Hi, we're Oscar. We're hiring a Senior Sales Executive to join our Sales team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

As a Senior Sales Executive, you will be responsible for driving membership growth through the management of traditional insurance sales channels, as well as the pursuit of innovative sales strategies. On the traditional side, the Senior Sales Executive is in charge of  driving the broker strategy, ensuring insurance brokers across our coverage area have the information and tools to effectively understand and sell our product. On the creative side, the Senior Sales Executive is responsible for iterating on ideas to drive buzz at a local level and create partnerships with local organizations.

You will report into a Director, Sales.

Work Location:  

This is a remote position based in the field, open to candidates who reside in Tennessee. Your daily work will involve a blend of work from your home office and frequent travel for client meetings. Occasional travel may be required for team meetings and company events. #LI-Remote

Pay Transparency:

The base pay for this role is: $96,876.00 - $127,149.75 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and sales commissions.

Responsibilities:

• Building and managing broker and GA (General Agent) relationships in the assigned geographic market and as required to support growth goals.
• Identifying distribution partners to invest in and building relationships over time.
• Training brokers and GA partners on our product.
• Representing our product in the market at local broker and community events, which may take place during evening and/or weekend hours.
• Identifying and testing new growth opportunities and sharing learnings with broader sales team.
• Partner with teams to build and improve tools and processes that make our product the easiest to work with in the market.
• Meeting or exceeding sales goals while providing great service to distribution partners.
• Providing local competitive intelligence and market research.
• Being the voice of brokers and consumers within our product.
• Compliance with all applicable laws and regulations. 
• Other duties as assigned. 

Requirements:

• 4+ years of healthcare industry in an outside sales role.
• 3+ years of experience presenting and communicating with stakeholders at all levels.
• Must be a licensed insurance professional.

Bonus points:

• Bachelor's Degree or 4 years of relevant experience.
• Proficient in Salesforce.

Travel Required:

• Up to 50%

Who we are

The real world is the next frontier, and at Metropolis, we are creating the artificial intelligence to make it responsive. We are pioneering the Recognition Economy — a future where mundane repetition disappears and being known unlocks access, comfort and belonging everywhere you go. From transforming parking into a seamless drive-in, drive-out experience for millions of Members to expanding our intelligence layer across retail and hospitality, we are building a world that feels instinctive and magical. The future isn’t coming; it’s here, and we need builders, innovators and problem solvers to help us create it.

Who you are

Metropolis is seeking an Financial Systems Administrator to join our team. You will manage, maintain, and optimize our Oracle Cloud EPM (EPBCS) ecosystem while serving as the strategic bridge between our Financial Planning & Analysis (FP&A) organization and our centralized Data Engineering teams. In our high-velocity, 5,000-location enterprise, financial accuracy is inextricably linked to operational data. You will not only handle traditional EPM administration but also partner directly with data and operational teams to define technical requirements for integrating non-financial KPIs—such as location churn, new facility onboardings, occupancy rates, and transaction counts—directly from our data warehouse into our financial forecasting models. The ideal candidate brings a strong grasp of EPM architecture, SQL data structures, and the communication skills required to translate complex operational metrics into actionable financial drivers.

What you'll do

• Oversee the end-to-end administration, configuration, and continuous optimization of the Oracle Cloud EPM suite (EPBCS)
• Design, build, and troubleshoot Essbase ASO/BSO cubes to support large-scale operational scenario planning
• Act as the primary technical translator between Finance and centralized Data/IT teams; partner with Data Engineering to define technical requirements, ensuring that data models in our data warehouse (e.g., Snowflake) are properly structured for seamless EPM ingestion
• Collaborate with data teams to ingest high-volume non-financial KPIs (e.g., transaction counts, location churn) into EPM planning cubes
• Troubleshoot integration workflows and perform root-cause analysis on data discrepancies using SQL and Python
• Replace static calculation scripts with dynamic, context-aware logic to optimize system performance across thousands of sparse locations
• Utilize EPM Automate alongside Python or batch scripting for complex job scheduling
• Manage the volatile lifecycle of 5,000+ operational locations; ensure location additions, divestitures, hierarchical changes and associated access permissions, synchronize flawlessly across ERP, CRM, and EPM environments
• Develop and maintain high-impact visualization dashboards (Tableau, Looker, Hex) with intuitive narratives to facilitate executive decision-making; provide user support, training, and documentation for supported applications

