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Energized technology transformation executive with 20+ years of experience modernizing…
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The Art of the Acquisition: Why Technology Due Diligence Is About More Than Technology
The Art of the Acquisition: Why Technology Due Diligence Is About More Than Technology
I’ve experienced acquisitions from all sides of the table. As the company being acquired, as the acquirer performing…
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Integrity Creates the Platform. Empowerment Drives the Results.
Integrity Creates the Platform. Empowerment Drives the Results.
Early in my career, success was personal and visible. As a software developer, progress was measured in features…
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Steven Thomas shared thisTechnology due diligence is about far more than the tech stack. Having experienced acquisitions from all sides of the table, I’ve learned that success hinges on operations, culture, governance, credibility, and people just as much as architecture. Here are a few lessons learned the hard way.The Art of the Acquisition: Why Technology Due Diligence Is About More Than TechnologyThe Art of the Acquisition: Why Technology Due Diligence Is About More Than Technology
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Steven Thomas shared thisWhat I Admire About Entrepreneurs Over the years I’ve had the privilege of working with several founder-led companies. If you’ve spent time in those environments, you recognize the energy immediately. It’s different from traditional corporate leadership. The urgency is real, the mission is personal, and the journey matters just as much as the destination. In fact, I often say it more bluntly: the journey ALWAYS matters as much as the destination. What I’ve always admired most about entrepreneurs is the clarity of purpose they bring to their work. There’s a focused energy that comes from building something that didn’t exist before. Decisions move faster because the mission is clear. Red tape is non-existent. Entrepreneurs are also uniquely comfortable with balanced risk. They know the difference between reckless decisions and necessary ones. Sometimes the right move is incremental progress; sometimes it’s a calculated “Hail Mary” when the opportunity window is closing fast. There’s also a strong overlap between entrepreneurial leadership and servant leadership. The best founders I’ve worked with understand that their job is not to be the hero of every story. It’s to create the conditions where talented people can do their best work. They remove friction, cut through bureaucracy, and keep the organization focused on what matters most. Perhaps most importantly, entrepreneurs tend to love the journey. The setbacks, the pivots, the late-night problem solving. It’s all part of the process of building something meaningful. How many of you have slept on a couch at work after powering through some late night issue or preparing for some customer demo first thing in the morning? These are the memories that remain long after corporate noise dissipates. The lesson I’ve taken from every founder I’ve worked with is the same: great organizations are built by people who care deeply about the mission, who move with intention, and who are willing to take the occasional bold step when the moment calls for it. Carry this into every role, not just leadership, and mountains will move.
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Steven Thomas posted thisTrust Is Infrastructure - Security Is a Culture, Not a Control In many organizations I’ve worked with security starts as a line item. An expense to be justified, reduced, or possibly deferred until the next audit cycle. Policies exist, tools are purchased, and certifications are pursued, but too often the reality sits behind a kind of “Wizard of Oz” curtain: everything looks secure when the auditors arrive, yet security isn’t truly embedded in how the organization operates day to day. Across global teams and portfolio companies, I’ve seen the same pattern repeat. Security budgets feel insufficient. Tooling and incident response investments compete with feature delivery and revenue pressures. In some organizations, policies exist but only to satisfy SOC or ISO audits. In others, there were no meaningful controls at all! No tooling. No training. No evangelists. The reasoning was always familiar: we didn’t have the budget, we lacked the expertise, or leadership didn’t see the urgency. A Solution Security cannot live as an annual project. It has to become part of the operating rhythm. One of the most effective shifts I’ve seen is treating security not as a compliance exercise but as a continuous practice. Something visible in every sprint, every goal-setting cycle, and every product discussion. That meant embedding secure development practices alongside delivery, running incident-response exercises as routinely as release planning (which can be fun), investing in training so that teams understood why controls existed, and making security outcomes part of how we measured success as leaders. A CISO once told me I might be overzealous in pushing multiple frameworks (SOC, ISO, NIST CSF/800-53, PCI), especially given how much they overlap. He wasn’t wrong. The goal was never to chase certifications, it was to keep security conversations active with our teams, our customers, and our leadership, always moving toward the next milestone, the next control, the next improvement. That’s how secure products become simply part of what we do. A Balance Of course, security investment should align with risk. Not every organization needs the same level of tooling or governance maturity but no organization can afford to be security-illiterate. The cost of inaction is not theoretical, it’s reputational, operational, and increasingly existential. Google recently warned us that "attackers are wiring AI directly into live cyberattacks". We are focusing on how Generative AI enhances our own productivity but we can't forget it's empowering the bad guys too. Security isn’t a control you bolt on at the end, it’s infrastructure you design from the start. The organizations that earn trust aren’t the ones with the most policies; they’re the ones where secure thinking is simply how work gets done, every sprint, every decision, every day. If this isn’t your organization, have the difficult conversation. Ground it in data. Deliver it with conviction.
