Job Description
Account Manager
Strategic Retention & Account Executive | Sales Organization
Sales — Account Management
Manager, Account Management
A Sales Role at Its Core
The Account Manager 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 — it is not a traditional customer service or client support role. Compensation includes incentive pay tied directly to business outcomes.
The Mission: A 90+% Renewal Rate
The single most important accountability of this role is achieving a 90+% renewal rate on all existing Roundstone business in the assigned portfolio. That is the target — and it would represent the highest renewal rate in the industry.
You will not pursue it alone. The Account Manager is backed by the full weight of Roundstone's Sales team: Regional Practice Leaders in every territory, the Chief Commercial Officer, and supporting departments across Underwriting, Partner Solutions, and Claims. When a renewal turns competitive, Roundstone fights for every account — and this role leads that fight with the entire organization behind you. You should expect to feel supported in this mission every day, because keeping a client is a team outcome, and this seat is the quarterback.
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 the Sales team as an Account Manager.
This role plays a critical part in our retention strategy. As an Account Manager, you'll own a portfolio of employer groups and advisor relationships, serving as the strategic quarterback who keeps clients engaged, informed, and confident in their decision to stay with Roundstone year after year. You'll go beyond reporting and renewal administration to bring an account executive mindset to every client interaction.
You'll work closely with Underwriting, Operations, 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.
A word about the environment: you will be operating in a highly competitive market, in a fast-paced organization with periods of the year that are demanding — especially during peak renewal seasons. If you do your best work when the stakes are real and the calendar is full, you'll thrive here.
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 competitive by nature and want to fight for every account, not just manage a queue
- 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
Strategic Account Leadership
- Own the full client relationship for an assigned portfolio from year-one transition to Roundstone 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
- Travel occasionally for in-person and 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 & Growth
- Deliver on the role's defining accountability: a 90+% renewal rate across the assigned book, with the support of Regional Practice Leaders, the CCO, and supporting departments
- Approach every client interaction with an account executive lens — listening for needs, positioning solutions, and reinforcing the value of the Roundstone offering
- 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 — escalating early and pulling in the full team when a renewal is at risk
- Identify opportunities to expand Roundstone's value proposition through enhanced cost containment solutions, plan optimization strategies, and deeper advisor engagement
- Maintain accountability for retention, premium preservation, and portfolio growth metrics
- Collaborate with advisors to align on renewal strategy, broker relationships, and employer group expectations
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
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 account management function with credibility and executive presence in client and advisor-facing settings
- Participate in multiple client-facing and advisor events throughout the year, representing Roundstone alongside the sales team
- 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 tied to business outcomes
- Highly organized and capable of managing a complex portfolio with competing timelines and priorities — including the demanding pace of peak renewal seasons
- Bachelor's degree from an accredited college or university preferred
- Bonus: prior experience in an account executive, strategic account management, or outcomes management role
To apply, please complete our mandatory 7–10 minute culture survey and submit your resume, cover letter, and salary requirements to
[email protected].
Culture 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.
