new world. 

We are all pulling in the same direction. 

Rogers Cybersecure Catalyst, Toronto Metropolitan University will offer every company in every Catalyst program strategic insights to help them explore and pursue opportunities in Canada’s growing defence sector.

Stay connected and pull together.

No alternative text description for this image

You know Canada is on the up when Dad sends you a TikTok (no i dont have an account) about the upcoming increase in defence spending.

What about Canada do you appreciate?

I like the cold...... what about you?

Building a cyber company is not for everyone.

Do you even have the commitment to do so?

I interviewed Eldon Sprickerhoff to get his insights for the next generation of founders. He is an Entrepreneur-in-Residence and a mentor at Rogers Cybersecure Catalyst, Toronto Metropolitan University. 


𝗧𝗵𝗲 𝗰𝘂𝗿𝗿𝗲𝗻𝘁 𝗰𝗵𝗮𝗽𝘁𝗲𝗿. 𝗦𝘁𝗶𝗹𝗹 “𝗖𝗼𝗺𝗺𝗶𝘁𝘁𝗲𝗱”

𝘘: 𝘞𝘩𝘢𝘵 𝘵𝘩𝘦𝘮𝘦𝘴 𝘰𝘳 𝘤𝘩𝘢𝘭𝘭𝘦𝘯𝘨𝘦𝘴 𝘬𝘦𝘱𝘵 𝘴𝘩𝘰𝘸𝘪𝘯𝘨 𝘶𝘱 𝘪𝘯 𝘤𝘰𝘯𝘷𝘦𝘳𝘴𝘢𝘵𝘪𝘰𝘯𝘴 𝘸𝘪𝘵𝘩 𝘧𝘰𝘶𝘯𝘥𝘦𝘳𝘴 𝘵𝘩𝘢𝘵 𝘶𝘭𝘵𝘪𝘮𝘢𝘵𝘦𝘭𝘺 𝘭𝘦𝘥 𝘺𝘰𝘶 𝘵𝘰 𝘸𝘳𝘪𝘵𝘦 𝘊𝘰𝘮𝘮𝘪𝘵𝘵𝘦𝘥 𝘢𝘯𝘥 𝘤𝘳𝘦𝘢𝘵𝘦 𝘵𝘩𝘦 𝘮𝘢𝘴𝘵𝘦𝘳𝘤𝘭𝘢𝘴𝘴?


I kept seeing the same patterns: some passionate and brilliant technical founders hitting predictable walls - raising capital without understanding dilution consequences, scaling teams without proper foundations, pursuing growth without sustainable unit economics, or worse: flailing in the market with a product/offering that didn’t have an obvious value or importance.

What frustrated me was that these weren't unsolvable problems. They were challenges we had faced and eventually figured out, often painfully. I realized this knowledge could help others avoid the same expensive mistakes.

The recurring theme was the gap between technical excellence and business fundamentals. Founders could build incredible technology but struggled with identifying their true “ideal client profile”, minimally viable offering, go-to-market strategy, fundraising dynamics, or organizational design. "Committed" became my way of sharing survival strategies that weren't readily available elsewhere.


𝘘: 𝘞𝘩𝘢𝘵 𝘢𝘳𝘦 𝘺𝘰𝘶 𝘮𝘰𝘴𝘵 𝘪𝘯𝘵𝘦𝘳𝘦𝘴𝘵𝘦𝘥 𝘪𝘯 𝘸𝘰𝘳𝘬𝘪𝘯𝘨 𝘰𝘯 𝘰𝘳 𝘤𝘰𝘯𝘵𝘳𝘪𝘣𝘶𝘵𝘪𝘯𝘨 𝘵𝘰 𝘳𝘪𝘨𝘩𝘵 𝘯𝘰𝘸, 𝘢𝘯𝘥 𝘩𝘰𝘸 𝘥𝘰𝘦𝘴 𝘵𝘩𝘦 𝘮𝘢𝘴𝘵𝘦𝘳𝘤𝘭𝘢𝘴𝘴 𝘧𝘪𝘵 𝘪𝘯𝘵𝘰 𝘵𝘩𝘢𝘵 𝘧𝘰𝘤𝘶𝘴?

