{"id":68751,"date":"2026-03-05T14:40:09","date_gmt":"2026-03-05T22:40:09","guid":{"rendered":"http:\/\/www.enxmag.com\/twii\/?p=68751"},"modified":"2026-03-05T14:40:11","modified_gmt":"2026-03-05T22:40:11","slug":"the-costs-to-be-the-boss-investments-necessary-to-sustain-managed-it-offering","status":"publish","type":"post","link":"https:\/\/www.enxmag.com\/twii\/feature-articles\/2026\/03\/the-costs-to-be-the-boss-investments-necessary-to-sustain-managed-it-offering\/","title":{"rendered":"The Costs to be the Boss: Investments Necessary to Sustain Managed IT Offering"},"content":{"rendered":"\n
\"\"<\/figure><\/div>\n\n\n\n

Set it and forget it? When it comes to being a managed IT provider, that\u2019s a charming thought. But as we all know, being successful and keeping up to date with the offering is a never-ending commitment to investments in time and resources. Providers are well aware of this fact when they embark on the king of managed services.<\/p>\n\n\n\n

The road to ROI scares off plenty of would-be providers, but a deliberate and well-planned blueprint, supported by advice from consultants and peer\/association colleagues, can be the catalyst to move forward. But after the managed services honeymoon ends, there are other considerations to bear in mind. As we open the March State of the Industry report on managed IT, our dealer panel adds insight into the continuing investments, from training to onboarding specialists and portfolio additions.<\/p>\n\n\n\n

\"\"
Travis Jack, Fraser\/Watchkeep<\/figcaption><\/figure><\/div>\n\n\n\n

In the past two years alone, Watchkeep\u2014the managed IT arm of Fraser Advanced Information Systems of West Reading, Pennsylvania\u2014dedicated significant investments, particularly in its cybersecurity portfolio. Travis Jack, director of service delivery, points out that due to the significant budgetary constraints that SMBs must reconcile, his company is prudent in vetting every new service on both its technical merits and measurable business impact.<\/p>\n\n\n\n

Identity protection, an area that is one of the most exploited vulnerabilities in the SMB space, has been a growth area for Watchkeep. To that end, they’ve added advanced identity and access management tools, in addition to capabilities around zero trust architecture, compliance management and ongoing risk assessment.<\/p>\n\n\n\n

\u201cWe\u2019ve also partnered with a trusted third-party provider to offer penetration testing, giving our clients deeper visibility into system weaknesses before attackers can exploit them,\u201d Jack said. \u201cThese aren\u2019t just upgrades; they\u2019re essential steps in helping our clients qualify for insurance, meet compliance standards and reduce the risk of costly downtime or data loss.<\/p>\n\n\n\n

\u201cAt Watchkeep, every investment ties back to outcomes. For clients that understand the link between cybersecurity and business performance \u2013 things like client trust, operational continuity and contract readiness \u2013 the value is clear. For those who haven\u2019t yet made that connection, we continue to educate, advise and lead them toward smarter, more sustainable decisions that strengthen their bottom line.\u201d<\/p>\n\n\n\n

Growth Markers<\/strong><\/p>\n\n\n\n

\"\"
Shelly Caldwell, Marco<\/figcaption><\/figure><\/div>\n\n\n\n

St. Cloud, Minnesota-based heavyweight Marco has pledged considerable resources to prepare for 2026 growth, notes Shelly Caldwell, managed service director. That includes expanding specialist roles, onboarding new technical expertise, and adding capabilities across cybersecurity, AI, modernization, and Insights\u2011based diagnostics.<\/p>\n\n\n\n

Among the highlights:<\/p>\n\n\n\n

  • Targeted upskilling programs<\/li>
  • Investments in engineers, analysts, and cybersecurity specialists<\/li>
  • New assessment tools and expanded Insights Platform functionality<\/li><\/ul>\n\n\n\n

