Role Description The Investments Senior Associate partners with the Head of Alternatives and Non-Core Specialty Mandates and the Alternative Investments team to support portfolio oversight, forecasting, reporting, and manager evaluation across the Alternatives and Non-Core portfolios. - Monitor existing external managers and underlying investments - Build and maintain asset models and financial plan projections - Support portfolio management, performance analysis, and stakeholder reporting - Execute manager due diligence, including evaluation and recommendation materials - Deliver ad hoc analyses and projects to support investment decision-making Enstar has 30+ managers across Alternatives (Private Equity, Private Credit, Real Estate, Infrastructure, Hedge Funds) and Non-Core (High Yield, Public Equity, CLO Equity) asset classes. These are targeted to represent 30% of approximately $20B in total investable assets and are expected to contribute a significant portion of projected investment return; the remainder is managed by core fixed income managers (outside the scope of this role). Qualifications - 4-6 years minimum experience in an institutional investment role focused on sourcing, due diligence, and monitoring external managers, with emphasis on the alternative strategies noted above. - Experience within an insurance company environment—such as an investment general account, CIO office, or insurance asset manager—is strongly preferred. - Demonstrated proficiency in screening and conducting due diligence on alternative investment funds. - Prior experience in tracking, monitoring, and reporting on a sub-portfolio or sub-strategy within a broader investment program. - Deep understanding of investment management, asset allocation (strategic and tactical), and capital markets. - Bachelor’s degree required; Master’s degree preferred. - Progress toward CFA and/or CAIA designations is preferred. - Applicable experience and understanding of non-core asset classes, including: public equity, private equity, real estate, hedge funds, infrastructure, CLO equity, high yield, bank loans, emerging market debt, and other alternative investments. - Deep understanding of statistical concepts, methods, and models, and their application to investments. - Knowledge of performance measurement and attribution, and benchmark construction required. - Proficient with calculating alternatives performance measures, and metrics such as TVPI, DPI, IRR, TWR, Unfunded, Exposure etc. - Proficiency in financial statement analysis, asset and portfolio NAV, Cash-flow, Gain-Loss forecast modelling, LBO modelling. - Excellent quantitative skills required for the asset modelling, performance measurement, portfolio construction and risk measurement processes. - Strong written communication is required for communications with the Investment Committee, Board of Directors, and various internal and external stakeholders. - Ability to prioritize commitments and time management is a significant requirement given the nature of our operations. - Ability to use Excel and PowerPoint is critical, given the requirement to develop investment analytics and proposals. - Strong collaborator with other functional areas and executive management to ensure consistency and efficiency of approach. - Ability to engage in crucial conversations to ensure effective decision making. Requirements - Ongoing Monitoring of Existing Managers, and Investments - Quarterly Monitoring: Support initial and ongoing relationships with assigned managers; produce quarterly investment updates; and ensure the accuracy of existing ratings. - Performance Measurement and Attribution: Analyze and explain absolute and relative performance; attribute results versus budget, assigned benchmarks, and peer groups. - Manager Scorecards: Maintain scorecards for funds, strategies, and managers using a combination of qualitative and quantitative analysis. - Peer Group Analysis: Deliver peer-group comparisons for existing and prospective managers and strategies. - Investment Data Management: Maintain up-to-date mandate, manager, and investment data across internal databases and third-party systems. - Asset Modelling and Financial Planning - Asset Modelling: Develop, maintain, and update NAV, cash flow, gain/loss, and return projection models for assigned investments and managers. - Plan Development: Support the setup, execution, and ongoing maintenance of Alternatives financial plan projections. - Portfolio Management and Reporting - Investment Execution Support: Support negotiations for new investments; coordinate with regional investment teams, risk management, investment operations, investment accounting, legal counsel, external vendors, and investment managers. - Onboarding and Setup: Onboard new managers and investments in coordination with regional investment teams, legal, investment accounting, investment operations, and IT, as well as external managers and vendors; ensure internal systems and databases are updated with complete and accurate manager and investment data. - Compliance: Monitor adherence to internal and external portfolio constraints; escalate and support remediation as needed. - Reporting: Prepare quarterly materials for the Group Investment Committee, Board of Directors, and/or CIO. - Manager Due Diligence - Pipeline Development: Develop market maps for Alternative and Non-Core asset classes; build and maintain an accurate forward fund pipeline for existing and prospective managers; produce peer-group comparison summaries for pipeline managers. - Manager Due Diligence: Support RFP development and end-to-end due diligence for current and prospective managers and funds, including investment structure review, tax considerations, insurance regulatory capital requirements across jurisdictions, and reference calls. - Investment Recommendation: Draft and/or contribute to investment memoranda and supporting analyses for Investment Committee review. - Ad-hoc Projects - Deliver additional analyses and special projects on an ad hoc basis, as business needs dictate. Benefits - Enstar offers best-in-class Medical, Dental, and Vision healthcare for single and family coverage. - Board-certified doctors and pediatricians are available virtually 24/7 for urgent care. - Access to Health Savings Account (HSA) or Flexible Spending Account (FSA). - Access to Dependent Care FSA to cover daycare expenses. - Access to Employee Assistance Programs (EAP) for health and well-being. - Optional Pet & Home/Auto Insurance. - Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses, i.e., gym memberships, massage, etc.). - 401K retirement plan (company matches up to 6% of employee contribution). - One paid annual volunteer day.

