Territory Sales Heathcare

Roundstone, Inc.; Cleveland (OH); Hybrid; USD 110,000 - 180,000; Full time

Benefits offered by this job

Annual bonus

Hybrid office schedule

401(k) plan with company match

Medical, dental and vision benefits

On-site gym

Job summary

Roundstone, Inc. is seeking a Regional Practice Leader to drive growth in the South Texas territory by expanding advisor relationships and winning new business.

The role leads the sales process and differentiates our captive stop‑loss program for employers seeking smarter benefit strategies. Ideal candidates will have 3–5 years in health insurance or advisor roles, strong communication skills, and a proven ability to simplify complex concepts for employers and agents.

Qualifications

• Experience building advisor relationships and pipelines.
• Ability to educate and win new business with confidence.
• Understanding of employee benefits and health insurance.
• Strong problem solving and communication skills.

Responsibilities

• Develop new advisor relationships to expand brand and market presence.
• Drive advisor growth by helping them win new binds and renewals.
• Collaborate with underwriting, marketing and customer success to deliver quotes.
• Maintain a robust sales pipeline across multiple geographies and agencies.

Skills

Relationship development

Pipeline management

Consultative selling

Proactive mindset

Communication skills

Problem solving

Employee benefits

Health insurance exp

Job description

Position:Regional Practice Leader, South Texas Territory

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

As a key driver of growth on our Sales team, the Regional Practice Leader (RPL) is responsible for building and expanding advisor relationships across their territory, with a relentless focus on winning new business. This role is about competing, educating, and binding new groups—positioning our captive stop-loss program as the go-to solution for employers seeking smarter employee health benefits strategies.

The RPL thrives in high-stakes, competitive situations. From engaging advisors to presenting directly to employer groups, including CEOs and CFOs, our RPL’s bring confidence, authority, alignment, and energy to every interaction. These leaders own the sales process, differentiate our program and driving results through their ability to simplify complex concepts and make them compelling.

This position requires exceptional communication skills, a deep commitment to learning about captive stop-loss programs, and the ability to convey complex information in a clear and compelling manner to advisors and employers.

Key Duties & Responsibilities

• Develop New Advisor Relationships:Proactively identify and establish relationships with new advisors to expand the Roundstone brand and market presence and drive growth.
• Drive Advisor Growth:Partner with advisors to develop their business, win new binds, and ensure successful renewals and continuous growth opportunities.
• Collaborate Across Departments:Work closely with internal teams, underwriting, marketing, and customer success to ensure timely and accurate delivery of quotes, enabling seamless communication and successful deal closures with agents and employer groups.
• Build and Maintain a Sales Pipeline:Strategically service multiple geographic markets and advisor agencies to develop a robust sales pipeline, fostering long‑term partnerships and consistent revenue generation.

Skills & Qualifications

• Relationship Development and Pipeline Management:Strong ability to establish and grow new or underutilized relationships, develop pipelines, and close opportunities by applying analytical insights and consultative sales techniques.
• Proactive and Confident Approach:A self‑motivated and results‑driven professional who thrives in competitive and sophisticated environments and takes initiative to meet and exceed goals.
• Strong problem‑solving skillsare essential, including the ability to identify root causes, analyze information thoroughly, brainstorm creative solutions, combat competitive noise, critically evaluate options, implement effective strategies, and adapt to changing circumstances.
• Ideally, a Deep Understanding of Employee Benefits:Demonstrated expertise in the intricacies of employee benefits, with the ability to communicate complex concepts effectively.
• Ideally, Health Insurance Industry Experience:3-5 years of proven success within the health insurance industry, ideally in roles with advisors, wholesalers, or related sectors.

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
• Annual bonus
• Dependent care 100% match up to max allowable
• Parental leave
• PTObeginning on Day 1
• 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.

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.