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Gusto · 12 hours ago

Government Affairs Lead (Small Business Healthcare, Benefits, and HR Policy)

New York, NY

Full-time

Hybrid

Senior Level

$150K/yr - $175K/yr

6+ years exp

Gusto is a modern, online people platform that helps small businesses take care of their teams. As a Government Affairs Lead, you will drive Gusto’s policy agenda focusing on small business healthcare, benefits, and HR policy, while utilizing AI to address complex policy challenges and influence legislative proposals.

Bookkeeping and PayrollEmployee BenefitsEnterprise SoftwareFinancial ServicesFinTechHuman ResourcesSaaSSoftware

Responsibilities

Develop comprehensive government affairs strategies with a strong focus on small business healthcare, tax, HR, and benefits policy, while aligning with Gusto’s broader business objectives

Use AI tools to monitor, summarize, and forecast legislative and regulatory developments, and to identify emerging policy risks and opportunities

Guide the creation of new policy approaches that position Gusto as a thought leader in areas such as healthcare affordability, payroll modernization, and the future of work

Proactively identify evolving policy areas that may impact Gusto customers as the company grows, and prepare the organization to engage effectively

Lead complex policy change initiatives using AI-driven research, synthesis, and scenario analysis across issues affecting healthcare, benefits, HR compliance, payroll, employment law, and other customer-relevant domains

Evaluate regulatory or legislative proposals, understand impact across Gusto’s products, and design strategies for navigating policy change from proposal to implementation

Serve as a subject-matter expert on small-business healthcare and employment policies and translate complex requirements into actionable recommendations

Partner with Product, Legal, Compliance, and Operations to translate policy developments—especially in healthcare, HR, and employment—into product roadmaps and operational plans

Embed AI-enabled workflows into policy monitoring, risk assessment, and internal communication to increase speed, coverage, and consistency

Provide creative solutions informed by the interconnected nature of healthcare, workforce benefits, taxation, payroll, and labor regulation

Represent Gusto before federal and state policymakers, regulators, and key stakeholders on issues including healthcare access, small business benefits, HR and employment compliance, and tax policy

Lead industry working groups and coalitions, shaping both strategy and substance

Communicate Gusto’s policy vision effectively in external forums, using AI-assisted preparation (briefing materials, talking points, comparative analysis) to maximize impact

Build and leverage networks across government, industry associations, think tanks, and small-business advocacy groups

Engage strategically to advance policies that improve the environment for small and medium-sized businesses

Maintain strong relationships with organizations working in healthcare affordability, benefits modernization, workforce issues, and small business resilience

Advise teams across Gusto on complex and emerging policy issues, particularly in healthcare, HR, tax, and employment

Promote a culture of responsible AI use within Government Affairs by sharing best practices, templates, and workflows

Provide mentorship and leadership, potentially directing team members and ensuring delivery of tactical and strategic policy objectives

Qualification

Government AffairsPublic PolicyAI ProficiencyHealthcare PolicyBenefits AdministrationHR ComplianceTax PolicyAnalytical ExcellenceLeadershipStrategic ThinkingRelationship BuildingCommunication Skills

Required

A minimum of 8 years in government affairs or public policy; or

6 years with a Master's degree; or

3 years with a PhD and demonstrated expertise in a relevant policy area

Strong preference for experience in small business healthcare, benefits, labor, HR/employment, and/or tax policy

Deep knowledge across multiple policy disciplines with a strong foundation in issues affecting small businesses, including healthcare and benefits, employment and labor regulation, payroll, taxation, and HR compliance

Demonstrated success navigating policy change management in contexts that impact business operations

Ability to recognize trends, anticipate policy shifts, and design strategic responses that strengthen customer resilience

Demonstrated proficiency using AI tools (e.g., large language models, AI research assistants, summarization tools) as an integral part of your policy work

Experience using AI to monitor and summarize legislation, regulation, and commentary

Draft, iterate, and refine policy materials (briefs, testimony, talking points, FAQs)

Analyze complex, multi-source information and model scenarios or impacts

Comfort experimenting with and improving AI-enabled workflows, while exercising strong judgment about accuracy, bias, and appropriate use

Experience developing and resolving complex policy models and procedures across healthcare, HR, and employment domains

Ability to understand cross-disciplinary policy interdependencies and guide development of innovative approaches

Proven ability to direct application of existing principles while advancing new solutions for emerging policy challenges

Expertise analyzing complex issues requiring evaluation of variable factors across healthcare, labor, benefits, tax, and HR frameworks

Proven ability to determine methods and procedures for new assignments and intricate policy challenges

Strong judgment in selecting, evaluating, and adapting methods—including AI-assisted approaches—to achieve optimal results

Skilled at representing an organization before senior government officials and industry stakeholders on issues central to small business operations

Able to adapt communication style and use persuasion effectively to align policy with business goals

Experienced in leading coalitions or working groups and providing strategic policy guidance

Demonstrated ability to build strategic relationships across diverse policy communities—especially in healthcare, employer benefits, workforce and HR issues, and small business advocacy

Proven success influencing policy outcomes through stakeholder engagement and credible thought leadership

Experience directing the work of others and being accountable for team or program outcomes

Ability to mentor and elevate colleagues on complex policy matters and on the effective use of AI in policy work

Track record of delivering results through effective leadership and cross-functional alignment