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Steven Thomas shared thisLeadership isn’t about crossing the line yourself. It’s about building the platform so others can.Integrity Creates the Platform. Empowerment Drives the Results.Integrity Creates the Platform. Empowerment Drives the Results.
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Steven Thomas posted thisPassion - Is Not a Side Hustle For a long time, we’ve perhaps treated passion as something separate from work, a reward at the edges of a demanding career. I’ve come to believe the opposite is true. Passion is foundational. It’s where energy, resilience, and clarity actually come from. Outside of technology, I play hockey and squash. I run. I boat. I hike. And I’m a musician, a drummer (so some might say…NOT a musician). However, none of these are hobbies I “fit in.” They are practices that sharpen focus, reinforce discipline, and remind me what it feels like to be fully engaged. Each one teaches something different. 1) Sport reinforces commitment and accountability - you show up, or you let the team down. 2) Endurance builds patience and perspective - progress happens one deliberate step at a time. 3) Time on the water and trail restores humility - nature has a way of resetting priorities. 4) And being a drummer demands listening, timing, and restraint - knowing when to drive momentum, when to hold the groove, and when to give others space. These experiences don’t distract from leadership; they inform it. They fuel the passion required to stay curious, grounded, and present, especially when the work is hard and the stakes are high. The leaders I admire most are not the busiest or loudest. They are the ones who bring energy, authenticity, and presence into the room. That kind of leadership doesn’t come from exhaustion; it comes from alignment. When passion is treated as core, not optional, work becomes more sustainable, decisions become clearer, and relationships deepen. Over time, that energy compounds into better outcomes for people and organizations alike. Leadership isn’t sustained by intensity alone, it’s sustained by the passions that keep us fully alive in the work.
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Steven Thomas posted thisLeadership – A Hall of Mirrors One of the most valuable leadership experiences I’ve had was a year-long program called Hall of Mirrors. Its core lesson was simple and uncomfortable: the hardest work in leadership isn’t changing organizations, it’s continuously examining ourselves. It’s easy to slip into autopilot. We convince ourselves we’re making intentional choices, until reflection forces the real question: Am I leading deliberately, or just repeating what’s familiar? Great leadership starts with integrity. Not just in outcomes, but in intent. It requires passion that’s steady, not performative. And it depends on relationship building, because trust is the only real accelerator of change. That same discipline applies to how we adopt AI. Responsible AI usage, grounded in transparency and accountability, can dramatically improve product centricity, operational discipline, and technical efficiency ... but only when leaders set a clear North Star. What is the strategy, and what are we trying to achieve? Done right, AI removes friction and sharpens focus. Done poorly, it simply automates noise, and teams recoil. Growth, whether personal or organizational, rarely comes from reinvention alone. It comes from conscious choice: what to preserve, what to evolve, and when to challenge ourselves to think differently. Technology is predictable. Humans aren’t ... and that’s the point.
