What Mid Market and SMB Leaders Faced, Fixed, and Learned Along the Way
By Jill Button, President & CEO, ProcurePro Consulting
As 2025 comes to a close, many mid market and SMB leaders are taking stock of a year that demanded more clarity, discipline, and resilience than most. This was not a year of chasing trends or experimenting for the sake of innovation. It was a year defined by pressure, competing priorities, and decisions that carried real consequences across technology, procurement, and operations.
Throughout the year, we worked alongside leaders navigating sourcing challenges, payroll and HR system risk, vendor oversight, payment infrastructure resilience, and the growing need for better project and financial visibility. What consistently made the difference was not speed or technology alone, but disciplined problem definition, stakeholder alignment, and structured decision making.
Across every engagement and every conversation, one theme kept coming up. The organizations that made the most progress were the ones willing to slow down just enough to define the problem properly before committing to a solution. That clarity reduced risk, avoided rework, and created momentum when it mattered most.
What follows is a look back at the work we were trusted with this year, along with the articles and videos that sparked the most engagement and conversation within our growing community.
Project Recap
The Work Our Clients Trusted Us With in 2025
This year, the organizations we worked with were not looking for theory, templates, or off the shelf answers. They were navigating real pressure, competing priorities, and meaningful risk. In every case, the ask was the same, help us bring clarity, structure, and confidence to decisions that mattered.
Our clients sat at the centre of every engagement. Our role was to support them, challenge assumptions when needed, and help them move forward with solutions that actually fit their business.
When Sourcing Needed to Support the Business, Not Just Reduce Cost
In one engagement, a growing manufacturing organization needed to rethink how it sourced a critical category tied directly to product quality and innovation. While cost mattered, the real challenge was reliability, supplier capability, and the ability to build longer term relationships that could scale with the business.
Stakeholders had different priorities, requirements were fragmented, and the market had not been tested in years. By taking the time to align teams, clearly define what success looked like, and run a disciplined sourcing process, the organization was able to move forward with confidence. The outcome was not just competitive pricing, but a sourcing approach better aligned to long term stability, growth, and collaboration.
When Payroll and HR Systems Became a Business Risk
Another organization reached out because their payroll and HR environment was no longer dependable. Errors were becoming too frequent, manual workarounds were routine, and confidence in year end reporting was eroding.
This was not simply a technology issue. It affected their ability to grow and expand, employee trust, compliance, and the credibility of leadership teams responsible for getting people paid accurately and on time.
Our work focused on helping the organization slow things down long enough to define what they actually needed, understand the options available in the market, and evaluate solutions in a structured and defensible way. By the end of our engagement, leadership had a clear understanding of the solutions and suppliers who could support them and renewed their confidence that their payroll and HR foundation could support both current operations and future growth.
When Vendor Oversight Needed to Be Practical, Not Bureaucratic
In regulated and risk sensitive environments, vendor management often becomes either overly complex or dangerously informal. One organization engaged us because their existing approach no longer reflected the risk profile of the business.
Onboarding was heavy and repetitive, ongoing oversight was inconsistent, and ownership across teams was unclear. Rather than adding more process for the sake of it, the focus has been on creating a practical, right sized framework that aligns with how the organization actually operates. The goal is clearer accountability, better visibility, and stronger governance without slowing the business down.
When Core Payment Infrastructure Needed to Become More Resilient
We are currently supporting an organization that recognized its payment platform needed to become more resilient, streamlined, and automated, without sacrificing risk and regulatory compliance. The risk was not hypothetical. It was operational, regulatory, and reputational.
Manual processes, limited redundancy, and growing complexity had introduced potential concern across the organization. Leadership understood that continuing as is was not sustainable, but moving forward required careful, well informed decision making.
Our role has been to help bring structure and clarity to that decision. Through focused requirements gathering, market assessment across banks and fintech providers, and a disciplined evaluation process, the organization is developing a clearer understanding of its options and the trade offs involved. The outcome will be a stronger foundation for decision making around a platform that sits at the heart of the business, and confidence that resilience, automation, and compliance can move forward together.
