Hiring is one of the most important growth decisions an MSP owner can make. The right person can create capacity, improve client experience, and support a stronger team. The wrong fit can create pressure across operations, profitability, and culture.
In a recent Stride Live, Casey Seaborn sat down with Terrell “TJ” Jackson, President and Founder of Culture Fits, to discuss what MSP owners should consider before making their next hire. TJ brings more than 15 years of experience helping MSPs and MSSPs find talent that fits both the technical needs of the role and the culture of the business.
The conversation focused on a practical question many MSP owners face: How do you know whether you are hiring the right person, for the right seat, at the right time?
Below are the key takeaways from the conversation.
1. The Most Expensive Hire Is Not Always the Highest Paid
When MSP owners think about the cost of a bad hire, salary is often the first number that comes to mind. But as TJ explained, the most expensive hire is not always the person with the highest compensation. It is often the wrong person in the wrong seat.
That cost can show up in several ways:
- Lower utilization
- More escalations
- Project delays
- Reduced gross margin
- Team frustration
- Client trust issues
For MSPs, hiring is not only a people decision. It is an operational and financial decision.
Key Insight: A bad hire does not stay isolated to one role. It can affect the team, the client experience, and the numbers.
2. Culture Fit Is About Accountability, Not Perks
Culture is often misunderstood. It is not just about benefits, team lunches, or whether people enjoy working together.
For MSPs, culture is about how the team shows up for clients, how they take ownership, and how they operate in a high-accountability environment. TJ emphasized that every hire either supports the culture or creates unnecessary friction within it.
This matters because MSP teams rely heavily on collaboration. When one person does not align with the company’s values or working style, it can create pressure across the entire department.
TJ shared that when someone complements the company’s core values, they are more likely to integrate well with the team and support the broader strategy of the business.
Tip: Before evaluating whether someone is a culture fit, define what your culture actually requires. For MSPs, that often includes ownership, accountability, communication, and client empathy.
3. Resumes Do Not Tell the Whole Story
Technical skills matter, but they are not enough.
TJ pointed out that many MSPs “interview for the resume and not for the role.” In other words, they focus heavily on past experience and technical qualifications without fully evaluating the behaviors required for success in the seat.
For example:
- A service desk engineer needs patience, empathy, and communication skills.
- A project engineer needs structure, planning, and follow-through.
- A sales hire needs relationship-building ability, curiosity, and alignment with the MSP’s growth model.
A candidate can look great on paper and still struggle if their working style does not match the realities of the role.
4. Bad Hires Eventually Show Up in the Financials
One of the most practical parts of the conversation was the connection between hiring and financial performance.
TJ explained that bad hires often show up in the numbers through lower billable utilization, more work being escalated to senior engineers, longer project timelines, and a lower effective hourly rate.
Casey added that Stride often sees this reflected in areas like:
- Poor time tracking
- Underutilized technician labor
- Labor not properly allocated to cost of goods sold
- Projects that are underscoped or over-resourced
- Administrative roles without clear accountability
- Lack of departmental reporting or itemized P&Ls
When those issues are not tracked clearly, an MSP owner may know something feels off but not be able to see exactly where margin is being lost.
Tip: If profitability is not improving as revenue grows, look closely at labor utilization, project margin, role clarity, and reporting structure.
5. Before You Hire, Decide Whether the Problem Is the Role or the Process
Not every hiring problem is solved by adding another person.
Casey and TJ discussed the importance of asking whether the business truly needs a hire, or whether it first needs a better process. This is especially important for MSP owners who are trying to build a second layer of leadership, offload operations, or scale beyond founder-led decision-making.
If the role is unclear, the onboarding is weak, or success has not been defined, even a capable hire may struggle.
TJ closed the conversation with a strong reminder: MSP owners need to have honest conversations about burnout, leadership gaps, and when to hire versus when to fix the process.
6. Define Success Before You Fill the Seat
One of the clearest takeaways from the conversation was the importance of defining success upfront.
Before hiring, MSP owners should be able to answer:
- What problem is this role solving?
- What does success look like in 30, 60, and 90 days?
- What metrics will show whether this person is working out?
- What traits matter most in this role?
- What support does this person need to succeed?
- How will this role affect client experience, team capacity, and margin?
Without those answers, it becomes difficult to evaluate whether the hire is actually on track.
Casey also emphasized the importance of building systems that help new hires succeed. Instead of assuming someone will “figure it out,” MSPs need processes, training, and check-ins that create a clear path forward.
Tip: A strong onboarding process protects both the company and the employee. It gives the new hire clarity and gives the owner a better way to measure progress.
7. The Right Hire Takes Ownership of Outcomes
Toward the end of the conversation, TJ described what a good MSP engineer looks like.
The right hire combines technical curiosity, ownership mentality, accountability, and client empathy. The best engineers do not just solve tickets. They take responsibility for the outcome and make sure the client feels supported along the way.
That mindset matters across the entire organization.
Whether the role is technical, operational, administrative, sales-focused, or leadership-oriented, the right person should help the business create more clarity, not more complexity.
Final Thoughts
Hiring is one of the biggest levers MSP owners have for growth. But it is also one of the easiest places to create unnecessary complexity if the business does not have the right structure in place.
A bad hire can affect utilization, margin, morale, project delivery, and client trust. But the solution is not to avoid hiring. The solution is to hire with more clarity.
That means defining the role, understanding the traits required for success, building strong onboarding systems, and knowing when the issue is a hiring need versus a process problem.
For MSP owners, the goal is not just to fill a seat. The goal is to build a stronger business.
Watch the Replay
Want to hear the full conversation with Casey Seaborn and Terrell “TJ” Jackson?
Watch the full Stride Live replay here:
https://www.linkedin.com/events/stridelive-thetruecostofabadhir7435361219307372544/theater/
About Culture Fits
Culture Fits is a national staffing partner serving the MSP and MSSP space. Led by Terrell “TJ” Jackson, Culture Fits helps MSPs identify candidates who align with both the technical requirements of the role and the culture of the organization. Their approach focuses on helping MSPs find the right person for the right seat, with an emphasis on operational fit, accountability, and long-term growth.
Learn more about Culture Fits:
https://www.culture-fits.com
About Stride Services
Stride Services is a comprehensive financial solutions provider specializing in outsourced bookkeeping, accounting, tax, and advisory services for Managed Service Providers. Stride helps MSP owners gain financial clarity, improve decision-making, and build a stronger foundation for growth.
If you’re interested in being a featured guest on Stride Live or if there’s a subject matter expert you’d like us to interview, please CLICK HERE and let us know.
Show Notes
Host: Casey Seaborn, Stride Services
Guest: Terrell “TJ” Jackson, President and Founder of Culture Fits
Topic: The True Cost of a Bad Hire in an MSP
Replay:https://www.linkedin.com/events/stridelive-thetruecostofabadhir7435361219307372544/theater/
