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In this role, you will own the systems, tools, and processes that enable our Legal &amp; Compliance teams to build and scale and be at the forefront of driving AI solutions for the teams.</p>\n<p>Responsibilities:</p>\n<ul>\n<li>Drive the Legal &amp; Compliance team’s operational strategy, understand operational challenges, identify opportunities to improve systems and workflows</li>\n<li>Maintain and optimize a best-in-class AI-driven tech stack. Partner cross-functionally with AI and Contract Operations to identify technologies, negotiate with vendors, and drive implementation</li>\n<li>Partner closely with Finance and Legal leadership to manage budget, forecasting, accruals, and track spend</li>\n<li>Work closely with leadership to own planning cycles, OKRs, and data reporting and metrics</li>\n<li>Manage outside counsel relationships, including new engagements, billing guidelines invoicing, and e-billing. Drive outside counsel management strategy with a focus on cost discipline and operational accountability</li>\n<li>Build and maintain knowledge management platforms and learning and development programs that keep the team current and operating effectively</li>\n<li>Run the day-to-day operations of the Legal &amp; Compliance team, driving efficiencies that enable the team to perform its best work</li>\n</ul>\n<p>Requirements:</p>\n<ul>\n<li>5+ years of legal operations experience at a high-growth technology company</li>\n<li>Hands-on expertise with legal tooling-selection, implementation, and day-to-day operation (CLM, e-billing, matter management, procurement systems)</li>\n<li>Experience implementing AI and technology within legal operations</li>\n<li>Hands-on experience with AI-assisted legal tools and a fluency (or path to fluency) in agentic/automated legal workflows</li>\n<li>Experience engaging and managing outside counsel, legal spend, budgeting, and program management</li>\n<li>Proven ability to build and maintain metrics and reporting frameworks, including operational KPIs</li>\n<li>Exceptional communication skills and the ability to influence stakeholders across Legal, Finance, IT, Security, and Procurement</li>\n</ul>\n<p>Nice to Have:</p>\n<ul>\n<li>Legal Operations community involvement (CLOC, Legal Suite)</li>\n<li>Experience at a SaaS or otherwise high-velocity technology company</li>\n<li>Creative problem-solving skills and the confidence to take smart risks</li>\n<li>Energy, curiosity, and a drive to be part of something groundbreaking</li>\n<li>A team-first approach, with no job too big or too small</li>\n</ul>\n<p>Salary: $133,000-$160,000 in San Francisco and $113,000-$139,000 in Denver</p>","enriched_at":1783789833284},{"id":"job_3f646af4-f9e","title":"Legal & Compliance Tech IT Product Manager","source_url":"https://job-boards.greenhouse.io/gusto/jobs/8039574","location":"San Francisco, CA","job_type":"full-time","experience_level":"senior","work_arrangement":"hybrid","category":"IT","description":"<h3>About the Role</h3>\n<p>As a key member of Enterprise Applications IT (EAIT), the Legal Tech IT Product Manager owns the AI-first strategy, roadmap, and delivery of the enterprise applications supporting Gusto’s Legal &amp; Compliance organization.</p>\n<p>This is an AI-forward product role: you will reimagine how legal and compliance work gets done by embedding generative AI, AI agents, and intelligent automation into systems like contract lifecycle management (CLM), matter and legal-spend management, e-signature, entity and corporate records management, legal hold and e-discovery, and governance, risk, and compliance (GRC) platforms.</p>\n<p>Acting as the primary interface between Legal &amp; Compliance teams and EAIT delivery resources, you will translate business needs into well-defined, AI-enabled product requirements, guide solution design, and drive continuous improvement across core legal and compliance processes.</p>\n<h3>Responsibilities</h3>\n<h4>AI-First Product Ownership &amp; Roadmap (Legal &amp; Compliance Technology)</h4>\n<ul>\n<li>Own the product vision, AI roadmap, and backlog for the legal and compliance technology portfolio within EAIT, with AI and automation as the default lens for every initiative.</li>\n<li>Set a multi-year vision for an AI-augmented legal function, identifying where generative AI, AI agents, and automation can eliminate manual effort, accelerate cycle times, and improve quality and risk outcomes.</li>\n<li>Align roadmap priorities with Legal &amp; Compliance leadership, EAIT’s AI transformation strategy, and enterprise architecture standards.</li>\n<li>Define success metrics and outcomes,including AI adoption, automation rate, accuracy, cycle-time reduction, and cost-to-serve,to measure business value and system effectiveness.</li>\n</ul>\n<h4>AI, Automation &amp; Agentic Workflows</h4>\n<ul>\n<li>Design and deliver generative-AI capabilities across the legal stack: AI-assisted contract drafting, review, redlining, clause extraction, and risk flagging; AI summarization of matters, contracts, and legal documents; and natural-language search across legal knowledge.</li>\n<li>Build and productize AI agents that execute or augment core legal and compliance processes,such as legal intake triage and routing, NDA and standard-contract self-service, obligation and renewal tracking, policy Q&amp;A, and regulatory-change monitoring.</li>\n<li>Define and prioritize Model Context Protocols (MCPs) and integrations that securely connect legal systems (CLM, matter management, document management, GRC) to large language models and orchestration frameworks.</li>\n<li>Apply retrieval-augmented generation (RAG) over contracts, policies, and legal knowledge bases to deliver grounded, citable answers for legal and business stakeholders.</li>\n<li>Evaluate, pilot, and scale AI legal-tech vendors and native AI features (e.g., contract AI, AI assistants, e-discovery AI), running structured proofs-of-concept and build-vs-buy assessments.</li>\n<li>Establish evaluation and quality processes for AI features,prompt design, model selection and tradeoffs, accuracy and hallucination testing, human-in-the-loop review, and continuous tuning.</li>\n</ul>\n<h4>Business Process &amp; Solution Design</h4>\n<ul>\n<li>Lead end-to-end, AI-augmented redesign of core legal workflows,contract lifecycle management, matter intake and management, outside-counsel and legal-spend (e-billing), e-signature, entity and corporate records management, and legal hold and e-discovery.</li>\n<li>Translate business requirements into clear functional specifications and solution designs,including where AI augments, automates, or fully owns a step, and where humans stay in the loop,for EAIT delivery teams.