About the Role

Our Product Pricing & Monetization team sits at the intersection of product and commercial strategy, responsible for holistic pricing and packaging across Gusto's full product suite.

We're looking for a Senior Pricing and Monetization Manager to focus across our platform. portfolio including Gusto Payroll, Gusto Time management and HR, and our suite of embedded financial services for employers and employees. You'll collaborate closely with product, sales, marketing, data, engineering, and finance, with work that is visible to Gusto leadership.

What You'll Do

• Work in partnership across Product, Finance, Marketing, and Go-to-Market to review and recommend monetization and pricing strategies for new product launches and our existing portfolio.
• Be a world-class operator, owning and delivering on cross-functional projects and commercial go-to-market initiatives. In an AI-native environment, strategy, ownership, and execution goes broad. You will be asked to learn, adapt and grow your range of expertise.
• Help shift from a commercial strategy and operations function, to an AI-powered builder program. You’ll ship MVPs, Proof of Concepts, and pilots right into market.
• Decide, Build, and Monitor the key Pricing and Monetization KPIs across our product and go-to-market portfolio.
• Be the pricing and monetization expert and go-to-partner for Monetization and Commercial strategy.
• Work closely with key stakeholders such as: Product, Product Marketing, Sales, Data Science, and Finance. Products will have direct executive line-of-sight and direct impact to our product and business.

What We're Looking For

• Background in fintech, business banking, retirement, E-commerce, payroll, or HR back office SaaS
• Background in B2B / B2C Saas in Payroll, HR, Fintech, ECommerce or related field.
• An AI-native operator who can go from strategy to execution quickly, building Agents instead of processes. You’ll be an expert in Claude.ai, Claude Code, and Cursor.
• A strong analytical mindset with strong attention to detail and creative problem-solving ability. Able to use AI tools to conduct end-to-end technical data analysis.
• Executive relationship management and communication. You’ll be presenting and working on topics for our executives, board, and senior leaders across Gusto.
• Exceptional cross-functional stakeholder management and relationship-building skills. Your success will be defined by your ability to move a broad set of stakeholders towards a common goal.
• Clear, concise communicator, able to distill complex ideas for any audience
• Thrives in fast-moving environments; able to pivot quickly and manage competing priorities
• Curious, growth-oriented, and genuinely passionate about pricing

Nice to Have

• Experience developing and delivering pricing and go-to-market recommendations in product, marketing, finance, or consulting.
• Experience with technical pricing research, like conjoint or max diff analysis, or other quantitative research techniques. 
• Expertise in technical data analysis skills, like SQL, Python or R. Expect underlying foundation coupled with ability to use AI to execute.
• Familiarity with the latest AI tools to help with coding or data analytics tools such as Claude, Cursor, Gumloop

Compensation

Our cash compensation amount for this role is targeted at $152,000 - $180,000/yr in Denver, Phoenix, and Atlanta, and $180,000 - $218,000/yr for San Francisco & New York. The salary range for Toronto is CAD 133,000 - 160,000. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

#LI-Hybrid

About the Role:

As the Head of Social and Influencer Marketing, you will define and lead Gusto's social and influencer strategy to significantly grow brand awareness, engagement, and consideration among small businesses and their advisors. You will be responsible for building, managing, and developing a high-performing team, overseeing all social channels, content strategy, and end-to-end influencer programs. You’ll work closely with brand, product marketing, sales, and PR teams to ensure a consistent, compelling, and integrated brand voice across all social touchpoints, driving measurable impact on our B2B growth objectives. You’re a visionary leader, deeply analytical, and customer obsessed, with a proven track record of scaling social and influencer initiatives. You will also serve as a leader in Gusto’s AI-native evolution, defining the standards for ethical and high-quality AI usage across all social and brand channels.

About the Team:

This role is a key leadership position within our marketing organization, vital for shaping Gusto's public presence and accelerating growth across direct and indirect channels. We are a team that combines creativity, data-driven insights, and cross-functional collaboration to design campaigns that reach, engage, and convert the right audiences at scale. You will build and empower a team dedicated to fostering vibrant communities and amplifying our message, contributing to Gusto's mission to serve over 400,000 small businesses, and we’re just getting started

Here’s what you’ll do day-to-day:

• Develop and execute a comprehensive social media and influencer marketing strategy aligned with business objectives, brand guidelines, and B2B audience needs.