Right now, I'm focused on helping the next generation of cybersecurity founders build enduring companies. Through my consulting and advisory roles, I'm seeing exceptional technical talent that needs guidance on the business side.

The masterclass is a way to scale that impact. I can only mentor a handful of founders directly, but the principles I learned building eSentire are broadly applicable. I want to help founders avoid the mistakes that nearly killed our company early on and accelerate their path to product-market fit and sustainable growth.

What excites me most is seeing founders take these lessons and apply them in ways I never imagined - solving problems that didn't exist when we started eSentire. The cybersecurity landscape keeps evolving, and I want to help the best founders navigate it successfully.


If you enjoyed this interview series, please follow Eldon and get his book at https://lnkd.in/gS2HNAnY


P.S. Have you read Committed? 
Get it already.

Having a brilliant idea is exciting.

But how you overcome uncertainty with conviction is key.

I interviewed Eldon Sprickerhoff to get his insights for the next generation of founders. Eldon is an active entrepreneur, investor, mentor, author, advisory and board member at the intersections of information security, computer science, machine learning, SaaS, and finance. He is an Entrepreneur-in-Residence and a mentor at Rogers Cybersecure Catalyst, Toronto Metropolitan University. 

He is best known for founding eSentire, a leading global cybersecurity Managed Detection and Response company.

𝗪𝗵𝘆 𝗮𝗻𝗱 𝗵𝗼𝘄 𝘄𝗮𝘀 𝗲𝗦𝗲𝗻𝘁𝗶𝗿𝗲 𝘀𝘁𝗮𝗿𝘁𝗲𝗱

𝘞𝘩𝘦𝘯 𝘺𝘰𝘶 𝘧𝘪𝘳𝘴𝘵 𝘴𝘵𝘢𝘳𝘵𝘦𝘥 𝘦𝘹𝘱𝘭𝘰𝘳𝘪𝘯𝘨 𝘵𝘩𝘦 𝘪𝘥𝘦𝘢, 𝘸𝘩𝘢𝘵 𝘧𝘦𝘭𝘵 𝘮𝘰𝘴𝘵 𝘶𝘯𝘤𝘦𝘳𝘵𝘢𝘪𝘯, 𝘢𝘯𝘥 𝘸𝘩𝘢𝘵 𝘨𝘢𝘷𝘦 𝘺𝘰𝘶 𝘦𝘯𝘰𝘶𝘨𝘩 𝘤𝘰𝘯𝘷𝘪𝘤𝘵𝘪𝘰𝘯 𝘵𝘰 𝘮𝘰𝘷𝘦 𝘧𝘳𝘰𝘮 ‘𝘪𝘥𝘦𝘢’ 𝘵𝘰 ‘𝘤𝘰𝘮𝘱𝘢𝘯𝘺’?

I suppose that the most uncertain part was whether organizations would actually pay for continuous security monitoring as a service. In 2001, companies were used to buying products or hiring consultants for projects - not ongoing security operations.

What gave me conviction was simple: I knew from my time in New York that security threats didn't take breaks, but most companies couldn't afford 24/7 security teams, even if they knew that the threats existed. The gap between the threat reality and what organizations could resource internally was massive and growing. That disconnect was the opportunity.


If you enjoyed this interview series, please follow Eldon and get his book at https://lnkd.in/gS2HNAnY

He aims to be the Rick Rubin of Canadian cybersecurity startups: helping the right teams sharpen their edge, amplify their strengths, and scale faster.

P.S. What is the current opportunity in Cyber?

Scaling Cybersecurity Companies: Strategic Advisor & Growth Architect

Rogers Cybersecure Catalyst, Toronto Metropolitan University

eSentire

Canada is in the top ten healthcare spenders in the world.
Leaders are drooling over potential AI efficiencies.
McKinsey & Company estimates CAD$14 - 26B net savings.

