by Terrance Ellis | Dec 12, 2025 | Uncategorized
This is a “build the brain of the company” product role. Not slide decks and stakeholder hugs. They want somebody who can ship agentic LLM systems into production, make them reliable, and make them feel human enough that care teams actually trust them.
About Pair Team
Pair Team is a public benefit, AI-enabled medical group serving Medicaid, Medicare, and safety-net populations. They partner with community orgs to deliver whole-person care and are scaling nationally after demonstrating significant reductions in ER visits and hospitalizations. They’re building an AI-first platform to coordinate care across medical, behavioral, and social services.
Schedule
• Full-time, 100% remote (United States)
• High-velocity build environment: product + engineering + clinical ops + design
• Human-in-the-loop, healthcare workflow heavy
What You’ll Do
• Design and deploy multi-agent systems for care coordination and patient engagement
• Define the “taste” of the agents: how they communicate, reason, and collaborate with care teams
• Build the agent ↔ care team interface inside the core platform (human-in-the-loop UX)
• Prototype and pilot new LLM use cases across intake, outreach, and member management
• Own internal data labeling and evaluation tooling, workflows, and integrations
• Run LLM operations: trace annotation, eval development, monitoring, and feedback loops
• Translate messy real-world healthcare workflows into scalable AI systems
What You Need
• Proven experience shipping conversational or AI-driven products to real users
• Deep familiarity with LLM product work: prompting, multi-agent orchestration, evaluation frameworks
• Comfort defining strategy and success metrics in ambiguous, early-stage problem spaces
• Strong cross-functional operating skills (engineering + ops + clinical)
• High ownership mindset and real mission alignment
Benefits
• Salary: $190,000 to $250,000
• Equity package
• Medical, dental, vision coverage
• 401(k) through Guideline
• Company-paid short and long-term disability and life insurance
• Backup childcare and caregiver support (Wellthy)
• Monthly $100 work-from-home stipend
• Equipment provided
• Flexible vacation policy
Backbone check: if you don’t have “I shipped LLM features to real users and built evals/monitoring so it didn’t fall apart” on your resume, this one will eat you alive. If you do, it’s a big swing role with real authority.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 12, 2025 | Uncategorized
This is a “first or early IT hire” kind of role where you own the whole IT function end-to-end, clean up the SaaS stack, tighten security, and make onboarding feel effortless. If you like startup chaos but want the authority to actually fix it, this one’s built for that.
About Pair Team
Pair Team is a public benefit, AI-enabled medical group serving Medicaid, Medicare, and safety-net populations. They partner with community orgs to deliver whole-person care and are scaling nationally after proving reduced ER visits and hospitalizations. The company is building an AI-first platform that connects healthcare and social-service orgs into a unified system.
Schedule
• Full-time, 100% remote (United States)
• Cross-functional, high-growth environment (People Ops, Finance, Legal, Engineering, clinical ops)
What You’ll Do
• Own IT end-to-end: onboarding/offboarding, device management, workflows, policies, security guardrails
• Refactor and optimize Rippling/HRIS and streamline the SaaS stack
• Build scalable IT fundamentals: MDM, access controls, documentation, repeatable processes
• Drive vendor management: select, negotiate, and manage MSP and SaaS vendors
• Security and compliance readiness: implement practical controls for HIPAA/SOC 2-style environments
• Lead incident response: run point, resolve quickly, document root causes, and prevent repeats
• Bring operational order: create simple systems that keep the business fast but secure
What You Need
• 7–10 years in IT, including 2–3 years in a lead or architect-level role
• Startup or high-growth experience (required)
• Hands-on experience with:
• Onboarding/offboarding and device management (MDM)
• SaaS administration
• SSO/IDP (Okta, Google Workspace, etc.)
