Oswald Companies
Would you like to take ownership in a dynamic, high-growth business that truly walks the talk?
Oswald Companies seeks goal-driven professionals ready to take their career to the next level.
Job Summary:
Unison Risk Advisors (URA) is seeking a dynamic and customer-focused, business-aligned Manager of IT End User Services to lead the development and continuous improvement of our distributed desktop support function. This role will be based in our
Oswald Companies,
Cleveland offices and will build and scale a service-first team that supports multiple URA brands and locations across the Eastern and Midwest United States. As a collaborative partner to the business, this leader will champion a culture of responsiveness, clear communication, and transparency-ensuring that IT is seen as a trusted ally. The successful candidate will bring technical depth with a hands-on approach, a strong sense of ownership, and a passion for mentoring regional teams and enhancing the user experience.
Key Responsibilities:
Team Leadership and Service Scaling:
Lead and expand a desktop support team across Eastern and Midwest U.S. locations, emphasizing quality, consistency, and cost-effectiveness. Strategic Business Partnership:
Act as a technology partner, engaging with stakeholders to align IT support with company objectives and delivering executive-level white-glove service. Cultivating Executive-Level IT Experience:
Provide white-glove support with professionalism, discretion, and urgency to ensure that executive users receive top-tier IT support that meets their specific needs and expectations. Enhancing User Communication and Service:
Ensure transparency throughout incident management, request tracking, and problem resolution with clear and effective communication. Process Improvement and Data-Driven Management:
Implement ITSM frameworks, manage incident and request processes, leverage metrics for service enhancement, and integrate automation and endpoint management tools. Mentoring and Coaching Regional Support Staff:
Mentor and coach regional support staff to elevate their technical expertise, customer service orientation, and confidence. Vendor and Third-Party Relationship Management:
Build strong vendor and third-party relationships, ensuring IT support resources are optimized and aligned. Ideal Candidate Profile:
Collaborative Business Partner:
Build relationships with non-technical teams and leadership, aligning IT support with business goals and daily operations. Exceptional Communicator:
Skilled at translating technical concepts for varied audiences and setting clear user expectations. Service Champion:
Passionate about delivering a seamless end-user experience and elevating the perception of IT. People-Oriented Leader & Team Builder:
Experienced in mentoring and empowering geographically distributed technicians to become high performers. Service-Minded and Data-Driven:
Passionate about continuous improvement and performance measurement. Operational Leader:
Skilled in formalizing scalable support processes across a complex multi-brand, multi-location environment.
Qualifications:
5+ years of IT desktop support and/or service management experience, with experience in a leadership or supervisory role being a plus. Demonstrated ability to lead and inspire distributed support teams across multiple physical locations. Strong knowledge of Windows and desktop technologies, collaboration tools (e.g., Microsoft 365, Teams), and endpoint support systems. Experience providing white-glove support to executive users. Excellent communication skills and proven ability to collaborate across business functions. Familiarity with ITIL, ITSM tools, and support performance metrics. Regional travel as required to visit offices and support onsite teams. Preferred Qualifications:
Experience in insurance, financial services, or professional services industries preferred but not required. Working knowledge of endpoint management (Intune, SCCM) and support automation. Prior success driving improvements in service transparency, response times, and user trust. Exposure to modern IT trends - remote support, collaboration transformation, and automation. ITIL certification or relevant technical certifications are a plus. Common Qualifications & Skills:
Technical Troubleshooting & Problem Solving Vendor/Supplier Management Documentation & Knowledgebase Development SLA Definition and Monitoring Active Directory & Collaboration Platform Expertise Project Planning & Coordination Proven Customer Service Excellence Empathy, Active Listening, and Conflict Resolution Adaptability and Continuous Learning Mindset Why Join Unison Risk Advisors?
At URA, we value partnership, transparency, and innovation. We believe IT should be empowering, visible, and aligned with our strategic goals. Your leadership will shape how our internal business customers experience and interact with technology, making a meaningful impact on our overall client's satisfaction, productivity, and company growth.