• Lead, mentor, and grow a team of social media and influencer marketing professionals, fostering a culture of innovation, collaboration, and continuous improvement. This includes acting as an Innovator to build repeatable, documented AI-assisted workflows (e.g., advanced prompt libraries for copy and content ideation, automated testing models) that increase the team’s effectiveness, and conducting regular training to elevate the team's AI fluency.

• Oversee content strategy, creation, and distribution across all owned social channels (e.g., LinkedIn, Meta, YouTube, Tik Tok), ensuring brand consistency and engagement. You are accountable for setting rigorous internal standards to Grade the Output of all AI-generated content for accuracy and brand voice.

• Design, launch, and manage end-to-end influencer programs that drive authentic advocacy, reach new audiences, and generate measurable results for B2B segments.

• Establish and evolve community management best practices, ensuring timely and engaging interactions with our audience.

• Partner closely with Brand, Product Marketing, PR, and Sales teams to integrate social and influencer efforts into broader campaigns and product launches.

• Define key performance indicators (KPIs), conduct regular analysis of social media and influencer performance, and provide actionable insights to optimize strategy and demonstrate ROI. You will strategically Give it to AI by identifying the highest-leverage opportunities for large language models and predictive tools to maximize campaign reach and targeting.

• Proactively champion the Guard the Trust principle by ensuring 100% compliance with Gusto's AI and data policies across all social, influencer, and community programs.

• Manage budgets, agency relationships, and social media tools/platforms effectively.

• Stay abreast of emerging social media trends, platforms, and technologies (including AI advancements) to identify new opportunities for growth and innovation.

Here’s what we're looking for:

• 12+ years of overall marketing experience, with at least 7+ years specializing in social media and influencer marketing, and 3+ years in a leadership role managing a team.

• Proven track record of building and scaling social media and influencer programs for B2B brands, demonstrating measurable growth in awareness, engagement, and lead generation.

• Deep expertise in developing content strategies tailored for various social platforms and audience segments.

• Strong understanding and hands-on experience with social media management platforms, analytics tools, and influencer marketing platforms.

• Exceptional analytical skills: ability to interpret complex social data, measure campaign effectiveness, and translate insights into strategic recommendations.

• A proven track record of operating at the Innovator or Amplifier level of AI fluency. This means moving beyond personal tool usage to define, deploy, and govern AI strategy for the entire function. You must demonstrate expertise in Guiding AI to produce highly effective and on-brand social content at scale, establishing quality assurance processes, and ensuring the team rigorously adheres to compliance and ethical standards.

• Outstanding leadership and people management skills, with experience coaching and developing marketing talent.

• Skilled collaborator with experience working closely with Brand, PR, Product Marketing, Sales, and RevOps teams.

• Exceptional written and verbal communication skills, with the ability to craft compelling narratives and present strategic plans to executive stakeholders.

• BA/BS degree required; MBA or advanced degree a strong plus

Our cash compensation amount for this role is targeted at $169,000 - $200,000/yr in Denver, Phoenix, and Atlanta, and $200,000 - $240,000/yr for San Francisco & New York. The salary range for Toronto is CAD 133,000 - 160,000. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

#LI-Hybrid

About the Role:

We are building AI-powered, agentic workflows to transform how service operations scale, resolve customer needs, and maintain quality in high-stakes environments. At Gusto, that means designing systems that can earn the trust of small business owners — where a wrong answer or a missed escalation has real consequences.

As an AI Solutions Architect, you will own the end-to-end design and performance of these workflows in production — where models, tools, data, and human judgment come together to deliver outcomes. This is not a traditional architecture role. You will design, prototype, deploy, and continuously improve AI-driven systems that directly impact customer experience and operational efficiency. You will also play a key role in shaping the evolution of our AI platform by identifying capability gaps, prototyping solutions, and informing the primitives required to scale agentic systems effectively.