</li>\n<li>Ensure solutions are scalable, auditable, and aligned with data privacy, security, internal controls, and compliance standards, including protection of privileged and sensitive information in all AI workflows.</li>\n</ul>\n<h4>Enterprise Applications Enablement</h4>\n<ul>\n<li>Partner with EAIT engineers, administrators, AI architects, and platform owners to design and deliver enhancements, integrations, MCPs, and AI agents across legal technology platforms.</li>\n<li>Review and approve configurations, workflows, integrations, prompts, and agent designs to ensure they meet business, legal, and IT governance requirements.</li>\n<li>Guide prioritization of enhancements, AI capabilities, upgrades, and technical-debt remediation across legal-managed platforms.</li>\n</ul>\n<h4>Stakeholder Partnership &amp; Delivery</h4>\n<ul>\n<li>Serve as the primary EAIT point of contact for Legal &amp; Compliance stakeholders and as a champion for AI-first ways of working across the legal function.</li>\n<li>Manage intake, prioritization, and delivery of requests, balancing stakeholder needs with EAIT capacity and the AI roadmap.</li>\n<li>Lead cross-functional initiatives from discovery through deployment, ensuring clear communication, change management, and timely execution.</li>\n</ul>\n<h4>Responsible AI, Controls, Privacy &amp; Insights</h4>\n<ul>\n<li>Govern the full lifecycle of AI agents and MCPs in the legal domain, ensuring responsible-AI practices: guardrails, privilege protection, data governance, access controls, auditability, and human oversight.</li>\n<li>Partner with Legal, IT risk, Security, and audit teams to ensure AI-enabled systems and processes support privacy, regulatory, and SOX-related requirements and safeguard attorney-client privilege and sensitive data.</li>\n<li>Define and oversee KPIs and operational metrics for legal and compliance systems, including AI accuracy, reliability, adoption, and ROI.</li>\n<li>Collaborate with data, BI, and AI teams to deliver dashboards, analytics, and AI-driven insights that support data-driven legal operations.</li>\n</ul>\n<h4>Change Management, AI Enablement &amp; Adoption</h4>\n<ul>\n<li>Drive successful adoption of new AI capabilities through training, documentation, prompt and playbook libraries, and hands-on change management.</li>\n<li>Coach legal and compliance teams on safe, effective, and confident use of AI tools, and act as the subject-matter expert for legal AI and technology within EAIT, promoting best practices and standardization.</li>\n</ul>\n<h3>Requirements</h3>\n<ul>\n<li>Bachelor’s degree in Information Systems, Business Administration, Legal Studies, or a related field.</li>\n<li>8+ years of experience in enterprise applications, legal operations / legal technology, business systems, or product management, with hands-on expertise supporting legal and/or compliance functions.</li>\n<li>Demonstrated experience delivering AI-powered products or features,generative AI / large language models, AI assistants, or intelligent automation,ideally within legal, compliance, or enterprise applications, with a clear bias toward applying AI to solve business problems.</li>\n<li>Working knowledge of leading LLM platforms (e.g., OpenAI, Anthropic, Gemini) and core GenAI techniques such as prompt engineering, retrieval-augmented generation (RAG), evaluation, and guardrails, with the ability to reason about model tradeoffs.</li>\n<li>Familiarity with AI agent and orchestration frameworks (e.g., LangChain, CrewAI, Semantic Kernel) and Model Context Protocols (MCPs), and experience integrating AI with enterprise systems is a strong plus.</li>\n<li>Hands-on experience with legal technology platforms such as contract lifecycle management (e.g., Ironclad, Agiloft, DocuSign CLM), matter management and e-billing (e.g., SimpleLegal, Brightflag, Legal Tracker), e-signature (e.g., DocuSign), entity management, legal hold / e-discovery, and/or GRC tools,including their native AI capabilities.</li>\n<li>Experience evaluating, selecting, and deploying AI legal-tech vendors and running proofs-of-concept and build-vs-buy assessments.</li>\n<li>Strong commitment to responsible, secure, and explainable AI, with experience embedding privacy, privilege protection, audit controls, and SOX-aligned governance into AI-enabled workflows.</li>\n<li>Experience owning or managing enterprise application products within an IT or EAIT-style organization, and the ability to translate business needs into product roadmaps, functional requirements, and delivered solutions.</li>\n<li>Strong stakeholder management skills and the ability to partner effectively across Legal, Compliance, IT, and executive leadership, with excellent written and verbal communication and the ability to influence without authority.</li>\n<li>Growth mindset and the ability to operate in ambiguity, define standards where none exist, and scale AI solutions from proof-of-concept to enterprise-wide adoption.</li>\n<li>Relevant certifications (PMP, product management, AI/ML, or legal operations / CLM certifications) are a plus.</li>\n</ul>\n<h3>Benefits</h3>\n<ul>\n<li>Cash compensation amount targeted at $221,000-247,000 in San Francisco Bay Area.</li>\n<li>Stock equity is additional.</li>\n<li>Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.</li>\n<li>Physical office spaces in Denver, San Francisco, and New York City.</li>\n<li>Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role).</li>\n</ul>","enriched_at":1783789809166},{"id":"job_3bf13806-4cc","title":"Business Money Engineering","source_url":"https://job-boards.greenhouse.io/gusto/jobs/8035802","location":"San Francisco, CA;New York, NY;Ontario, CAN - Remote;Toronto, Ontario, CAN - Remote;United States - Remote","job_type":"full-time","experience_level":"senior","work_arrangement":"remote","category":"Engineering","description":"<p>As a Staff Engineer, you&#39;ll play a significant role in building new products and scaling existing ones to further evolve Gusto&#39;s product offerings.</p>\n<p>Your work will focus on improving our customers&#39; financial tools, helping them spend less time managing their finances and more time focusing on their businesses.</p>\n<p>You will collaborate with a team of highly skilled professionals, contributing engineering expertise throughout the product development lifecycle,from ideation and design to architecture, development, release, and post-release monitoring and scaling.</p>\n<p>The Business Money team is on a mission to support small and medium-sized businesses by providing financial tools that help them manage cash flow and run their businesses with confidence.