In Staffing, the Exit Clock Starts the Day You Open the Doors

Too many owners treat selling like a light switch, flip it when you’re ready. But real value isn’t built at closing. It’s built in the trenches, long before the first buyer ever knocks.

The truth?
Great exits are the result of years of discipline:

  • Building systems that don’t rely on you.
  • Hiring people who can lead without you.
  • Landing contracts that keep renewing—even when you’re golfing.
  • Making decisions that increase transferable value, not just short-term profit.

It’s not about timing the market. It’s about being ready when the timing finds you. Buyers reward readiness, not effort.

And in staffing, readiness means:

  • Clean books.
  • Recurring gross profit.
  • Low churn.
  • Documented process.
  • Clear scale potential.

These are the currency of a strong multiple. You’re always one recession, client loss, or internal resignation away from sliding backward, and losing ground you can’t easily recover.

So if you think your exit is “someday,” start acting like it’s already on the calendar. Because it is. You just haven’t been told the date yet.

Build like you’re not selling.
Prepare like you are.
Win either way.

Thinking of selling your staffing firm someday? Then get started today.

We help staffing firm owners turn uncertainty into strategy, and strategy into strong exits.
No guesswork. No panic. Just a business that’s ready when the time comes.

We engineer the kind of exits that don’t “just happen”, they work. Let’s talk now, so you’re ready when the moment finds you.


Schedule a confidential valuation or reach out directly, no pressure, just clarity.

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Working IN vs. ON Your Business: You Might Be the Problem

“In” vs.” On”?  The Hard Truth for Staffing Company Owners: Maybe You’re the Problem.

As an Owner/Leader, you pour your energy into growing your business. But here’s the paradox: the very hands-on approach that built your success can become your biggest obstacle, especially when preparing for growth or an eventual sale. Buyers aren’t just looking for a profitable business; they’re looking for one that can thrive without you.

Transitioning from working “in” the business to “on” it is a critical shift that separates good Owner/Leaders from great ones. Working on the business means focusing on high-level strategy, growth opportunities, and building systems that allow the organization to thrive independently of your daily involvement. Here are 8 practical steps to make the leap and set your business up for long-term success, whether you’re scaling for growth or positioning for a sale.

1. Delegate Decision-Making Authority

  • Identify key managers and empower them to own decisions in their areas of expertise. Start with smaller decisions and build up to more critical ones.
  • Use delegation as a coaching opportunity, providing feedback and guidance to help your team grow in confidence and capability.

2. Document Core Processes

  • Focus on documenting high-level operational, financial, and strategic workflows to ensure consistency and scalability. For example, create detailed playbooks for client onboarding, weekly revenue reporting, and sales pipeline management, key decision-making frameworks and processes critical to staffing firms looking to maintain consistency and growth.
  • Use tools like playbooks or checklists to make these workflows accessible and easy for your leadership team to follow, reducing dependency on you.

3. Diversify Client Relationships

  • Assign key clients to team members and ensure they take the lead in meetings, communication, and account management.
  • Develop a system where no single person (including you) holds more than 20% of client relationships to minimize risk.

4. Build Leadership Depth

  • Identify high-potential employees and invest in their development through mentorship, leadership training, and stretch assignments.
  • Cross-train your leadership team to ensure they can cover multiple roles if needed, demonstrating stability to potential buyers.

5. Shift Focus to Strategy

  • Dedicate specific time each week to focus solely on high-level goals, market trends, and growth opportunities rather than operational tasks.
  • Use group strategic planning sessions and an Advisory Board to align your team around long-term objectives and track progress.

6. Adopt Scalable Systems

  • Implement automation tools for repetitive tasks like payroll, invoicing, and scheduling to free up time for strategic work.
  • Invest in robust ATS, CRM, and AI-driven platforms to improve efficiency and support growth in staffing operations.

7. Create a Transition Plan

  • Define a clear timeline and roadmap for your exit, including milestones for shifting responsibilities to your team.
  • Share the plan with key stakeholders early to ensure alignment and minimize disruptions during the transition.

8. Make Yourself Replaceable

  • Gradually step back from daily operations, starting with minor tasks and moving toward critical functions over time. For example, begin by delegating recurring tasks like weekly reports within the first six months, then progress to strategic responsibilities such as client negotiations over the next year.
  • Position yourself as a mentor and advisor rather than the go-to problem solver, ensuring the business thrives without your constant involvement.

