Underwriter – Manager – Remote

This is a pricing-and-deal desk leadership role. You’re basically the person who helps Sales win while making sure CVS doesn’t price itself into a bad marriage. Heavy modeling, fast deadlines, exec presentations, and a lot of “answer that question right now” energy.

About CVS Health

CVS Health is a Fortune 5 health solutions company serving millions through retail presence, digital channels, and large-scale health services.

Schedule

  • Full-time, 40 hours/week
  • Remote (Work at Home), Illinois

What You’ll Do

  • Lead Specialty Drug pricing strategy and build financial models for comprehensive pricing offers
  • Review RFP financial sections to spot client needs, concerns, and deal risks
  • Partner with Sales + Account Services on pricing and negotiation strategy to hit revenue/profit targets
  • Identify, evaluate, and manage underwriting risk to maximize revenue, membership, and earnings
  • Own the underwriting workflow end-to-end: from RFP/pricing request intake to internal communication of final financial agreements
  • Present to executive leadership on underwriting approval calls, and defend the numbers live

What You Need

  • 5+ years pricing or financial analysis experience
  • 1+ year building financial models
  • Strong analytical mindset + comfort working at speed with tight turnarounds
  • Ability to communicate clearly with senior leaders (because you will get challenged)

Preferred

  • Contract and/or RFP experience
  • Master’s degree (not required)

Pay

  • Typical range: $66,330 – $145,860/year (plus potential bonus/short-term incentives)

Benefits

  • Medical plan options
  • 401(k) with matching
  • Employee stock purchase plan
  • Wellness programs, counseling, financial coaching
  • PTO, family leave, tuition assistance, dependent care resources (eligibility varies)

Deadline: application window expected to close 12/31/2025.

My blunt take: if you don’t already have pricing/modeling chops (Excel heavy, sometimes actuarial-adjacent thinking), this is a stretch role. But if you do and you’ve dealt with RFPs, it’s a clean “remote manager” lane with real influence.

Happy Hunting,
~Two Chicks…

APPLY HERE.