</p>\n<p>Here&#39;s what you&#39;ll do day-to-day:</p>\n<ul>\n<li>Build products &amp; services and scale the platform that powers business money and accounting experiences at Gusto</li>\n<li>Take ownership of projects, ensuring they meet high standards of quality and performance</li>\n<li>Adopt the latest best practices for using AI technologies across all aspects of product development</li>\n<li>Collaborate on complex and ambiguous problems with partnerships from Engineering, Product Management, Design, Data Science, Compliance, Operations, and other cross-functional teams</li>\n<li>Engage in a highly supportive environment working with others to drive productivity and innovation</li>\n<li>Help drive the product development process from concept to launch</li>\n</ul>\n<p>We&#39;re looking for:</p>\n<ul>\n<li>8+ years of professional software development experience</li>\n<li>Experience architecting, building, and testing large-scale and resilient distributed systems and/or software platforms</li>\n<li>Maximizes the use of AI tooling while guiding the team in adopting modern AI practices</li>\n<li>Comfortable dealing with ambiguity and working with quick iteration cycles</li>\n<li>Ability to communicate technical complexity and help facilitate informed tradeoffs</li>\n<li>Willingness to collaborate across different functions</li>\n<li>An aptitude and interest in bringing clarity and simplicity to complex and ambiguous problems</li>\n<li>Experience as a technical lead, leading the work of multiple engineers on multi-quarter projects</li>\n</ul>\n<p>Nice, but not required:</p>\n<ul>\n<li>Experience in the Fintech industry building scalable backend systems to power financial services and products</li>\n<li>Experience with accounting, bookkeeping, tax, or financial reporting systems and a strong understanding of accounting workflows</li>\n<li>Familiarity with small business accounting or tax domains, including concepts such as ledgers, reconciliations, financial statements, payroll accounting, or tax compliance</li>\n<li>Ruby/Ruby on Rails, GraphQL, React, Typescript, AWS</li>\n</ul>\n<p>Our cash compensation amount for this role is targeted at $163,000–$204,000 in Denver &amp; most remote locations, and $197,000–$247,000 for San Francisco &amp; New York.</p>\n<p>Stock equity is additional.</p>","enriched_at":1783789746853},{"id":"job_02b4df24-2e2","title":"Benefits Care Advocate, Phoenix","source_url":"https://job-boards.greenhouse.io/gusto/jobs/8055761","location":"Phoenix, Arizona","job_type":"full-time","experience_level":"mid","work_arrangement":"hybrid","category":"Customer Experience","description":"<p>At Gusto, we&#39;re on a mission to grow the small business economy by handling the hard stuff , payroll, health insurance, 401(k)s, and HR , so owners can focus on their craft and customers.</p>\n<p>As a Benefits Care Advocate at Gusto, you will guide customers to solutions, answering queries via phone and email each day. You&#39;ll own each customer experience from start to finish, ensuring exceptional service and accurate resolution.</p>\n<p>Responsibilities:</p>\n<ul>\n<li>Own customers&#39; inquiries from start to finish while keeping them updated during the resolution process.</li>\n<li>Work a full-time 40-hour/week schedule during operational hours.</li>\n<li>Meet quality and productivity standards for superior customer service and performance progression.</li>\n<li>Collaborate with other advocates and across the company to influence product development.</li>\n<li>Deliver exemplary customer service using a &#39;search first&#39; mentality.</li>\n<li>Expand critical thinking skills and knowledge to answer complex customer inquiries.</li>\n<li>Stay up-to-date with new products/features and communicate updates to customers.</li>\n<li>Be flexible to accommodate annual volume spikes from December through March.</li>\n</ul>\n<p>Requirements:</p>\n<ul>\n<li>Minimum 2+ years of experience within the call center, technology, retail, or hospitality space.</li>\n<li>At least 1-year experience in a Customer-facing benefits role with a Broker, Carrier, or Benefits provider.</li>\n<li>Highly preferred: 2 years experience in the Benefit space.</li>\n<li>Comfortable working with multiple technologies in a digital-first environment (tools such as Salesforce, Slack, Confluence, and NICE Workstation).</li>\n<li>Collaborative, accountable, and effective stress management.</li>\n<li>Great written and verbal communicator.</li>\n</ul>\n<p>Benefits:</p>\n<ul>\n<li>Competitive base pay</li>\n<li>Benefits</li>\n<li>Equity (RSUs)</li>\n<li>Cash compensation range: $19.231/hr,$21.63/hr in Phoenix</li>\n</ul>\n<p>Gusto is an equal opportunity employer and considers qualified applicants with criminal histories.</p>","enriched_at":1783789718188},{"id":"job_4230d80b-cde","title":"Legal Operations Manager","source_url":"https://job-boards.greenhouse.io/gusto/jobs/8047260","location":"Denver, CO;San Francisco, CA","job_type":"full-time","experience_level":"senior","work_arrangement":"hybrid","category":"Legal","description":"<p>We are seeking a hands-on Legal Operations Manager to join the Legal &amp; Compliance team at Gusto. In this role, you will own the systems, tools, and processes that enable our Legal &amp; Compliance teams to build and scale and be at the forefront of driving AI solutions for the teams.</p>\n<p>Responsibilities:</p>\n<ul>\n<li>Drive the Legal &amp; Compliance team’s operational strategy, understand operational challenges, identify opportunities to improve systems and workflows</li>\n<li>Maintain and optimize a best-in-class AI-driven tech stack. Partner cross-functionally with AI and Contract Operations to identify technologies, negotiate with vendors, and drive implementation</li>\n<li>Partner closely with Finance and Legal leadership to manage budget, forecasting, accruals, and track spend</li>\n<li>Work closely with leadership to own planning cycles, OKRs, and data reporting and metrics</li>\n<li>Manage outside counsel relationships, including new engagements, billing guidelines, invoicing, and e-billing. Drive outside counsel management strategy with a focus on cost discipline and operational accountability</li>\n<li>Build and maintain knowledge management platforms and learning and development programs that keep the team current and operating effectively</li>\n<li>Run the day-to-day operations of the Legal &amp; Compliance team, driving efficiencies that enable the team to perform its best work</li>\n</ul>\n<p>Requirements:</p>\n<ul>\n<li>5+ years of legal operations experience at a