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Our Coaches

Get to know our team a little better

Jamison West

Jamison has been a serial entrepreneur for 25 years. He built Arterian (formerly JWCS), an MSP that he grew from a 1 man shop to 40 staff through both organic growth and the acquisition of 4 other IT Services companies.


He went on to Co-Found 3 SaaS companies including Teamatics, SmileBack, and TimeZest and currently serves as a fractional CEO for SmileBack and Chairman of TimeZest. He enjoys his role as a Strategic Coach and Consultant for several clients in the US.


His background includes:

  • Founding and operating companies in the SaaS and IT Services space

  • Participating in and moderating professional peer groups (HTG and EO)

  • Coaching and Consulting for organizations in the SaaS and IT Services verticals

  • Speaking on a range of topics from Cloud to M&A to People

  • Former EOS® Implementer

Jamison currently lives in Las Vegas, NV and travels constantly. 

Brett Jaffe

Over a period of 25 years, Brett built and sold three companies (including an MSP, cloud reseller, and digital forensics business), led hundreds of soldiers as an officer in the US Army, and built an international channel partner program from inception to over $30M in revenue.


Brett is an accomplished speaker, consultant, and advisor and has worked with hundreds of businesses in varying capacities, giving him a unique understanding of what it takes to succeed at varying levels of business growth.  Brett has also been involved in several M&A deals as a buyer, seller, and advisor.


He is excited to be a part of the talented team of coaches at ConnectStrat and looks forward to making a difference in the ITSP space helping others achieve their dreams.

Brett is a former EOS® Implementer and certified DISC trainer and continues to serve the IT community as CEO of audIT Sales Presentation System.

Brett is an avid skier and mountain biker.  He currently lives in beautiful Bedford, NH with his wife, two daughters, and slightly crazy dog.

Jason Knight

Jason Knight is an experienced leader with 30 years creating and managing companies in Information Technology, Software Development, Construction Technology, and Aviation industries.


Jason began his entrepreneurial journey in the mid-1990s when he founded an IT security group which he ultimately grew to over $30mm in revenue.


In 2005 Jason started a Houston based technology solutions provider which he grew to $50mm in revenue and in 2014 sold as part of a roll-up. While integrating the various companies involved in the roll-up it quickly became evident that there was a need for consistency in vision, execution, and culture, which lead him to EOS.


Since the conclusion of the roll-up integration, Jason has discovered his passion for working with other entrepreneurs to bring balance to their lives and help them achieve the most from their business using the Entrepreneurial Operating System.

Fred Jentgen

Fred grew up in Indiana as a young entrepreneur starting his own paper route, teaching tennis lessons at the neighborhood swim & tennis club, and coaching both swim and tennis teams that competed with other city clubs. He followed his father’s engineering footsteps, graduating with an Electrical & Electronics Engineering degree from Purdue University, May 1992.


Intel snatched Fred off campus and brought him to Phoenix, AZ, starting a fast-paced, exciting technology career as a sales & marketing leader. One of Fred's primary roles was working with the technology partner channel where he discovered his passion for IT entrepreneurship!   After a short side-step, where he spent 18 months as the VP of Marketing for Avnet, Fred decided to pursue working with technology entrepreneurs full-time.


Fred founded Unleashed Consulting Group LLC in Sept 2019 with a focus on helping technology businesses through Professional EOS® Implementation and Certified LifePlan Facilitation for leaders. In 2020, Fred joined forces with the ConnectStrat Team to scale vision, strategy, and execution services to the IT services industry.


Fred has been married 27 years to his high school sweetheart, Julie. They live in Phoenix, Arizona, with their three teenagers Tim, Ally, and Jared and a growing number of their extended family who love the Arizona outdoors.

Doug Hall

Doug Hall is a Professional EOS Implementer® with deep roots in the IT business. His career started at Burroughs Corporation (now UNISYS) in business computers and mainframes then he jumped into the young PC industry and managed business units for Entre Computer Centers and EDS. In the early 1980’s as a general manager at Entre’ he grew annual sales from $2 million to $12+ million while increasing technical capabilities in software and networking solutions. At EDS his team delivered perhaps the first Managed Services for PCs in the IT services industry. At Intermec Technologies (now Honeywell AIDC) he managed $50+ million product business units that developed barcode and RFID hardware and software sold through the VAR channel.

Doug is passionate about helping business owners get what they want from their business. He serves as Professional EOS Implementer® with several Seattle-area MSPs and concentrates on the Pacific Northwest for in-person implementation. 