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Steven Thomas shared thisThe entrepreneurial spirit at work! Get firsthand insight from those shaping exceptional companies.Steven Thomas shared this🚀 Introducing the CEO Spotlight Series ---- At Edelweiss Software Group, our mission is simple: to help great software companies thrive for the long term. Behind every software business we partner with, there's someone who's poured years - often decades - into building something extraordinary. These are the entrepreneurs who've chosen to join the Edelweiss family, and in this series, we're sharing their stories. 💡 Why did they join Edelweiss? 💬 What does partnership look like in practice? 🌱 How have their businesses evolved since joining? Over the next few weeks, we'll introduce you to the CEOs leading our 12 (and growing) portfolio companies - beginning with Donnie Beer, CEO of Wisys. Their journeys are unique, but the theme is the same: a belief in sustainable growth, autonomy, and community. Follow along as we highlight the people and passion driving Edelweiss Software Group (an operating group of Valsoft Corporation). 🔗 Learn more: https://edelweisscorp.com/ #EdelweissSoftwareGroup #CEOspotlight #Entrepreneurship #SoftwareGrowth #Valsoft #FounderStories #LongTermPartnerships
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Steven Thomas shared thisBig announcements and exciting times! P.S. We're hiring...check out open positions posted by Alizée Leizerovici. #valsoftway #growth #edelweisssoftwaregroupSteven Thomas shared thisWe’re proud to share an important milestone in our journey. To strengthen portfolio management and drive sustainable long-term growth, Valsoft Corporation has established seven dedicated operating groups to support our expanding ecosystem of software companies: Aspire Software, Lighthouse Software Group, Helios Software Group, Fluent Software, TAG Software Group, Manos Software Group, and Edelweiss Software Group. These operating groups will oversee the support, maintenance, and operations of our portfolio companies—ensuring each one receives tailored guidance, resources, and expertise while preserving its entrepreneurial DNA. "As our portfolio has grown significantly, we recognized the need for a structure that would give our companies the dedicated attention they deserve, while staying true to our decentralized model," said Sam Youssef, Founder and CEO of Valsoft Corporation. Learn more: https://lnkd.in/e7a3Bney #VMS #PortfolioManagement #Entrepreneurship #Growth
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Steven Thomas shared thisProud to be part of this amazing journey! #valsoftway #growthSteven Thomas shared thisWe’re proud to share an important milestone in our journey. To strengthen portfolio management and drive sustainable long-term growth, Valsoft Corporation has established seven dedicated operating groups to support our expanding ecosystem of software companies: Aspire Software, Lighthouse Software Group, Helios Software Group, Fluent Software, TAG Software Group, Manos Software Group, and Edelweiss Software Group. These operating groups will oversee the support, maintenance, and operations of our portfolio companies—ensuring each one receives tailored guidance, resources, and expertise while preserving its entrepreneurial DNA. "As our portfolio has grown significantly, we recognized the need for a structure that would give our companies the dedicated attention they deserve, while staying true to our decentralized model," said Sam Youssef, Founder and CEO of Valsoft Corporation. Learn more: https://lnkd.in/e7a3Bney #VMS #PortfolioManagement #Entrepreneurship #Growth
Steven Thomas replied to a comment
3mo
Dylan Turner An approach taken a couple of times is your exact observation. Most companies I've worked for, and with, gauge business health using a variety of KPIs. A couple of obvious non-proprietary examples would be EBITA and organic growth (OG)....the really smart companies add Security (and now AI related) KPIs to the key operating ratios. Essentially the 'desire to be secure' now becomes mandatory and the path-forward is cleared. The difficult conversation still remains if HQ isn't pushing a strong security-first mindset. This is where your evangelists can help craft the message to leadership as to what is needed and why.
