by Terrance Ellis | Jan 23, 2026 | Uncategorized
If you love building strong teams and clean systems, this role puts you right at the center of it. You’ll own onboarding and training for Pomelo’s outreach specialists, drive quality during ramp, and keep operations tight so new hires hit the ground running and stay on track.
About Pomelo Care
Pomelo Care delivers evidence-based virtual healthcare for women and children, spanning reproductive care, pregnancy, infant and pediatric care, and hormonal health through perimenopause and menopause. Their 24/7 multispecialty model supports medical, behavioral, and social needs, partnering with payers, employers, and providers to improve outcomes and expand access.
Schedule
United States (Remote)
Willingness to work some nights and weekends as needed
May flex into inbound and outbound calling coverage as needed
What You’ll Do
- Train all new outreach hires through live trainings, shadowing sessions, and training material creation
- Performance manage new hires through onboarding, ensuring 100% milestone completion during ramp
- Project manage training operations: equipment delivery, training cycles, and onboarding schedules
- Own onboarding quality assurance by listening to calls, scoring them, and providing clear, actionable feedback to people managers
- Build and maintain knowledge bases inside internal software systems
- Support outreach operations through admin work such as eligibility checks, process documentation, and fixing call documentation errors
- Manage support tickets with the telephony vendor and handle time card support tasks
- Manage inbound calls from prospective patients
- Conduct outbound calls and digital outreach (SMS/email) to educate patients on Pomelo services when needed
What You Need
- Experience training in a call center environment
- Experience performance managing in a call center environment
- Bachelor’s degree in education, healthcare, or a related field (health coaching certification is a plus)
- Strong organizational and time-management skills
- High-quality execution, reliability, and attention to detail
- Ability to work independently and as part of a team
- Remote-ready: reliable internet and ability to work from home
- Willingness to work some nights and weekends as needed
Benefits
- Competitive healthcare benefits
- Generous equity compensation
- Unlimited vacation
- Membership in the First Round Network (events, guides, Q&A library, mentorship)
This role is estimated at $70,000–$85,000, with total compensation also including equity and benefits.
If you’re the person who can turn onboarding into a repeatable machine, while still coaching humans like a human, this is your shot.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 23, 2026 | Uncategorized
If you love leading from the front, coaching teams to hit goals, and using data to tighten up the operation, this role is built for you. You’ll manage and motivate an outreach team to drive enrollment and activation, while keeping quality, compliance, and patient experience rock solid.
About Pomelo Care
Pomelo Care delivers evidence-based virtual healthcare for women and children, spanning reproductive care, pregnancy and postpartum, infant care and pediatrics, and perimenopause and menopause. Their 24/7 multispecialty model combines clinical, behavioral, and social support, partnering with payers, employers, and providers to expand access and improve outcomes.
Schedule
United States (Remote)
Monday–Friday, 8:30am–5:00pm CT
Some evening hours required to supervise and coach outreach specialists during evening shifts
What You’ll Do
- Lead, coach, and manage a team of outreach specialists to achieve enrollment and activation KPIs
- Onboard and train new specialists, including facilitating ongoing training and performance coaching
- Analyze outreach performance metrics (qualitative and quantitative) to spot trends and improve KPIs like enrollments and CAC
- Monitor call quality and protocol adherence through audits of call recordings and specialist interactions
- Ensure accurate documentation of outreach interactions, outcomes, and follow-ups while maintaining privacy and confidentiality standards
- Identify and implement process improvements to strengthen inbound and outbound calling efficiency and effectiveness
- Conduct regular performance evaluations of specialist calls and documentation
- Build and maintain team schedules to ensure consistent coverage
- Ensure compliance with government regulations and guidelines across all outreach activities
- Foster a supportive, inclusive team culture that encourages growth and development
What You Need
- Bachelor’s degree in healthcare management, public health, or a related field
- Proven experience in healthcare management with a focus on outbound calling and proactive outreach
- Strong knowledge of Medicaid policies, procedures, and value-based care
- Demonstrated leadership experience managing and motivating teams
- Strong communication and interpersonal skills with diverse patient populations
- Comfortable using metrics and reporting to drive performance improvement
- Detail-oriented with strong organization and documentation habits
- Ability to adapt quickly in a fast-paced, evolving environment
- Familiarity with healthcare software systems and CRM tools
Benefits
- Competitive healthcare benefits
- Generous equity compensation
- Unlimited vacation
- Membership in the First Round Network (events, guides, Q&A library, and mentorship)
Compensation for this role is estimated at $90,000–$115,000 base plus bonus, with total comp also including equity and benefits.