But it's not a straight golden ticket.

Here are 3 problems for small-med health organizations.

𝗣𝗿𝗼𝗯𝗹𝗲𝗺 𝟭:
Unmanaged health data breach risk undermines trust, compliance, and growth.

𝗣𝗿𝗼𝗯𝗹𝗲𝗺 𝟮:
Limited ability to adopt AI and advanced technologies securely and ethically.

𝗣𝗿𝗼𝗯𝗹𝗲𝗺 𝟯:
Resource-constrained resilience posture: small teams are under-prepared for cyber incidents and resulting in operational disruption.


This is a problem for the entire ecosystem.
It is not going to be solved overnight.
But we can take steps in the right direction.

Join us for an expert panel discussion on 𝗙𝗲𝗯 𝟭𝟭, 𝟭𝟬𝟯𝟬𝗮𝗺.

𝗣𝗿𝗼𝘁𝗲𝗰𝘁𝗶𝗻𝗴 𝗛𝗲𝗮𝗹𝘁𝗵 𝗗𝗮𝘁𝗮 𝗮𝗻𝗱 𝗟𝗲𝘃𝗲𝗿𝗮𝗴𝗶𝗻𝗴 𝗔𝗜: 𝗕𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝗖𝘆𝗯𝗲𝗿-𝗥𝗲𝘀𝗶𝗹𝗶𝗲𝗻𝘁 𝗦𝗠𝗘𝘀 𝗶𝗻 𝗢𝗻𝘁𝗮𝗿𝗶𝗼

Patricia Thaine - Co-founder, Private AI
Gila Pyke - VP Enterprise Risk, WELL Health Technologies Corp. (TSX: WELL) 
Loreen Wales - Founder & CEO, My Viva Inc.
Anne Genge - CEO, Myla Training | AI Privacy for Healthcare 

This webinar will explore the intersection of cybersecurity, privacy, and AI. The expert panel will cover topics such as specific challenges for health-data custodians, privacy and regulatory context and AI adoption risks and opportunities.



𝟲 𝗪𝗲𝗲𝗸 𝗕𝗼𝗼𝘁𝗰𝗮𝗺𝗽 𝗦𝗲𝗿𝗶𝗲𝘀

This will be followed by a hands-on and interactive bootcamp co-developed and co-led by health privacy expert Patrick Lo, CISSP, CIPP/C and myself.

Offered virtually for 2 hours/week for 6 weeks, this bootcamp launches on Feb 17 and Mar 31 - but don't wait, we've already had to close the first cohort and added new dates.

Learn more and register: https://lnkd.in/ghdVa4XE

Offered in partnership by Rogers Cybersecure Catalyst, Toronto Metropolitan University and Canadian Cyber Threat Exchange (CCTX) , with funding from the Ontario Government | Gouvernement de l’Ontario.

McKinsey & Company

Co-Founder and Chairwoman @ Private AI | Building the Privacy Layer for Data | Host of The Data Frontier Podcast | World Economic Forum Technology Pioneer 2023 | Maclean’s magazine Power List 2024 🇨🇦

Private AI

Passionate about risk management, privacy, cybersecurity and healthcare interoperability compliance. Harmonized technology is how we let clinicians and technologists focus on their dayjob of improving patient outcomes.

WELL Health Technologies Corp. (TSX: WELL)

Founder & CEO at My Viva Inc.

My Viva Inc.

Use AI Without Blowing up Privacy, Compliance, or Common Sense. — Practical Training for Scams, Hackers & AI Risks* Professional Speaker* Risk Management Professional• AI Privacy & Security Training Healthcare + SME

Myla Training | AI Privacy for Healthcare

CEO, Privacy Horizon Inc.

Canadian Cyber Threat Exchange (CCTX)

Ontario Government | Gouvernement de l’Ontario

Every company begins by solving a problem.

Do you have clarity of exactly what that is?