Who is Oswald?
Oswald is a 129-year-old company that creates a world of protection around the lives and businesses of our clients.
We are an independent, employee-owned company. So, essentially, you own your own success in a personally and financially rewarding opportunity.
Inclusivity is a priority. We foster an environment of collaboration and belonging where our Employee-Owners thrive on their unique path. Our diverse talent reflects the communities and clients we serve, while driving unmatched risk and insurance innovations.
Our people-first culture and client service excellence have built our reputation of integrity, resourcefulness, and a relentless care for our clients and employees. Don't believe us? Ask your friends, colleagues, and mentors about Oswald. There's a reason Oswald has been named a Top Workplace for nine consecutive years.
What you'll get...
At Oswald, you will have the opportunity to build a long-term career with unlimited growth potential. Aim high, work hard and we'll help you achieve your goals.
At Oswald, you will experience our caring work environment. We care about our Employee-Owners, we care about our customers, and we care about the world around us. Our caring personality comes to life in the form of volunteering in the community. We even give employees paid time off to volunteer with an organization of their choice.
At Oswald, you will achieve a work-life balance. We care about your physical and emotional well-being, so work-life balance is encouraged and practiced. We understand you have a life outside of work, and we want you to live it.
At Oswald, you will have access to a world-class Total Rewards package. We truly value our people, which shows in our compensation, benefits, and perks.
In addition to competitive pay, we have designed a performance-based annual incentive program. All employees are eligible to earn a bonus by meeting performance objectives. Comprehensive medical, dental and vision plans and numerous supplemental benefit offerings. Paid time off annually and a sabbatical at every 10-year service anniversary. Ownership in the company in the form of company stock (discretionary profit-sharing and 401(k) match contribution) Assistance with parking expenses, discount programs for area services/experiences, and financial support for professional development and licensure/designations Access to specialized leadership development programming designed to take your career to the next level. And so much more!
To learn more about Oswald, our culture and everything we have to offer, visit us on LinkedIn.
Oswald, a Unison Risk Advisors company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic.
Oswald Companies seeks goal-driven professionals ready to take their career to the next level.
Job Summary:
Unison Risk Advisors (URA) is seeking a dynamic and customer-focused, business-aligned Manager of IT End User Services to lead the development and continuous improvement of our distributed desktop support function. This role will be based in our
Oswald Companies,
Cleveland offices and will build and scale a service-first team that supports multiple URA brands and locations across the Eastern and Midwest United States. As a collaborative partner to the business, this leader will champion a culture of responsiveness, clear communication, and transparency-ensuring that IT is seen as a trusted ally. The successful candidate will bring technical depth with a hands-on approach, a strong sense of ownership, and a passion for mentoring regional teams and enhancing the user experience.
Key Responsibilities:
Team Leadership and Service Scaling:
Lead and expand a desktop support team across Eastern and Midwest U.S. locations, emphasizing quality, consistency, and cost-effectiveness. Strategic Business Partnership:
Act as a technology partner, engaging with stakeholders to align IT support with company objectives and delivering executive-level white-glove service. Cultivating Executive-Level IT Experience:
Provide white-glove support with professionalism, discretion, and urgency to ensure that executive users receive top-tier IT support that meets their specific needs and expectations. Enhancing User Communication and Service:
Ensure transparency throughout incident management, request tracking, and problem resolution with clear and effective communication. Process Improvement and Data-Driven Management:
Implement ITSM frameworks, manage incident and request processes, leverage metrics for service enhancement, and integrate automation and endpoint management tools. Mentoring and Coaching Regional Support Staff:
Mentor and coach regional support staff to elevate their technical expertise, customer service orientation, and confidence. Vendor and Third-Party Relationship Management:
Build strong vendor and third-party relationships, ensuring IT support resources are optimized and aligned. Ideal Candidate Profile:
Collaborative Business Partner:
Build relationships with non-technical teams and leadership, aligning IT support with business goals and daily operations. Exceptional Communicator:
Skilled at translating technical concepts for varied audiences and setting clear user expectations. Service Champion:
Passionate about delivering a seamless end-user experience and elevating the perception of IT. People-Oriented Leader & Team Builder:
Experienced in mentoring and empowering geographically distributed technicians to become high performers. Service-Minded and Data-Driven:
Passionate about continuous improvement and performance measurement. Operational Leader:
Skilled in formalizing scalable support processes across a complex multi-brand, multi-location environment.
