Position: Customer Outcomes Manager (COM III)
About Roundstone
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.
Role Description
Do you thrive on building trust, owning outcomes, and turning complex data into a winning renewal strategy? Roundstone is looking for a strategic, consultative, and relationship-driven professional to join our customer success team as a Customer Outcomes Manager (COM 3).
This is a critical member of Roundstone’s Commercial organization, while this role is not responsible for new business prospecting. The COM III owns the retention, growth, and strategic management of an assigned book of business. Success is measured through client retention, premium preservation, advisor engagement, identification of growth opportunities, and the ability to strengthen long-term employer and advisor relationships. This is a consultative sales role focused on expanding value within existing relationships rather than acquiring new ones.
You'll work closely with Underwriting, Cost Containment and our Clinical teams to ensure every employer group is fully informed and set up for the best possible outcome, while building the kind of trusted advisor relationships that turn renewals into long-term partnerships. With an established book of business and a runway for growth, this role rewards strategic thinking, clear communication and a genuine drive to win and keep every account.
This Job is for you If...
- You get energy from owning your outcomes
- You can look at a data set and tell a client a story that changes how they see their path forward
- You’re comfortable being the one who has to deliver hard news and skilled enough to do it in a way that keeps trust intact
- You’re curious, coachable, and motivated by outcomes rather than activity for activity’s sake
- You want a seat where your judgment and consultative instincts matter as much as your follow-through
- You’re comfortable in client-facing and advisor events throughout the year
- You’re energized by ongoing training and development opportunities to sharpen, reinforce, and enhance your sales skills and introduce new techniques.
Key Duties & Responsibilities
Strategic Account Leadership
- Own the full client relationship for an assigned portfolio from onboarding through renewal with a proactive, retention-first approach
- Serve as the primary point of contact and trusted advisor for employer groups, advisors, and Regional Practice Leaders
- Occasional travel to make in-person or pop-up visits to employer groups and advisors, reinforcing relationships and positioning Roundstone as the stronger choice
- Develop and maintain deep knowledge of each employer group’s goals, workforce demographics, and benefit priorities
- Lead strategic account planning to identify risks, opportunities, and customized solutions
Consultative Selling & Retention
- Identify opportunities to expand Roundstone’s value proposition through enhanced cost containment solutions, plan optimization strategies, and deeper advisor engagement.
- Lead renewal conversations with confidence, using data, utilization trends, and cost containment insights to build compelling narratives that drive retention
- Overcome objections and manage competitive threats through consultative dialogue and evidence-based positioning
- Maintain accountability for retention, premium preservation, and portfolio growth metrics.
- Ability to operate in a highly competitive market, fast paced environment with periods of the year that are demanding, especially during the peak renewal seasons, with a target account retention of 90%.
Data Analysis & Outcomes Storytelling
- Retrieve, analyze, and present employer reporting in a clear, outcomes-driven format for both internal and external stakeholders
- Translate complex utilization data and cost drivers into accessible insights that support informed employer decision-making
- Partner with the Underwriting team to optimize renewal timing and financial positioning
- Collaborate with the Cost Containment Consultant and CSI team to ensure health plan design and cost containment solutions are fully optimized
Stakeholder Engagement & Communication
- Establish a consistent, proactive communication cadence with all stakeholders to stay ahead of client needs and renewal timelines
- Navigate complex service escalations with professionalism, urgency, and a solution-oriented mindset
- Represent the outcomes management function with credibility and executive presence in client and advisor-facing settings
- Maintain detailed, organized records of client interactions, renewal strategy, and next steps within CRM or outcomes tracking tools
Skills and Qualifications
- 5–7 years of experience in health insurance, employee benefits, or a related industry, with demonstrated exposure to client-facing, sales, or account management functions
- Account executive or consultative sales mindset, with a track record of influencing, retaining, and growing client relationships
- Entrepreneurial and outcomes-driven motivated by ownership of a portfolio and its growth
- Strong ability to analyze data and translate findings into compelling, client-ready narratives
- Excellent verbal and written communication skills, including executive-level presentation ability
- Familiarity with CRM or outcomes tracking tools; comfort adopting new sales enablement technology a plus
- Curious, coachable, and motivated by commission incented income
- Highly organized and capable of managing a complex portfolio with competing timelines and priorities
- Bachelor’s degree from an accredited college or university preferred
- Bonus: prior experience in an account executive, strategic account management, or outcomes management role
Better Benefits:
We’re leaders in our industry, so naturally, we look out for our employees’ best interests with a robust benefits package. Roundstone employees are eligible for:
- Medical, dental and vision benefits
- Dependent care 100% match up to max allowable
- Healthy work/life balance
- 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, please take a minute, click on the link and take the really brief survey:
https://go.cultureindex.com/p/aV2vIUWBQKpuW3
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.