The Bottom Line

The paradox of Owner/Leadership is this: the more indispensable you are, the harder it is to scale or sell your business. For example, we’ve seen deals fall apart when buyers realize the owner is the only one maintaining client relationships or making critical decisions. Buyers don’t want to inherit a dependency, they want a business that runs on systems, not a single person. Great Owner/Leaders focus on building businesses that can thrive without them.

By following these 8 steps, you’ll set the foundation for a business that’s not only resilient and scalable but also positioned to thrive, with or without you at the helm.

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Cybersecurity in Staffing Industry Mergers and Acquisitions

By: Brian Kennedy

 

What if a $30 mistake cost you millions and killed your M&A deal?

It sounds extreme, but it happens more often than you’d think, especially when it comes to cybersecurity. A small vulnerability that seems insignificant can open the door to catastrophic consequences. Just ask the owner of a staffing company who was on the verge of closing a lucrative deal after years of hard work, only to see everything fall apart, because of a fish tank thermometer. 

The company had a beautiful saltwater aquarium in its office, and the owner installed a WiFi-connected thermometer to monitor the water temperature remotely. What he didn’t realize was that the device had no security controls and was connected to the company’s network. A hacker exploited this tiny vulnerability, gained access to the firm’s entire system, and deployed ransomware, locking down all their data, including payroll records, candidate information, and client contracts.

The company was forced to pay the ransom, but the damage was done. The buyer walked away from the deal, citing cybersecurity negligence as a major risk factor. The seller’s firm, once highly valuable, had lost millions in potential deal value over a $30 mistake.

This is not a hypothetical scenario. It really happened. And it underscores why cybersecurity is no longer just an IT issue, it’s an M&A dealbreaker.

 

Meet the Experts

To explore how cybersecurity impacts staffing M&A and what firms must do to protect themselves, I spoke with two of the leading experts in cybersecurity and enterprise architecture from Charter, a company which has driven successful digital transformations for clients globally since 1997.

Mike Glover – One of Canada’s most highly regarded enterprise architects, with deep expertise in business strategy, technology integration, and large-scale cybersecurity transformations. He has advised companies facing high-stakes M&A transactions where data integrity and risk management are paramount.

Krisann McDonnell – An M&A and cybersecurity leader specializing in assessing and mitigating risks in high-value transactions. Holding TOGAF, CISM, and NIST certifications, she leads security practice at Charter and works directly with firms to uncover hidden vulnerabilities and ensure compliance.

Both Mike and Krisann have seen firsthand how cybersecurity can turn an acquisition from a growth opportunity into a financial and operational nightmare.

What This Series Will Cover

Over the next four articles, we’ll take a deep dive into the most critical cybersecurity challenges facing staffing firms in M&A transactions:

  • Why Cybersecurity is Now a Dealbreaker in Staffing M&A – Understanding how cyber risks influence valuations and transaction terms.
  • Hidden Cybersecurity Risks in Staffing Acquisitions – Identifying the most overlooked vulnerabilities that could compromise a deal.
  • Post-Acquisition Cybersecurity Integration – Addressing challenges in merging security systems and ensuring a smooth
  • How to Strengthen Cybersecurity Before Entering the M&A Market – Practical steps staffing firms can take to protect themselves and enhance their marketability.

Cybersecurity is no longer optional in staffing M&A. It is a core business risk that must be addressed proactively. By leveraging the expertise of Mike Glover and Krisann McDonnell, this series will equip staffing firm owners, buyers, and investors with the critical insights needed to execute secure and successful transactions.

Keep reading for Part 1, where we explore why cybersecurity has become a deciding factor in staffing M&A deals.

 

Part 1 – Why Cybersecurity is Now a Dealbreaker in Staffing M&A

Mergers and acquisitions in the staffing industry have always been driven by financial performance, client contracts, and operational efficiency. However, in today’s market, cybersecurity has become a major factor in deal success or failure. Buyers are scrutinizing security postures more than ever, and firms with weak cybersecurity protocols are increasingly facing reduced valuations or even deal cancellations.

To understand why cybersecurity is now a make-or-break issue in staffing M&A, I sat down with Mike Glover, one of Canada’s most experienced enterprise architects and a leader in cybersecurity for M&A transactions, and Krisann McDonnell, an M&A and security expert at Charter.

Brian Kennedy: Mike, cybersecurity wasn’t always a top priority in staffing acquisitions. What changed?

Mike Glover: “A few years ago, buyers treated cybersecurity as an IT issue they could deal with after the acquisition. That’s no longer the case. Now, buyers want proof of strong security practices before closing a deal. If they uncover security gaps, they’ll either walk away or use them as leverage to lower the valuation.”