You will report into the Service Transformation org and work at the intersection of AI governance, service quality, and operational transformation — operating as the connective tissue between Engineering, CX, Legal, and Compliance as Gus, Gusto's AI assistant, scales.

About the Team:

The mission of our Service Transformation (CXT) team is to quickly evolve and scale how Gusto delivers outstanding service experiences and leverages AI to do so. Our team designs the systems, governance frameworks, and feedback loops that allow Gusto's service model to improve continuously, operate reliably, and earn the trust of the customers and employees who depend on it.

Here’s what you’ll do day-to-day:

• Architect, prototype, and own end-to-end agentic service workflow frameworks, from scoping through production deployment and iteration — including solve and assist targets, HITL protocols, override logic, and downstream quality safeguards
• Analyze SOPs, operational metrics and interaction data to identify and prioritize high-impact automation opportunities based on volume, risk, and customer impact
• Design and implement multi-agent orchestration patterns across tools, data sources, and decision steps within a single end-to-end workflow
• Apply and influence AI platform capabilities in partnership with CoreX (Gusto's AI Platform team) — including orchestration, retrieval, and evaluation — helping define what needs to be built to support production workflows at scale
• Identify platform gaps, prototype workflow-level solutions, and partner with engineering to shape the primitives required for reliable, scalable AI systems
• Serve as the primary CX voice in Legal, Security, Compliance, and CoreX forums — translating CX quality stakes and workflow risk into terms each audience acts on, and ensuring governance requirements are embedded in design, not retrofitted after launch
• Strengthen evaluation frameworks and feedback loops to ensure quality, compliance, and continuous improvement; contribute to Gusto's human evaluation programs and AI governance practices through deep partnership with our internal CX Labs team
• Partner with Data teams to define and track workflow performance — including solve and assist rate, AHT, rework rate, and customer effort score — clearly distinguishing between model-level, workflow-level, and operational drivers
• Build ROI models to quantify workflow impact across efficiency, quality, and cost before and after deployment
• Represent workflow performance and risk to senior stakeholders with appropriate precision and brevity; communicate in a way that drives action, not overwhelm
• Lead through ambiguity and rapid change: the function is still being defined, and you will help define it

Here’s what we're looking for:

• 8+ years in operations, product, or AI roles — with at least 2 years designing and deploying AI-assisted or agentic workflows
• Strong fluency with LLM systems, including prompt design, evaluation, and production behavior at scale
• Hands-on experience with agentic tooling, orchestration frameworks, or MCP-style integrations — conceptual familiarity is not sufficient at this level
• Experience designing human-in-the-loop (HITL) systems with clear escalation logic, override controls, and compliance-aware checkpoints
• Working knowledge of multi-agent systems and tool coordination
• Strong operational judgment: able to define and diagnose workflow metrics 
• Proven track record influencing cross-functional stakeholders — including Product, Engineering, Legal, Security, and Compliance — in writing, in design reviews, and in high-stakes forums
• Familiarity with Responsible AI practices, governance, and risk management in production environments
• Proven ability to operate in high ambiguity, create clarity, and drive alignment across technical and non-technical audiences
• Strong systems thinking with a bias toward execution and measurable outcomes
• Deep empathy for small business customers and the employees who serve them

Our cash compensation amount for this role is $133,470/yr to $173,511/yr in Denver & most major metro locations, and $157,145/yr to $204,289/yr for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

About the Role:

As a Expansion Sales Account Executive at Gusto, you will be a platform advisor to drive expansion revenue by engaging customers through both inbound and outbound outreach. Using a structured, multi‑touch cadence, you will secure quality connects and generate incremental ARR growth.

Key Responsibilities:

• Execute a multi‑touch outreach cadence (calls + emails) to connect with customers
• Fast responsiveness to inbound opportunities combined with smart outbound prospecting into our customer base
• Conduct at least 60 consultative calls daily to uncover upsell and cross‑sell opportunities.
• Leverage your deep knowledge of the People Platform to demonstrate additional product value.
• Update Salesforce with detailed notes and collaborate with cross‑functional teams (Sales, Product, Marketing) to optimize messaging.
• Ownership of a monthly ARR quota achieved via upsell and cross-sells
• Use AI-powered workflows as a core part of how you sell: running assigned tools daily, surfacing friction and inefficiencies as you find them, and collaborating with your team to influence what gets built or improved next.