Job Title: Investment Banking Associate Position Type: Full-Time, Remote Working Hours: U.S. client business hours (with flexibility for transaction timelines and late-stage deal requirements) About the Role: Our client is seeking an Investment Banking Associate to support mergers & acquisitions (M&A), capital raising, and strategic advisory transactions. This role involves building complex financial models, drafting marketing materials, managing due diligence processes, and working closely with senior bankers and clients. The Associate is a critical link between analysts, vice presidents, and clients, ensuring that deals move forward smoothly, accurately, and on time. Responsibilities: Financial Modeling & Valuation: - Build and maintain detailed discounted cash flow (DCF), leveraged buyout (LBO), and merger models. - Conduct comparable company and precedent transaction analyses. - Perform sensitivity and scenario testing to stress-test assumptions. Transaction Support: - Manage due diligence checklists, coordinate data rooms, and track requests. - Liaise with clients, accountants, lawyers, and consultants to gather information. - Ensure deliverables are complete, accurate, and aligned with deadlines. Marketing & Client Materials: - Draft confidential information memoranda (CIMs), pitch books, teasers, and management presentations. - Prepare investor decks and client-ready reports with high attention to detail. Research & Analysis: - Conduct industry and market research to identify trends, risks, and opportunities. - Summarize findings in briefing notes and incorporate into valuation assumptions. Collaboration & Mentorship: - Work closely with analysts, reviewing their work and providing guidance. - Support VPs and MDs by preparing materials and presenting findings. Compliance & Governance: - Ensure all documentation adheres to internal controls, regulatory requirements, and confidentiality standards. - Maintain audit-ready records of models and deliverables. What Makes You a Perfect Fit: - Exceptional financial modeling and analytical skills. - Strong communicator with executive presence in client settings. - Organized and detail-oriented under tight deadlines. - Able to balance multiple live transactions simultaneously. Required Experience & Skills (Minimum): - 2–4 years experience in investment banking, corporate finance, or private equity. - Advanced Excel (financial modeling, VBA macros preferred) and PowerPoint. - Experience with valuation methodologies (DCF, LBO, comparables, precedent transactions). - Familiarity with Bloomberg, Capital IQ, FactSet, or PitchBook. Ideal Experience & Skills: - MBA, CFA, or CPA credential. - Exposure to both buy-side and sell-side transactions. - Experience across multiple industries (tech, healthcare, real estate, financial services). - Prior mentorship or leadership of analysts. What Does a Typical Day Look Like? An Associate’s day revolves around managing deal execution and producing high-quality analysis and materials.You will: - Update and refine models with client financials and assumptions. - Draft marketing materials such as pitch books, CIMs, and presentations. - Manage the due diligence process, ensuring all requests and data room uploads are completed. - Support live deals, coordinating with lawyers, accountants, and client executives. - Review analyst outputs, checking for accuracy and clarity. - Prepare senior bankers for client meetings, ensuring they have insights, models, and materials at hand. In essence: you ensure deals move forward efficiently and flawlessly, with clients and senior bankers confident in the accuracy of the work. Key Metrics for Success (KPIs): - Accuracy of financial models and assumptions. - Timely delivery of pitch books, CIMs, and investor decks. - Smooth execution of due diligence and transaction processes. - Positive feedback from clients and senior bankers on quality and reliability. - Effective mentorship of junior team members. Interview Process: - Initial Phone Screen - Video Interview with Pavago Recruiter - Technical Assessment (e.g., build a DCF or M&A model based on case study data) - Client Interview with Senior Bankers - Offer & Background Verification

• Drive and close high‑ticket tax strategy transactions ($2M+) with HNWI and business owners • Lead the full sales cycle from qualification to close, consistently exceeding revenue targets • Serve as the primary point of contact for clients throughout the transaction process • Review and approve all client documents for accuracy and compliance • Communicate complex federal tax code implications in a clear, compelling manner • Develop and refine policies, procedures, and sales processes to increase close rates • Implement strategies to convert qualified leads into long‑term clients • Collaborate with internal teams to ensure seamless client service and satisfaction • Maintain expert‑level knowledge of industry trends, tax strategies, and competitor offerings • Document all activities, communications, and deal progression in the CRM for accurate reporting

Department: 13298 Enterprise Revenue Cycle - Eligibility: Illinois Status: Full time Benefits Eligible: Yes Hours Per Week: 40 Schedule Details/Additional Information: Schedule: Virtual position. Standard hours are 10:30 AM–7:00 PM, with one weekday off (Tuesday or Thursday). Every other weekend is required (8:00 AM–5:00 PM). Schedule determined at hire. No holidays. Pay Range $22.90 - $34.35 Major Responsibilities: - Calculates and provides patients with personalized estimates of their financial responsibility based on their insurance coverage prior to service. - Communicates patient liability clearly and accurately while adequately explaining concepts such as deductibles, coinsurance, and/or copayments and how they may affect the cost of care. Explains how non-covered and out-of-network services factor into the out-of-pocket cost. - Requests upfront payment toward self-pay amounts, including estimated out-of-pocket costs and outstanding previous balances. Establishes