Doug is a Board Director for Ventures, a Seattle-based nonprofit that trains and enables underprivileged people to start their own business. He is an accomplished public speaker on leadership, management, team health and alternative business exit.  Doug lives on beautiful Lake Union in the heart of Seattle and is a golfer, hiker, boater and certified ski instructor.

Glenn Bergsma

From tech startups and SME’s to large global corporations across Australasia and North America, Glenn has supported leaders and their companies to achieve high-value strategic growth for over 15 years.

With that demonstrated success, Glenn's deep insight and breadth of international and cross-cultural experience have resulted in accelerated leadership and business performance for his highly motivated clients. Glenn’s strategic approach and practical leadership training have supported authentic performance assessment, planning and execution.

Glenn’s expertise includes:


  • Strategy & Execution Coaching

  • Leadership Training & Development

  • High Performing Teams & Culture Development

  • Change Management & Continuous Improvement

  • Executive Leadership Coaching

  • Governance Development & Board Directorships

  • Keynote Speaking & Facilitation


Glenn currently lives in Perth, Western Australia with his wife, Allie and two sons, Chase & Jack. When he’s not working, he’s fishing, cooking bbq, throwing weights around the gym, pretending to be a rock star on the guitar or relaxing with his family and friends.

Richard Anderson

As an avid reader, Rich represents a hand-picked, greatest-hits, best-practice amalgamation of Michael Gerber's E-Myth; Patrick Lencioni's focus on teams, culture and leadership; Marcus Buckingham's focus on what great teams do differently and Simon Sinek's "Start with Why". Add in a layer for Gino Wickman's Traction and the Wickman/Paton co-authored, "Get a Grip" -- and you have a blended leadership development approach that can accomplish great things - while also honoring culture and vision.

Rich has worked with hundreds of MSP industry leaders and believes that one of the greatest responsibilities of leaders is developing new and existing leaders. His greatest passion is facilitating that leadership journey.  

Rich was also a former public accountant - so he believes that a healthy layer of accountability is needed to obtain measurable Traction -- and he will help your organization create a culture of accountability by measuring what matters - and then 'managing to the numbers'. summarized list of Rich's background is included below:

  • Executive Coach (5 years)

  • Advisory Board member (10+ companies)

  • Executive Peer Group Facilitator (10 years)

  • Executive Peer Group Member (12 years)

  • Merger & Acquisition (5 personal deals; MANY consulted deals)

  • Financial Analyst (former public accountant)

  • Motorcycle & Mountain Biking Enthusiast.

  • Son. Brother. Husband. Father.


Rich currently lives in Minneapolis, MN with his wife and daughter.

Gerwai Todd

Gerwai Todd is a seasoned executive consultant and StratOp-certified business strategist who works with MSPs and business owners to build high-performance teams and drive operational efficiency. Gerwai has 25 years of expertise in mergers and acquisitions, worked with hundreds of MSPs, and is an entrepreneur himself. He knows firsthand that the definition and execution of a strategic plan is critical to reducing operational cost, simplifying corporate structure, and increasing performance. 


Gerwai recently spent 10 years on the leadership team at ConnectWise and assisted in the hyper growth from 50 employees to 1200+ before being acquired by Thoma Bravo for $1.5 billion.


Gerwai is certified in the Patterson Group StratOp Strategic Planning Framework, a CEO Peer Group Facilitator, and serves as a Board Member & Capital and Investor Relations Committee Chairman of the Tampa Bay Wave tech incubator.


Gerwai holds a Bachelor of Science in Business Administration with a minor in economics from the University of Oregon. 

Jena Knight

Jena Knight is an experienced Social Worker and Kolbe Certified Consultant that focuses on bringing” Healthy” to the workplace. Jena is able to help organizations release and leverage the natural instincts of their current talent force through the Kolbe System™. With a special emphasis on complementing the EOS process, Jena is able to help leaders and teams  leverage their natural instincts to:


  • Be more productive

  • Reduce stress

  • Get better results with less effort 

  • Enjoy greater personal satisfaction


Recently, Jena completed her Kolbe Youth Specialist ( KYS- 6/2020) credential to work with students ages 10+.  As a KYS, Jena is able to help students identify their natural strengths and use them to achieve more naturally with less stress, grow in confidence and purpose, and set a course towards the future. Jena is excited to add a dimension of “Whole Health” that extends beyond the workplace to families. 

We are growing!  Are you a former ITSP Owner with leadership, coaching, and facilitation experience looking to join our team?  Please reach out to see if there is a fit.