MSP Sales Partners

We help IT and MSP businesses transform sales into their superpower. 

Our services include: 

- Sales training & coaching for closers
- Sales community and training for SDRs/BDRs
- Fractional sales and marketing leadership
- Sales audits and process assessments
- And more

Whether you need strategy, execution, or team development, we deliver results that move the needle.

Founder & Chief Revenue Officer

Repeatable Revenue Ventures

Elite Growth Studio + Venture Fund For B2B Founders Ready To Scale

We select a handful of ambitious B2B companies each year, providing the expertise, capital and resources needed to achieve 3-5Х growth and build a premium exit-ready asset.

Managing Partner

RJG Incubator

Courses, Community & Coaching to build valuable, scalable assets through proven systems and frameworks.

Some results from inside the RJG Incubator:

✔️ Close rates increasing from 26% to 44%
✔️ Doubled pipeline conversion
✔️ Millions in predictable revenue
✔️ Real enterprise value through systematic growth

We have 3 ways to help you grow:

1: Get The Roadmap Course

Our proven course for systematic revenue growth on LinkedIn, sales and internal processes. 10+ hours of practical, actionable training. 

2: Join The Community

 250+ B2B founders scaling together in a community, with access to a complete training library (100+ hours). 
 
3: Join The Accelerator

Monthly 1:1 strategy sessions with me. Providing unlimited async support, feedback and custom growth roadmap development.

Founding Member

Sales and sales management advisor for small and midsize IT business.

Expert In Residence: Sales & Sales Management

SaaS Academy

Advisor, consultant, and fractional sales executive for SaaS Academy, the largest B2B SaaS coaching & consulting program in the world.

Sales Consultant

LAW Publications

Recruited by investors to determine scalability of company and drive growth through operational and sales improvements. 

Key wins included:  
- Highest month of revenue in co.'s 45-year history
- Rebuilding of executive team
- Introduction of principles-based management culture
- Overhaul and improvement of products (including Gold Davey Award Winning product)
- Installation of company-wide CRM
- Integration of a company operating system
- Development of analytics capabilities, tools, and resources
- Professionalization of key functions in HR, production, finance, operations, and sales
- Replaced handwritten, manual processes and paperwork with automation and technology, including integration of a company-wide CRM, national rollout of iPads, installation of VOIP systems, and collaboration software.

Chief Executive Officer

U.S. Chamber of Commerce

During my career with the US Chamber of Commerce, I ascended through roles of increased scope and responsibility for the world’s largest business federation representing 3M+ businesses, associations, and organizations. 

In this role, I held primary P&L accountability for a nation-wide SME unit. I directed multiple sales and membership acquisition channels, including outside, inside, direct mail, and online sales, as well as customer services. I defined and executed the business unit’s long-term strategic direction. 

Highlights include…

~  Secured first year-over-year growth in small business membership by launching new membership model. 

~  Spearheaded initiative to boost political and special issue fundraising, which would go on to surpass membership fundraising for the first time. 

~  Increased membership engagement rates by 33x through new digital communications strategies. 

~  Relaunched Chamber’s small business online presence and deployed new digital model to acquire members.

Managing Director, Small and Midsize Business

I received a promotion to assume P&L accountability over the Chamber’s national sales and fundraising center, which oversees political fundraising, special issue fundraising, membership sales, customer service, and membership operations. 

Highlights include…

~  Achieved first revenue increase in 11 years, positioning center to become largest SME fundraising operation in the Chamber. 

~  Doubled revenue-per-sale of specific-issue fundraising by generating substantial new sales and delivering comprehensive fundraising best practice training. 

~  Fostered culture of achievement through strategic hiring, training, and motivational compensation plans.

Managing Director, National Small Business Sales & Contact Center

I advanced the company’s sales and revenue growth objectives by managing an inside sales team of the National Small Business Membership Center. In addition to recruiting, hiring, and coaching Sales Directors (as well as other sales personnel), I defined and executed sales and fundraising messaging. I managed all aspects of sales operations and quality assurance. 

Highlights include…

~  Met and surpassed ambitious sales objectives every month of tenure. 

~  Diversified and grew sales by integrating novel and innovative sales programs. 