    \u201cThis investment ensures we can support more customers, accelerate recurring revenue growth, and deliver faster, clearer recommendations,\u201d Caldwell said.<\/p>\n\n\n\n

    \"\"
    Keith Adams, Les Olson IT<\/figcaption><\/figure><\/div>\n\n\n\n

    Although not an MSSP, Les Olson IT of Salt Lake City takes great pains to ensure it maintains a front-line role when it comes to cyber protection. It begins during the onboarding phase, with a thorough sweep for old accounts, stale passwords and misconfigured or poorly configured protections, notes Keith Adams, vice president of IT.<\/p>\n\n\n\n

    Beyond bolstering its team and tools, the dealer has introduced local system management tools to all new managed IT accounts. \u201cWe have integrated the tools into the stack with the goal of hardening the customer\u2019s environment with safeguards that are set to remove local admin status, stop common exploits of normal system functions, as well as cross platform exploits,\u201d Adams remarked. \u201cWith that included platform, we have put numerous people through training and have reached the highest level of support for that product.\u201d<\/p>\n\n\n\n

    \"\"
    Jeff Dotzler, GFC\/Elevity<\/figcaption><\/figure><\/div>\n\n\n\n

    Education and certifications are budgeted annually to ensure the ability to meet client expectations, notes Jeff Doztler, president of Elevity, a division of Gordon Flesch Company in Madison, Wisconsin. The long-term strategy is to further develop a practice for those clients that require advanced compliance and governance.<\/p>\n\n\n\n

    \u201cRegarding the solution, we are constantly evaluating what is necessary to protect our clients as the threat landscape evolves,\u201d Doztler noted. \u201cOur primary investment has been in people and education with the right experience.\u201d<\/p>\n\n\n\n

    Deeper Dive<\/strong><\/p>\n\n\n\n

    \"\"
    Lindsay Usherwood, Usherwood Office Technology<\/figcaption><\/figure><\/div>\n\n\n\n

    For providers such as Usherwood Office Technology in Syracuse, New York, the main thrust has been expanding its portfolio beyond pure technology. One of the cornerstones has been attaining SOC 2 certification and fortifying specialized talent around security and compliance, notes Lindsay Usherwood, general counsel for the dealer.<\/p>\n\n\n\n

    \u201cSOC 2 forced us to document and operationalize what \u2018good\u2019 looks like: think documented controls, repeatable processes and real accountability, and thereby directly refining our consulting to clients,\u201d she noted. \u201cAt the same time, we solidified our midmarket co-managed product as a standalone business, as both our MIT clients grow, and we continue to grow across the northeast. By also investing in talent in the security and compliance space, we raised our internal standards and level of confidence we can offer the market.\u201d<\/p>\n","protected":false},"excerpt":{"rendered":"