What we're looking for

• 7+ years of Oracle EPM (EPBCS/Planning) System Administration and development experience in a high-growth, multi-location enterprise
• Bachelor’s degree in Computer Science, Finance, Economics, Accounting, Information Systems, or a related field
• Strong knowledge of data integration tools (EPM Integration Agent, Data Management, EPM Automate) and deep understanding of dependencies between functional components of Oracle EPM
• Proficiency in SQL and Python with a proven track record of automating financial processes
• Must understand modern cloud data structures well enough to perform "handholding" and meaningful collaboration with Data Engineers
• Exceptional ability to bridge the gap between technical data architecture and functional financial insights
• Strong experience partnering with Senior Leadership and the ability to translate "big picture" financial concepts into tactical execution plans for IT
• Ability to work independently or with a low-ego, highly collaborative, cross-functional team in a fast-paced, deadline-driven environment
• Experience leveraging AI tools to transform static workflows into responsive, high-output processes

While not required, these are a plus:

• Experience with Groovy scripting

4 Days in Office: Metropolis values in-person collaboration to drive innovation, strengthen culture, and enhance the Member experience. Our corporate team members hold to our office-first model, which requires employees to be on-site at least four days a week, fostering organic interactions that spark creativity and connection.

When you join Metropolis, you'll join a team of world-class product leaders and engineers, building an ecosystem of technologies at the intersection of parking, mobility, and real estate. Our goal is to build an inclusive culture where everyone has a voice and the best idea wins. You will play a key role in building and maintaining this culture as our organization grows. The anticipated base salary for this position is $120,000.00 USD to $130,000.00 USD annually. The actual base salary offered is determined by a number of variables, including, as appropriate, the applicant's qualifications for the position, years of relevant experience, distinctive skills, level of education attained, certifications or other professional licenses held, and the location of residence and/or place of employment. Base salary is one component of Metropolis' total compensation package, which may also include access to or eligibility for healthcare benefits, a 401(k) plan, short-term and long-term disability coverage, basic life insurance, a lucrative stock option plan, bonus plans and more. #LI-AW1 #LI-Onsite

Title of role: Program Manager, Member Services Content & Communications
Location: Remote but if in NY/ Boston (2 days in office)
Approved Salary Range: $95,000-$115,000

About the Role:

The Program Manager, Content & Communications plays a critical role in enabling a luxury customer experience by developing clear, engaging, and effective content for both member services agents and members. This role is responsible for training content creation, agent-facing knowledge resources, and member-facing help content.

This role partners closely with MS Training, MS Operations, and MS Operations Excellence teams to ensure content is accurate, timely, scalable, and aligned with both operational needs and luxury brand standards.

Key Responsibilities:

• Training & Agent Enablement

  • Design, develop, and maintain training materials for customer service agents, including onboarding, refresher training, process updates, and learning modules.
  • Develop refresher modules and tips/tricks series to keep tenured agents sharp and engaged
  • Translate complex policies, systems, and workflows into clear, actionable training content that supports agent confidence and performance.
  • Partner with Training and Operations leaders to identify content gaps and continuously improve learning effectiveness and agent readiness.
  • Move beyond text-heavy desks and create engaging content using videos, interactive modules, infographics, and gamified learning that caters to diverse learning styles

  Agent-Facing Knowledge & Help Content

  • Own and maintain agent-facing knowledge base articles, job aids, and standard operating procedures ensuring ease of navigation, accuracy, and optimization
  • Collaborate with cross-functional partners to create content related to policy updates, tool enhancements, and operational changes.
  • Ensure agent-facing content is structured, standardized, and optimized for AI-powered tools to enable accurate, consistent, and context-aware support at scale while maintaining a high-quality agent & member experience.