~  Significantly enhanced sales capacity by launching recruitment and training programs to repeatedly add sales directors who performed in the upper quartile.

Division Manager, Inside Sales

Promoted three times from direct fundraising to support, manage, and lead special projects, sales divisions, and growth initiatives.

Key wins included:
- Creatively developed solutions to monetize non-paying members through partnerships with Fortune 500 companies.
- Exceeded every sales and fundraising goal.
- Supported senior management initiatives, including program to enter midmarket membership with new products, services, and offers. 
- Developed framework for the Corporate Leadership Advisory Council, a policy council for midmarket sized companies.

Fundraising - Special Projects - Corporate Relations

Various Companies

Started, sold, worked for, and advised 10+ ventures, including: 

Operating Partner - Like My Mother Does: LMMD is an entrepreneurial venture that began when the founder started making custom baby bedding on Etsy. Within months, demand dramatically exceeded capacity and the waiting list stretched almost four months long. I helped the founder turn her hobby into a boutique referral only business and discover profitability by developing financial, shipping, and inventory models; developing a pricing strategy that resulted in quadrupling prices; and updating and automating digital strategies. 

Operating Partner - After Hours Flowers: Family owned, retail florist that I co-led the turnaround of, took online, pivoted the business model away from third party wire services, and sold. 

Founder - Imagine Promotions: Founded and later sold a music promotions company that represented 20+ artists and organized  or co-organized dozens of concerts and festivals. 

Worked for and advised numerous other startups, ventures, and independent businesses.

Founder - Managing & Operating Partner Roles (RJG)

Napster (Rhapsody International)

Customer Success Specialist

Repeatable Client Acquisition & Fulfillment | Our mastermind community helps you convert online income into a real business | Book a call or DM to apply

In 2019, I walked away from the C-Suite and moved my family to a remote Mexican beach, leaving behind a successful corporate career to pursue a new path.

Prior to going out on my own, I had:

• Been recruited by private equity groups to lead turnarounds as CEO

• Spent 10 years as a senior sales executive, never missing a quota or bonus

• Received 7 promotions in 7 years, rising from sales rep to Managing Director at the U.S. Chamber of Commerce, the world's largest business federation

• Earned my Executive MBA and was invited to Beta Gamma Sigma as a top 20% student at a top 5% business school

• Founded and turned around several small businesses, two of which we sold

But I got tired of building other people's dreams while putting mine on hold. 

So, my wife and I extended a family vacation to Baja indefinitely, determined to build a new kind of business and lifestyle on our own terms.

As an independent consultant, I've had the pleasure of working with world-class clients like Dan Martell, the world's largest B2B SaaS coach; Robin Robins, the world's largest IT business coach; and other well-known names.

Through my company MSP Sales Partners, we help IT companies and MSPs scale sales through our fractional sales management and strategic consulting services that start with a proprietary 360º Sales Audit. 

Through my community, I coach other B2B founders through the process building and scaling their businesses. 

And through Repeatable Revenue Ventures, I lead the process of providing all the resources a select number of B2B businesses need to 3-5x their business, systematize growth, and exit--including the necessary expertise, people, and capital.

Visit www.RayJGreen.com to learn more.

Ray J. Green

Don’t confuse activity with productivity. 

If you have 1 person hitting your “100 call a day minimums” and missing quotas.

And another person missing your call activity minimums but consistently hitting your quotas.

The answer is NOT make the person hitting quotas start hitting minimum activity targets. 

It’s to figure out HOW they’re getting more output with less input—and operationalize it. 

That’ll make everything you’re doing better. 

More value from your list. 
More revenue from every unit of input. 

And your team will probably like the job better. 

So they’ll stay longer. 
Burnout less. 
And allow you to attract better people. 

Activity is just a means to the end. 

Work backwards from what you REALLY want: productivity.

CEO @ MSP Sales Partners | Helping MSP Founders Build Sales Teams That Actually Sell | Ex-PE Backed CEO | Former U.S. Chamber Managing Director

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It's Nov 12. If you're NOT going to hit your annual sales goal this year, read this. 

First, don't give up. 

The work you put in at the end of the year determines how you start the next. 

Start 2026 with momentum, regardless of where 2025 ends. 