high-growth technology company</li>\n<li>Hands-on expertise with legal tooling selection, implementation, and day-to-day operation (CLM, e-billing, matter management, procurement systems)</li>\n<li>Experience implementing AI and technology within legal operations</li>\n<li>Hands-on experience with AI-assisted legal tools and a fluency (or path to fluency) in agentic/automated legal workflows</li>\n<li>Experience engaging and managing outside counsel, legal spend, budgeting, and program management</li>\n<li>Proven ability to build and maintain metrics and reporting frameworks, including operational KPIs</li>\n<li>Exceptional communication skills and the ability to influence stakeholders across Legal, Finance, IT, Security, and Procurement</li>\n</ul>\n<p>Nice to Have:</p>\n<ul>\n<li>Legal Operations community involvement (CLOC, Legal Suite)</li>\n<li>Experience at a SaaS or otherwise high-velocity technology company</li>\n<li>Creative problem-solving skills and the confidence to take smart risks</li>\n<li>Energy, curiosity, and a drive to be part of something groundbreaking</li>\n<li>A team-first approach, with no job too big or too small</li>\n</ul>\n<p>Salary: $133,000-$160,000 in San Francisco and $113,000-$139,000 in Denver</p>","enriched_at":1783748298991},{"id":"job_f466e029-734","title":"Legal & Compliance Tech IT Product Manager","source_url":"https://job-boards.greenhouse.io/gusto/jobs/8039574","location":"San Francisco, CA","job_type":"full-time","experience_level":"senior","work_arrangement":"hybrid","category":"IT","description":"<h3>About the Role</h3>\n<p>As a key member of Enterprise Applications IT (EAIT), the Legal Tech IT Product Manager owns the AI-first strategy, roadmap, and delivery of the enterprise applications supporting Gusto’s Legal &amp; Compliance organization.</p>\n<p>This is an AI-forward product role: you will reimagine how legal and compliance work gets done by embedding generative AI, AI agents, and intelligent automation into systems like contract lifecycle management (CLM), matter and legal-spend management, e-signature, entity and corporate records management, legal hold and e-discovery, and governance, risk, and compliance (GRC) platforms.</p>\n<p>Acting as the primary interface between Legal &amp; Compliance teams and EAIT delivery resources, you will translate business needs into well-defined, AI-enabled product requirements, guide solution design, and drive continuous improvement across core legal and compliance processes.</p>\n<h3>Responsibilities</h3>\n<h4>AI-First Product Ownership &amp; Roadmap (Legal &amp; Compliance Technology)</h4>\n<ul>\n<li>Own the product vision, AI roadmap, and backlog for the legal and compliance technology portfolio within EAIT, with AI and automation as the default lens for every initiative.</li>\n<li>Set a multi-year vision for an AI-augmented legal function, identifying where generative AI, AI agents, and automation can eliminate manual effort, accelerate cycle times, and improve quality and risk outcomes.</li>\n<li>Align roadmap priorities with Legal &amp; Compliance leadership, EAIT’s AI transformation strategy, and enterprise architecture standards.</li>\n<li>Define success metrics and outcomes,including AI adoption, automation rate, accuracy, cycle-time reduction, and cost-to-serve,to measure business value and system effectiveness.</li>\n</ul>\n<h4>AI, Automation &amp; Agentic Workflows</h4>\n<ul>\n<li>Design and deliver generative-AI capabilities across the legal stack: AI-assisted contract drafting, review, redlining, clause extraction, and risk flagging; AI summarization of matters, contracts, and legal documents; and natural-language search across legal knowledge.</li>\n<li>Build and productize AI agents that execute or augment core legal and compliance processes,such as legal intake triage and routing, NDA and standard-contract self-service, obligation and renewal tracking, policy Q&amp;A, and regulatory-change monitoring.</li>\n<li>Define and prioritize Model Context Protocols (MCPs) and integrations that securely connect legal systems (CLM, matter management, document management, GRC) to large language models and orchestration frameworks.</li>\n<li>Apply retrieval-augmented generation (RAG) over contracts, policies, and legal knowledge bases to deliver grounded, citable answers for legal and business stakeholders.</li>\n<li>Evaluate, pilot, and scale AI legal-tech vendors and native AI features (e.g., contract AI, AI assistants, e-discovery AI), running structured proofs-of-concept and build-vs-buy assessments.</li>\n<li>Establish evaluation and quality processes for AI features,prompt design, model selection and tradeoffs, accuracy and hallucination testing, human-in-the-loop review, and continuous tuning.</li>\n</ul>\n<h4>Business Process &amp; Solution Design</h4>\n<ul>\n<li>Lead end-to-end, AI-augmented redesign of core legal workflows,contract lifecycle management, matter intake and management, outside-counsel and legal-spend (e-billing), e-signature, entity and corporate records management, and legal hold and e-discovery.</li>\n<li>Translate business requirements into clear functional specifications and solution designs,including where AI augments, automates, or fully owns a step, and where humans stay in the loop,for EAIT delivery teams.</li>\n<li>Ensure solutions are scalable, auditable, and aligned with data privacy, security, internal controls, and compliance standards, including protection of privileged and sensitive information in all AI workflows.</li>\n</ul>\n<h4>Enterprise Applications Enablement</h4>\n<ul>\n<li>Partner with EAIT engineers, administrators, AI architects, and platform owners to design and deliver enhancements, integrations, MCPs, and AI agents across legal technology platforms.</li>\n<li>Review and approve configurations, workflows, integrations, prompts, and agent designs to ensure they meet business, legal, and IT governance requirements.</li>\n<li>Guide prioritization of enhancements, AI capabilities, upgrades, and technical-debt remediation across legal-managed platforms.</li>\n</ul>\n<h4>Stakeholder Partnership &amp; Delivery</h4>\n<ul>\n<li>Serve as the primary EAIT point of contact for Legal &amp; Compliance stakeholders and as a champion for AI-first ways of working across the legal function.</li>\n<li>Manage intake, prioritization, and delivery of requests, balancing stakeholder needs with EAIT capacity and the AI roadmap.</li>\n<li>Lead cross-functional initiatives from discovery through deployment, ensuring clear communication, change management, and timely execution.