Careers at Boundless

Team Lead II

At Boundless | RapidVisa Phils. Inc.

Onsite, Cebu, Philippines

About Boundless Immigration

We’re a team of immigrants and experts who have struggled with our own journeys through the complex, high-stakes U.S. immigration system. That is why we are building deeply customer-centric products and experiences to become the default trusted partner for all families through their entire immigration journey and their first ten years of life in a new country.

Since 2020, Boundless has become the largest player in the family immigration industry, helping tens of thousands of families every year achieve their dreams and becoming the first brand in an industry that has never had one before.

We're backed by influential early-stage venture investors around the country, including Foundry Group (led by Brad Feld), Emerson Collective (Laurene Powell Jobs’ foundation), Pioneer Square Labs, Two Sigma Ventures, Trilogy Equity Partners, and Jerry Yang, and are well-capitalized for years of growth.

What You Will Do

• As a Team Lead II within the Payment Solutions Team, you will lead and coach a group of 4-5 Payment Solutions Specialists and Agents responsible for day-to-day Accounts Receivable & Accounts Payable execution.
• You will own a team of 3 specialists managing $1 million in AR with a target of reducing customer defaults down to 10% & 1 specialist managing the customer AP process. You ensure your team executes consistently against SLAs, quality standards, and financial targets. You are accountable for frontline performance, workload management, and first-level issue resolution. You translate priorities set by the Finance Operations Manager into clear daily actions and ensure your team has the support and structure needed to succeed.

This role is hands-on and execution-focused, combining people leadership with operational oversight and continuous improvement.

Key Responsibilities

Team Leadership & Coaching

• Lead and coach team members through daily standups, weekly 1:1s, and ongoing performance feedback.
• Own onboarding and ramp-up for new hires on the team
• Set and reinforce expectations around ownership, quality, and professional customer communication.

Performance Management & Execution

• Monitor individual and team performance against KPIs, SLAs, and quality benchmarks.
• Identify performance gaps early and implement corrective actions.

Operational Oversight (AR & AP)

• Oversee daily AR and AP operations across the Individual segments, ensuring adherence to SLAs, policies, and financial controls.
• Serve as 1st AP Approver prior to release of any “money-out”.
• Monitor workload distribution, execution quality, and backlog based on volume, complexity, and performance data.
• Ensure operational consistency across platforms and workflows.
• Provides support for the Senior Team Lead and Manager when they are out of office

Escalation Management (Level 1)

• Handle Level 1 payment-related escalations across channels (email, calls, chat).
• Resolve standard escalations independently and escalate complex or high-risk issues to the Senior Team Lead with context and recommendations.

Quality Control & Compliance

• Conduct regular audits of case handling, documentation, and customer communications to ensure compliance with SOPs and policies.
• Ensure accurate processing and adherence to financial and operational controls.

Reporting & Operational Visibility

• Create, maintain, and update operations trackers and agent-level reporting.
• Use AI (e.g., Claude) and data tools (e.g., Sigma, PowerBI, Looker, KNIME, Google Sheets) to monitor trends, flag risks, and support performance discussions.
• Share regular performance updates with the Senior Team Lead.

Process Improvement

• Identify process gaps, bottlenecks, and recurring issues within team workflows.
• Initiate and support improvement efforts that enhance efficiency, accuracy, and customer experience.
• Ensure process changes and best practices are documented and communicated to the team.

Who You Are

• You are a people-first leader who keeps execution tight and consistent.
• You are comfortable balancing coaching with accountability.
• You handle day-to-day issues calmly and know when to escalate.
• You think in terms of execution quality, risk, and throughput not just task completion.
• You lead by example and create clarity in fast-moving environments.

What You Bring

• 2+ years of experience leading financial operations and collections teams within a B2C and/or B2B Setting
• Comfortable working with financial and AR concepts; a degree in Accountancy, Management Accounting, Finance, or a related field is preferred but not a hard requirement if you can demonstrate the skill directly
• Proven experience using data tools (e.g., Claude, Sigma, PowerBI, Looker Studio, Google Workspace) to drive decisions and monitor team performance
• A proactive, strategic mindset - you anticipate risks, identify gaps early, and take action before issues escalate
• Strong communication skills, with the ability to simplify complex topics for teams and cross-functional partners
• A driver mentality - you influence others, lead with clarity, and hold the team accountable for results
• Experience with CRM and ticketing tools, paired with strong operational discipline
• A passion for building a high-performance, customer-first culture focused on clarity, ownership, and continuous improvement

What We Offer

You will be part of a dynamic workforce in an environment where you will collaborate with the expert and elite talents in the online immigration services industry. 