I interviewed Eldon Sprickerhoff to get his insights for the next generation of founders. Eldon is an active entrepreneur, investor, mentor, author, advisory and board member at the intersections of information security, computer science, machine learning, SaaS, and finance. He is an Entrepreneur-in-Residence and a mentor at Rogers Cybersecure Catalyst, Toronto Metropolitan University. 

He is best known for founding eSentire, a leading global cybersecurity Managed Detection and Response company.

𝗪𝗵𝘆 𝗮𝗻𝗱 𝗵𝗼𝘄 𝘄𝗮𝘀 𝗲𝗦𝗲𝗻𝘁𝗶𝗿𝗲 𝘀𝘁𝗮𝗿𝘁𝗲𝗱

𝘞𝘩𝘢𝘵 𝘸𝘦𝘳𝘦 𝘺𝘰𝘶 𝘥𝘰𝘪𝘯𝘨 𝘢𝘯𝘥 𝘯𝘰𝘵𝘪𝘤𝘪𝘯𝘨 𝘪𝘯 𝘵𝘩𝘦 𝘮𝘢𝘳𝘬𝘦𝘵 𝘣𝘦𝘧𝘰𝘳𝘦 𝘦𝘚𝘦𝘯𝘵𝘪𝘳𝘦 𝘦𝘹𝘪𝘴𝘵𝘦𝘥, 𝘢𝘯𝘥 𝘩𝘰𝘸 𝘥𝘪𝘥 𝘵𝘩𝘢𝘵 𝘦𝘹𝘱𝘦𝘳𝘪𝘦𝘯𝘤𝘦 𝘪𝘯𝘧𝘭𝘶𝘦𝘯𝘤𝘦 𝘸𝘩𝘢𝘵 𝘺𝘰𝘶 𝘥𝘦𝘤𝘪𝘥𝘦𝘥 𝘵𝘰 𝘣𝘶𝘪𝘭𝘥?

Before starting eSentire, I was providing information security consulting at a prime broker in New York, supporting both the brokerage itself and the hedge funds they hosted. I was building out defensive processes and systems to protect their Internet-connected infrastructure from increasingly sophisticated threats.

What I kept noticing was the gap between what organizations needed and what they could actually sustain. Security didn't operate on business hours - threats were 24/7 - but very few organizations could afford dedicated security operations teams. Even well-funded financial institutions struggled to staff and maintain continuous monitoring. Smaller firms had no chance.

I also saw that traditional consulting wasn't solving the core problem. Companies would hire us for projects, we'd implement solutions, then leave. But security isn't a project - it's an ongoing operational challenge. The defensive systems I built needed constant attention, tuning, and response capabilities.

This experience became the foundation for eSentire. I realized that if sophisticated financial firms couldn't solve this problem internally, there had to be a better model - one where security expertise and continuous operations could be delivered as a service rather than a one-time project or expensive internal build-out. That insight, combined with the operational knowledge I gained in New York, gave me the platform to build something fundamentally different.


If you enjoyed this interview series, please follow Eldon and get his book at https://lnkd.in/gS2HNAnY

He aims to be the Rick Rubin of Canadian cybersecurity startups: helping the right teams sharpen their edge, amplify their strengths, and scale faster.

P.S. What other qns would you ask him?

4 types of people in tabletop exercises.

And how to deal with them.

It is every facilitator's nightmare. You spend hours designing and scheduling a tabletop exercise and you practice and envision every conversation, pushback, scenario.

Yet you still feel unprepared because you don't fully know who the audience is, what they are like, and whether they will chew you up and spit you out.

Here are the 4 archetypes and how to manage these characters.

1. The Know-it-all

If we all conduct a blind survey in the room and ask everyone to close their eyes and point to the person who "Knows-it-all", they will all point to the same person.

How to tell who this person is?

Don't worry. When the exercise reaches the first discussion point, this person will start talking about Step A to Z on what he or his team will do. He knows his plans, critical processes, who to call, what to ask, what to investigate, how long it takes, priorities etc

How do you handle the "Know-it-all"?

This is a good thing.
Don't discourage the sharing. Instead leverage what the person is sharing and post some of the things he raised to other teams.

Example:
Know-it-all: For this particular incident, we will triage and send out the initial report within 30 mins

You: That is excellent. Operations team (or any other team that should receive the report), is the information within the initial report sufficient or what other types of info will help your team's processes?

Know-it-alls are good for keeping the flow of the exercise. Leverage them well.

2. The Forever-Skeptic (FS for short)

Signs of the FS.
- This will never happen
- We have implemented tools for this
- This inject is not applicable for our env

I know. 
You may find yourself sweating at this point. But don't worry, leverage your exercise design partner to help expand on the inject to make it relevant.

OR if all else fails. 
This is one trick that works.

Ask the FS straight up. 
"Is there a similar inject or scenario where in your experience and expertise, you know will triggers an event/incident that needs your team's response?"

1. This strokes FS's ego.
2. You have trapped FS. He can't say there is no such scenario.
3. Smile and pivot from FS's suggestion.
4. Rem to tie it back to the overall scenario.

3. The Conversation Hogger

Signs of the Hogger
- This is a no brainer. If you record the whole, the hogger probably took up 70% of the air time.

It is likely that the hogger has gone too far down a rabbit hole. 

Acknowledge the hogger's contribution and bring others in the convo.

4. The silent ones

No sound. No inputs. No involvement.
Ask them directly what they think or they would do. 
Do it with every inject.

What other characters are there and how do you deal w them?

Basic TTX design: Start w scenario. 
Advanced TTX: Start w objectives. 
Expert TTX: Start w decision points. 

Simple trick. 
Work in this order. 

Start with decision points. 
Build up the objectives. 
Fit the scenario in. 

This makes the exercise effective. 

Sounds simple. 
Until you try it out. 

What have you seen teams start with when designing exercises?

It’s 2026 and it’s still a VUCA world. 

Volatilite
Uncertain
Complex
Ambiguous 

No wonder there is a continued demand for crisis mgmt professionals. 

VUCA was introduced in 90s to describe the post Cold War period. 
Still as relevant today. 


In fact, things may escalate. 

BANI is added to the frame with pandemics, AI, and whatever’s next. 

Brittle
Anxious
Nonlinear 
Incomprehensible


Stay safe out there. 

P.S Just saw the missile attack on the base in Bahrain where I was stationed back in the day.

Imagine exercising the exact scenario a couple of weeks before an incident. 

This is how some teams would have managed the lead up to this weekend. 

The sharpest teams would have tracked the escalation and highlighted the threat scenarios weeks ago. This can only happen if your threat intel teams covers beyond just cyber. 

The risk teams would be pulled in and have a quick reassessment. This can only happen if your intel and risk teams know how to work together. 

The exercise and security teams collaborate to rapidly design and develop exercise scenarios. This can only happen if leaders carve out time. 

The leadership team prepare briefs to the executive leadership and board. This can only happen if there is trust. 

Can you predict when something kicks off? Nope but you can certainly prep for it in advance. 

And when you run the exact scenario weeks before it actually happens. 

Imagine the credibility your team gains. This doesn’t happen by chance but by an intricate and established machinery. 

P.S 
how are you actively managing risks?

If the message is still unclear, do this. 
- review last few major incidents 
- identify the most relevant scenarios
- refresh or recirculate response plans
- stand up a quick incident drill 
- plan for a near term exercise 
- run the exercise and note lessons
- update leadership on readiness


Write a quick doc on this process. 
That is your response playbook. 
Don’t fumble the next crisis.

Running the Naval Wargaming & Simulation Centre provided a strong foundation for running cyber exercises.

Here was what a typical week looked like.

• detailing injects
• designing exercise scenarios
• preparing exercise with instructors
• running exercises for warfare teams
• keeping up to date with naval tactics
• tracking and assessing performances
• planning out future exercise schedules
• conducting pre and post-exercise briefs
• discussing the ship's exercise objectives
• ensuring teams are up to date on Red Team tactics

Now you can understand the transferable skills in Cybersecurity exercises.

If you’re a cybersecurity CEO going to RSAC 2026, this will either save you… or cost you.

Most teams treat RSAC like a 4-day sprint.

But the CEOs who win RSAC treat it like a 6-week runway:

• build familiarity in the feed
• earn trust with proof and POV
• then make the meeting ask easy
  
If you skip the runway, you’ll feel it:

• you’ll be “just another booth”
• you’ll get lots of “send me info”
• your SDRs will grind cold outreach at peak noise

So I built a free package for cyber CEOs:

RSAC 2026: 6-Week LinkedIn Content Package

Mon: Authority
Wed: Trust
Fri: Leads (value-driven CTA to meet at RSAC)

Inside:

• 18 complete posts (ready to copy/paste)
• multiple post formats (checklists, lessons, mistakes)
• CTAs tied to real buyer pain and outcomes

Designed for a mid-size cybersecurity company CEO.

Want it?

Comment PACKAGE and I’ll DM it to you.

(Tag someone who you know will benefit from this.)

Most cyber CEOs ask:

What shld I write about on LinkedIn?

Here’s a simple filter I give clients 

Write about this:
- Reason for product pivots
- Questions boards asks
- Insights from clients 
- Investor concerns 
- Tough decisions

Avoid writing this:

- Repost cyber news
- Random infographics 
- Vague “AI is risky” takes
- Generic breach commentary

If another cyber CEO could copy-paste your post and it still works, it’s probably not helping your positioning.

The best way to avoid mistakes is to learn from others who have trodden a similar path. 

I interviewed Eldon Sprickerhoff to get his insights for the next generation of founders. He is an Entrepreneur-in-Residence and a mentor at Rogers Cybersecure Catalyst, Toronto Metropolitan University. 

He is best known for founding eSentire, a leading global cybersecurity Managed Detection and Response company.

𝗘𝗮𝗿𝗹𝘆 𝘆𝗲𝗮𝗿𝘀 𝗼𝗳 𝗯𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝗲𝗦𝗲𝗻𝘁𝗶𝗿𝗲

𝘘: 𝘐𝘯 𝘵𝘩𝘦 𝘦𝘢𝘳𝘭𝘺 𝘺𝘦𝘢𝘳𝘴, 𝘸𝘩𝘢𝘵 𝘸𝘦𝘳𝘦 𝘵𝘩𝘦 𝘮𝘰𝘴𝘵 𝘪𝘮𝘱𝘰𝘳𝘵𝘢𝘯𝘵 𝘭𝘦𝘴𝘴𝘰𝘯𝘴 𝘺𝘰𝘶 𝘭𝘦𝘢𝘳𝘯𝘦𝘥 𝘢𝘣𝘰𝘶𝘵 𝘣𝘶𝘪𝘭𝘥𝘪𝘯𝘨 𝘵𝘩𝘦 𝘣𝘶𝘴𝘪𝘯𝘦𝘴𝘴, 𝘢𝘯𝘥 𝘸𝘩𝘦𝘳𝘦 𝘥𝘪𝘥 𝘵𝘩𝘰𝘴𝘦 𝘭𝘦𝘴𝘴𝘰𝘯𝘴 𝘤𝘰𝘮𝘦 𝘧𝘳𝘰𝘮?

Three lessons stand out:

First, product-market fit isn't a one-time achievement - it's continuous. What worked for early customers often needed to evolve as we scaled. This came from painful experience watching our initial approach struggle as we tried to expand.

Second, in security, trust is everything but takes years to build. This lesson came from losing deals early on simply because we were unknown, regardless of our technical capabilities. We had to earn credibility one customer at a time.

Third, technical founders need to learn business fundamentals or find partners who have them. We learned this through trial and error - understanding unit economics, founder-led sales processes, and operational scaling didn't come naturally but became critical to our survival.