    Set it and forget it? When it comes to being a managed IT provider, that\u2019s a charming thought. But as we all know, being successful and keeping up to date with the offering is a never-ending commitment to investments in time and resources. Providers are well aware of this fact when they embark on the king of managed services. The road to ROI scares off plenty of would-be providers, but a deliberate and well-planned blueprint, supported by advice from consultants and peer\/association colleagues, can be the catalyst to move forward. But after the managed services honeymoon ends, there are other considerations to bear in mind. As we open the March State of the Industry report on managed IT, our dealer panel adds insight into the continuing investments, from training to onboarding specialists and portfolio additions. In the past two years alone, Watchkeep\u2014the managed IT arm of Fraser Advanced Information Systems of West Reading, Pennsylvania\u2014dedicated significant investments, particularly in its cybersecurity portfolio. Travis Jack, director of service delivery, points out that due to the significant budgetary constraints that SMBs must reconcile, his company is prudent in vetting every new service on both its technical merits and measurable business impact. Identity protection, an area that is one of the most exploited vulnerabilities in the SMB space, has been a growth area for Watchkeep. To that end, they’ve added advanced identity and access management tools, in addition to capabilities around zero trust architecture, compliance management and ongoing risk assessment. \u201cWe\u2019ve also partnered with a trusted third-party provider to offer penetration testing, giving our clients deeper visibility into system weaknesses before attackers can exploit them,\u201d Jack said. \u201cThese aren\u2019t just upgrades; they\u2019re essential steps in helping our clients qualify for insurance, meet compliance standards and reduce the risk of costly downtime or data loss. \u201cAt Watchkeep, every investment ties back to outcomes. For clients that understand the link between cybersecurity and business performance \u2013 things like client trust, operational continuity and contract readiness \u2013 the value is clear. For those who haven\u2019t yet made that connection, we continue to educate, advise and lead them toward smarter, more sustainable decisions that strengthen their bottom line.\u201d Growth Markers St. Cloud, Minnesota-based heavyweight Marco has pledged considerable resources to prepare for 2026 growth, notes Shelly Caldwell, managed service director. That includes expanding specialist roles, onboarding new technical expertise, and adding capabilities across cybersecurity, AI, modernization, and Insights\u2011based diagnostics. Among the highlights: Targeted upskilling programs Investments in engineers, analysts, and cybersecurity specialists New assessment tools and expanded Insights Platform functionality \u201cThis investment ensures we can support more customers, accelerate recurring revenue growth, and deliver faster, clearer recommendations,\u201d Caldwell said. Although not an MSSP, Les Olson IT of Salt Lake City takes great pains to ensure it maintains a front-line role when it comes to cyber protection. It begins during the onboarding phase, with a thorough sweep for old accounts, stale passwords and misconfigured or poorly configured protections, notes Keith Adams, vice president of IT. Beyond bolstering its team and tools, the dealer has introduced local system management tools to all new managed IT accounts. \u201cWe have integrated the tools into the stack with the goal of hardening the customer\u2019s environment with safeguards that are set to remove local admin status, stop common exploits of normal system functions, as well as cross platform exploits,\u201d Adams remarked. \u201cWith that included platform, we have put numerous people through training and have reached the highest level of support for that product.\u201d Education and certifications are budgeted annually to ensure the ability to meet client expectations, notes Jeff Doztler, president of Elevity, a division of Gordon Flesch Company in Madison, Wisconsin. The long-term strategy is to further develop a practice for those clients that require advanced compliance and governance. \u201cRegarding the solution, we are constantly evaluating what is necessary to protect our clients as the threat landscape evolves,\u201d Doztler noted. \u201cOur primary investment has been in people and education with the right experience.\u201d Deeper Dive For providers such as Usherwood Office Technology in Syracuse, New York, the main thrust has been expanding its portfolio beyond pure technology. One of the cornerstones has been attaining SOC 2 certification and fortifying specialized talent around security and compliance, notes Lindsay Usherwood, general counsel for the dealer. \u201cSOC 2 forced us to document and operationalize what \u2018good\u2019 looks like: think documented controls, repeatable processes and real accountability, and thereby directly refining our consulting to clients,\u201d she noted. \u201cAt the same time, we solidified our midmarket co-managed product as a standalone business, as both our MIT clients grow, and we continue to grow across the northeast. By also investing in talent in the security and compliance space, we raised our internal standards and level of confidence we can offer the market.\u201d<\/p>\n","protected":false},"author":166,"featured_media":68752,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":[],"categories":[1650,82,87,1638],"tags":[2738,2023,4400,545,3932],"_links":{"self":[{"href":"https:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/posts\/68751"}],"collection":[{"href":"https:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/users\/166"}],"replies":[{"embeddable":true,"href":"https:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/comments?post=68751"}],"version-history":[{"count":1,"href":"https:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/posts\/68751\/revisions"}],"predecessor-version":[{"id":68753,"href":"https:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/posts\/68751\/revisions\/68753"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/media\/68752"}],"wp:attachment":[{"href":"https:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/media?parent=68751"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/categories?post=68751"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/tags?post=68751"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}