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

Gusto, Inc.•Washington, DC

27d•Hybrid

About The Position

As a Government Affairs Lead, you are a senior policy leader with deep expertise in small business healthcare, benefits, and HR policy and are highly proficient in using AI as a core part of your work. You will drive Gusto’s policy agenda with a focus on strengthening the regulatory and legislative environment for small and medium-sized businesses—especially in areas that shape how they hire, pay, retain, and provide benefits for their teams. You will apply in-depth functional knowledge and AI-enabled analysis to develop solutions to complex policy challenges, particularly those impacting healthcare affordability and access, payroll and HR operations, benefits administration, workplace compliance, and the evolving employer–employee relationship. As Gusto’s product suite expands, you will also work across the organization to anticipate and engage on other policy issues affecting Gusto’s customers, using AI to surface trends, synthesize information quickly, and model potential impacts. This role requires understanding the interrelationships between policy disciplines—from healthcare and labor regulation to taxation, benefits, and the future of work—and the ability to deliver creative, effective strategies for multifaceted issues. You will position Gusto to anticipate and influence legislative and regulatory proposals, develop and promote best-practice frameworks for policy change management, and ensure Gusto is consistently recognized as a leading voice for small business. You will represent Gusto before government officials, lead industry coalitions, and serve as a senior advisor to internal leaders navigating complex policy matters. This may include directing the activities of others and requires someone who can see around corners, recognize policy trends, and guide the organization through the full lifecycle of public policy change—from idea to implementation—with AI as a key enabler. This role requires understanding the interrelationships between different policy disciplines and providing creative and effective solutions to multifaceted issues. You will be responsible for positioning Gusto proactively to respond to and influence proposed regulatory and legislative policy changes, while developing and promoting best practices for policy change management that optimize outcomes for Gusto and our customers. You will represent Gusto before government officials, lead industry association working groups, and serve as a senior advisor on complex policy matters across the organization. This position may include directing the activities of others and requires someone who can see around corners, recognize policy trends, and understand the full spectrum of public policy change from proposal through implementation.

Requirements

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.

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.