  Member-Facing Service Content

  • Create and update member-facing content, including Help Center articles, FAQs, policy explanations, and transactional messaging to reduce friction and promote self-service
  • Ensure all member-facing content reflects the luxury brand voice while clearly setting expectations and helping reduce inbound contacts.
  • Ensure member-facing content is structured, standardized, and optimized for AI-powered tools to enable accurate, consistent, and context-aware support at scale while maintaining a high-quality member experience.

  Agent Facing Communication

  • Support internal communications and engagement initiatives within the Member Service organization, including change communications, operational updates, and recognition content.
  • Curate Flash Alerts and Reminders to ensure agents are aware of recent changes, outages, or policy shifts.

  Content Governance & Optimization

  • Establish content standards, templates, and best practices across training, agent-facing, and member-facing materials.
  • Track content performance and engagement metrics (e.g., article usage, training completion, contact drivers) and use insights to iterate and improve effectiveness.
  • Manage content calendars, updates, and version control to ensure consistency across channels and audiences.

Experience and Background Needed:

• • Strong writing and editing skills with the ability to adapt tone for agents, internal stakeholders, and luxury consumers.
  • Experience in creating training materials, knowledge base content, or internal communications in a customer service or e-commerce environment.
  • Strong cross-functional collaboration and stakeholder management skills.
  • Comfort working in a fast-paced, evolving environment with multiple priorities.
  • Proficiency with content creation tools (e.g., Gemini, LM Notebook, Canva, Loom, Camtasia, or Articulate) to build visually compelling content and training.

• Education

  • Bachelor’s degree in communications, marketing, education, organizational development or related field required

  Years of experience

  • 3-5 years’ experience in content creation, communications, knowledge management, training, curriculum design

  Technical skills

  • Knowledge management platforms
  • Experience leveraging AI tools to support content creation, editing, summarization, and optimization while maintaining quality, accuracy, and brand voice.
  • Experience optimizing content for AI-driven search and automation
  • Ability to use data to inform content gaps and performance

The above statements are intended to describe the general nature and level of work being performed by employee(s) assigned to this job. They are not intended to be an exhaustive list of all responsibilities, duties and skills required of employee(s) assigned to this job. Rue Gilt Groupe reserves the right at any time, with or without notice, to alter or change job responsibilities, reassign or transfer job position or assign additional job responsibilities within your general skill set or capabilities. Rue Gilt Groupe is proud to be an Equal Opportunity workplace. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

What We Offer:

Rue Gilt Groupe is committed to providing Associates with equal pay for equal work and carefully considers a wide range of compensation factors, including but not limited to, prior experience, education, certification(s), license(s), skills and expertise, location, internal equity, and other factors that are job related and consistent with business need. Our goal is to support, reward and compensate the entire individual. Depending on role eligibility, your offer may also include bonus/commission, stock options, 401(k) participation, paid time off, medical, dental, vision and basic life insurance. Therefore, final offer amounts may vary from the amount stated.

We Encourage You to Apply:

At Rue Gilt Groupe, diversity enriches our passion, collaboration, kindness and innovation. We’re committed to fostering an inclusive environment where every Associate is empowered to learn, grow and bring their full self to work. Even if you don't check off every qualification in the job description, that's okay. We encourage you to apply to any role that excites you and sparks delight! We can't wait to learn more about you.

Work Authorization
Rue Gilt Groupe requires all applicants to be currently authorized to work in the United States on a full-time basis. This position is not eligible for visa sponsorship now or in the future. Rue Gilt Groupe is an Equal Opportunity Employer and will consider all qualified applicants without regard to race, color, religion, sex, national origin, disability, or protected veteran status.