• HRIS (Rippling preferred)
• Vendor management experience: selection, contract negotiation, ongoing performance management
• Security and compliance exposure: practical controls, compliance readiness, secure-by-default processes
• Incident response leadership: coordination, RCA, and prevention planning
• Strong cross-functional collaboration with People Ops, Finance, Legal, and Engineering
• Ability to communicate IT decisions clearly and support non-technical users with patience
Benefits
• Salary: $165,000 to $205,000
• Equity package
• Medical, dental, vision coverage
• 401(k) through Guideline
• Company-paid short and long-term disability and life insurance
• Backup childcare and caregiver supports (Wellthy)
• Monthly $100 work-from-home stipend
• Equipment provided
• Flexible vacation policy
Real talk: this role is not “keep the helpdesk moving.” It’s “be the IT department and the architect,” and they’re clearly expecting someone who can lead security posture and vendor strategy without building a big team first.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 12, 2025 | Uncategorized
Build product that actually changes lives, not just dashboards. Pair Team is scaling an AI-first, whole-person care platform for Medicaid, Medicare, and public assistance, and they need a senior engineer who can own full-stack product work end-to-end.
About Pair Team
Pair Team is a public benefit corporation and AI-enabled medical group building a unified care model that connects healthcare and social services. They partner with community organizations to support high-need populations and use technology to coordinate care, automate operations, and improve outcomes at scale.
Schedule
• Full-time, 100% remote (United States)
• Occasional in-person onboarding/orientation and annual retreats may be required
• Cross-functional collaboration with product, design, and platform engineering teams
What You’ll Do
• Own core product initiatives and lead full-stack feature development from concept to deployment
• Build scalable, high-performance web applications supporting both clinical and patient experiences
• Improve platform speed, reliability, and usability through thoughtful iteration
• Collaborate with product managers, designers, and platform engineers to ship user-centered solutions
• Contribute to architectural decisions that support growth and long-term maintainability
• Deliver iteratively, breaking complex work into shippable steps without over-engineering
• Mentor junior and mid-level engineers, participate in reviews, and help raise team standards
• Implement metrics that measure impact and drive operational improvements
What You Need
• 2+ years of software development experience as a high-performing individual contributor (startup experience)
• Experience in both backend and frontend engineering
• Experience building complex web applications (required)
• Relational database data modeling (required)
• Ruby on Rails preferred
• React preferred
• AWS services preferred
• Strong system design skills for moderate to high-complexity problems
• Ability to operate in ambiguity, balance speed with quality, and make smart trade-offs
• Mission alignment: passion for supporting people facing homelessness, severe mental illness, and substance use disorder
Benefits
• Salary: $165,000 to $220,000
• Equity compensation package
• Comprehensive health, vision, and dental insurance
• 401(k) through Guideline
• $50 employer contribution to active HSA accounts
• Life insurance and AD&D
• Flexible vacation policy
• Monthly $100 work-from-home stipend
• Equipment provided (laptop, monitor, etc.)
• Strong growth runway with rapid career progression opportunities
Senior engineers who can ship, lead, and mentor in one package are rare, and Pair Team is clearly paying for the real thing.
If you’re ready to build full-stack product that powers better outcomes for the people who need it most, apply.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 12, 2025 | Uncategorized
This is for specialists who can write clearly, think precisely, and help shape what AI “knows” through high-quality content. If you’ve got deep domain expertise and strong English chops, this contract gig lets you turn your knowledge into real paid output.
About Firstsource
Firstsource Solutions is a provider of Business Process Management services focused on helping organizations improve efficiency, insight, and outcomes through transformational solutions. They support customers by reimagining business processes with a tech-forward approach.
Schedule
• Remote (United States)
• Contract, gig-based work (not a guaranteed full-time role)
• Potential for future full-time opportunities
What You’ll Do
• Develop and optimize AI-generated content in your area(s) of expertise
• Produce clear, accurate, well-structured written content that improves AI outputs
• Apply domain knowledge across one or more listed subjects (examples include STEM, computer science, law, humanities, languages, and more)
• Maintain high standards for clarity, correctness, and consistency
What You Need
• Bachelor’s, Master’s, or Ph.D.
• Expert written and verbal English skills
• Proven expertise in one or more domain areas (from the role’s listed subjects)
• AI content creation experience is preferred
Benefits
• Fully remote, flexible contract-style opportunity
• Work aligned to your expertise (you’re not writing fluff)
• Possible pathway to future full-time openings
These gig roles tend to fill with people who move quickly and can demonstrate real expertise.
