• Jason E. Schlegel

    Senior Operations Executive | Marine Corps Veteran | Scaling Multi-Entity Organizations with People-First Leadership, Systems Design & Operational Excellence

  • Leading with People, Systems, and Precision. Operational Excellence, Scaled.

    Senior operations executive, servant leader, and US Marine Corps veteran with a history of scaling complex, multi-entity organizations while maintaining cultural cohesion, operational precision, and strong financial outcomes. Adept at translating vision into systems and execution, with domain fluency across HR, IT, and facilities. Proven success driving rapid revenue growth—from $5M to $70M—and property expansion from 64 to 1,550 units through structured workflows, data visibility, and accountable team leadership.

    Known for implementing enterprise platforms and automation tools that reduce costs, improve clarity, and enable aligned action on a high scale. Track record of leadership success, from leading teams in business operations to leading over 45 US Marines in multiple deployments. Brings a people-first, systems-oriented approach to building teams, growing organizations, and implementing systems.

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    Current Position

    Chief Operating Officer | 2024 – Present

    Lead all operations for a turnkey real estate investmentsolutions company offering passive investors diversified opportunities in residential and multi-family properties backed by decades of expertise and secured assets with a portfolio of 2,708 apartment units in joint ventures, overseeing $100 million in capital under management and $230 million in assets under management.

    • AI & Automation Leadership: Drive the development anddeployment of custom GPTs to train employees on AI applications spanning formula creation, code generation, executive content development, and business process automation. Lead creation of AI agents that reduce manual workload and embed advanced automation across core functions.
    • HR Strategy & Talent Infrastructure: Design andexecute comprehensive HR and talent strategies that elevated retention, engagement, and performance across a 200+ employee organization. Leveraged a 1,000+ resident network, referral programs, and high-impact recruitment events to attract top talent. Spearheaded benefits enhancements, including expanded PTO, upgraded insurance, and a $250 annual swag stipend, while implementing a Microsoft Teams–based performance management system (TeamFlect) to integrate goal setting, feedback, and reviews. Instituted stay interviews and weekly 1:1s, driving measurable gains in employee satisfaction, cultural alignment, and organizational stability.
    • Operational Oversight & Organizational Excellence: Directday-to-day operations, elevate service delivery standards, and reinforce Freeland Ventures’ reputation for excellence. Lead cross-functional process improvement initiatives to streamline administrative workflows and accelerate internal decision-making.
    • IT Systems & Infrastructure: Launch and optimize ITinfrastructure and support protocols to improve system uptime, reliability, and user experience across the organization.
    • Facilities & Real Estate Management: Negotiateand manage commercial leases and facilities operations to secure cost-effective solutions while maintaining high standards for operational continuity and workspace quality.
    • Strategic Planning & Executive Engagement: Providecritical input in senior leadership forums to shape strategic investments, growth initiatives, and expansion roadmaps.

  • Career Highlights

    Operational Scale-Up: Expanded property operations from 64 to 1,550 multifamily units across 18 sites in 24 months. Increased occupancy from 87% to 94% while reducing marketing spend through integrated SEO and third-party tools. Scaled workforce from 11 to 70 employees and revenue from $5M to $70M within three years.

    Technology & AI Modernization: Executed enterprise-wide IT overhaul, deploying Microsoft 365, Teams, Planner, Jamf, and Apple Business Manager to unify 17+ sites. Pioneered early adoption of AI tools—including ChatGPT Plus and Microsoft Copilot—resulting in a 3x execution efficiency gain and 60% performance lift across departments. Integrated CRM systems and APIs to streamline customer experience, generating recurring incremental revenue.

    Workforce Strategy & HR Leadership: Directed HR operations across multiple entities, including recruiting, onboarding, payroll, compliance, and performance systems. Implemented OKRs, 1:1s, and structured review cycles via Teamflect, building scalable infrastructure that maintained high retention and cultural alignment during rapid expansion.

    Revenue Growth & Innovation: Launched monetized Resident Benefits Program (insurance, bundled services, and ancillary products) to boost revenue and satisfaction. Negotiated employee health benefits, reducing costs by $35K annually. Expanded digital product fulfillment and national events strategy, driving $3.1M in new sales and improving subscription retention from 1.8 to 3 months.

    Financial & Operational Excellence: Delivered $100K in cost savings by automating manual processes and deploying BI systems for analytics-driven decisions. Forecasted budgets 18+ months ahead to align with investor expectations and business cycles. Achieved a 92% customer satisfaction rating and an A+ accreditation score through rigorous staff training and service standards.

    Leadership & Culture: Strengthened employee engagement by launching a branded swag store, creating an e-learning catalog across five companies, and establishing bonus and mentorship programs. Successfully led multiple corporate office relocations on time and within budget.

    Early Career Impact: Transformed a restaurant operation from a $250K loss to an $80K profit in three years, boosting sales by $1.1M and reducing turnover by 90%. Recognized nationally for achieving a single-day sales record of $70K at a flagship restaurant.

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    Kolbe A Index Assessment

    Identify. Discuss. Solve.

  • Community Outreach

    Rahab Ministries

    Street Team · Protective Services

    Safe House Liaison

    Volunteered as part of a committed weekly small street team that would search out, speak with, and encourage women who were caught up in the world of sex trafficking to offer hope and safety. Rahab would assist with a safe place to offer physical, spiritual and emotional needs for these young women. My main task was to protect the women on our team on the streets of the inner city as we walked late at nights (9pm-11pm) or very early mornings (5am-7am). I also assisted as being a liaison between our grace groups and other organizations to coordinate with the Rahab Director and CEO for their needs for specialized safe housing areas.

    Grace Church of Greater Akron

    Grace Group Leader · Safety Team

    Haiti Missionary · Count Team

    I have led leading several Grace Groups over the years where we met weekly to discuss the sermon and go in-depth into the Bible. I have also been an active member of multiple campus safety teams to ensure the protection of our pastors and the congregation, as well as, financial count team. I have participated in a mission trip to Haiti in 2015 as well as serving on a meal and bereavement ministry. I continue to serve our local community through other outreach programs and church partners.

    Akron-Canton Regional Foodbank

    Global | Local Humanitarian Meal Needs

    Led a team of two groups of volunteers to help organize and pack hundreds of pounds of food items to be delivered for humanitarian relief across the globe.

  • Resume

    Download a copy of my resume or contact me below for more information.

  • Let's Connect

    Direct Message, Call, or Email.

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