Join Horace Mann: Empower Educators, Achieve Financial Success

Ready to Make a Difference?

Join Horace Mann today and take the first step toward achieving your career and financial goals while making a meaningful impact on the educators you serve. Together, we can help educators secure their future while empowering you to achieve your own.

As an Insurance Producer at Horace Mann, you’ll receive mentorship from an experienced agent while gaining hands-on experience in the industry. Our insurance products are tailored to meet the unique needs of educators, and we provide outstanding training, competitive rates, and flexible work options. With an unparalleled compensation structure, exciting incentives, and bonus opportunities, top performers have the chance to earn all-expenses-paid trips to amazing destinations.

Why Join Us?

• Performance-Based Compensation [1099] with a 36-month incentive plan and enhanced commissions
• Monthly incentives based on sales volume for the first 36 months
• Quarterly production bonuses for the first 36 months
• Leverage established books of business while learning the business
• Access to a niche market that increases your potential for success
• Value-added services to connect you with ideal clients
• Simple, streamlined products and sales processes for quick success
• Networking, community, and industry events to expand your connections
• A comprehensive, multi-line product portfolio in a ‘One-Stop Shop’ model

What You Will Do:

• Solve financial challenges faced by educators through tailored solutions
• Present with confidence—one-on-one or in large groups—to educate potential clients on products
• Engage in community and networking events, expanding your professional connections
• Stay current with industry trends and apply new knowledge to help clients
• Cultivate strong market relationships and build a solid client base
• Invest time and resources in ensuring the success and growth of your business

What We’re Looking For:

• A commitment to helping educators achieve financial prosperity
• Strong interpersonal and presentation skills
• Self-motivation and the ability to manage your own business
• The ability to obtain or currently hold state licenses in Life & Health and Property & Casualty

Compensation and Benefits:

• Sign-On Bonus
• Uncapped Earnings/Commission
• Structured Incentive & Bonus Pay to reward your hard work
• Work Environment—work in-person, in the field, and/or from an office setting

Support and Accountability:

As an Insurance Producer, you'll be guided by a mentor agent who will support you every step of the way to ensure your success.

We make a difference!

At Horace Mann, we are driven by our mission to support the educators who shape the future of our children. We believe that educators deserve someone who looks after their financial well-being just as they do for their students. Our passion lies in providing tailored solutions that protect what educators have today and help them achieve long-term financial security and happiness.

#LI-WR1  #LI-MN1

#VIZI#

Join Horace Mann and Unlock Your Financial Potential

Ready to take control of your financial future? At Horace Mann, we are here to support you in achieving your goals and making a meaningful difference in the lives of the educators who trust you. Join us and take the first step toward building a brighter, more prosperous future.

If you're ready to take the next step toward realizing your financial goals, we invite you to join our team as an Exclusive Agent. With Horace Mann’s expertise and your ambition, together, we can help you unlock your full potential.

What We Offer:

• Competitive, performance-based [1099] compensation with an industry-leading 48-month incentive package
• Earning incentives tied to your activity and success during the first 48 months
• Quarterly production incentives for the first 48 months, rewarding consistent performance
• Dedicated Premier Service Representative to handle client service work, allowing you to focus on building your business
• Exclusive niche market designed to increase your opportunities for success
• Cutting-edge technology and ongoing training to support and grow your operations
• A comprehensive multiline product portfolio to meet a variety of client needs
• Market and relationship-building programs to help you establish and grow your network

Your Path to Success:

Several factors will contribute to your success in this role, including:

• A commitment to identifying and implementing solutions that help educators achieve affordable insurance solutions and financial security

• A focus on achieving market access and building strong relationships
• The ability to confidently present products to both groups and individuals
• Active engagement in networking, community, and industry events
• A dedication to investing time and resources to ensure the long-term success of your business

What We’re Looking For:

• Strong interpersonal and business management skills to build and manage your agency
• 2-5 years of experience in the insurance and financial services industry (preferred)
• Resident State General Lines Insurance Licenses:
• Life and Health Insurance License
• Property and Casualty Insurance License
• Ability to obtain FINRA Series 6 & 63 licenses (if applicable in your region)

Join Horace Mann and Unlock Your Financial Potential

Ready to take control of your financial future? At Horace Mann, we are here to support you in achieving your goals and making a meaningful difference in the lives of the educators who trust you. Join us and take the first step toward building a brighter, more prosperous future.