𝘘: 𝘓𝘰𝘰𝘬𝘪𝘯𝘨 𝘣𝘢𝘤𝘬, 𝘸𝘩𝘢𝘵 𝘸𝘦𝘳𝘦 𝘢 𝘧𝘦𝘸 𝘱𝘪𝘷𝘰𝘵𝘢𝘭 𝘮𝘰𝘮𝘦𝘯𝘵𝘴 𝘵𝘩𝘢𝘵 𝘴𝘩𝘢𝘱𝘦𝘥 𝘵𝘩𝘦 𝘤𝘰𝘮𝘱𝘢𝘯𝘺’𝘴 𝘥𝘪𝘳𝘦𝘤𝘵𝘪𝘰𝘯, 𝘢𝘯𝘥 𝘩𝘰𝘸 𝘥𝘪𝘥 𝘺𝘰𝘶 𝘥𝘦𝘤𝘪𝘥𝘦 𝘸𝘩𝘢𝘵 𝘵𝘰 𝘥𝘰 𝘯𝘦𝘹𝘵 𝘢𝘵 𝘵𝘩𝘰𝘴𝘦 𝘱𝘰𝘪𝘯𝘵𝘴?

A few moments were definitive:

The decision to focus on MDR as its own category rather than trying to be a general security consultancy. This came from recognizing we needed to own a specific problem rather than compete in a commoditized services market.

Choosing to build certain technology components rather than resell others' tools - and this changed throughout the life of the company. This was risky and capital-intensive, but it became our moat. We decided based on the belief that you can't deliver differentiated outcomes with commoditized tools; we made the choice to build on well-established frameworks (enterprise-level plumbing) and then build our own solutions on top.


The choice to pursue enterprise clients over SMB at a certain stage. This shift required completely rethinking our go-to-market, but the economics and retention made it necessary. We made this call when customer acquisition costs versus lifetime value forced us to evolve.


P.S. Are you capturing these moments in your journey?

I have been writing here for 3.5 years. 

These 3 events forced me to start. 

Perhaps you are on the fence and thinking about whether you should start making your thoughts public. 

Over-analysing the risk v reward. 

I know. I was once in your shoes. 

Perhaps you have been through these events that changed my mind and got me started writing on LinkedIn. 

1. “Wasted” work

I remember preparing a presentation. Missed dinners and worked over weekends. In the end, I sent it to my boss who took a 5 min look, deleted 50% and sent it upwards. 

His boss takes a 3 min look and says “cut it down to 2 slides”.

Those hours of work, thought process, analysis, critical thinking 

All gone to “waste”. 

I wanted to articulate my efforts. 

2. Muted Network

I asked myself, within my org,
how many people knew me. 

And how many fewer knew about the quality of work that I produce. 

I was in a role that needed to interact with many other departments. 

Yet. I counted. 
Maybe 40 ppl knew me. 
And maybe 7 knew my work. 

That needed to change. 
So I took matters into my own hands and started writing and sharing. 

3. Watched others flourish

I started reading what others wrote. 
No the mindless scrolling that u do. 

But reading and diving into posts. 

Soon I realized that I do have valuable things and experiences to share. 


If you are reading this, you probably have similar experiences. 

Start writing. 

P.S what encouraged you to start writing here on LinkedIn ?

P.S.S whose ready for summer?

CEOs are holding back their team if they have no presence on LinkedIn. 

You need to take the lead. 

When your team sees you being active, it gives them the encouragement to grow their own presence and inevitably draw attention to your organization. 

But if you barely bother, they will hesitate and may even be worried. 

What does being active bring?

- more warm leads, less cold spam 
- awareness for the company
- increased partnership opps
- better organic marketing 
- advocacy for yr team

What’s holding CEOs back?

A Mag 7 acquires your Cyber company for Billions.

No wonder everyone is now a cyber founder... BUT

I interviewed Eldon Sprickerhoff to get his insights for the next generation of founders. He is best known for founding eSentire, a leading global cybersecurity Managed Detection and Response company.