About the Team:

The Platform Sales team is dedicated to supporting our existing customers as their businesses evolve, ensuring their needs are met at every stage of growth. Through proactive outreach during key lifecycle moments, we drive greater product adoption, enhance customer engagement, and extend customer lifetime value with Gusto.

Here’s what you’ll do day-to-day:

• Daily Outreach:
• Make approximately 60 dial attempts per day (targeting 6 quality connects; ~10 call attempts per connect).
• Send personalized follow‑up emails per dial attempt/connect and leverage additional touchpoints as needed.
• Consultative Engagement:
• Conduct a minimum of 6 consultative calls each day—balancing inbound scheduled calls with targeted outbound efforts.
• Pipeline & Collaboration:
• Update Salesforce with detailed call notes, track opportunities, and plan follow‑up actions.
• Participate in daily huddles with your PE to review priorities and discuss top‑priority opportunities.
• Feedback:
• Collect insights from customer conversations to help refine outreach strategies and product messaging.
• Results
• Contribute to achieving monthly incremental ARR targets of approximately $109,000

Here’s what we're looking for:

• 3+ years in consultative sales or account management focused on expansion.
• Proven success in a high‑velocity sales environment managing numerous customer interactions.
• Proficiency in Salesforce and modern sales engagement tools.
• Excellent communication, negotiation, and time‑management skills.
• Proven, day-to-day experience integrating AI into how you work - across writing, research, prep, and summarization as a core part of your workflow, with a track record of giving clear, useful feedback that helps improve your tools and processes.

Our cash compensation range for this role is $95,000 to $120,000 OTE in Denver, Atlanta, Phoenix, Chicago and most remote locations. Remote locations will vary based on our geographical pay approach. Final offer amounts are determined by multiple factors, including candidate location, experience and expertise, and may vary from the amounts listed above.

About the Role:

Gusto is searching for a builder. Not a manager of an existing PEO sales team — a founder-minded sales leader who will design the motion, write the playbook, hire the team, and carry a personal book of business in the early months. This is a 0→1 opportunity to establish Gusto's PEO sales org from the ground up, and we're looking for someone who is energized by that challenge.

You will drive new PEO revenue by selling Gusto's co-employment solution to both prospects and our existing base of 400,000+ customers — Gusto's single biggest competitive advantage over legacy PEOs. The pace is fast, the market opportunity is real, and we're looking for someone who will bring experience, creativity, and a genuine passion for building to the table every single day. You align with our company values and have a knack for building for the long haul. If you're excited to roll up your sleeves, lead by example, and architect something from scratch, let's talk.

About the Team:

You will be the founding leader of Gusto's PEO sales function. In the first 6–12 months, you'll operate as a true player-coach — personally closing deals while simultaneously building the team, tooling, and infrastructure around you. You'll define the ideal customer profile, build out the sales stages and pipeline architecture in Salesforce, and establish the channel strategy (including broker and accountant referral partnerships) that will drive scalable new business over time.

This team will serve as Subject Matter Experts on PEO, guiding prospects through complex buying decisions and partnering closely with HR, benefits, and payroll counterparts to deliver a seamless customer experience. Your biggest unfair advantage: Gusto's existing install base. Like the best scaled PEOs, a meaningful share of your pipeline will come from converting existing payroll customers — and you'll be the one to design and build that on-ramp.