</li>\n</ul>\n<h4>Responsible AI, Controls, Privacy &amp; Insights</h4>\n<ul>\n<li>Govern the full lifecycle of AI agents and MCPs in the legal domain, ensuring responsible-AI practices: guardrails, privilege protection, data governance, access controls, auditability, and human oversight.</li>\n<li>Partner with Legal, IT risk, Security, and audit teams to ensure AI-enabled systems and processes support privacy, regulatory, and SOX-related requirements and safeguard attorney-client privilege and sensitive data.</li>\n<li>Define and oversee KPIs and operational metrics for legal and compliance systems, including AI accuracy, reliability, adoption, and ROI.</li>\n<li>Collaborate with data, BI, and AI teams to deliver dashboards, analytics, and AI-driven insights that support data-driven legal operations.</li>\n</ul>\n<h4>Change Management, AI Enablement &amp; Adoption</h4>\n<ul>\n<li>Drive successful adoption of new AI capabilities through training, documentation, prompt and playbook libraries, and hands-on change management.</li>\n<li>Coach legal and compliance teams on safe, effective, and confident use of AI tools, and act as the subject-matter expert for legal AI and technology within EAIT, promoting best practices and standardization.</li>\n</ul>\n<h3>Requirements</h3>\n<ul>\n<li>Bachelor’s degree in Information Systems, Business Administration, Legal Studies, or a related field.</li>\n<li>8+ years of experience in enterprise applications, legal operations / legal technology, business systems, or product management, with hands-on expertise supporting legal and/or compliance functions.</li>\n<li>Demonstrated experience delivering AI-powered products or features,generative AI / large language models, AI assistants, or intelligent automation,ideally within legal, compliance, or enterprise applications, with a clear bias toward applying AI to solve business problems.</li>\n<li>Working knowledge of leading LLM platforms (e.g., OpenAI, Anthropic, Gemini) and core GenAI techniques such as prompt engineering, retrieval-augmented generation (RAG), evaluation, and guardrails, with the ability to reason about model tradeoffs.</li>\n<li>Familiarity with AI agent and orchestration frameworks (e.g., LangChain, CrewAI, Semantic Kernel) and Model Context Protocols (MCPs), and experience integrating AI with enterprise systems is a strong plus.</li>\n<li>Hands-on experience with legal technology platforms such as contract lifecycle management (e.g., Ironclad, Agiloft, DocuSign CLM), matter management and e-billing (e.g., SimpleLegal, Brightflag, Legal Tracker), e-signature (e.g., DocuSign), entity management, legal hold / e-discovery, and/or GRC tools,including their native AI capabilities.</li>\n<li>Experience evaluating, selecting, and deploying AI legal-tech vendors and running proofs-of-concept and build-vs-buy assessments.</li>\n<li>Strong commitment to responsible, secure, and explainable AI, with experience embedding privacy, privilege protection, audit controls, and SOX-aligned governance into AI-enabled workflows.</li>\n<li>Experience owning or managing enterprise application products within an IT or EAIT-style organization, and the ability to translate business needs into product roadmaps, functional requirements, and delivered solutions.</li>\n<li>Strong stakeholder management skills and the ability to partner effectively across Legal, Compliance, IT, and executive leadership, with excellent written and verbal communication and the ability to influence without authority.</li>\n<li>Growth mindset and the ability to operate in ambiguity, define standards where none exist, and scale AI solutions from proof-of-concept to enterprise-wide adoption.</li>\n<li>Relevant certifications (PMP, product management, AI/ML, or legal operations / CLM certifications) are a plus.</li>\n</ul>\n<h3>Benefits</h3>\n<ul>\n<li>Cash compensation amount targeted at $221,000-247,000 in San Francisco Bay Area.</li>\n<li>Stock equity is additional.</li>\n<li>Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.</li>\n<li>Physical office spaces in Denver, San Francisco, and New York City.</li>\n<li>Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role).</li>\n</ul>","enriched_at":1783748262165},{"id":"job_7deca765-16c","title":"Business Money Engineering","source_url":"https://job-boards.greenhouse.io/gusto/jobs/8035802","location":"San Francisco, CA;New York, NY;Ontario, CAN - Remote;Toronto, Ontario, CAN - Remote;United States - Remote","job_type":"full-time","experience_level":"senior","work_arrangement":"remote","category":"Engineering","description":"<p>As a Staff Engineer, you&#39;ll play a significant role in building new products and scaling existing ones to further evolve Gusto&#39;s product offerings.</p>\n<p>Your work will focus on improving customers&#39; financial tools, helping them spend less time managing finances and more time focusing on their businesses.</p>\n<p>You will collaborate with a team of highly skilled professionals, contributing engineering expertise throughout the product development lifecycle,from ideation and design to architecture, development, release, and post-release monitoring and scaling.</p>\n<p>The Business Money team supports small and medium-sized businesses by providing financial tools to manage cash flow and run their businesses with confidence.</p>\n<p>Responsibilities:</p>\n<ul>\n<li>Build products &amp; services and scale the platform that powers business money and accounting experiences at Gusto</li>\n<li>Take ownership of projects, ensuring they meet high standards of quality and performance</li>\n<li>Adopt the latest best practices for using AI technologies across all aspects of product development</li>\n<li>Collaborate on complex and ambiguous problems with partnerships from Engineering, Product Management, Design, Data Science, Compliance, Operations, and other cross-functional teams</li>\n<li>Engage in a highly supportive environment working with others to drive productivity and innovation</li>\n<li>Help drive the product development process from concept to launch</li>\n</ul>\n<p>Requirements:</p>\n<ul>\n<li>8+ years of professional software development experience</li>\n<li>Experience architecting, building, and testing large-scale and resilient distributed systems and/or software platforms</li>\n<li>Maximizes the use of AI tooling while guiding the team in adopting modern AI practices</li>\n<li>Comfortable dealing with ambiguity and working with quick iteration cycles</li>\n<li>Ability to communicate technical complexity and help facilitate informed tradeoffs</li>\n<li>Willingness to collaborate across different functions</li>\n<li>An aptitude and interest in bringing clarity and simplicity to complex and ambiguous problems</li>\n<li>Experience as a technical lead, leading the work of multiple engineers on multi-quarter projects</li>\n</ul>\n<p>Nice, but not required:</p>\n<ul>\n<li>Experience in the Fintech industry building scalable backend systems to power financial services and products</li>\n<li>Experience with accounting, bookkeeping, tax, or financial reporting systems and a strong understanding of accounting workflows</li>\n<li>Familiarity with small business accounting or tax domains, including concepts such as ledgers, reconciliations, financial statements, payroll accounting, or tax compliance</li>\n<li>Ruby/Ruby on Rails, GraphQL, React, Typescript, AWS</li>\n</ul>\n<p>Benefits:</p>\n<ul>\n<li>Competitive base pay</li>\n<li>Benefits</li>\n<li>Equity (RSUs)</li>\n<li>A two-day travel to a Gusto office for onboarding is required for this position.