𝗔𝗱𝘃𝗶𝗰𝗲 𝗮𝗻𝗱 𝗽𝗲𝗿𝘀𝗽𝗲𝗰𝘁𝗶𝘃𝗲 𝗳𝗼𝗿 𝘁𝗼𝗱𝗮𝘆’𝘀 𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀

𝘘: 𝘍𝘳𝘰𝘮 𝘺𝘰𝘶𝘳 𝘱𝘦𝘳𝘴𝘱𝘦𝘤𝘵𝘪𝘷𝘦, 𝘸𝘩𝘢𝘵’𝘴 𝘥𝘪𝘧𝘧𝘦𝘳𝘦𝘯𝘵 𝘢𝘣𝘰𝘶𝘵 𝘣𝘶𝘪𝘭𝘥𝘪𝘯𝘨 𝘢𝘯𝘥 𝘴𝘤𝘢𝘭𝘪𝘯𝘨 𝘢 𝘤𝘺𝘣𝘦𝘳𝘴𝘦𝘤𝘶𝘳𝘪𝘵𝘺 𝘤𝘰𝘮𝘱𝘢𝘯𝘺 𝘵𝘰𝘥𝘢𝘺 𝘤𝘰𝘮𝘱𝘢𝘳𝘦𝘥 𝘵𝘰 𝘦𝘢𝘳𝘭𝘪𝘦𝘳 𝘦𝘳𝘢𝘴?


The biggest difference is that the market now better understands the category. When we started, we had to explain why continuous monitoring mattered, let alone explaining what we meant by “Embedded Incident Response” or “Collaborative Threat Management” (two early terms we used to describe what benefit we were bringing to the market).

Today, MDR is established - founders don't need to educate the market on the concept, but they face different challenges.

The bar for differentiation is much higher. Buyers are more sophisticated and have many options. You can't win just by being "better" - you need to solve a problem fundamentally differently or serve an underserved segment.

Capital availability has changed dramatically. In the early 2000s, cybersecurity funding was extremely scarce. Today, capital is somewhat more abundant (especially when addressing the market from the perspective of AI), which means you can scale faster but also face better-funded competition earlier. The pressure to grow quickly can actually hurt companies that haven't found true product-market fit.


𝘘: 𝘞𝘩𝘦𝘯 𝘺𝘰𝘶 𝘮𝘦𝘦𝘵 𝘧𝘰𝘶𝘯𝘥𝘦𝘳𝘴 𝘰𝘧 𝘤𝘺𝘣𝘦𝘳𝘴𝘦𝘤𝘶𝘳𝘪𝘵𝘺 𝘴𝘵𝘢𝘳𝘵𝘶𝘱𝘴 𝘰𝘳 𝘴𝘤𝘢𝘭𝘦-𝘶𝘱𝘴, 𝘩𝘰𝘸 𝘥𝘰 𝘺𝘰𝘶 𝘵𝘦𝘭𝘭 𝘸𝘩𝘦𝘵𝘩𝘦𝘳 𝘵𝘩𝘦𝘺’𝘳𝘦 𝘰𝘯 𝘢 𝘩𝘦𝘢𝘭𝘵𝘩𝘺 𝘱𝘢𝘵𝘩?

I look for a few signals:

Do they have deep conviction about a specific problem, or are they chasing a market opportunity? The best founders I meet can articulate exactly why their solution needs to exist based on real experience, not market sizing slides.

Are their customers renewing and expanding? Revenue growth matters, but retention and expansion tell you if you're actually solving the problem. Churn hides in early-stage metrics.

Can the founder articulate their unit economics clearly? If they can't explain their CAC, LTV, and path to profitability, they're likely building on quicksand regardless of how impressive the top-line growth looks.

Finally, are they learning and adapting? The founders who succeed aren't the ones who execute their original plan perfectly - they're the ones who recognize when something isn't working and adjust intelligently. This has been coined as a new flavour of MVP: Minimally eVolveable Product.



If you enjoyed this interview series, please follow Eldon and get his book at https://lnkd.in/gS2HNAnY

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