Full-Time

Underwriting Senior Associate

Updated on 9/10/2026

Deadline 9/18/26
CVS Health

CVS Health

10,001+ employees

Healthcare, insurance, PBM, and retail pharmacy

Compensation Overview

$18.50 - $38.82/hr

+ Bonus + Commission + Short-term incentive

Company Historically Provides H1B Sponsorship

Northbrook, IL, USA + 2 more

More locations: Hartford, CT, USA | Woonsocket, RI, USA

Hybrid

Hybrid work is required.

Bachelor's

Category
Insurance (1)
Required Skills
Microsoft Office
Forecasting
Financial analysis
Risk Management
Data Analysis
Excel/Numbers/Sheets

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Requirements
  • Strong analytical and quantitative skills with the ability to interpret data and make informed business recommendations.
  • Demonstrated problem-solving and critical thinking abilities.
  • Strong attention to detail and commitment to accuracy.
  • Proficiency in Microsoft Office applications, including Excel.
  • Effective written and verbal communication skills.
  • Ability to prioritize work, manage multiple deadlines, and perform in a fast-paced environment.
  • Ability to work independently while collaborating effectively with cross-functional partners.
  • Demonstrated ability to learn new systems, processes, and technical concepts.
  • Basic understanding of financial analysis, business mathematics, accounting principles, or related quantitative concepts.
  • Bachelor's degree or equivalent experience.
Responsibilities
  • Perform underwriting analysis and risk assessments for new and renewal large-group business.
  • Evaluate pricing, funding arrangements, and contract structures to ensure appropriate risk selection and profitability.
  • Support revenue and membership growth through sound underwriting recommendations.
  • Manage assigned cases and book of business while balancing competitive positioning with financial performance objectives.
  • Develop expertise across multiple product lines, funding arrangements, and rating methodologies.
  • Collaborate with internal business partners to deliver underwriting solutions that align with company goals and customer needs.
  • Contribute to earnings growth by maintaining underwriting discipline and identifying opportunities to improve account profitability.
  • Prepare and deliver routine to moderately complex new business quotes, renewal proposals, and accounting reconciliations for large-group customers.
  • Perform detailed financial analysis and underwriting assessments to support pricing decisions, profitability targets, and business growth objectives.
  • Independently review work products to ensure accuracy, completeness, and compliance with underwriting guidelines and company standards.
  • Partner with managers and mentors to develop pricing strategies and accounting balance recommendations that align with financial goals, risk tolerance, and market competitiveness.
  • Utilize underwriting systems, tools, rating platforms, and reference materials to produce accurate and timely customer deliverables.
  • Apply established underwriting principles and guidelines while appropriately escalating exceptions, financial variances, and non-standard risks.
  • Support sales and account teams by explaining rate development, fee calculations, accounting balances, and underwriting policies to internal and external stakeholders.
  • Produce customer-specific reports, documentation, and financial deliverables within established service and quality standards.
  • Conduct audits of premiums, fees, claim wires, and receivable activity to ensure financial accuracy and proper accounting treatment.
  • Monitor customer allowances and Minority/Women Business Enterprise goals to ensure compliance with applicable guidelines and reporting requirements.
  • Participate in departmental projects, cross-functional workgroups, and operational initiatives.
  • Identify opportunities for process improvement and support automation, workflow enhancements, and efficiency initiatives that improve accuracy, productivity, and customer experience.
Desired Qualifications
  • Experience in underwriting, insurance, healthcare, finance, accounting, analytics, risk management, or a related field.
  • Experience analyzing data, identifying trends, and making recommendations based on findings.
  • Exposure to pricing, forecasting, budgeting, financial reporting, or account reconciliation activities.
  • Experience working with large data sets and performing quantitative analysis.
  • Knowledge of healthcare insurance products, underwriting principles, or funding arrangements.
  • Advanced Microsoft Excel skills, including Pivot Tables and data analysis functions.
  • Demonstrated success collaborating across teams to achieve business objectives.
  • Interest in developing a career in underwriting and risk management.

CVS Health operates as a diversified health services company in the United States, organized into Health Care Benefits, Pharmacy & Consumer Wellness, and Health Services. Its offerings include medical insurance products, retail and mail-order prescription drugs, and pharmacy benefit management (PBM) services, all connected through its integrated platform. By combining insurance, retail pharmacy, PBM, and health solutions, CVS Health coordinates care and controls costs across touchpoints for individuals, employers, and government programs. The company aims to lower health care costs while improving access and health outcomes for customers.

Company Size

10,001+

Company Stage

IPO

Headquarters

Woonsocket, Rhode Island

Founded

1963

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Simplify Jobs

Simplify's Take

What believers are saying

  • Q2 2026 revenue hit $106.1 billion, up 7.3%, with adjusted EPS $2.58.
  • CVS raised 2026 adjusted EPS guidance to $7.90-$8.10 and cash flow to $11.5 billion.
  • Walgreens' 1,200-store closures through 2027 funnel prescriptions toward CVS locations.