</li>\n</ul>\n<p>Salary:</p>\n<ul>\n<li>$163,000–$204,000 in Denver &amp; most remote locations</li>\n<li>$197,000–$247,000 for San Francisco &amp; New York</li>\n</ul>","enriched_at":1783748143063},{"id":"job_544e3670-c7c","title":"Benefits Care Advocate, Phoenix","source_url":"https://job-boards.greenhouse.io/gusto/jobs/8055761","location":"Phoenix, Arizona","job_type":"full-time","experience_level":"mid","work_arrangement":"hybrid","category":"Customer Experience","description":"<p>At Gusto, we&#39;re on a mission to grow the small business economy.</p>\n<p>As a Benefits Care Advocate at Gusto, you will guide our customers to solutions, answering queries via phone and email each day.</p>\n<p>Here&#39;s what you&#39;ll do day-to-day:</p>\n<ul>\n<li>Own customers&#39; inquiries from start to finish while keeping the customer updated at all times during the resolution process.</li>\n<li>Work a full-time 40-hour/week schedule during our hours of operation.</li>\n<li>Meet the quality and productivity standards necessary to meet Gusto&#39;s business standards for superior customer service and performance progression.</li>\n<li>Collaborate closely with other advocates and across the company to influence product development.</li>\n<li>Deliver exemplary customer service using a &#39;search first&#39; mentality, ensuring comprehensive research of a question is carried out through our various internal resources channels before asking for further support.</li>\n<li>Expand your critical thinking skills and knowledge in order to answer progressively more challenging/complex customer inquiries.</li>\n<li>Stay up-to-date with new products/features and be able to consistently communicate these updates to customers in a way that ensures an exceptional customer experience.</li>\n<li>Be flexible to accommodate annual volume spikes from December through March when we require additional weekend overtime and blackout periods for paid time off to provide the best service possible to our customers during the most critical time of the year for small business owners.</li>\n</ul>\n<p>Here&#39;s what we&#39;re looking for:</p>\n<ul>\n<li>Experience: Minimum 2+ years of experience within the call center, technology, retail, or hospitality space and are seeking a new challenge.</li>\n<li>At least 1-year experience in a Customer-facing benefits role with a Broker, Carrier, or Benefits provider.</li>\n<li>Highly preferred, 2 years experience in the Benefit space.</li>\n<li>Technical Ability,You must feel comfortable working with multiple and perhaps new technologies in a digital-first environment (tools such as Salesforce, Slack, Confluence, and NICE Workstation are often used).</li>\n<li>Collaborative: A consummate teammate, ready to wear multiple hats, inspire those around you and work collectively while priding yourself in maintaining a professional brand and image.</li>\n<li>Accountable: A proactive problem solver with incredible critical thinking skills, comfortable with a role heavy in customer interaction.</li>\n<li>Manages Stress Effectively: You&#39;re an autonomous problem solver with a personality that thrives in a dynamic environment.</li>\n<li>Reliable: Individuals should take pride in showing up to work not only for themselves but for their customers.</li>\n<li>Ethical: You hold true to your values of providing top-tier customer service.</li>\n<li>Great written and verbal communicator: You are a confident communicator and methodical thinker.</li>\n</ul>\n<p>Our cash compensation range for this role is $19.231/hr,21.63/hr in Phoenix and most locations.</p>","enriched_at":1783748099678},{"id":"job_3a8e60d8-838","title":"IT Applications Support Analyst - Order to Cash","source_url":"https://job-boards.greenhouse.io/gusto/jobs/8039570","location":"San Francisco, CA","job_type":"full-time","experience_level":"senior","work_arrangement":"hybrid","category":"IT","description":"<h3>About the Role</h3>\n<p>As part of the Enterprise IT Applications team, the IT Applications Support Analyst owns the day-to-day support, configuration, and continuous improvement of the enterprise applications that power Billing, Order-to-Cash (O2C), and Cash Reconciliation.</p>\n<p>This role keeps these business-critical finance systems running reliably , troubleshooting incidents, fulfilling change requests, and partnering with Finance stakeholders to translate business needs into well-supported application solutions.</p>\n<p>A core focus of this role is applying AI and automation to modernize how finance applications are supported.</p>\n<h3>Responsibilities</h3>\n<h4>Application Support &amp; Incident Management</h4>\n<ul>\n<li>Provide support for billing, O2C, and cash-reconciliation applications, owning complex incidents and escalations.</li>\n<li>Triage, investigate, and resolve application issues within agreed SLAs, performing root-cause analysis to prevent recurrence.</li>\n<li>Manage the incident, problem, and change lifecycle in the ITSM tool, keeping tickets and documentation current.</li>\n<li>Coordinate with vendors and internal teams to resolve defects, raise support cases, and track fixes through to closure.</li>\n<li>Support the month-end billing run , monitoring billing jobs/batches, troubleshooting failures, and ensuring invoices generate completely and on time for close.</li>\n</ul>\n<h4>AI &amp; Automation</h4>\n<ul>\n<li>Identify and build AI- and automation-driven solutions to reduce manual effort, accelerate issue resolution, and lower ticket volume.</li>\n<li>Apply automation to repetitive support, configuration, and reconciliation tasks.</li>\n<li>Leverage AI tooling for intelligent ticket triage, root-cause analysis, anomaly detection, and knowledge-base assistance.</li>\n<li>Partner with Finance and IT to automate reconciliations, exception handling, and cash-application logic.