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Steven Thomas liked thisSteven Thomas liked thisWe just completed our latest Volaris Group AI accelerator in Palm Beach Florida. Companies are really starting to get ambitious. People are really leaning into how to transform end user experiences. Finding things people loath but tolerate. And then shocking them when you can solve this in scalable and reliable ways in a matter of weeks. A key learning is that businesses need to focus more broadly than the development process. Product, Development, QA, Devops, Support, Marketing all need to be factored in if you are going to ship exceptional experiences rapidly. Our next accelerator in Berlin 8 days from now is going to be an interesting one ;)
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Steven Thomas liked thisSteven Thomas liked this🚀 EQ Bank is hiring Forward Deployed AI Engineers to completely rewrite the playbook for digital banking. We are looking for a rare breed: a brilliant technical builder who can step out of the codebase and lead the conversation. If you want to ship AI solutions that disrupt traditional finance, this is your playground. The Mission Location: Toronto-based, working in a flexible hybrid model. Deploy on Cloud: Build and scale impactful AI systems leveraging our modern Azure and GCP stacks. Translate AI: Effortlessly teach and communicate complex technical concepts to non-technical partners and engineers alike. Drive Pure Value: Move past the AI hype to co-create solutions that deliver measurable business impact. Stay Hungry: Bring a passion for intense collaboration and life-long learning to a fast-moving team. We have the scale of a top digital bank and the soul of a startup. Let’s change the industry together. 👉 Apply now: https://lnkd.in/gUipu9vT #Hiring #AI #AppDev #AgenticAI #AIEngineering #Fintech #ChallengerBank #TorontoJobs #Cloud #DigitalTransformation #AppliedAI #TorontoTech
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Steven Thomas liked thisSteven Thomas liked thishttps://lnkd.in/g2GfTKrw CIOs and CISOs just ran out of excuses. When the Five Eyes say “the timeline is months, not years,” they aren’t warning about sci‑fi AI. They’re telling you that the way you’ve been rolling out automation is about to become a liability at national‑security speed. If you have agents and copilots wired into production without a hard, shared control surface, you did not “innovate.” You built a weapons‑grade attack surface and handed the playbook to whoever gets the next model checkpoint. This isn’t an AI story. It’s a story about ungoverned autonomy inside systems you already know are fragile. The only surprising part is that intelligence agencies were the first ones to say it plainly. So here’s the new bar: If you cannot point to one governed substrate that constrains, verifies, and audits all automated work in your estate, you are not “transforming.” You are gambling. Helix is our bet—and our challenge (3Pillar.ai). We built Helix to be that substrate: the thing every agent and automated workflow must pass through if it wants to touch your systems. No side channels, no “special exemptions for pilots,” no “we’ll bolt security on later.” No knowledge graph? You are defending an architecture the attacker’s model understands better than you do. No verification layer in the path? You are letting untrusted code and config land in production because a demo looked good. No telemetry loop? You’re giving your systems infinite chances to fail in the same way, just faster each time. If you’re proud of your AI pilots but can’t answer, in one sentence, “Where does all this automation get compromised?"—you’re not ahead. You’re exposed. The Five Eyes just put a clock on that exposure. Helix is how we plan to stop the clock.'Five Eyes' intelligence alliance warns that new AI models pose urgent cyber risk'Five Eyes' intelligence alliance warns that new AI models pose urgent cyber risk
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Steven Thomas liked thisSteven Thomas liked thisGoes to show how much can change in a few years. Stepping into the unknown in the first training academy all them years ago, I didn't know what to expect but all I knew was I had a clear motivation to make something out of my life. Surrounded by a team of young, driven & like minded people from day one and a leader with a clear vision pushed me to progress to where I have now. Throughout the years I continuously learnt how to be better, saw what success looked like and how to embed the right standards into everything, but most importantly never settle and always strive for more. Looking back at the photos of myself alongside others across the business demonstrates how much we've grown across the years together, with the biggest achievements still to come. Going from a trainee in London to SVP in our Miami office and a shareholder of the business is a trajectory that I wouldn't have possibly imagined 7 years ago, and I'm grateful to where I've got to so far but also proud to have seen so many others in the business progress and be involved in building something special. Happy 10 years InterEx