When Project and Financial Visibility Needed to Improve
In another engagement, leadership was frustrated by how difficult it was to understand the financial health of active projects. Information existed, but it lived across too many spreadsheets, tools, and manual handoffs.
The challenge was not data availability, but coherence. By helping define what actually matters to their project and leadership teams and evaluating tools through that lens, the organization is moving toward a simpler, more integrated approach to project and financial management. The focus is on reducing friction for teams and giving leaders clearer, more timely insight to support better decisions.
The work above reflects what many leaders are facing right now. Complexity is not going away, but clarity is achievable with the right structure and support.
Most Popular Substack Articles of 2025
What We Kept Hearing From Leaders This Year
The IT ProcurePro Substack launched in April 2025 as a place to have more honest, practical conversations about procurement, technology, and decision making. What surprised us most was not just the growth, but how quickly the community engaged.
In less than a year, the newsletter grew to 1,251 subscribers, with 98 percent of engagement happening directly in your inbox and an average open rate close to 35 percent. That tells us leaders are not just skimming headlines. They are reading, reflecting, and applying what they learn.
The articles that resonated most were not the most technical. They were the ones that named real frustrations and helped leaders think more clearly about decisions they are accountable for.
Some of the most read and shared pieces included:
- How to Select ERP Software: https://theitprocurepro.substack.com/p/how-to-select-erp-software-a-guide?r=44n78
- How to Buy HR and Payroll Software: https://theitprocurepro.substack.com/p/how-to-buy-hrpayroll-software?r=44n78
- How to Negotiate Like a Pro: https://theitprocurepro.substack.com/p/how-to-negotiate-like-a-pro?r=44n78
- How Smart IT Leaders Evaluate RFPs: https://theitprocurepro.substack.com/p/how-smart-it-leaders-evaluate-rfps?r=44n78
- 8 Steps to Build a Winning IT RFP: https://theitprocurepro.substack.com/p/8-steps-to-build-a-winning-it-rfp?r=44n78
What these articles have in common is a focus on outcomes, not activity. They sparked thoughtful conversations with CIOs, CFOs, project leaders, and operators who are responsible for results.
We love Substack as a platform and the community that is forming here. In the year ahead, we are excited to continue evolving this space with more exclusive paid content, deeper training, and practical digital assets, tools, and templates.
Most Popular Videos of 2025
Where the Conversation Went Deeper
Video became an important means of reaching SMB leaders on YouTube this year. For many, it was an opportunity to explore topics in a deeper way, grounded in real experience rather than theory.
What resonated most was not polish or production. It was honesty. These videos worked because they addressed the questions leaders are actually asking behind closed doors.
The themes were consistent.
How do we avoid getting this wrong
How do we make better decisions with imperfect information
How do we protect the business while still moving forward
Some of the most watched and shared videos included:
- Writing Effective RFP Requirements: https://youtu.be/lkIpfooZ94E
- The Shocking Truth About Canadian Supply Chains: https://youtu.be/yNUfHuuCrAA
- How Canadian Businesses Can Respond to U.S. Tariffs: https://youtu.be/rcBjNAedHNw
- How to Reach a Fair Market Deal: https://youtu.be/4J-Gup_ngww
These videos resonated because they reflected real world complexity. They did not offer shortcuts or silver bullets. Instead, they helped leaders think more clearly, ask better questions, and avoid decisions they would later have to unwind.
Looking Ahead to 2026
As we move into 2026, the pressure on leaders is not easing. Budgets remain tight. Risk expectations are higher. And the margin for error continues to shrink.
The opportunity lies in doing fewer things better. In being more intentional about problem definition, governance, and decision making before technology or suppliers enter the conversation. And in building internal capability alongside external solutions.
In the year ahead, we will continue focusing on practical guidance, deeper insight, and tools that help leaders move forward with confidence. That includes more in depth content on Substack, expanded training, and hands on resources designed to support real world decision making.
Thank you for reading, watching, and being part of this community. The conversations you have with us shape the work we do and the direction we take. We look forward to continuing the journey with you in 2026.
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