If you're ready to take the next step toward realizing your financial goals, we invite you to join our team as an Exclusive Agent. With Horace Mann’s expertise and your ambition, together, we can help you unlock your full potential.

What We Offer:

• Competitive, performance-based [1099] compensation with an industry-leading 48-month incentive package
• Earning incentives tied to your activity and success during the first 48 months
• Quarterly production incentives for the first 48 months, rewarding consistent performance
• Dedicated Premier Service Representative to handle client service work, allowing you to focus on building your business
• Exclusive niche market designed to increase your opportunities for success
• Cutting-edge technology and ongoing training to support and grow your operations
• A comprehensive multiline product portfolio to meet a variety of client needs
• Market and relationship-building programs to help you establish and grow your network

Your Path to Success:

Several factors will contribute to your success in this role, including:

• A commitment to identifying and implementing solutions that help educators achieve affordable insurance solutions and financial security

• A focus on achieving market access and building strong relationships
• The ability to confidently present products to both groups and individuals
• Active engagement in networking, community, and industry events
• A dedication to investing time and resources to ensure the long-term success of your business

What We’re Looking For:

• Strong interpersonal and business management skills to build and manage your agency
• 2-5 years of experience in the insurance and financial services industry (preferred)
• Resident State General Lines Insurance Licenses:
• Life and Health Insurance License
• Property and Casualty Insurance License
• Ability to obtain FINRA Series 6 & 63 licenses (if applicable in your region)

Join Horace Mann and Unlock Your Financial Potential

Ready to take control of your financial future? At Horace Mann, we are here to support you in achieving your goals and making a meaningful difference in the lives of the educators who trust you. Join us and take the first step toward building a brighter, more prosperous future.

If you're ready to take the next step toward realizing your financial goals, we invite you to join our team as an Exclusive Agent. With Horace Mann’s expertise and your ambition, together, we can help you unlock your full potential.

What We Offer:

• Agency owner with an exclusive niche, defined territory — no overlap with other agents
• Competitive, performance-based [1099] compensation with an industry-leading 48-month incentive package
• Earning incentives tied to your activity and success during the first 48 months
• Quarterly production incentives for the first 48 months, rewarding consistent performance
• Dedicated Service Representative to handle client service work, allowing you to focus on building your business
• Cutting-edge technology and ongoing training to support and grow your operations
• A comprehensive multiline product portfolio to meet a variety of client needs
• Market and relationship-building programs to help you establish and grow your network

Your Path to Success:

Several factors will contribute to your success in this role, including:

• A commitment to identifying and implementing solutions that help educators achieve affordable insurance solutions and financial security
• A focus on achieving market access and building strong relationships
• The ability to confidently present products to both groups and individuals
• Active engagement in networking, community, and industry events
• A dedication to investing time and resources to ensure the long-term success of your business

What We’re Looking For:

• Strong interpersonal and business management skills to build and manage your agency
• 2-5 years of experience in the insurance and financial services industry (preferred)
• Resident State General Lines Insurance Licenses:
• Life and Health Insurance License
• Property and Casualty Insurance License
• Ability to obtain FINRA Series 6 & 63 licenses (if applicable in your region)

#LI-WR1

#LI-MN1

#VIZI#

Join Horace Mann and Unlock Your Financial Potential

Ready to take control of your financial future? At Horace Mann, we are here to support you in achieving your goals and making a meaningful difference in the lives of the educators who trust you. Join us and take the first step toward building a brighter, more prosperous future.