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Steven Thomas liked thisSteven Thomas liked thisStrong leaders come in many forms, and some of the most important lessons in leadership start long before the boardroom. Today, we celebrate the fathers, father figures, mentors, and role models who lead with patience, resilience, integrity, and heart. A special thank you to the dads across Portfolio+ and our Vencora family. The leadership, dedication, and care you bring to your teams, your families, and our communities make a lasting impact every day. Thank you for the guidance you share, the example you set, and the countless ways you help others grow and succeed. From all of us at Portfolio+, Happy Father's Day! 💚 💙 #FathersDay #Leadership #Mentorship #PortfolioPlus
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Steven Thomas liked thisSteven Thomas liked thisPllease join us in welcoming Santhosh Balakrishnan to Portfolio+ as our new Enterprise Security Specialist! 👋 His collaborative mindset, attention to detail, and commitment to building secure, resilient environments align perfectly with how we work at Portfolio+: balancing innovation with responsibility while keeping our customers, partners, and teams protected every step of the way. ✨ Welcome to Portfolio+, Santhosh! We're glad to have you on the team. ✨ #WeArePortfolioPlus #CyberSecurity #InformationSecurity #EnterpriseSecurity #FinTech #PortfolioPlus
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Steven Thomas liked thisSteven Thomas liked thisBetter to disrupt your industry than watch a competitor do it first. That's the mindset Crystal Germond, MBA brings to AI transformation as the GM at eQuip — and it starts with recognizing that inaction isn't neutral. In a competitive environment, standing still means falling behind. But getting "unstuck" isn't only a technology problem. Crystal has found that the harder work is human — helping everyone at every level of the organization, and even customers, find comfort in uncertainty, ambiguity, and the questions that don't yet have clear answers. Want more insights? Hear from GMs leading through uncertainty in our webinar: https://lnkd.in/gWeMRmU4 #ForeverInvested AssetWorks Inc Greg Richards Ryan Saxby Hill
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Steven Thomas liked thisSteven Thomas liked thisToday was a meaningful day. On behalf of our Teams Vertus Group and Jonas Software, we were proud to donate $1,305 to Yellow Brick House in Richmond Hill, Ontario. Yellow Brick House provides life-saving services and prevention programs for individuals, families, women, and children impacted by violence. This donation came from a simple internal initiative, but it reflects something much bigger: the importance of showing up for the communities where we live and work. Thank you to everyone across Vertus and Jonas who contributed. Your generosity made this possible. #CommunitySupport #GivingBack #YellowBrickHouse #RichmondHill #YorkRegion #TeamVertus #JonasSoftware #ConstellationSoftware
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Steven Thomas liked thisCongrats to all the 2026 #ORBIE CIO and CISO finalists! Thanks to InspireTORONTO for your impact keeping industry CIO and CISOs together. Great to see my friends Tatiana Gribanovskaia Ali Razavi Bill Pearce Irene Zaguskin ICD.D Sarah Willock ❤️Steven Thomas liked thisSome rooms just feel different. Last week's Toronto #ORBIE Leadership Reception was one of them. There's something that happens when the Toronto CIO and CISO community gathers not to network, but instead to genuinely celebrate each other. That energy filled the room as leaders celebrated and learned from great leaders. Every nomination tells a story of teams who showed up to move their organizations forward. Not because it was easy. Because it mattered. That's the kind of work that earns recognition from the only people who truly understand it: fellow leaders who look across the room and say: "What you carried mattered. What you built mattered." Our InspireTORONTO Awards Chair, Neeraj Mathur of SickKids Foundation guided the panel discussion right to the heart of it, asking the question every technology leader is thinking about: "How do we build for the future when the future is arriving faster than ever?" Uma Gopinath of Porter Airlines Inc., Farshad Kajouii of the City of Toronto, Clinton McFadden of Canadian Tire Corporation, and Alex Coleman of @Children, Youth, Social Services I&IT Cluster didn't just answer it, they opened up about what it actually looks like to scale innovation while carrying the weight of public trust, governance, and institutional responsibility. Becoming a Finalist means your peers see you. They understand the complexity, the decisions, the weight of leading through transformation and they're saying it out loud. 🌟 Congratulations to all of the 2026 Toronto ORBIE Finalists. We are so proud to celebrate you and can't wait for what's ahead. https://lnkd.in/diwbhzbC Global Shannon Bell, OpenText Martin Jepil, Avison Young Nishat Jessa, Oxford Properties Alfredo C. M. Tan, Canada Goose Irene Zaguskin ICD.D, PwC Canada Large Enterprise Donna Kidwell, University of Toronto Kin Lee-Yow, CAA Club Group Alex Ricordi, EMBA, PMP, HSS Enterprises Sarah Shortreed, P.Eng, FCAE, ICD.D, Metrie Peter Singh, Toronto District School Board Sarah Willock, Coca-Cola Canada Enterprise Andrew Cree, Canada Cartage Janet Lin, EQ Bank Ali Razavi, 407 ETR Alicia Samuel CIO.D, Holt Renfrew Dhaksayan Shanmuganayagam, Toronto Transit Commission Brad Strom, York University Corporate Scott Briggs, MMSc, C.Dir., Humber Polytechnic Kalyan Chakravarthy, MBA, ICD.D, Electrical Safety Authority Alistair Forsyth, VHA Home Healthcare Geoff Hogan, Nature Conservancy of Canada Venky Rajaraman, Equifax Canada Eric Westerby, Arterra Canada Thank you to all our 2026 ORBIE season partners, Cloudflare, Nutanix, SHI International Corp., Amazon Web Services (AWS), and especially the continued support of our underwriters, Sidi Goutam at Slalom and Neil Bunn at Google. #ORBIE #Toronto #CIO #CISO #Leadership #TechnologyLeadership #BetterTogether