You can cultivate your skillfulness and dexterity amongst us as you experience a highly creative culture built on loyalty and responsibility to our partners while having a lot of fun at work. 

Great company perks and benefits await you!

Assistant Manager, Operations

Cebu, Philippines

About Boundless Immigration

We’re a team of immigrants and experts who have struggled with our own journeys through the complex, high-stakes U.S. immigration system. That is why we are building deeply customer-centric products and experiences to become the default trusted partner for all families through their entire immigration journey and their first ten years of life in a new country.

Since 2020, Boundless has become the largest player in the family immigration industry, helping tens of thousands of families every year achieve their dreams and becoming the first brand in an industry that has never had one before.  In 2023, Boundless entered into employment-based immigration services by acquiring Bridge. With Bridge, Boundless provides a holistic solution to the immigration journey, addressing both corporate immigration strategies and the personal challenges faced by the global workforce and their families.

We're backed by influential early-stage venture investors around the country, including Foundry Group (led by Brad Feld), Emerson Collective (Laurene Powell Jobs’ foundation), Pioneer Square Labs, Two Sigma Ventures, Trilogy Equity Partners, and Jerry Yang, and are well-capitalized for years of growth.

What You Will Do

In this role, you will: 

• Work with US and Europe immigration experts, Attorneys, Project Managers and Sr. SMEs to support and guide our Data Reviewers and Case Production Specialists, offering constructive feedback to enhance quality and consistency across all deliverables, ensuring alignment with USCIS requirements and standards.
• Continuously evaluate and refine workflows to optimize operational efficiency, drive better outcomes, and enhance client satisfaction.
• Serve as the go-to expert for questions and challenges related to the services we offer to our corporate clients, providing insights and solutions to complex case scenarios under attorney oversight.
• Collaborate with attorneys to define, refine, and update templates, ensuring they reflect the latest best practices, regulatory updates, and legal strategies.
• Assist in the development and delivery of training programs for new DRS or CPS, focusing on best practices, case type-specific strategies, and ongoing professional development.
• Conduct detailed reviews of related forms, requirements and supporting evidence and audits of written materials to ensure accuracy, clarity, and persuasiveness, and make revisions as needed to uphold the highest standards of client service.
• Adapt to shifting business priorities by taking on ad-hoc leadership projects and expanded operational responsibilities as company needs evolve.
• Support organizational growth and scaling initiatives, including the operational integration and alignment of newly acquired subsidiaries or business units.

Other responsibilities include:

• Adhere to internal service level agreements (SLAs) on timely preparation of cases
• Follow protocol to maintain the strict security and privacy of our clients’ information

Who You Are

We are seeking a highly skilled and detail-oriented Writing SME to join our dynamic corporate immigration team in the Philippines. This role requires strong subject matter expertise in EB1A, EB1B, NIW, O-1A, and O-1B case types. The Writing SME will provide mentorship and guidance to junior writers, collaborate with attorneys to refine templates and drafting processes, and play a pivotal role in training and knowledge-sharing initiatives.

What You Bring

• Experience: 2+ years of leadership experience managing an on-site team (preferred).
• People Leadership: Proven ability to mentor, empower, and hold staff accountable while driving team engagement and skill development.
• Operational Excellence: Strong background in optimizing workflows/SOPs, managing metrics and SLAs, and maintaining strict adherence to USCIS and legal compliance standards.
• Cross-Functional Communication: Skilled at translating executive and attorney strategies into daily team tasks while smoothly navigating priorities between Legal, PMs, and Operations.
• Problem-Solving & Adaptability: Resourceful under pressure when managing complex edge cases, process scaling, organizational shifts, and new tools (including AI and dashboards).

What We Offer

You will be part of a dynamic workforce in an environment where you will collaborate with expert and elite talents in the online immigration services industry. 

You can cultivate your skillfulness and dexterity amongst us as you experience a highly creative culture built on loyalty and responsibility to our partners while having a lot of fun at work. 

Great company perks and benefits await you!

Principal Architect

Hybrid Seattle preferred 
Full-Time

We're hiring a Principal Architect to reinvent how legal work gets done in the age of AI.


Boundless is a Series C legal tech company based in Seattle, backed by Foundry Group (Brad Feld) and Silver Lake. We operate in 10+ countries and have helped over 100,000 people and companies navigate immigration. We build tech-powered immigration solutions for two audiences: corporate HR teams managing high volumes of employer-sponsored cases, and individuals navigating family and naturalization cases. We have in-house lawyers and are building a world-class AI-powered services firm.