Here’s what you’ll do day-to-day:

• Sell and build simultaneously. For the first 6–12 months, carry a personal book of business while building the team and infrastructure around you. This is a player-coach role that requires someone comfortable operating at both levels.
• Design the sales motion from scratch. Define sales stages, lead routing, funnel metrics, and pipeline architecture in Salesforce. This org doesn't have a pre-built RevOps foundation — you'll build it.
• Own the full talent lifecycle. Partner closely with Recruiting to define hiring profiles, run interviews, and select top PEO sales talent. Onboard new hires for fast ramp and continuously assess team capacity to stay ahead of headcount needs.
• Build and leverage the channel ecosystem. Develop a point of view on broker, GA, and accountant referral channels. Even if you don't own these relationships day one, you'll be expected to shape the strategy and lay the groundwork for a scalable partner channel.
• Convert the install base. Develop the playbook for converting Gusto's existing 500K+ payroll customers to PEO. Understand the unique motion, objections, and value proposition for in-base selling vs. cold-start prospecting.
• Operate with selling season fluency. Understand and plan around PEO's concentrated selling window (Sept–Dec, with ~50–60% of new business landing Jan 1). Build team capacity, pipeline targets, and go-to-market rhythms accordingly.
• Collaborate cross-functionally with Sales, Marketing, and Product leadership to identify market opportunities, drive pipeline, and help shape PEO product strategy.
• Use data to drive decisions — from advisor skill development to team-level initiatives. Track, measure, and report on sales effectiveness; adjust programs as needed.
• Lead with AI fluency. As a people leader at Gusto, you're expected to actively model and drive AI adoption across your team — not just as a user, but as a champion. This means leveraging AI tools to surface pipeline insights, accelerate coaching, improve forecast accuracy, and identify at-risk deals earlier. You'll help your team integrate AI into daily workflows (outreach, call prep, follow-up), experiment with new tooling, and share learnings across the broader sales org. We expect our leaders to stay ahead of the curve and bring a point of view on how AI can make the team meaningfully better.
• Build a culture of excellence. Cultivate each individual's skill set and guide career pathing as they grow within the organization. Ensure the team maintains deep knowledge of PEO compliance, co-employment regulations, and applicable state and federal employment law requirements.

Here’s what we're looking for:

• PEO Expertise: 5+ years of experience in PEO sales, with direct experience standing up a PEO sales org or building a sales team 0→1 in a high-growth environment. We're prioritizing builder profiles over tenure in a mature org.
• Player-Coach Experience: Proven ability to carry personal quota while simultaneously building team, process, and infrastructure. This is not a pure management role in the early stages.
• Selling Season Fluency: Direct experience operating within PEO's Jan 1 selling cycle — Sept–Dec pipeline build, renewal dynamics, and capacity planning. This is a key screen for PEO-specific operating experience vs. generic HCM.
• Install Base Conversion: Experience developing or executing strategies to convert an existing customer base to a higher-tier or adjacent product. Familiarity with in-base PEO conversion motions is a strong plus.
• Channel Strategy: Understanding of broker, GA, and accountant referral channels in the PEO or benefits space. Ability to develop a POV and lay groundwork for scalable partner-sourced pipeline.
• RevOps & Pipeline Architecture: Experience building or significantly contributing to Salesforce pipeline design — sales stages, lead routing, funnel reporting — from an early-stage starting point.
• Management Experience: 5+ years of people management in a sales organization, including direct involvement in recruiting and hiring.
• Results-Oriented: Consistent track record of establishing and exceeding measurable goals.
• Sales Acumen: Strong working knowledge of inbound and outbound sales methodologies in SMB SaaS or HCM/PEO environments.
• Collaboration: Ability to work effectively across Sales, HR, Benefits, and Product teams; excellent interpersonal skills.
• AI Leadership: Demonstrated ability to evaluate, adopt, and champion AI and automation tools in a sales environment. Comfortable going beyond personal usage — setting expectations, building habits, and holding the team accountable to AI-enabled ways of working.
• Technical Proficiency: Salesforce.com (SFDC) experience required, including pipeline and funnel design; familiarity with HCM platforms and benefits administration tools preferred.

Our target on-target earnings (OTE) compensation for this role is $270,000/yr to $280,000/yr in Denver & most remote locations, and $295,000/yr to $318,000/yr for San Francisco, & New York. This OTE is structured with a target 60% base pay and 40% commission pay with an uncapped commission structure. Final offer amounts and the exact base/commission split are determined by multiple factors including candidate location, experience, and expertise and may vary from the amounts listed above.