If you're ready to take the next step toward realizing your financial goals, we invite you to join our team as an Exclusive Agent. With Horace Mann’s expertise and your ambition, together, we can help you unlock your full potential.

What We Offer:

• Agency owner with an exclusive niche, defined territory — no overlap with other agents
• Competitive, performance-based [1099] compensation with an industry-leading 48-month incentive package
• Earning incentives tied to your activity and success during the first 48 months
• Quarterly production incentives for the first 48 months, rewarding consistent performance
• Dedicated Service Representative to handle client service work, allowing you to focus on building your business
• Cutting-edge technology and ongoing training to support and grow your operations
• A comprehensive multiline product portfolio to meet a variety of client needs
• Market and relationship-building programs to help you establish and grow your network

Your Path to Success:

Several factors will contribute to your success in this role, including:

• A commitment to identifying and implementing solutions that help educators achieve affordable insurance solutions and financial security
• A focus on achieving market access and building strong relationships
• The ability to confidently present products to both groups and individuals
• Active engagement in networking, community, and industry events
• A dedication to investing time and resources to ensure the long-term success of your business

What We’re Looking For:

• Strong interpersonal and business management skills to build and manage your agency
• 2-5 years of experience in the insurance and financial services industry (preferred)
• Resident State General Lines Insurance Licenses:
• Life and Health Insurance License
• Property and Casualty Insurance License
• Ability to obtain FINRA Series 6 & 63 licenses (if applicable in your region)

#LI-MN1

#VIZI#

Horace Mann is seeking a motivated insurance professional to join our team serving the educator market. This opportunity is designed for individuals looking to build or grow their own business while being supported by a strong brand, established resources, and a niche educator market.

Based on experience and background, this opportunity has an existing book of business and may be aligned as either an Exclusive Agent (EA) or an Enhanced Exclusive Agent. Both opportunities require a Property & Casualty and Life & Health license.

Role Options

• Exclusive Agent (EA):
  Focused on continuing to build from an existing book of business while expanding market access within the educator community through school events, networking, and referrals, with renewal income earned as new business is written.
• Enhanced Exclusive Agent:
  Assumes and expands an existing book of educator clients with in-force policies and immediate renewal income, while continuing to grow relationships and deepen market presence. Must also have, at minimum, the SIE prior to start; Series 6 and/or Series 63 required or to be obtained after hire, as applicable.

What You’ll Do

• Build and maintain relationships with educators and school employees
• Identify client needs and recommend insurance and financial solutions
• Generate new business through referrals, school partnerships, and networking
• Retain and renew policies while delivering exceptional service
• Cross-sell auto, home, life, and retirement products
• Participate in community and educator-focused events

What We Offer

• 1099 compensation with uncapped earning potential with renewals
• Industry-leading incentive compensation during the first 48 months while you grow your book (Exclusive Agent)
• Book of business with immediate renewal income (Enhanced Agent)
• Exclusive territory within a niche educator market
• Dedicated service support so you can focus on growth
• Ongoing training, technology, and business development resources
• Flexibility to manage your own schedule and business

Qualifications

• Active Life & Health and Property & Casualty licenses (Exclusive & Enhanced Agent)
• Ability to obtain FINRA licenses (SIE, Series 6 & 63, if applicable) (Enhanced)
• Insurance or financial services experience preferred
• Strong relationship-building and communication skills
• Entrepreneurial mindset and self-motivation

Why Horace Mann?

• Exclusive access to the educator market
• Opportunity to build a meaningful, long-term business
• Strong earning potential with stability and growth
• Ability to make a real impact supporting educators’ financial futures

Whether you’re looking to build from a small book, assume an established one, or grow into a future leadership role, Horace Mann offers a path designed to support your success.

#LI-MN1

#VIZI#