Anthropic is not coming for this. Immigration is vertical, regulated, and workflow-deep, and we are racing to build the defining AI product in the

category.

Why this role exists

We are rebuilding our software platform and engineering infrastructure from the ground up, and we need a Principal Architect to lead that transformation and set the technical vision that ties it together.

You will have a real customer base and a real platform - and the autonomy to reshape both - on day one. We are looking for someone who loves the speed and impact of startups, but wants their work to be immediately scaled on day one.

Immigration is complex, with endless edge cases and global scale. We are building intelligent automation, orchestration, and decision-making to support the agentification of legal workflows, with the checks and balances required to ensure accuracy in a regulated domain and to enable the lawyers who ultimately own legal decisions. The challenge is systems and data infrastructure that can handle this complexity without sacrificing accuracy, observability, or speed, at the scale required to reliably serve thousands of people every year.

We are looking for someone who can hold the whole technical picture: the platform, the AI layer, the data infrastructure, the engineering infrastructure - and how they interact. Someone who makes hard calls, thinks in years not months, and partners with our engineering team to build a durable, world-class AI platform that helps millions of people achieve their immigration dreams.

We are a remote-first team with a small in-person office in Seattle. Our ideal applicant is based in Seattle and will be in the office two-days per week, although we are open to fully remote for the right person.

What you will do

• Own the platform architecture end to end: service boundaries, API design, multi-tenancy, data modeling, and the shift to agent-orchestrated legal work.
• Design the AI layer: how LLMs, retrieval systems, and structured tools connect to case data; how we evaluate quality; how we handle failure modes that matter in a regulated domain.
• Build and own foundational agent infrastructure that product teams use to deploy, monitor, and manage agents independently.
• Define how context is structured and managed: what gets persisted, how customer and session state is scoped, and how agents share or isolate domain knowledge.
• Build agents that handle legal tasks, communications, data hygiene, payments, and the full operational surface of an immigration case, from intake to government submission to resolution.
• Define how data moves, from transactional systems to the warehouse to the operational tooling case managers and legal teams rely on every day.
• Transition our engineering infrastructure into a software factory, overhauling dev processes, systems, tools, and culture in partnership with product and engineering.
• Be the senior technical voice in design reviews and hard tradeoff conversations. Write architecture decision records that give the team durable context.
• Mentor engineers on architectural thinking by doing the work visibly and giving direct feedback on design proposals.
• Ship code and lead from the front.

Who you are

• You have 10+ years in engineering, with meaningful time as a principal, staff, CTO, or architect-level IC. You have owned real architectural decisions on production systems people depend on.
• You think in systems. You can hold the platform, the AI layer, the data infrastructure, and the business constraints in your head at once and see where they don't line up.
• You are a builder. You set new benchmarks for output and want a role where you ship with autonomy and speed, with immediate impact on thousands of existing customers. Not a role where you wait for consensus or others to write the code.
• You move fast by making decisions quickly, not by cutting corners. You know the difference between a reversible call and one that will cost the team six months to unwind.
• You have shipped AI into production. You have views on retrieval, evaluation, latency, and where LLMs break down, and you know when to use AI and when another tool is the right call.
• You have taste. You can build systems where agents and humans work in harmony without overbuilding.
• You write well. The most durable output of this role is documentation that helps engineers make the right call when you are not in the room.
• You have worked in a domain where correctness has consequences: legal, healthcare, financial services, or public safety. You understand why accuracy and auditability are non-negotiable.

Good signals, not requirements

• You have worked at both large and small companies and have a preference for small. You understand speed and impact but also know what matters at scale.
• Founder or CTO experience.
• Experience with workflow automation, case management, or document processing pipelines.
• Prior work with vector search, semantic retrieval, or document understanding systems at production scale.

Compensation

At Boundless, we believe compensation is more than just a paycheck. We invest in our team’s health, flexibility, and future:

Salary

• Seattle Base Pay Range: $236k - $275k
• Our Approach: The applicable base pay range will depend on what ultimately is determined to be the candidate’s primary work location, complexity and responsibility of role, job duties/requirements, and relevant experience and skills.

Health & Wellness

• Comprehensive Coverage: Robust medical, dental, and vision insurance.
• Financial Protection: Life insurance, plus short- and long-term disability coverage.
• Well-being: Access to holistic health benefits and wellness programs.

Time Off & Flexibility

• Work Flexibility: Hybrid and remote work options.
• Unlimited PTO and generous Leave policies

Financial Security

• Retirement: A 401(k) plan with a competitive company match.