About the Role

Gusto is looking for a Paid Social Marketing Lead to own our paid social program end-to-end, from brand awareness through conversion, across social channels such as Meta, LinkedIn, Reddit, and TikTok. This is a high-visibility, high-impact role at the intersection of performance marketing, creative strategy, and AI-powered workflow design. You will serve as the strategic lead for paid acquisition across paid social and adjacent channels, setting the framework for how paid media operates within Gusto's demand generation engine. You'll have full strategic and creative latitude over one of Gusto's most important acquisition channels, with direct influence on pipeline and revenue. If you're a full-funnel paid social operator who thinks in systems, holds creative and data rigor in equal measure, and uses AI as a genuine daily tool, we want to meet you.

About the Team

As a member of Gusto’s Demand Generation team, you will be embedded specifically within Paid Acquisition, a focused group responsible for driving awareness and pipeline through paid media. This team operates with high autonomy, a bias for experimentation, and a culture of cross-functional partnership. We hold ourselves to a high standard, move fast, and genuinely believe that being AI-native is part of what it means to do this job well today.

Here's what you'll do day-to-day:

• Own paid social strategy and execution across Meta, LinkedIn, Reddit, Quora, and TikTok, driving full-funnel campaigns from brand awareness through retargeting and conversion, with accountability to pipeline and revenue targets.
• Manage significant, multi-million dollar budgets with rigor, including campaign pacing, forecasting, budget-vs-actuals analysis, and making the case for paid social investment in imperfect attribution environments.
• Define and socialize Gusto's paid acquisition measurement framework, including attribution philosophy and budget allocation principles, establishing this as the standard for the broader marketing team.
• Lead creative strategy and testing at scale: briefing creative studios and agencies, structuring meaningful experiments, interpreting complex data sets to drive actionable insights, and building a clear learning roadmap.
• Act as Gusto's internal subject matter expert on paid social and AI-powered marketing workflows, developing playbooks and frameworks adopted across the marketing org.
• Partner with Web Marketing to align on landing page strategy, message match, and post-click conversion, because paid social performance doesn't end at the click.
• Manage agencies and contractors, and an IC by setting clear expectations, reviewing quality, and holding partners accountable to results.
• Use AI tools as a consistent, habitual part of your workflow: generating campaign briefs, developing copy variants, accelerating audience research, and building reusable systems that raise the bar for the whole team.
• Collaborate cross-functionally with Integrated Marketing, Communications, and Web to align paid social with integrated campaigns, product launches, and earned media moments, and bring performance data back upstream to influence creative production and asset strategy.

Here's what we're looking for:

• 12+ years of paid social experience or equivalent at a B2B SaaS, performance marketing agency, or high-growth consumer organization.
• Full-funnel ownership across two or more major paid social platforms (Meta, LinkedIn, Reddit, Quora, TikTok) with significant budget responsibility and a track record of driving measurable pipeline impact.
• Demonstrated experience managing external agencies and/or contractors, setting expectations, measuring performance, and holding partners to a high bar.
• Strong creative strategy and testing instincts: you know how to structure a test, distinguish a learning from a result, and translate performance data into creative direction.
• AI-fluent in practice, not just in theory; you use AI tools consistently in your day-to-day workflow to accelerate briefs, copy, and analysis, and have a track record of implementing AI-driven efficiencies for your team.
• Excellent cross-functional collaborator who can translate integrated briefs into paid social strategy, advocate for what the channel needs, and work effectively alongside brand, web, and comms partners.
• You are analytical and data-driven, with a clear point of view on attribution in imperfect measurement environments and comfort communicating paid social's contribution to business outcomes.

Compensation

Our cash compensation amount for this role is $151,020/yr to $180,000/yr in Denver, Phoenix/Scottsdale, Las Vegas, Chicago, and Atlanta, and $177,550/yr to $210,000/yr for San Francisco & New York. The cash compensation range for Toronto is (CAD) $134,285 - $158,000. Final offer amounts are determined by multiple factors including candidate location, experience and expertise, and may vary from the amounts listed above.

The Opportunity

Gusto Embedded Payroll (GEP) is one of Gusto's highest-growth bets — a platform business that enables software companies to offer Gusto-powered payroll directly within their own products. We're looking for a Head of Partner Growth to lead the team responsible for making our embedded partners successful: driving go-to-market execution, growing partner revenue, and building the operational and strategic frameworks that will scale this business toward $100M+.