If you’re ready to lead a team that turns outreach into real access and real outcomes, jump on it.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 23, 2026 | Uncategorized
Help expand access to women’s and pediatric care by getting clinicians credentialed quickly and accurately with health plans. If you’re detail-obsessed, fast with portals and CAQH, and you love turning messy timelines into clean approvals, this role matters.
About Pomelo Care
Pomelo Care delivers evidence-based, virtual care for women and children across pregnancy, postpartum, infant care, pediatrics, and hormonal health through perimenopause and menopause. Their 24/7 multispecialty model partners with payers, employers, and providers to improve outcomes and reduce overall healthcare spend.
Schedule
- Remote role (United States)
- High-volume, milestone-driven workload with cross-functional coordination
What You’ll Do
- Complete group and practitioner health plan credentialing for Pomelo’s telehealth clinic and care team
- Track applications from submission through approval, contracting, and agreement with clear milestone visibility
- Proactively prevent and resolve delays or denials through rigorous follow-up and workflow improvements
- Partner with licensing, credentialing, and enrollment teams to ensure clinician licensure and up-to-date CAQH profiles
- Collaborate with nurses, NPs, physicians, therapists, and dietitians to answer credentialing questions and support navigation
- Maintain cross-functional alignment on timelines, roadblocks, and deliverables
What You Need
- 2–4 years of high-volume credentialing specialist experience
- Strong expertise in commercial health plan credentialing, including portals and CAQH
- High attention to detail with strong organization and documentation habits
- Proactive, resourceful problem-solving mindset with comfort in ambiguity
- Strong written and verbal communication and collaborative working style
- Strong prioritization and time management with clear ownership of timelines and escalation
Benefits
- Competitive healthcare benefits
- Generous equity compensation
- Unlimited vacation
- Membership in the First Round Network
- Salary range: $55,000–$75,000/year (plus equity and benefits)
Apply now if you’re ready to move fast, keep it accurate, and help more families access care.
If you’re the kind of person who lives for clean credentialing files and faster approvals, this is your lane.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 23, 2026 | Uncategorized
Negotiate delinquent accounts on behalf of clients and help them get real savings on the path to becoming debt-free. If you’re persuasive, organized, and thrive in a fast-paced queue, this role lets your communication skills turn into measurable impact.
About Beyond Finance
Beyond Finance helps everyday Americans break free from debt through compassionate support, compliance-first practices, user-centric technology, and customized financial solutions. They’ve helped over 1 million clients and continue to grow with a mission-driven, people-first culture.
Schedule
- Remote role
- Full-time position
- Fast-paced, queue-based workload with multitasking expectations
What You’ll Do
- Build and maintain relationships with external partners to negotiate delinquent accounts for client savings
- Oversee client finances and determine effective strategies for addressing inquiries and requests
- Consolidate common debts across multiple clients to strengthen negotiation leverage with agencies
- Manage account queues with strong time management and multitasking
- Maintain a client-first mindset focused on meeting needs and driving outcomes
- Support additional duties and special projects as assigned
What You Need
- Preferred bachelor’s degree in a relevant field (Business Administration, Finance, Banking, Actuarial Science)
- Strong communication skills (listening, verbal, and written)
- Ability to thrive in a fast-paced environment
- Strong teamwork mindset and commitment to collaboration and inclusion
- Client-focused approach with a passion for helping others
- Strong tech proficiency; Salesforce or similar CRM experience is a plus
Benefits
- $21/hour base pay
- Monthly commission based on amount of debt negotiated (per company commission plan)
- Health, dental, and vision coverage with strong employer contributions
- Generous PTO, paid holidays, and paid parental leave
- 401(k) matching program
- Career development, training, and advancement opportunities
Apply now if you’re ready to negotiate hard, stay organized, and help clients win.
If you can balance relationship-building with results-driven negotiation, you’ll thrive here.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 23, 2026 | Uncategorized
Help clients in financial hardship stay committed to a real path toward becoming debt-free. This is a high-call, high-empathy retention role for someone who can deescalate, negotiate, and guide people through tough moments without losing their cool.
About Beyond Finance
Beyond Finance helps everyday Americans break out of the debt cycle through individualized support, compliance-first practices, user-centric technology, and customized financial solutions. They’ve helped over 1 million clients and continue to grow with a mission-driven culture focused on doing the right thing.
Schedule
- Remote role
- High inbound call volume, fast-paced environment
- Weekend availability required
What You’ll Do
- Educate clients on the financial hardship debt program, including benefits, process, and available options
- Deescalate upset clients using empathy, active listening, and confident negotiation
- Use a CRM to access client details and document interactions and progress accurately
- Assess client financial situations and identify the best options to support their debt-free goals
- Create customized retention solutions aligned with client needs and encourage program continuation
- Meet or exceed retention targets and earn commissions based on performance
- Deliver best-in-class customer service across phone and other communication tools
What You Need
- Experience in retention, sales, or collections (required)
- High school diploma or equivalent (degree a plus)
- Ability to handle high call volumes in a fast-paced environment
- Strong deescalation, negotiation, and problem-solving skills
- CRM proficiency and strong technical aptitude
- Resilience and ability to stay calm under pressure
- Strong verbal and written communication skills with excellent active listening
- Ability to multitask, prioritize, and manage time effectively
Benefits
- $19–$20/hour base pay (plus commission opportunities)
- Health, dental, and vision coverage with strong employer contributions
- Generous PTO, paid holidays, and paid parental leave
- 401(k) matching program
- Career development, training, and advancement opportunities
Apply now if you’re ready to help people stay in the fight and deliver results on every call.
If you can balance empathy with firmness and keep clients moving forward, you’ll thrive here.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 23, 2026 | Uncategorized
Help people in real financial trouble stay the course toward becoming debt-free, one call at a time. This is a high-impact retention role built for someone who can deescalate, negotiate, and guide clients with empathy and confidence.
About Beyond Finance
Beyond Finance helps everyday Americans break free from crippling debt through individualized support, compliance-first practices, and user-centric technology. They’ve helped over 1 million clients and are continuing to grow with a mission-driven, people-first culture.
Schedule
- Remote role
- High inbound call volume, fast-paced environment
- Weekend availability required
What You’ll Do
- Educate clients on Beyond Finance’s financial hardship debt program, including benefits, process, and options
- Deescalate upset clients using empathy, active listening, and calm negotiation
- Use a CRM to review client status, document interactions, and track program progress accurately
- Assess client financial situations and recommend the best path toward becoming debt-free
- Create customized retention solutions aligned with client goals and encourage program continuation
- Meet or exceed retention targets and earn commissions tied to outcomes
- Deliver best-in-class customer service across phone and other communication tools
What You Need
- Bilingual Spanish (required)
- Experience in retention, sales, or collections (required)
- High school diploma or equivalent (degree a plus)
- Strong deescalation, negotiation, and problem-solving skills
- CRM proficiency and strong overall tech skills
- Ability to handle high call volumes and stay calm under pressure
- Strong verbal and written communication with excellent active listening
- Ability to multitask, prioritize, and manage time effectively
Benefits
- $19–$21/hour base pay (plus commission opportunities)
- Health, dental, and vision coverage with strong employer contributions
- Generous PTO, paid holidays, and paid parental leave
- 401(k) matching program
- Career development, training, and advancement opportunities
Apply now if you’re ready to work the calls that actually change somebody’s life.
If you can keep your cool, keep it human, and keep clients moving forward, you’ll thrive here.
Happy Hunting,
~Two Chicks…
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