MSP Staffing Challenges: How to Solve Them with Insights from Matthew Pincus on the WIN Podcast
Managed Service Providers (MSPs) are facing a staffing crisis. Finding, training, and keeping skilled technicians has become one of the biggest hurdles in the industry. Help desk roles, in particular, experience high turnover rates, employee burnout, and operational inefficiencies that leave MSPs scrambling to fill the gaps.
On a recent episode of the WIN Podcast, hosted by Carrie Richardson of Fox and Crow Group, Matthew Pincus, co-founder of Helpt, shared real-world insights on how MSPs can address these hiring and retention issues while improving service quality.
If your MSP is struggling with an overloaded support team, unreliable staffing, or recruitment bottlenecks, this article will outline actionable strategies that can help.
Why MSP Staffing Is More Challenging Than Ever
Hiring has always been a challenge, but for MSPs, the nature of the business makes it even harder. Technical support roles demand specialized knowledge, strong customer service skills, and the ability to handle high-pressure situations—yet these positions are often considered entry-level stepping stones rather than long-term careers.
According to Matthew Pincus, the frontline support role is particularly difficult to fill and retain:
“The hardest thing is hiring and retaining talent. The person who is that front line taking the call—it’s a thankless position. There’s no world in which that person makes everyone happy.”
This reality creates a constant cycle of hiring, training, and replacing staff, which drains an MSP’s resources and slows business growth.
Another key issue is that most technicians don’t want to stay in entry-level positions for long. Many expect a promotion within six months, leading to frustration when growth opportunities don’t come fast enough. MSPs often feel stuck between trying to develop talent in-house and facing constant turnover.
The result? Poor service quality, slow response times, and dissatisfied clients.
To solve these problems, MSPs need to rethink how they approach hiring, training, and team structure.
Outsourcing: A Scalable Solution for MSP Help Desk Support
One of the most effective ways MSPs can overcome staffing challenges is by outsourcing help desk functions to a trusted partner.
Rather than constantly recruiting and onboarding new hires, MSPs can tap into an established team of trained technicians who can handle support requests seamlessly.
How Outsourcing MSP Help Desk Support Helps
Pincus explains how Helpt is designed to fill this gap:
“Helpt is outsourced tech support. We provide services ranging from technical call answering—where a team takes inbound calls and does triage—to fully embedded technicians who handle level 1 tickets on behalf of our clients.”
This outsourcing model provides several key benefits:
✔ Reduces turnover headaches – No more constantly hiring and training new help desk staff.
✔ Improves service reliability – Clients get faster responses and more consistent support.
✔ Allows MSPs to focus on growth – Freeing up internal resources for higher-level projects.
By partnering with an outsourced provider like Helpt, MSPs can reduce operational stress and improve customer experience without being caught in the never-ending hiring cycle.
Building a Smarter MSP Hiring & Onboarding Process
For MSPs that prefer to hire in-house, strengthening the hiring and onboarding process is crucial to improving employee retention and long-term job satisfaction.
Best Practices for Hiring & Retaining MSP Staff
One of the biggest mistakes MSPs make is hiring reactively—only looking for staff when there’s an immediate need. This leads to rushed decisions and poor hires. Instead, MSPs should take a proactive approach by:
✔ Defining clear career paths – New hires should see long-term growth opportunities, not just a job.
✔ Providing competitive compensation & benefits – Attracting and keeping top talent requires a strong offer.
✔ Investing in professional development – Regular training and upskilling keep employees engaged.
Pincus highlighted how having a structured hiring strategy made a difference at Helpt:
“My co-founder, David, worked in recruiting before this, so he understands HR. When we needed consultants, we had the advantage of getting expert HR guidance from people who worked in both corporate and startup environments.”
MSPs without dedicated HR expertise may benefit from working with HR consultants or staffing specialists to optimize their recruitment processes. A well-structured hiring plan leads to better hires, longer retention, and a stronger team.
Balancing Speed & Strategy in MSP Growth
A common challenge for MSPs is balancing rapid growth with operational stability. Many business owners feel pressured to hire quickly and implement new tools immediately—but moving too fast can create more problems than it solves.
Why Strategic Hiring Matters
Pincus shared an example of how rushing a major system launch backfired:
“We launched an improved ticket management system, thinking we could spin it up overnight. But we didn’t put enough time into backend reporting. On day 1, we realized it wasn’t tracking billable time properly. That’s a massive problem in our business.”
This experience underscores the importance of strategic decision-making when it comes to staffing and operations. As Carrie Richardson pointed out:
“Yeah, I can hear Ian saying: ‘Slow is smooth, and smooth is fast.’”
For MSP staffing, this means:
✔ Don’t rush hiring just to fill seats – Prioritize quality over speed.
✔ Take time to implement efficient workflows – Ensure new hires have the tools they need.
✔ Build scalable systems that grow with your business – Avoid short-term fixes that create long-term problems.
By balancing speed and strategy, MSPs can grow their teams effectively without sacrificing service quality.
The Power of Community Engagement in MSP Hiring & Growth
One of the most underutilized strategies for MSPs is active engagement in industry communities. Many hiring and sales opportunities come from networking and building trust rather than traditional job postings.
How MSPs Can Build Trust in the Industry
Pincus shared how Helpt has built credibility in the MSP space:
“We’re in the MSP community, in Discords, on Reddits, on Slack—having real conversations. Not shilling, not selling, just engaging.”
For MSPs looking to expand their network and attract top talent, this means:
✔ Joining industry forums (Reddit’s r/MSP, Slack groups, Discord communities).
✔ Attending key events (ASCII, ChannelPro, IT Nation).
✔ Focusing on knowledge-sharing, not just selling.
By being present and engaged, MSPs can connect with potential hires and build a reputation that attracts top talent.
Learn More About MSP Staffing Strategies
To hear more insights from Matthew Pincus, check out the full WIN Podcast episode:
🎙️ Listen Now →
For expert consulting on MSP growth & marketing, visit:
💡 Fox and Crow Group
Want to connect with the experts?
🔗 Carrie Richardson
🔗 Matthew Pincus