</li>\n<li>Stay current on emerging AI and automation capabilities and champion their adoption across the supported application portfolio.</li>\n</ul>\n<h4>Configuration, Enhancements &amp; Releases</h4>\n<ul>\n<li>Configure and maintain application settings supporting billing rules, pricing, order workflows, payment application, and reconciliation logic.</li>\n<li>Gather requirements from Finance stakeholders and translate them into configuration changes, enhancements, or functional specifications.</li>\n<li>Support testing, deployments, and release cycles, including regression testing for patches and upgrades.</li>\n<li>Maintain technical and functional documentation, SOPs, and knowledge-base articles for the supported applications.</li>\n</ul>\n<h4>Integrations, Data &amp; Reconciliation Support</h4>\n<ul>\n<li>Monitor and support integrations and interfaces between billing/O2C/cash systems and the ERP, banks, payment gateways, and data warehouse.</li>\n<li>Investigate data and interface failures and drive timely resolution.</li>\n<li>Write and run queries/reports to analyze issues, validate data, and support audit and month-end close activities.</li>\n<li>Partner with Finance to ensure system controls, automated reconciliations, and cash-application logic operate accurately and reliably.</li>\n</ul>\n<h4>Stakeholder &amp; Continuous Improvement</h4>\n<ul>\n<li>Act as a trusted point of contact between Enterprise IT and Finance Operations for the supported application portfolio.</li>\n<li>Identify automation, AI, configuration, and process-improvement opportunities to reduce manual effort and ticket volume.</li>\n<li>Support compliance, security, and audit requirements for in-scope applications.</li>\n</ul>\n<h3>Requirements</h3>\n<ul>\n<li>Bachelor&#39;s degree in Information Technology, Computer Science, Information Systems, or a related field , or equivalent practical experience.</li>\n<li>8–12 years of experience supporting enterprise/finance applications, ideally within billing, O2C, AR, or cash-reconciliation domains.</li>\n<li>Demonstrated experience applying AI and/or automation to streamline support, operations, or finance processes.</li>\n<li>Hands-on experience supporting or administering Zuora and NetSuite, and the integration between them.</li>\n<li>Strong working knowledge of end-to-end Order-to-Cash processes and the systems that support them.</li>\n</ul>\n<h3>Nice to Haves</h3>\n<ul>\n<li>Experience building automations with scripting, workflow platforms, or RPA tools, and applying AI/ML to support or finance operations.</li>\n<li>Experience acting as a senior/escalation resource within an IT applications support team.</li>\n<li>Familiarity with reconciliation or automation platforms and payment/banking integrations.</li>\n<li>Exposure to integration technologies and reporting/BI tools.</li>\n<li>ITIL certification and/or experience supporting SOX-controlled or audited financial applications.</li>\n</ul>\n<h3>Benefits</h3>\n<ul>\n<li>Competitive base pay</li>\n<li>Benefits</li>\n<li>Equity (RSUs)</li>\n<li>Work-from-office expectations: 2-3 days per week</li>\n</ul>","enriched_at":1783725852739},{"id":"job_105b750a-d2f","title":"IT Applications Support Analyst - Order to Cash","source_url":"https://job-boards.greenhouse.io/gusto/jobs/8039570","location":"San Francisco, CA","job_type":"full-time","experience_level":"senior","work_arrangement":"hybrid","category":"IT","description":"<h3>About the Role</h3>\n<p>As part of the Enterprise IT Applications team, the IT Applications Support Analyst owns the day-to-day support, configuration, and continuous improvement of the enterprise applications that power Billing, Order-to-Cash (O2C), and Cash Reconciliation.</p>\n<p>This role keeps these business-critical finance systems running reliably , troubleshooting incidents, fulfilling change requests, and partnering with Finance stakeholders to translate business needs into well-supported application solutions.</p>\n<p>A core focus of this role is applying AI and automation to modernize how finance applications are supported. You&#39;ll look for opportunities to automate manual processes, reduce ticket volume through self-service and intelligent tooling, and leverage AI-driven approaches to triage, analysis, and reconciliation.</p>\n<p>You&#39;ll act as a subject-matter expert on the billing and cash application landscape, including the integrations that connect these systems to the wider ERP and data ecosystem.</p>\n<h3>Responsibilities</h3>\n<h4>Application Support &amp; Incident Management</h4>\n<ul>\n<li>Provide support for billing, O2C, and cash-reconciliation applications, owning complex incidents and escalations.</li>\n<li>Triage, investigate, and resolve application issues within agreed SLAs, performing root-cause analysis to prevent recurrence.</li>\n<li>Manage the incident, problem, and change lifecycle in the ITSM tool (e.g., ServiceNow, Jira), keeping tickets and documentation current.</li>\n<li>Coordinate with vendors and internal teams to resolve defects, raise support cases, and track fixes through to closure.</li>\n<li>Support the month-end billing run , monitoring billing jobs/batches, troubleshooting failures, and ensuring invoices generate completely and on time for close.</li>\n</ul>\n<h4>AI &amp; Automation</h4>\n<ul>\n<li>Identify and build AI- and automation-driven solutions to reduce manual effort, accelerate issue resolution, and lower ticket volume.</li>\n<li>Apply automation (scripting, workflow tools, RPA) to repetitive support, configuration, and reconciliation tasks.</li>\n<li>Leverage AI tooling for intelligent ticket triage, root-cause analysis, anomaly detection, and knowledge-base assistance.</li>\n<li>Partner with Finance and IT to automate reconciliations, exception handling, and cash-application logic.</li>\n<li>Stay current on emerging AI and automation capabilities and champion their adoption across the supported application portfolio.</li>\n</ul>\n<h4>Configuration, Enhancements &amp; Releases</h4>\n<ul>\n<li>Configure and maintain application settings supporting billing rules, pricing, order workflows, payment application, and reconciliation logic.</li>\n<li>Gather requirements from Finance stakeholders and translate them into configuration changes, enhancements, or functional specifications.</li>\n<li>Support testing (unit, SIT, UAT), deployments, and release cycles, including regression testing for patches and upgrades.</li>\n<li>Maintain technical and functional documentation, SOPs, and knowledge-base articles for the supported applications.