payment arrangements in advance of scheduled services when applicable, communicating due dates and the amount of each installment. - Interviews uninsured patients to assess for qualifying financial needs. Identifies available assistance programs and coordinates with patient to complete paperwork and applications for any potential coverage(s). Continues follow-up efforts to obtain a funding source for patient’s health services. - Initiates credit scoring to determine each patient’s eligibility for Medicaid, hospital-sponsored charity care, and other programs through a comprehensive patient interview. - Works in conjunction with state social worker and/or outside eligibility vendor to assist in the appropriate completion of Medicaid applications, ensuring this funding source is maximized based on patients’ eligibility. - Demonstrates working knowledge of insurance benefits, insurance companies, and Marketplace insurance options, and stays informed of other payer sources entering the markets. - Educates physician office/patient on the organization’s applicable policies such as Financial Assistance Policy, Patient Financial Responsibility, Non-Covered Services, and Deferral of Care. Coordinates with provider office to determine scheduling options based on the need to secure funding and clarify patient’s financial responsibility. - Stays current on regulations and eligibility requirements for government funding, especially Medicare and Medicaid. Understands and complies with all internal charity care policies and processes. Understands, complies with, and can articulate federal regulations around 501R. Performs in a HIPAA-compliant manner with all pertinent patient interviews, including management of demographic data, topics discussed, and actions taken. - Collaborates with peers in the operational flow for uninsured patients or patients that are concerned about costs for upcoming services. Serves consumers in various settings, including virtual, bedside, Emergency Department room, clinic exam room, Urgent Care, consult space, or a Financial Resource Specialist office. Licensure, Registration, and/or Certification Required: - None Required. Education Required: - High School Graduate, or - Certificate of General Educational Development (GED) or High School Equivalency Diploma (HSED). Experience Required: - Typically requires 2 years of experience in Patient Access, health care, insurance industry, or in a customer service setting. Knowledge, Skills & Abilities Required: - Ability to communicate clearly and proactively to management about issues involving customer service and process improvement opportunities. - Ability to articulate explanations of HIPAA and EMTALA regulations as they relate to all patient interactions within the operational flow involving the Financial Advocate, either virtually or in person. - Has solid knowledge of how various types of insurances operate related to denials and appeals processes. - Basic medical coding knowledge. - Understanding of insurances, billing and denials - Ability to use a combination of scripted notes and clear, written communication when documenting in patients’ accounts. Physical Requirements and Working Conditions: - This position requires travel, therefore, will be exposed to weather and road conditions. - Operates all equipment necessary to perform the job. - Exposed to a normal office environment. - Must be able to sit a majority of the workday - Occasionally lift up to 10 lbs. This job description indicates the general nature and level of work expected of the incumbent. It is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities required of the incumbent. Incumbent may be required to perform other related duties. Our Commitment to You: Advocate Health offers a comprehensive suite of Total Rewards: benefits and well-being programs, competitive compensation, generous retirement offerings, programs that invest in your career development and so much more – so you can live fully at and away from work, including: Compensation - Base compensation listed within the listed pay range based on factors such as qualifications, skills, relevant experience, and/or training - Premium pay such as shift, on call, and more based on a teammate's job - Incentive pay for select positions - Opportunity for annual increases based on performance Benefits and more - Paid Time Off programs - Health and welfare benefits such as medical, dental, vision, life, and Short- and Long-Term Disability - Flexible Spending Accounts for eligible health care and dependent care expenses - Family benefits such as adoption assistance and paid parental leave - Defined contribution retirement plans with employer match and other financial wellness programs - Educational Assistance Program About Advocate Health Advocate Health is the third-largest nonprofit, integrated health system in the United States, created from the combination of Advocate Aurora Health and Atrium Health. Providing care under the names Advocate Health Care in Illinois; Atrium Health in the Carolinas, Georgia and Alabama; and Aurora Health Care in Wisconsin, Advocate Health is a national leader in clinical innovation, health outcomes, consumer experience and value-based care. Headquartered in Charlotte, North Carolina, Advocate Health services nearly 6 million patients and is engaged in hundreds of clinical trials and research studies, with Wake Forest University School of Medicine serving as the academic core of the enterprise. It is nationally recognized for its expertise in cardiology, neurosciences, oncology, pediatrics and rehabilitation, as well as organ transplants, burn treatments and specialized musculoskeletal programs. Advocate Health employs 155,000 teammates across 69 hospitals and over 1,000 care locations, and offers one of the nation’s largest graduate medical education programs with over 2,000 residents and fellows across more than 200 programs. Committed to providing equitable care for all, Advocate Health provides more than $6 billion in annual community benefits.