Second, don't adjust the annual goal. 

Your goals need to have integrity. Modifying them right before you miss destroys that integrity. 

Revising goals last minute is addictive. It becomes a habit really easily, so avoid at all costs. 

Third, set a "between now and end of year" goal. 

Make it one you can actually hit. Even if it it's embarrassingly low. 

End the year on a win. 

Lastly, perform an autopsy on sales and set a 2026 goal you WILL NOT MISS come hell or high water. 

You don't want to establish a culture of missing goals. 

So take this year's learnings and apply them to make sure that doesn't happen. 

Winning is a habit. Start small and ratchet up over time.

I work out 7x a week—and have for 15+ years.

A friend just asked me what my favorite fitness books are.

I scanned my entire library.

Something interesting I learned about myself today:

I own ONE book on fitness: Tim Ferriss' 4 Hour Body. 

I bought it 15 years ago.

I thought, well let me scan my YouTube history for a recommendation.

None there either, except some bodyweight workouts I pull up while traveling.

Legitimately surprised to realize that as much as I read and learn, I don’t consume fitness content.

I’ve used the same few regimens for more than 15 years:

• Walk 6-10 miles a day
• Strength training 1-4x a week
• Jog 1-2x a week
• Eat decent (not perfect)
• Revisit a sports I love like boxing occasionally 

I’m not going to win a bodybuilding competition, spar with real fighters or place in a triathlon anytime soon.

But at 45, I feel pretty damn good about where I’m at.

Guess that one book was all I needed.

Implementation > Consumption

"𝗖𝘂𝗹𝘁𝘂𝗿𝗲" is one of those things that's hard to define in business. But you definitely know a good one or a bad one when you experience it.

And it's one of the highest leverage tools you have as a leader. Because culture influences how your team communicates, executes, and ultimately how much value they add to the business.

Here are three types of cultures:

𝟭. 𝗗𝗲𝗳𝗮𝘂𝗹𝘁 𝗖𝘂𝗹𝘁𝘂𝗿𝗲: The owner is oblivious to the fact that culture even exists. A culture develops by default, not by design.

𝟮. 𝗗𝗲𝗹𝘂𝘀𝗶𝗼𝗻𝗮𝗹 𝗖𝘂𝗹𝘁𝘂𝗿𝗲: The owner talks about how great the environment is, but employees have a very different perspective. Culture becomes a liability because it erodes trust.

𝟯. 𝗗𝗲𝗹𝗶𝗯𝗲𝗿𝗮𝘁𝗲 𝗖𝘂𝗹𝘁𝘂𝗿𝗲: A leader has a vision for who the team is and how they operate. It's healthy, productive, and compels people to give discretionary effort.

Fifteen years ago, at the US Chamber of Commerce, I inherited a sales team in decline. Losing people. Missing numbers. Toxic culture.

I took one of my biggest career risks and completely changed the culture.

I fired half my team within 90 days. Created core values. Changed how we hired. Fired top salespeople who didn't align.

At first, it didn't look good. Morale was rough. Numbers kept declining.

But then the uptick started.

After the initial uptick, we never missed a goal for 10 years straight.

When I eventually left, it was one of the hardest decisions I'd made. Because I didn't want to leave the culture we'd built. 

I break down the warning signs your culture needs a turnaround and the exact 3D Framework we use at MSP Sales Partners in the full article: https://lnkd.in/e5VTC3sF

Christmas came early for me. 

I was recording a YouTube video when my cell phone rang with a cold call. 

First of all, if you know me, you know that’s weird. I keep my phone on DND permanently and it only gets turned on by accident. 

Second, I answered it. Also rare.

But best of all, this happened while I was already recording—so I just let ot run and captured the whole call on camera. 

I turned it into a video because it’s actually a good call, but there’s a handful of really common mistakes I share with you when the call is done. 

Check it out here:

Open video: https://youtu.be/2QyhQfpq0N4?si=oGSgA4ZEkejOs7Ba on youtu.be

https://youtu.be/2QyhQfpq0N4?si=oGSgA4ZEkejOs7Ba

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

Another reason to be active on LinkedIn and you won’t like this. 

People are too busy to notice you. 