</li>\n</ul>\n<h4>Integrations, Data &amp; Reconciliation Support</h4>\n<ul>\n<li>Monitor and support integrations and interfaces between billing/O2C/cash systems and the ERP, banks, payment gateways, and data warehouse.</li>\n<li>Investigate data and interface failures (e.g., failed payment files, posting errors, reconciliation breaks) and drive timely resolution.</li>\n<li>Write and run queries/reports (e.g., SQL) to analyze issues, validate data, and support audit and month-end close activities.</li>\n<li>Partner with Finance to ensure system controls, automated reconciliations, and cash-application logic operate accurately and reliably.</li>\n</ul>\n<h4>Stakeholder &amp; Continuous Improvement</h4>\n<ul>\n<li>Act as a trusted point of contact between Enterprise IT and Finance Operations for the supported application portfolio.</li>\n<li>Identify automation, AI, configuration, and process-improvement opportunities to reduce manual effort and ticket volume.</li>\n<li>Support compliance, security, and audit requirements (e.g., access reviews, SOX-relevant controls) for in-scope applications.</li>\n</ul>\n<h3>Requirements</h3>\n<ul>\n<li>Bachelor&#39;s degree in Information Technology, Computer Science, Information Systems, or a related field , or equivalent practical experience.</li>\n<li>8–12 years of experience supporting enterprise/finance applications, ideally within billing, O2C, AR, or cash-reconciliation domains.</li>\n<li>Demonstrated experience applying AI and/or automation to streamline support, operations, or finance processes.</li>\n<li>Hands-on experience supporting or administering Zuora and NetSuite (billing, subscriptions, and ERP), and the integration between them.</li>\n<li>Strong working knowledge of end-to-end Order-to-Cash processes and the systems that support them.</li>\n<li>Experience supporting New Product Introductions (NPIs) , setting up new products, SKUs, and rate plans in billing and ERP.</li>\n<li>Experience supporting financial close activities, including bank reconciliations and AR/cash sub-ledger to GL tie-outs.</li>\n<li>Experience with an ITSM tool and structured incident/problem/change management practices.</li>\n<li>Ability to read/write SQL and analyze data to investigate application and interface issues.</li>\n</ul>\n<h3>Nice to Haves</h3>\n<ul>\n<li>Experience building automations with scripting, workflow platforms, or RPA tools, and applying AI/ML to support or finance operations.</li>\n<li>Experience acting as a senior/escalation resource within an IT applications support team.</li>\n<li>Familiarity with reconciliation or automation platforms (e.g., BlackLine, HighRadius) and payment/banking integrations.</li>\n<li>Exposure to integration technologies (APIs, middleware, file-based interfaces) and reporting/BI tools.</li>\n<li>ITIL certification and/or experience supporting SOX-controlled or audited financial applications.</li>\n</ul>\n<h3>Compensation and Benefits</h3>\n<p>The cash compensation amount for this role is targeted at $169,000-189,000 in San Francisco Bay Area. Stock equity is additional. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.</p>","enriched_at":1783656711496}],"category_normalised":[{"category":"engineering","count":60},{"category":"sales","count":19},{"category":"operations","count":17},{"category":"finance","count":15},{"category":"design","count":10},{"category":"hr","count":9},{"category":"legal","count":8},{"category":"it","count":6},{"category":"marketing","count":4}],"velocity":{"weeks":[{"week_start":"2026-04-13","count":7},{"week_start":"2026-04-20","count":28},{"week_start":"2026-04-27","count":2},{"week_start":"2026-05-04","count":5},{"week_start":"2026-05-11","count":8},{"week_start":"2026-05-18","count":4},{"week_start":"2026-05-25","count":5},{"week_start":"2026-06-01","count":18},{"week_start":"2026-06-08","count":2},{"week_start":"2026-06-15","count":27},{"week_start":"2026-06-22","count":16},{"week_start":"2026-06-29","count":12},{"week_start":"2026-07-06","count":16}],"trend":"accelerating","wow_pct":33},"momentum":{"recent_14d":28,"prior_14d":43,"growth_pct":-35,"classification":"decelerating"},"salary_vs_industry":{"company_median":205000,"industry_median":null,"percentile":null,"sample_size":106,"by_region":[{"region":"United States","company_median":205000,"industry_median":null,"sample":105}],"transparency_pct":79,"industry_transparency_pct":0,"transparency_warning":false},"market_share":{"company_jobs":150,"industry_total":150,"share_pct":100,"rank":1,"peer_count":1},"ai_exposure":{"occupation_weighted_score":0.23,"skill_weighted_score":0.341,"top_exposed_titles":[{"title":"Staff Software Engineer, Core Products","count":4,"score":0.288},{"title":"Future Opportunities: Dedicated Service Advisor","count":4,"score":0},{"title":"Staff Software Engineer, Tax Experiences","count":2,"score":0.288},{"title":"Staff Software Engineer, Pricing and Packaging Engineering","count":2,"score":0.288},{"title":"Staff Software Engineer, Growth (Revenue Enablement)","count":2,"score":0.288},{"title":"Staff Software Engineer, Growth (Orchestration Platform)","count":2,"score":0.288},{"title":"Staff Software Engineer, Developer Productivity Async","count":2,"score":0.288},{"title":"Staff Software Engineer, Database Infrastructure","count":2,"score":0.288},{"title":"Staff Software Engineer, Core Platforms","count":2,"score":0.288},{"title":"Staff Software Engineer,  AI Developer Tools","count":2,"score":0.288}],"top_exposed_skills":[{"skill":"CI/CD","count":4,"score":0.473},{"skill":"AWS","count":6,"score":0.411},{"skill":"Python","count":8,"score":0.389},{"skill":"API Design","count":7,"score":0.337},{"skill":"SQL","count":9,"score":0.318},{"skill":"Claude Code","count":4,"score":0.315},{"skill":"Large Language Models","count":6,"score":0.298},{"skill":"Javascript/React","count":6,"score":0.288},{"skill":"Scalable Platforms","count":3,"score":0.288},{"skill":"Performance And Reliability Issues","count":5,"score":0.288}]},"peer_set":[],"skills_lq":[],"geographic_shift":{"current":[{"region":"United States","count":148,"share_pct":98.7},{"region":"Unknown","count":2,"share_pct":1.3}],"emerging":[{"region":"United States","recent_30d":69,"prior_30d":30,"growth_pct":130}],"shrinking":[]},"seniority_anomalies":{"exec_recent_30d":2,"exec_prior_90d_avg":1.7,"exec_growth_pct":18,"notable_exec_hires":[{"title":"Head of Accountant Partner Program","location":"Denver, CO;San Francisco, CA;New York, NY; Atlanta, GA; Chicago, IL; Toronto ON","posted_at":"2026-06-19"},{"title":"Head of Client Experience, Symmetry","location":"Scottsdale, AZ","posted_at":"2026-06-18"}]},"posting_dynamics":{"median_days_open":32,"industry_median_days_open":null,"long_open_count":0,"closure_rate_pct":49}}}}