Experience & Education
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Valsoft Corporation
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Licenses & Certifications
Volunteer Experience
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Soccer Coach
Byron Optimist Soccer Club
- 7 years 6 months
Children
I coached Timbits soccer with the Byron Optimist Soccer Club, working primarily with children ages 6–12. It was a great opportunity to help young players build confidence, teamwork, and a love of the game while creating a fun, supportive environment where they could learn, grow, and enjoy being part of a team.
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Cub Leader
Scouts Canada
- 6 years 8 months
Children
I volunteered with Cubs and Scouts Canada for six years, supporting youth development through mentorship, outdoor activities, teamwork, and community engagement. It was a rewarding experience that reinforced the importance of leadership, service, and helping young people build confidence, resilience, and life skills.
Patents
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Advanced Resource Manager for Television Set-top Boxes
60/566,837
In the current generation of set top boxes (STBs), when multiple resources are needed to perform a single activity, these resources are allocated separately by application or system software. If the system detects conflicts during these allocations, each conflict is presented individually to the user or to conflict handler software. When multiple resources are required for a single activity this may cause more than one conflict to be presented to the user or conflict handler software.…
In the current generation of set top boxes (STBs), when multiple resources are needed to perform a single activity, these resources are allocated separately by application or system software. If the system detects conflicts during these allocations, each conflict is presented individually to the user or to conflict handler software. When multiple resources are required for a single activity this may cause more than one conflict to be presented to the user or conflict handler software. However, when more than one conflict is presented to the user, this may cause confusion to the user. Additionally, the conflict handler may resolve one conflict in favor of the new activity and another conflict against the new activity. In this case, the new activity cannot proceed since it requires all the conflicts it generated to be resolved in its favor, but some existing activities may already have been terminated
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RESOURCE ACCESS CONTROL
LIBE APP 61US
Various problems in the prior art are addressed by the present invention of a method and system that enable multiple applications to access a physical resources by way of multiple resource proxies, while still enabling exclusive control of the physical resource by one application. Moreover, the invention contemplates marking methods, such as Java application programming interface (API) methods, with an access control attribute so that a virtual machine (VM) such as Java VM may intercept…
Various problems in the prior art are addressed by the present invention of a method and system that enable multiple applications to access a physical resources by way of multiple resource proxies, while still enabling exclusive control of the physical resource by one application. Moreover, the invention contemplates marking methods, such as Java application programming interface (API) methods, with an access control attribute so that a virtual machine (VM) such as Java VM may intercept invocations of these methods and selectively permit a resource manager to determine whether a resource proxy of an invoking application has or is associated with an access or control token.
Languages
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English
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Organizations
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ISACA
Member
ISACA (formerly the Information Systems Audit and Control Association) is a global professional association, founded in 1969, focused on IT governance, risk, assurance, security, and privacy. With over 185,000 members in 188 countries, it provides industry-leading certifications (CISA, CISM, CRISC), frameworks (COBIT), and educational resources to help individuals and enterprises build a trusted digital world
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