Top Talent. Right Plan. Healthier You
Are you an
entrepreneur at heart?
Do you thrive on building your own success, taking ownership of your work, and making a real impact? At
WiseChoice,
we’re looking for visionary self-starters to join our remote-first team—where you’re in control of your growth, your income, and your future.
At
WiseChoice
, our mission is to expertly guide consumers through their health insurance and related options when, where, and how they prefer. We’re creating a better way – one that’s transparent and trustworthy for both our consumers externally and our employees internally.
As a Sales Enablement Coach, you will monitor sales team interactions, providing training, feedback, and guidance to enhance and improve the skills of sales agents, resulting in increased conversion rates, quality scores, policy effectuations, and member retention.
**This position is fully remote**
Quick Facts About WiseChoice Senior Solutions
Founded: April 2024
Mission: Redefining Medicare by putting people first (Talent & Senior), one WiseChoice at a time.
Vision: Earn More. Work Less. No Micromanagement.
Traction
:
One of the fastest-growing insure-tech start-up teams.
Key investors:
Innovative Financial Group (IFG), FYM Financial, Humana
Team size: 45 + agents & full-time equivalent (April 2025) and targeting 300+ by end of 2026
Location: 100% remote (US required, preferably Midwest/Eastern Time Zone
)
What you’ll do:
Monitor the performance of all Sales Agents and identify areas of improvement in key areas of sales process, quality assurance, policy effectuation, and member retention.
Provide one-on-one sales coaching sessions to agents and managers to improve identified leading and key performance indicators.
Cultivate and foster an environment of open communication with the sales team to ensure their ideas and challenges are heard and addressed.
Identify sales process enhancements by observing sales encounters, studying sales performance qualitative/quantitative behaviors, reports, and data.
Stay up-to-date with new market trends and demands of a corporate sales environment.
Work closely with managers/business support to help investigate and resolve complaints, escalations, trends, and more.
Leverage multiple reporting tools to identify high-risk submissions and target sales agents who are at risk of a lower retention or issuance projection.
Have thorough knowledge of products and services that WiseChoice offers.
Additional duties as assigned (sales facilitation, meetings, etc.).
Who are you:
Bachelor's degree in Human Resources, Marketing, or related field.
2 years of work experience as a Sales Coach or Sales Trainer.
License in Health Insurance Sales
Professional certification in sales training: Certified Inside Sales Professional (CISP).
Preferred
Strong knowledge of the sales process and its best practices.
Strong ability to champion and adapt to process changes consistent with new/modified organizational goals.
Excellent presentation and coaching skills.
Excellent verbal and written communication skills.
Computer proficiency, including Microsoft Office and Webinar/Video chat tools.
Active listening skills with the ability to quickly and accurately respond to inquiries and requests.
Detail-oriented and well-organized with strong interpersonal skills.
Ability to work well alone or as part of a team.
Why WiseChoice?
Join an organization that values boldness, ambition, collaboration, and a customer-centric approach.
Work in a dynamic, entrepreneurial environment with a strong team spirit.
Career advancement opportunities in a high-growth startup
Enjoy competitive compensation + performance bonus
About Us:
WiseChoice
was founded in 2024 , and we’re more than just a company—we’re a team dedicated to simplifying Medicare for seniors nationwide. Built by Agents for Agents. With a focus on integrity, innovation, and exceptional service, we empower our agents to succeed while making a real impact. Join us and be part of a supportive culture that puts you first. Ready to Get Started? If you’re driven to succeed and passionate about helping others, we want to hear from you!