Head of Engineering

Location: Seattle, WA, Full-Time

We're hiring a Head of Engineering to reinvent how legal work gets done in the age of AI.

Boundless is a Series C legal tech company based in Seattle, backed by Pioneer Square Labs, Trilogy, Foundry Group (Brad Feld) and Silver Lake. We operate in 10+ countries and have helped over 100,000 people and companies navigate immigration. We build tech-powered immigration solutions for two audiences: corporate HR teams managing high volumes of employer-sponsored cases, and individuals navigating family and naturalization cases. 

We have in-house lawyers and are building a world-class AI-powered services firm. Anthropic is not coming for this. Immigration is vertical, regulated, and workflow-deep, and we are racing to build the defining AI product in the category.

Why this role exists

We are rebuilding our software platform and engineering infrastructure from the ground up, and we need a Head of Engineering to lead the team.

You will inherit a real customer base, a real platform, and a great team of engineers. 

Immigration is complex, with endless edge cases and global scale. We are building intelligent automation, orchestration, and decision-making to support the agentification of legal workflows, with the checks and balances required to ensure accuracy in a regulated domain and to enable the lawyers who ultimately own legal decisions. The engineering challenge is a team and a system that can handle this complexity without sacrificing accuracy, observability, or speed, at the scale required to reliably serve thousands of people every year.

However,  this is not a caretaker role. The world is changing around us and the team is in the midst of transitioning to both an AI-native customer product and an AI-native development process. You will need to drive change with us, and partner with our existing engineering, product, design, legal and operations teams to build a world-class AI-native platform for legal services, and continue to evolve our development infrastructure towards being a truly AI-native “software factory”.

We are looking for someone who can hold the whole picture: the customer, the team, the platform, the AI layer, the delivery system - and how they interact. Someone who makes hard calls, thinks in years not months, and builds an organization that top-tier engineers find exciting and satisfying to be part of. 

We are a remote-first team with a small in-person office in Seattle. We want someone based in Seattle and expect you to be in the office a minimum of 2-days per week.

What you will do

• Build the team. Retain our top performers, hire more top-tier engineers, and lead, inspire, challenge, level, structure, and grow the team. 
• Own engineering delivery end to end. Roadmap execution, quality, on-call, and the operational health of a platform that customers depend on daily.
• Evolve team design as the work changes. Service boundaries and team boundaries move together. 
• You’ll be a true player-coach: expected to ship code yourself while leading the team and staying close to the details of everything we build. 
• Drive the AI transition through the team, not around it. Every engineer should be building with LLMs, retrieval, and structured tools as a default.
• Build the foundational infrastructure that operating teams use to deploy, monitor, and manage agents and LLM-powered customer features at enormous scale. 
• Continue our transition towards a “software factory” engineering model, overhauling dev processes, systems, tools, and culture.
• Partner with product, design, legal and operations as a peer. Engage thoughtfully in tradeoff conversations about scope, sequencing, and what "done" means in a regulated domain.
• Set the technical bar in design reviews and hard tradeoff conversations. Make sure architecture decisions get written down and give the team durable context. Help us build a platform that both engineers and operating teams pine for after they leave.
• Grow engineers into architectural thinking by giving them opportunities to step up, and pushing their thinking constructively. 
  
  

Who you are

• You are a builder. You set new benchmarks for output and want a role where your team ships with autonomy and speed. Not a role where you wait for consensus.
• You have 10+ years in engineering and 4+ years managing engineers, including managing managers or senior ICs. 
• You move fast by making decisions quickly, not by cutting corners. You know the difference between a reversible call and one that will come back to haunt us. 
• You hire well and manage out when you need to. You have built a team you were proud of and you can describe what made it work.
• You have shipped AI into production and led a team through the shift. You have views on retrieval, evaluation, latency, and where LLMs break down, and you know when to use AI and when another tool is the right call.
• You have been the technical decision-maker, not just the person who runs the process. You can lead a design review and change the answer.
• You think in systems. You can hold the team, the platform, the AI layer, and the business constraints in your head at once and see where they don't line up.
• You have taste. You can build teams and systems where agents and humans work in harmony without overbuilding.
• You have worked in a domain where correctness has consequences: legal, healthcare, financial services, or public safety. You understand why accuracy and auditability are non-negotiable.
  
  

Good signals, not requirements

• You have worked at both large and small companies and have a preference for small. You understand speed to impact but also know what matters at scale.
• Founder or CTO experience.
• You have scaled a team through a platform rebuild or replatforming, and can talk about what you got wrong.
• Experience with workflow automation.
• Prior work with vector search, semantic retrieval, or document understanding systems at production scale.