What critics are saying

  • FTC settlement on Caremark insulin practices forces transparency changes through 2036.
  • CVS expects 340B pressure and Caremark membership declines in 2027.
  • $175 billion liabilities and $3.12 billion annual interest burden constrain strategic flexibility.

What makes CVS Health unique

  • Caremark, Aetna, and 9,000 stores create unmatched U.S. pharmacy-insurance integration.
  • CVS handled 87 million PBM members and 37 million insured people in June 2026.
  • CVS app now prices Eli Lilly Zepbound and Mounjaro for same-day pickup.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

401(k) Retirement Plan

Company Equity

Wellness Program

Professional Development Budget

Paid Vacation

Paid Holidays

Company News

Yahoo Finance
Sep 12th, 2026
CVS quietly gains market share as Walgreens closes 1,200 US stores following $10B private equity sale

Walgreens is closing roughly 1,200 of its approximately 8,500 US locations through 2027, with many customers being redirected to nearby CVS pharmacies. The pattern is reshaping suburban pharmacy markets without direct competition. In August 2025, Walgreens completed a $10 billion sale to private equity firm Sycamore Partners, taking the 124-year-old chain private for the first time. Mike Motz was named chief executive, replacing Tim Wentworth. CVS is gaining market share without active expansion efforts. Federal and state rules require orderly prescription transfers when pharmacies close, often directing patients to the nearest CVS location. CVS and Walgreens together now handle nearly 40% of all US retail prescription sales. CVS benefits from owning Caremark, a dominant pharmacy benefit manager, providing vertical integration advantages.

Yahoo Finance
Aug 28th, 2026
CVS stock down 12% in a month despite 34% annual gain, faces 2027 headwinds

CVS Health stock has declined 12.3% over the past month, sitting about 15% below its 52-week high, though it remains up 34% over the trailing twelve months. The company's revenue reached approximately $415 billion, up 7.4% year-over-year. Management raised its full-year 2026 adjusted earnings per share guidance by $0.60 to a range of $7.90 to $8.10. For 2027, the company anticipates membership declines at Caremark and continued 340B programme pressure, offset by Aetna's recovery, which added over $2 billion in adjusted operating income in the first half of 2026. Management considers a 2027 adjusted EPS outlook of at least $8.44 reasonable. Historically, CVS has experienced varied recovery periods following market downturns, with some rebounds taking years rather than months.

Yahoo Finance
Aug 25th, 2026
CVS and Roche stocks could benefit from expanding GLP-1 drug market

CVS Health and Roche could benefit from the growing GLP-1 drug market, alongside current leaders Eli Lilly and Novo Nordisk. CVS Health has improved its financial performance, with second-quarter revenue rising 7.3% year-over-year to $106.1 billion and adjusted earnings per share increasing 42.5% to $2.58. The pharmacy chain offers all approved GLP-1 medicines in the US, including Eli Lilly's Zepbound and Foundayo, plus Novo Nordisk's Wegovy. CVS also provides low-cost online consultations at $29 to assess patient eligibility for GLP-1 drugs. Beyond GLP-1 initiatives, CVS is addressing previous business challenges and is positioned to capitalise on rising healthcare spending in the US over the next decade.

Yahoo Finance
Aug 19th, 2026
CVS Health appoints JPMorgan data executive to board as focus shifts to digital healthcare

CVS Health has appointed Teresa Heitsenrether, a senior executive from JPMorgan Chase with extensive data and analytics experience, to its board of directors. The move follows the resignation of board member Larry M. Robbins. The appointment signals CVS Health's focus on technology and data-driven healthcare at the governance level. The company, valued at approximately $120bn, operates an integrated healthcare model spanning insurance, pharmacy benefits, and retail services. Heitsenrether's data expertise aligns with CVS Health's strategy to leverage digital capabilities and operational efficiency across its businesses, including Aetna and Caremark. The company faces challenges including high debt levels and reimbursement pressures in a competitive market alongside UnitedHealth Group and Cigna.

Yahoo Finance
Aug 14th, 2026
CVS Health beats Q2 revenue and profit estimates but faces questions on sustainability

CVS Health reported second quarter revenue of $106.1 billion, beating analyst estimates of $99.41 billion by 6.7%. Adjusted earnings per share came in at $2.58, surpassing expectations of $1.85 by 39.4%. Management attributed strong performance to specialty pharmacy and Medicare Advantage, with CEO David Joyner noting improvements from actions taken in Aetna and Caremark. The company raised its full-year adjusted EPS guidance to $8 at the midpoint. However, analysts raised concerns about sustainability. Management acknowledged ongoing challenges in the 340B program and normalisation of script share gains from Rite Aid. To offset these headwinds, executives pointed to biosimilars and investments in service technology. The company has committed $20 billion over a decade to AI and technology investments, with operational savings already being realised.