If your knowledge is sharp and your writing is even sharper, get your name in.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 12, 2025 | Uncategorized
Own the blueprint, not just the backlog. If you’re the kind of architect who can connect cloud, DevOps, middleware, and security into one clean, scalable story, this BPaaS role is built for you.
About Firstsource
Firstsource is a global business process management partner delivering tech-led, transformational services across the customer lifecycle. Their work spans industries like healthcare, banking and financial services, communications, media, and technology, helping enterprises modernize operations and digital capabilities.
Schedule
• Full-time, Remote (United States)
• You’ll collaborate with cross-functional teams (DevOps, InfoSec, vendors, client stakeholders) in a fast-paced, multi-vendor environment
What You’ll Do
• Define and maintain the BPaaS architecture blueprint with scalability, security, and performance in mind
• Design integration patterns using middleware gateways (Edifecs, Informatica, MuleSoft) for enterprise connectivity
• Translate business and technical requirements into detailed solution designs
• Drive cloud-native adoption across Azure, AWS, or GCP for hosting, integration, and data services
• Partner with DevOps to strengthen CI/CD pipelines, infrastructure as code (IaC), and automated deployments
• Architect for resilience: high availability, disaster recovery, and capacity planning
• Set API and data exchange governance standards (security, transformation, message patterns)
• Guide network and security design (VPN, routing, firewalls, IAM, encryption, monitoring) and embed compliance best practices (HIPAA, SOC2, HITRUST)
• Present architectural options and recommendations to leadership and client teams
• Mentor and support development, infrastructure, and operations teams
What You Need
• Bachelor’s or Master’s in a related field, or equivalent experience (10–15 years progressive IT architecture/solution design)
• 8+ years in IT architecture and solution design, including 3+ years in cloud and BPaaS environments
• Hands-on experience with integration/middleware tools: Informatica, MuleSoft, and/or Edifecs
• Strong DevOps background with CI/CD and IaC tools like Terraform and/or Ansible
• Solid network architecture skills (VPNs, load balancers, firewalls, enterprise connectivity)
• Strong communication skills and comfort working across business, technical, and vendor stakeholders
• Bonus points for Edifecs suite experience (XEngine, IG, TM), healthcare payer/BPaaS background, and cloud certifications (AWS or Azure Solutions Architect)
Benefits
• Remote role supporting US-based programs
• High-impact architecture ownership across cloud, DevOps, integration, and security
• Strong runway for growth in BPaaS and compliance-focused architecture (HIPAA, SOC2, HITRUST)
Roles like this don’t sit open forever, especially remote.
If you’re ready to build secure, cloud-native BPaaS solutions that actually scale, get your name in the mix.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 12, 2025 | Uncategorized
If you can write natural, believable e commerce conversations and explain the logic behind the “right answer,” this is a creative, writing heavy role that helps train AI. It’s structured, quota driven work where quality matters just as much as speed.
About Firstsource
Firstsource is a global business process management partner supporting clients across industries like healthcare, banking, and technology. This project focuses on creating training data to help AI understand e commerce interactions.
Schedule
• Remote (must be U.S. based)
• Contract temp project
• 20 hours per week minimum
• Pay: $10 per unit (each unit takes about 15 minutes)
What You’ll Do
• Write original user and agent conversations from scratch based on provided scenarios
• Create a final user message plus a step by step Reasoning Trace showing how an agent should reach the correct outcome
• Follow detailed written instructions and hit daily or weekly productivity targets
• Meet quality standards consistently
What You Need
• Bachelor’s degree or higher
• Native or near native U.S. English
• Strong writing, editing, and logical reasoning skills (you can break decisions into clear steps)
• Familiarity with online shopping language and common e commerce situations
• Basic understanding of how AI and LLM style systems behave
• Comfortable working in web based tools and structured task submission workflows
• Important: you must write everything yourself, use of LLMs is prohibited
Benefits
• Fully remote (U.S.)
• Predictable, task based workload (20 hours weekly minimum)
• Clear performance expectations with measurable targets
If you want a remote role where your writing and reasoning are the product, get your application in while the project is actively staffing.
Bring your best “human sounds human” writing and your clean, step by step thinking.
Happy Hunting,
~Two Chicks…