Brian: Why is cybersecurity an even bigger concern in staffing M&A than in other industries?

Mike: “Staffing firms handle enormous amounts of personally identifiable information: candidate resumes, payroll details, client contracts. If that data gets compromised, the entire business model is at risk. A breach doesn’t just impact one company; it can expose thousands of candidates and clients. Buyers don’t want to inherit a data security mess, and they’re going to pay less, or not buy at all if they sense risk.”

Brian: So how does cybersecurity affect valuation in real-world deals?

Krisann McDonnell: “Buyers aren’t just looking at EBITDA anymore. Cybersecurity risk is now a major factor in valuation. A firm with a strong security posture can command a premium price, while one with poor security might see its valuation drop overnight. I’ve seen firms lose millions in potential deal value simply because they didn’t have proper security controls in place.”

Mike: “I worked on a deal where the seller assumed security wouldn’t impact valuation, but when the buyer’s tech team did a deep dive, they found unencrypted payroll records and no multi-factor authentication. The buyer immediately cut their offer by 20%. The seller was blindsided, but in today’s market, buyers aren’t willing to take that risk.”

Brian: What security red flags are most likely to make buyers reconsider a deal?

 Mike: “There are a few major ones:

  • Outdated software – Staffing firms often use legacy applicant tracking and payroll systems that lack modern security controls.
  • No multi-factor authentication (MFA) – If employees can log into critical systems with just a password, it’s an easy target for attackers.
  • Third-party vendor risk – Many staffing firms use third-party providers for payroll, background checks, and CRM tools. If those vendors have weak security, the risk extends to the buyer.”

Krisann: “I’d add past security incidents to that list. A lot of sellers don’t realize that previous breaches, even if they were resolved, can still impact valuation. Buyers want full disclosure, and if they find out about a breach the seller didn’t mention, it immediately raises trust issues.”

Brian: So for staffing firms thinking of selling, what should they do now to avoid cybersecurity hurting their valuation?

Mike: “Start preparing early. Sellers should:

  1. Conduct a cybersecurity audit before a buyer Fixing problems before due diligence prevents last- minute deal surprises.
  2. Ensure regulatory Staffing firms operate across multiple jurisdictions, and buyers don’t want compliance headaches.
  3. Harden access controls. Remove ex-employee access to critical systems and require multi-factor authentication for sensitive data.”

Krisann: “Also, be ready to prove your security maturity. Buyers love seeing a cybersecurity due diligence package that outlines your policies, recent audits, and security improvements. It signals that security is a priority, which builds confidence and protects valuation.”

Brian: Final thoughts? What should staffing firms take away from this conversation?

Mike: “Cybersecurity isn’t just an IT issue anymore. It’s an M&A deal factor that can determine whether a transaction moves forward or collapses. Sellers who ignore it risk losing millions.”

Krisann: “Security preparedness isn’t just about avoiding penalties, it’s an opportunity to increase valuation and buyer confidence. The firms that address cybersecurity early will have the most leverage when negotiating a deal.”

Conclusion

Cybersecurity is no longer optional, it’s mandatory in today’s M&A environment. For staffing firms looking to enter the market, taking proactive steps to strengthen cybersecurity before the process begins can make a world of difference.

By conducting audits, upgrading systems, training employees, and ensuring compliance, firms can increase their marketability, protect their valuation, and set themselves up for a successful transaction.

Take Action Now.

If you’re considering selling your staffing firm, don’t let cybersecurity be the reason you lose value or delay your deal. The risks you overlook today could be the very reason your deal falls apart tomorrow.

As someone who specializes in selling staffing companies, I can tell you that the firms that address cybersecurity issues upfront are the ones more likely to get top dollar. It’s a marketable characteristic of your enterprise. If you want to make your business as attractive as possible to buyers, it’s crucial to address any cybersecurity vulnerabilities now.

Charter can make that process easier. They offer confidential cybersecurity assessments that help firms identify weaknesses, improve their digital hygiene, and ensure they’re ready for a successful transaction.

No cost. No pressure. Just real insights.

Schedule a complimentary, confidential consultation with Charter today: [kmcdonnell@charter.ca]

You can also ask us your M&A  questions: brian@racohenconsulting.com and be sure to check our Resources Library out here: https://racohenconsulting.com/library

Your business value depends on it.

 

In the Part 2, we’ll examine hidden cybersecurity risks in staffing acquisitions and how buyers can uncover potential threats before closing a deal.

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