Venture Analyst, Healthcare Strategy

Founded in 2003, Roundstone is not your typical insurance company. We’re on a mission to help employers save on healthcare benefits so they can put those savings towards bettering their businesses and taking care of their employees. The Venture Analyst supports the evaluation, diligence, and monitoring of investment opportunities across Roundstone’s healthcare ecosystem with a particular focus on operator quality, business model durability, financial projections, and forecast credibility. This role also contributes to strategic initiatives related to expanding access to healthcare carrier networks and evaluating alternative network strategies, helping the organization assess how investments and partnerships can improve cost while growing access for employers in the Captive model. Key Duties & Responsibilities: Conduct operator vetting and diligence on founders, management teams, and strategic partners, including background research, reference calls, and assessment of execution capability. Synthesize and evaluate findings, presenting in clear materials. Build and maintain financial models, operating models, and forecast scenarios to evaluate investment opportunities and portfolio company performance. Analyze market size, competitive landscape, business model durability, unit economics, return potential, and operational viability across prospective investments. Ensure regular Operator financial and performance reporting is aggregated and monitor portfolio company performance against forecast, identifying risks and upside, and recommended actions. Forecast portfolio cashflow based on investment exit and distribution timelines. Partner with internal stakeholders to drive opportunities to expand access to healthcare carrier networks or create network alternatives that improve affordability, access, and member experience in target geographies. Support strategic analysis of alternative network models, including tiered networks, cash-pay, value-based arrangements, narrow networks, and other access-expansion strategies. Quantify the pricing, access, and operational implications of networks and network alternatives and work with UW to ensure updated, accurate discounts are represented on proposals. Manage network onboarding, launch, and adoption. Internal and external communication and education (SME) on network strengths and options by geography. Qualifications 2–5+ years of experience in venture capital, corporate development, investment banking, consulting, healthcare analytics, or related roles. Strong financial modeling, forecasting, and valuation skills. Excellent research, synthesis, and written communication skills. Familiarity with healthcare payer, provider, network, or employer-benefit dynamics strongly preferred. Ability to translate ambiguous strategic questions into structured analyses and actionable recommendations. Better Benefits Medical, dental and vision benefits Annual bonus Dependent care 100% match up to max allowable Parental leave PTO beginning on Day 1 Tuition reimbursement Healthy work/life balance Hybrid office schedule 401(k) plan with company match Employee Assistance Program On-site gym with personal trainer access Life insurance and short term disability insurance More About Roundstone Headquartered in Rocky River, Ohio, Roundstone is proud to be a Northeast Ohio Top Workplace as recognized by The Plain Dealer and cleveland.com, based on anonymous employee feedback. We foster a supportive, values-driven culture where employees feel engaged, valued, and celebrated. Roundstone has also been named an Inc. 5000 award recipient for eight consecutive years, reflecting our continued growth and success. Our Core Values Live well: Be healthier and bring positive energy to all you do. Work smarter: Get things done, better. Own it: Accountability is your middle name. Be on time, do what you say, and finish what you start. Be intellectually curious: Always be learning. See opportunity everywhere and have a drive to know. Culture and fit are integral to success and in an effort to achieve a better match both from a candidate's perspective and our organization, Don’t meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they meet every single qualification. At Roundstone Insurance we are dedicated to building a diverse, inclusive, and authentic workplace, so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to apply anyways. You may be just the right candidate for this or other roles. #J-18808-Ljbffr