Qualifications:
5+ years of IT desktop support and/or service management experience, with experience in a leadership or supervisory role being a plus. Demonstrated ability to lead and inspire distributed support teams across multiple physical locations. Strong knowledge of Windows and desktop technologies, collaboration tools (e.g., Microsoft 365, Teams), and endpoint support systems. Experience providing white-glove support to executive users. Excellent communication skills and proven ability to collaborate across business functions. Familiarity with ITIL, ITSM tools, and support performance metrics. Regional travel as required to visit offices and support onsite teams. Preferred Qualifications:
Experience in insurance, financial services, or professional services industries preferred but not required. Working knowledge of endpoint management (Intune, SCCM) and support automation. Prior success driving improvements in service transparency, response times, and user trust. Exposure to modern IT trends - remote support, collaboration transformation, and automation. ITIL certification or relevant technical certifications are a plus. Common Qualifications & Skills:
Technical Troubleshooting & Problem Solving Vendor/Supplier Management Documentation & Knowledgebase Development SLA Definition and Monitoring Active Directory & Collaboration Platform Expertise Project Planning & Coordination Proven Customer Service Excellence Empathy, Active Listening, and Conflict Resolution Adaptability and Continuous Learning Mindset Why Join Unison Risk Advisors?
At URA, we value partnership, transparency, and innovation. We believe IT should be empowering, visible, and aligned with our strategic goals. Your leadership will shape how our internal business customers experience and interact with technology, making a meaningful impact on our overall client's satisfaction, productivity, and company growth.
Who is Oswald?
Oswald is a 129-year-old company that creates a world of protection around the lives and businesses of our clients.
We are an independent, employee-owned company. So, essentially, you own your own success in a personally and financially rewarding opportunity.
Inclusivity is a priority. We foster an environment of collaboration and belonging where our Employee-Owners thrive on their unique path. Our diverse talent reflects the communities and clients we serve, while driving unmatched risk and insurance innovations.
Our people-first culture and client service excellence have built our reputation of integrity, resourcefulness, and a relentless care for our clients and employees. Don't believe us? Ask your friends, colleagues, and mentors about Oswald. There's a reason Oswald has been named a Top Workplace for nine consecutive years.
What you'll get...
At Oswald, you will have the opportunity to build a long-term career with unlimited growth potential. Aim high, work hard and we'll help you achieve your goals.
At Oswald, you will experience our caring work environment. We care about our Employee-Owners, we care about our customers, and we care about the world around us. Our caring personality comes to life in the form of volunteering in the community. We even give employees paid time off to volunteer with an organization of their choice.
At Oswald, you will achieve a work-life balance. We care about your physical and emotional well-being, so work-life balance is encouraged and practiced. We understand you have a life outside of work, and we want you to live it.
At Oswald, you will have access to a world-class Total Rewards package. We truly value our people, which shows in our compensation, benefits, and perks.
In addition to competitive pay, we have designed a performance-based annual incentive program. All employees are eligible to earn a bonus by meeting performance objectives. Comprehensive medical, dental and vision plans and numerous supplemental benefit offerings. Paid time off annually and a sabbatical at every 10-year service anniversary. Ownership in the company in the form of company stock (discretionary profit-sharing and 401(k) match contribution) Assistance with parking expenses, discount programs for area services/experiences, and financial support for professional development and licensure/designations Access to specialized leadership development programming designed to take your career to the next level. And so much more!
To learn more about Oswald, our culture and everything we have to offer, visit us on LinkedIn.
Oswald, a Unison Risk Advisors company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic.