Personal Risk Advisor – Remote

This is a build-your-own-book role for people who want autonomy and long-term commission income, not a scripted call-center grind. If you can prospect, market yourself, and build trust fast, Pyron Group is offering the tools and support while you control the pace.

About Pyron Group
Pyron Group is a people-first insurance agency built on empathy, simplicity, and service. They help clients navigate personal insurance decisions with clarity and confidence, and they support teammates with training, marketing resources, and a collaborative culture.

Schedule
Fully remote (Mississippi residents only, more states expected later)
Full-time, entrepreneurial structure with flexible scheduling
No fixed quotas, income scales with your effort and book growth
Agency provides technology and marketing assets

What You’ll Do
• Prospect and sell personal insurance products (auto, home, renters, umbrella, and more)
• Generate leads through your personal network, community presence, and social platforms
• Guide clients from quote through renewal with a strong, service-first experience
• Manage and service your book of business with agency support as needed
• Maintain required state licensing and follow regulatory guidelines
• Participate in optional mentorship and development resources

What You Need
• Mississippi resident (required)
• Strong interpersonal skills and comfort with self-promotion and relationship selling
• Independent work style with consistent follow-through
• Digital comfort using CRM and quoting platforms
• Experience in insurance, real estate, direct sales, or customer service (helpful but not required)
• Property & Casualty license or ability to obtain one (Mississippi preferred)

Benefits
• Commission-based with the ability to choose a compensation track based on your goals and sales confidence
• Residual income from renewals as your book grows
• Full tech setup provided (laptop, phone system, remote tools)
• Training, onboarding, and marketing support
• Benefits package available depending on compensation track, including:
• Medical, dental, vision
• HSA/FSA with employer contributions
• Wellness program
• 401(k) with match
• Company-paid life and short-term disability
• Optional long-term disability and supplemental life insurance

Real talk: this role is only a good fit if you’re willing to hunt. If you want a guaranteed base and a predictable day, this will feel stressful. If you want freedom and you can sell, it could be a strong long-term play.

If you’re serious about it, your next move is simple: apply today, and be ready to speak clearly about how you’ll generate leads in your first 30 days.

Happy Hunting,
~Two Chicks…

APPLY HERE

Clinical Scheduling Specialist – Remote

Own the schedule. Keep the practice flowing. If you’re the kind of person who can build clinician templates, manage waitlists, and keep Athena running like a well-oiled machine across time zones, Midi wants you as their master scheduler.

About Midi Health
Midi is a digital healthcare company focused on delivering a kind, human-centered care experience. They’re a fast-growing startup practice offering fully remote work, strong benefits, and a chance to get in early and help shape how the operation scales.

Schedule
Fully remote
Full-time, 40 hours per week
Required shift: Monday to Friday, 9:30 AM to 6:00 PM PST (8-hour shift plus 30-minute unpaid lunch)

What You’ll Do
• Build and manage every Midi clinician’s schedule in athenaHealth
• Monitor clinician schedules daily to ensure accuracy and availability
• Manage patient waitlists to backfill openings as time becomes available
• Reschedule patients as needed and adjust clinician schedules when changes come up
• Support Care Coordinator team coverage as assigned to keep operations moving

What You Need
• Availability for the required M–F 9:30 AM–6:00 PM PST shift
• 3+ years of experience building clinician schedules (not just booking patients), preferably in athenaHealth
• 1+ year of experience working at a digital healthcare company
• Proficiency scheduling across multiple time zones
• Strong attention to detail, ownership mindset, and ability to self-direct in a remote environment

Benefits
• $30/hour (non-exempt)
• Medical, dental, vision, and 401(k)
• Fully remote work-from-home setup
• A human-centered culture at a growing healthcare startup

This kind of scheduling seat is high-trust and high-impact. If you’ve got Athena expertise and the “nothing slips through the cracks” mindset, apply now.

You’ll be the reason the care stays smooth.

Happy Hunting,
~Two Chicks…

APPLY HERE

Account Manager – Remote

Own a book of business, grow revenue, and turn customers into raving fans. If you’re strong at relationship-building, renewals, and consultative upsell and cross-sell, Fleetworthy wants you driving retention and expansion.

About Fleetworthy
Fleetworthy (rebranded in September 2024 from Bestpass, Fleetworthy, ExpressTruckTax, and Drivewyze) simplifies fleet safety, compliance, toll management, and efficiency under one connected platform. Their tools help fleets reduce risk, improve performance, and operate beyond compliant, supporting millions of drivers and vehicles across the industry.

Schedule
Remote or hybrid role (based on location and team needs)
Full-time, customer-facing position supporting account growth, renewals, and product adoption
Work includes managing multiple customers and priorities in a fast-paced environment

What You’ll Do
• Grow revenue within an existing customer base through strategic upsell, cross-sell, and renewals
• Build and maintain a strong pipeline of expansion opportunities while hitting sales targets
• Manage customer engagement end-to-end, using customer journey mapping and proactive outreach
• Strengthen customer lifetime value by understanding segmentation, behaviors, and account insights
• Deliver a superior customer experience through consistent communication, follow-through, and customer advocacy
• Act as the voice of the customer, sharing feedback and feature requests to influence product improvements
• Drive customer adoption by educating clients on new capabilities and best practices
• Collect customer insights through surveys, interviews, and focus groups to improve satisfaction and retention
• Help generate customer references and case studies that support growth

What You Need
• 3 to 5 years of account management experience (or closely related customer growth role)
• Strong interpersonal skills and the ability to work well with internal and external stakeholders
• Customer-first mindset with the ability to manage expectations and build trust
• Ability to juggle high volume across multiple accounts and priorities without dropping details
• Excellent written and verbal communication skills
• CRM experience preferred (Salesforce or similar)
• Comfort with Microsoft Office tools (PowerPoint, Word, Excel a plus)
• A results-oriented mindset with the creativity and initiative to exceed targets

Benefits
• Base salary range: $50,000 to $65,000 USD plus commission
• Remote or hybrid flexibility (role-dependent)
• High-impact role with clear ownership of retention and revenue growth

If you’re the type who can keep customers happy and still grow the account, this one’s worth moving on quickly. Apply while it’s still open.

Be the advocate. Be the closer. Be the reason they renew.

Happy Hunting,
~Two Chicks…

APPLY HERE

Support Operations Coordinator – Remote

If you’re the type who loves cleaning up messy processes, keeping details tight, and making sure customers get the right outcome fast, this role is built for you. It’s a strong entry point at Fleetworthy where you’ll learn toll operations while supporting internal teams and customers with precision.

About Fleetworthy
Fleetworthy (rebranded in September 2024 from Bestpass, Fleetworthy, ExpressTruckTax, and Drivewyze) simplifies fleet safety, compliance, toll management, and efficiency under one connected platform. Their technology helps fleets reduce risk, save money, and stay beyond compliant, supporting millions of drivers and vehicles across the U.S.

Schedule
Remote or hybrid role (depending on location and team needs)
Full-time position supporting internal and external customers
Work involves coordinating across teams, CRM communication, and process documentation

What You’ll Do
• Process toll and violations data for existing customers as needed
• Research and troubleshoot issues, sometimes partnering with toll agencies and internal cross-functional teams
• Use Salesforce CRM to support internal and customer communications
• Support new account setup tasks and operational workflows
• Update existing SOPs and collaborate on new SOPs as processes evolve
• Identify process improvements, recommend efficiencies, and share ideas with the team

What You Need
• High school diploma or GED (Associate or Bachelor’s degree is a plus)
• Strong organization skills and sharp attention to detail
• Comfort working in evolving processes with a mindset for continuous improvement
• Proficiency with Microsoft Office (Excel, Word, Outlook preferred)
• Ability to deliver accurate work, communicate clearly, and stay focused on outcomes
• Alignment with Fleetworthy’s values: People First, Trust, Every Trip Matters, Always Innovating, and Growth Mindset

Benefits
• Compensation range: $35,000 to $40,000 USD annually
• Remote or hybrid flexibility (role-dependent)
• Entry point opportunity with room to grow while learning toll operations and support workflows

These ops roles don’t stay open long because they’re a launchpad. If you want in, apply while it’s still available.

Come in organized. Leave things better than you found them. That’s the job.

Happy Hunting,
~Two Chicks…

APPLY HERE

Account Based Marketing Manager – Remote

Build an ABM engine that actually moves pipeline, not just impressions. If you love aligning Marketing, Sales, and RevOps around high-value accounts and can prove impact with clean metrics, Fleetworthy is hiring for exactly that.

About Fleetworthy
Fleetworthy (rebranded in September 2024 from Bestpass, Fleetworthy, ExpressTruckTax, and Drivewyze) is simplifying fleet safety, compliance, and toll management under one connected platform. Their command center approach delivers real-time insights so fleets can reduce risk, improve efficiency, and operate beyond compliant. Supporting millions of drivers and vehicles, Fleetworthy is pushing road safety and fleet tech into its next era.

Schedule
Remote within the United States
Full-time, cross-functional role partnering closely with Sales, SDRs, RevOps, Marketing Ops, and Content/Digital teams
Fast-paced environment with accountability to marketing-sourced pipeline goals

What You’ll Do
• Build and execute Fleetworthy’s next-generation Account-Based Experience (ABX) program
• Partner with Sales and RevOps to define target account lists, segmentation strategies, and ICP refinement
• Launch tailored ABM campaigns (1:1, 1:few, 1:many) across priority accounts and verticals
• Translate account insights into multi-channel plays (email, paid media, SDR sequences, events, direct mail)
• Own performance tracking and optimization across engagement, pipeline influence, velocity, and conversion
• Align with SDRs and Sales on pre- and post-engagement plans to convert interest into meetings and pipeline
• Create playbooks and processes that clarify roles and touchpoints across Marketing, Sales, and RevOps
• Partner with Marketing Ops to build reporting, dashboards, and ABX data visibility across teams
• Document wins, losses, and learnings to help build an internal ABM center of excellence

What You Need
• 4–5+ years in B2B SaaS demand gen, growth marketing, or ABM roles
• Proven track record running full-funnel ABM programs in partnership with Sales and SDR teams, with measurable pipeline impact
• Experience with ABM and data platforms (Demandbase, 6sense, Clay, ZoomInfo, or similar)
• Strong analytical skills with the ability to connect marketing activity to pipeline and revenue outcomes, including attribution and ROI
• Excellent cross-functional communication skills and the ability to influence without authority
• Self-starter mindset with structure, process, and accountability in ambiguous situations

Benefits
• Remote work in the United States
• Opportunity to build a modern ABX program from the ground up with real executive visibility
• Values-driven culture centered on teamwork, trust, innovation, and growth mindset

If you’ve been waiting for a role where ABM is the strategy, not a side project, this is your shot. Apply while the seat’s still open.

Go build the engine. Make the pipeline prove it.

Happy Hunting,
~Two Chicks…

APPLY HERE

Medicaid Claims Processor – Remote

If you’re good at moving claims quickly without getting sloppy, this is a clean, structured work-from-home role. You’ll process Medicaid claims, verify completeness, and keep work flowing with the right balance of speed and accuracy.

About BroadPath
BroadPath builds remote teams that support health plans and healthcare operations across claims, utilization management, and member services. They’re known for steady work-from-home roles with clear procedures, quality standards, and consistent schedules.

Schedule
Training: 1 week, Monday–Friday, 8:00 AM–5:00 PM AZ time
Production: Monday–Friday, 8:00 AM–5:00 PM AZ time (no weekends)

What You’ll Do
• Process incoming Medicaid claims following established policies, procedures, and client guidelines
• Confirm required data fields are complete and medical records are included when needed
• Refer claims for medical review when appropriate
• Work independently in a virtual environment while maintaining accuracy and consistency

What You Need
• 2+ years of recent health insurance claims processing experience
• Ability to meet expectations for both production and quality
• Strong professionalism, confidentiality, and attention to detail
• Reliable work habits and the ability to work independently from home while collaborating with a team
• Positive, steady attitude in a process-driven workflow

Preferred
• Prior Medicaid claims processing experience (preferred, not required)
• Prior work-from-home experience
• IDX and/or AHCCCS system experience
• Experience with Citrix, Siebel, HPIS, DataNet, Excel, and SharePoint

Benefits
• $18.00/hour base pay
• Weekly pay
• Weekday schedule with no weekends
• Inclusive workplace and equal opportunity employer
• Accommodation support available through HR (upon request)

If you’ve already got claims experience and you want a predictable remote schedule, this is a solid “steady check” role.

Happy Hunting,
~Two Chicks…

APPLY HERE