- social media doom scroll
- Netflix and chilling 
- project deadlines
- kids schedule 
- home stuff  
- life events 

And there you are, typing away on your keyboard, working your bum off. Spending all your hours and energy delivering the best work that you can. 

But you forgot to spend time on yrself. 

Time to learn more. 
Time to recuperate. 
Time to invest in you. 

Use LinkedIn to share just abit more of
- what you do
- what you think
- what you are like 

You work hard enough to be noticed. 

Don’t let all that go to waste because you are afraid of what yr colleagues and friends think. 

Let them live with their insecurities. 

You have a career + reputation to build.

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?

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.

Getting into Cyber feels like winning the lottery.

Here’s how to increase your odds.

I interviewed my friend Zinet Kemal, who is an immigrant, mother of four, author, TEDx speaker & Cybersecurity professional. She is passionate about educating and empowering children on online safety and cybersecurity careers.

Journey & Motivation

Q1: You started in law before moving into cybersecurity. What inspired that switch?

I wanted a career where I could make a tangible impact and continuously learn. Cybersecurity offered that blend of purpose, challenge, and growth that instantly drew me in.

Q2: Hands-on experiences like competitions helped launch your career — what advice would you give to others trying to break into cyber?

Don’t wait to feel “ready.” Jump in, join competitions, try extra curricular stuff and learn by doing. Real-world practice builds confidence faster than any certification alone.

Cloud Security Expertise

Q3: What’s one common mistake organizations make when moving to the cloud?

Rushing migration without embedding security from the start. Security shouldn’t be an afterthought. It should guide every design and decision.

Q4: How do you balance speed and security in fast-paced cloud environments?

By automating what you can and baking security into the pipeline. That way, teams can move fast and stay secure without friction.
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If you enjoyed this interview series, please follow Zinet. She frequently shares about her cybersecurity journey and is a gem to the industry.


P.S Have you seen her award list!

“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.

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.

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.

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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?

Data is absolutely vital for effective healthcare.

But how do we manage the risk and liability?

Managing data and addressing privacy issues are major risk areas for many healthcare organizations. Add AI to that picture and it can be messy very quickly.

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 Evolution of Privacy in the Health Sector

Q1: You’ve worked across both government and private healthcare environments. How has the concept of “privacy by design” evolved in the health sector over the past decade?

In the last ten years, privacy by design has evolved from a compliance trend to a core design principle integrated into digital health innovations and an operational imperative. It’s now focused on instilling trust and resilience in systems rather than merely fulfilling regulatory requirements.


Q2: What are some persistent privacy misconceptions you still encounter among healthcare organizations today?

A common misconception is that privacy is the same as security or that having a lawyer create an agreement and terms of use ensures protection and compliance. Effective privacy management requires ongoing governance that aligns people, processes, and technologies to foster accountability and manage data throughout its lifecycle.
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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 other privacy mistakes do you see healthcare organizations make?

Privacy mgmt shouldn't be an afterthought.

Yet many choose to only address it later.

That is a risk startups should address early in their journey, especially if they handle sensitive information. Add AI to that picture and it can be messy very quickly.

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.

Operationalizing Privacy — From Compliance to Trust


Q3: Many healthcare startups treat privacy as a barrier to speed. How do you help founders operationalize privacy without slowing innovation?

I encourage them to view privacy as an enabler rather than an impediment. We help clients establish strong privacy foundations and clear growth plans. We offer Virtual Privacy Officer service to help them navigate privacy-related challenges and implement best practices, allowing them to concentrate on their core business. Embracing privacy can not only benefit their bottom line but also set them apart from the competition. Effective privacy management builds customer trust and differentiates them from competitors.


Q4: What frameworks or approaches have proven most effective in embedding privacy into day-to-day clinical or product operations?

The NIST Privacy Framework, ISO 27701, and the CSA Model Code for the Protection of Personal Information provide a solid foundation, but achieving success often requires creating and executing a well-organized privacy management program. This program should encompass an accountability framework, functional tools such as privacy impact assessments (PIAs) and risk registers, and training that ensures everyone is responsible for privacy, not just the compliance team.
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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 other privacy frameworks would you recommend?

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.
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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. 
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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.

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?

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?

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?

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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