Strategic Coaching Program

Design a comprehensive operating system to transform your IT/MSP business with industry experts

 What got you here, won't get you there. 
 We know, because we've been there. 

Each member of our team brings a wealth of leadership, expertise, and industry experience - because we have suffered through the pain you are currently experiencing. We have bought & sold ITSPs, built channel programs, and run large divisions. We've worked with hundreds of companies.

More importantly, we are here to share our wisdom from those experiences.


Our coaching philosophy revolves around "The Four Pillars"



We coach & train leaders on aligning teams to support one unified vision.



Working with your team to focus, prioritize & align on vision - to create a success strategy.



syncCreating discipline & accountability by executing to achieve every part of the vision.



global-business-team (1)Intentionally investing yourself in a way that is fulfilling, creating significant impact.

 At MSP+OS, we understand 
 the intricacies of the IT and   MSP  landscapes. 

Coaching isn't just generic advice; it's tailored guidance built upon years of industry-specific experience. With a focus on authenticity and results, our coaching methods are geared to drive transformative change, positioning leaders and their organizations for lasting success.


What's Included:

 MSP+OS Implementation 
  • >> Owners Session
  • >>

 Dedicated Integrator 
  • >> 
 Quarterly Meetings 
  • >> 



One Solution, Customized for Your Company

MSP+OS provides tailored solutions to meet the diverse needs of fast-growing technology companies.

is an invitation to engage deeply with a dedicated coach, providing personalized insights over a year-long engagement. Owners and Executive will find solace in monthly one-on-one sessions, quarterly planning, and regular check-ins that prioritize their company's unique dynamics & challenges. 

For those who thrive in a collaborative setting, our Executive Accelerator Bootcamp brings together a community of coaches and experts. Over an intensive 12-week program, Business Executives and their second-in-command participate in a mix of group coaching sessions, benefiting from the collective wisdom of multiple companies. The journey commences with a two-day in-person meeting, followed by nine virtual sessions that promise not just learning, but an exchange of experiences & best practices. 


Want To Meet Our Strategic Coaches?

Find out about the services we offer by clicking the link below to get in touch with our team.


 Jamison has been a serial entrepreneur for 25 years. Formerly 
 an EOS® Implementer, has deep roots in the IT/MSP community. 

Participating and moderating professional peer groups (HTG and EO), coaching and consulting across various SaaS and IT companies, and speaking on a range of topics from Cloud to M&A.  Jamison built Arterian (formerly JWCS), an MSP that he grew from a 1 man shop to 40 team members through both organic growth and the acquisition of four IT Services companies.

He went on to co-found 3 SaaS companies including Teamatics, SmileBack, and TimeZest and currently serves as Co-Founder and Chief Strategy Officer of TimeZest -- and now, MSP+OS.


 With a rich journey spanning over 30 years, Brett Jaffe has 
 launched from inception to sale three pioneering ventures. 

Brett founded an MSP, a compliance-based cloud solution, and a cutting-edge digital forensics enterprise. Brett stands out as a seasoned speaker, consultant, and trusted advisor. His interactions with a multitude of businesses have granted him a panoramic perspective on the nuances of diverse business growth stages. His adeptness in M&A has seen him don multiple hats, be it as a purchaser, vendor, or a guiding counselor.

His prowess is further highlighted through 3 successful business exits and the architecture of an international channel partner program, ushering it from a mere idea to a staggering $30M in recurring revenue in under 5 years.


 Brian has been part of the Managed Services industry since the 
 early 2000s. He earned both his Bachelor’s and MBA from 
 Baylor University. 

He’s been everything from a technician to Ops Manager to CFO to CEO. He has grown multiple MSPs to over $5 million in revenue and run MSPs in excess of $15 million in revenue. Brian has a thorough understanding of all the ins and outs of running a highly successful MSP. More importantly, he understands how to help MSP leaders get the most from their business.

His expertise in leadership and coaching can help any MSP owner or CEO achieve the results they want in both business and life.


We get it.

Identifying the specific areas where improvement is needed can be challenging. Especially when you are deeply involved in your own operations.

 This is where MSP+OS can provide valuable expertise. 

As consultants, we bring an experienced and objective perspective to your business. Our team will conduct a comprehensive evaluation of your current systems, operations, and processes. By gaining a deep understanding of your business, we can identify potential blind spots.

Once we identify areas for improvement, we can work collaboratively with your team to create a plan of action.

 Our goal is to help you discover and implement 
 a better way of doing things.

While you may not be aware of all the possibilities yet, together we can uncover areas for improvement and drive your business forward. 


"What is executive coaching and how does it differ from traditional training?"

Executive coaching is a personalized, one-on-one approach to professional development. Unlike traditional training that follows a set curriculum for all, executive coaching is tailored to the individual's unique needs, challenges, and goals. It's about unlocking potential, refining leadership skills, and navigating complex business situations with expert guidance.

"Who can benefit from executive coaching?"

While executive coaching is often associated with top-tier leadership, it's beneficial for anyone in a managerial or leadership position. Whether you're a CEO, department head, or an emerging leader, coaching can provide insights, tools, and strategies to enhance your leadership capabilities and achieve organizational goals.

"How long does a typical coaching engagement last?"

Our Growth Accelerator Coaching program has a 12-month minimum engagement. However, the actual duration can vary based on individual needs and objectives. Some executives might seek coaching for specific short-term goals, while others engage in a more extended relationship for ongoing development.

"What's the difference between Growth Accelerator Coaching and Growth Accelerator Bootcamp?"

Growth Accelerator Coaching is a one-on-one, tailored experience with a dedicated coach focusing on your company's unique challenges. In contrast, the Growth Accelerator Bootcamp is a group setting where multiple companies come together for collective learning, sharing experiences, and insights over a 12-week intensive program.

"Will the content discussed in our coaching sessions remain confidential?"

Absolutely. Confidentiality is paramount in executive coaching. Anything discussed between the coach and the executive remains private, ensuring a safe and open environment for candid conversations and genuine growth.

"How do I know if executive coaching is right for me or my organization?"

If you or your leadership team is facing challenges in decision-making, strategy formulation, team dynamics, or simply want to refine leadership skills for the next phase of business growth, executive coaching might be an excellent fit. It's about recognizing the need for an external perspective and expert guidance to reach new heights.

Blog posts

Navigating the Unique Features of Wise-Sync: A Guide for Efficient ConnectWise Integration
5 minute read
In the realm of professional service automation (PSA) and accounting integration, Wise-Sync stands out as a beacon of efficiency...
ConnectWise & QuickBooks: Our Answers to Your Top Questions
3 minute read
Are your revenue numbers integrating into QuickBooks the way you want them to? This post will highlight ConnectWise and...
Unleashing the Full Potential of Your RMM: Advanced Alerting
7 minute read
In the rapidly evolving world of IT and Managed Service Providers (MSPs), optimizing your Remote Monitoring and Management (RMM)...