This is a player-coach leadership role. You'll manage a cross-functional team spanning Partner Success Management (PSM) and Partner enablement— while also staying deeply hands-on with our most strategic partner relationships. You'll own the partner growth playbook end-to-end: from GTM planning and launch sequencing through ongoing optimization, escalation management, and executive relationship development.

Gusto's partnerships organization focuses on evaluating and executing strategic partnerships in new categories. Gusto Embedded Payroll allows us to bring our people platform to thousands more businesses than those we serve directly and will play a key role in Gusto's growth.

What It's Like to Work in This Role

Lead & Develop

• Build, lead, and develop a high-performing team of Partner Success Managers and Partner Enablement
• Set the operational rhythm for the partner growth function — including planning cadences, escalation workflows, and performance management
• Coach team members on partner strategy, executive communication, and cross-functional navigation
• Drive Enablement with the ideation, creation, and execution of enablement frameworks and materials.
• Drive AI fluency across the team — embedding AI tools and workflows into day-to-day partner operations, GTM planning, and internal knowledge management to accelerate output and decision quality

Strategize & Plan

• Own the partner growth strategy across the GEP portfolio, including partner segmentation, prioritization, and resource allocation
• Develop and maintain per-partner operating plans with clear success metrics, in collaboration with Product, Engineering, Marketing, and Sales Enablement
• Build repeatable GTM playbooks — covering co-marketing motions, sales enablement, content roadmaps, and launch sequencing — tailored to each partner's distribution model and ICP
• Translate portfolio-level data (revenue, attach rates, funnel performance) into strategic narratives for leadership

Operate & Execute

• Drive success for our partners and their end customers through adoption, activation, and retention of Gusto-powered embedded products
• Own the full marketing funnel and sales motion with partners — from top-of-funnel demand generation through conversion, onboarding, and expansion
• Manage complex, high-stakes partner relationships directly — including contract negotiations, executive escalations, and cross-functional alignment on roadmap priorities
• Lead partner incident response and escalation management with structured, cross-functional workflows

Build for Scale

• Create and expand the feedback loop between partners, their end users, and Gusto's internal product, marketing, engineering, and operations teams
• Design frameworks, templates, and processes that enable the team to manage a growing partner portfolio without linear headcount growth
• Identify and implement AI-powered workflows and tools that improve team efficiency, partner reporting, and knowledge management

What We're Looking For

• 12-15 years of experience, with 8+ years in a people management role and 7+ years in partner-facing or channel-facing roles
• Partner-side perspective: Has operated on the partner or channel side of the table — understands how partners evaluate, prioritize, and activate embedded or referral relationships
• Farmer mentality: Wired to grow and deepen existing partner relationships through trust-building, strategic account planning, and proactive expansion — not just hunting new deals
• Methodical operator: Builds repeatable playbooks, escalation frameworks, and operational rhythms rather than relying on one-off heroics. Strong systems thinker
• GTM playbook experience: Hands-on experience building go-to-market plans from scratch — including co-marketing, keyword strategies, content roadmaps, and launch sequencing
• Full-funnel fluency: Understands the complete marketing and sales journey from demand gen through conversion, activation, and retention. Can diagnose where a partner motion is leaking value and prescribe the right intervention
• AI fluency: Actively uses AI tools (e.g., LLMs, automation platforms) to accelerate workflows, improve decision quality, and build team capability. Comfortable leading an AI adoption agenda within a team
• Executive communicator: Strong ghostwriter and strategic communicator who can represent the partnership function credibly with C-suite stakeholders — both internally and at partner organizations
• Strong sense of ownership and resilience: Thrives in ambiguity, takes initiative, and drives outcomes without waiting for permission
• Exceptional written and verbal communication: Can shift register fluently between partner-facing emails, internal Slack, leadership documents, and board-level narratives

Strong Nice-to-Haves

• Experience with embedded or platform business models (APIs, developer tools, B2B2B)
• Knowledge of payroll, HR tech, or fintech software ecosystems
• Experience managing partner P&Ls, cost-to-manage models, or portfolio-level financial analysis
• "Gets" the building-mode opportunity — has scaled a partner function from early stage, not just inherited a mature program

Our cash compensation amount for this role is targeted at:
$230,215 - $270,500 in San Francisco, CA; New York, NY 
$195,745 - $230,000 in Denver, CO;  Phoenix, AZ; Atlanta, GA; Chicago, IL; Las Vegas, NV

If you are outside of the geographic areas above, your application will not be considered at this time.

Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

The Role: 

The Sales Enablement team sits within our Revenue Operations organization, the linchpin of our world-class sales experience. Learning Partners play a critical role in executing enablement strategies to drive revenue growth and feature adoption across sales. This role owns the learning lifecycle for business insurance products (e.g., Workers’ Comp, BOP, Commercial Auto, E&O) and PEO sales and partners closely with leaders on onboarding, continuous education, and high-performance skill development. You will design and implement learning solutions that include high-impact learning assets, self-paced content, and facilitated experiences.

We are seeking an individual with expertise in learning science, strong consulting capability, and experience in professional sales or business development. You are passionate about enabling HR solution sellers with the content, tools, insights, and training they need to win more business while exceeding the expectations of our existing clients. You align with our company values, are highly self-motivated to drive results, and bring a relentless curiosity to continuously deepen product knowledge and scale enablement at pace in a fast-moving environment.

Responsibilities:

• Collaborate with stakeholders and partners including revenue, revenue operations and other cross functional leads to determine sellers learning and performance needs and priorities to achieve business results
• Diagnose skill and knowledge gaps and independently design and deliver enablement solutions that drive measurable improvements in capability, productivity, and revenue—often with limited information, tight timelines, and minimal support.
• Apply learner-centered design principles while balancing speed, pragmatism, and impact, tailoring solutions based on observation, stakeholder input, and the depth of learning required for performance.
• Define and track KPIs to measure the impact of enablement initiatives, including time-to-performance, and use data to quickly iterate and refine solutions.
• Design, build, and deliver onboarding, continuous training, and just-in-time learning experiences with a bias toward action, rapid development, and scalable execution to keep our sales teams on the cutting edge
• Partner cross-functionally to ensure enablement content remains current and optimized for seller workflows, even as priorities and product capabilities evolve quickly
• Cultivate a community of expert practitioners, crowdsourcing best practices and user-generated content to continuously improve enablement
• Monitor industry trends and competitive dynamics, adapting enablement priorities quickly as business needs change
• Research and apply emerging AI tools and methodologies to accelerate design, development, and delivery while maintaining quality and effectiveness.

Here’s what we're looking for:

• 12+ years of experience in sales enablement, training, or sales leadership supporting high-volume HR solution sales, ideally in PEO or licensed business insurance sales (EG: Workers’ Comp, BOP, Commercial Auto, E&O).
• Proven track record of designing and delivering highly effective enablement programs that drive measurable improvements in sales performance and productivity
• Demonstrated ability to independently lead learning initiatives end-to-end, from needs analysis through delivery and post-program evaluation, while managing multiple competing priorities.
• Experience designing and facilitating new hire training and continuous education training for licensed sales teams focused on growth 
• Strong analytical, communication, and presentation skills, with the ability to influence stakeholders and work cross-functionally to ensure learning objectives translate into real performance outcomes 
• Solid foundation in instructional design and adult learning theory, with the judgment to select appropriate modalities based on speed, scale, and impact
• Hands-on experience with content creation, curation, and knowledge management platforms, paired with a genuine passion for sales and finding creative ways to make sellers more effective
• Comfort operating in urgency and ambiguity, with the resilience, conflict management skills, and composure required to thrive in a fast-paced environment
• Willingness to travel up to 20% annually

Preferred Qualifications:

• Knowledge of the payroll industry 
• An advanced degree or certificate in enablement, education or organizational science 
• Experience with GSuite, Salesforce, Slack, Notion, AI tools along with various learning management systems and authoring tools

Our cash compensation amount for this role is targeted at:
$177,000 - $200,000 in San Francisco, CA; New York, NY 
$150,000 - $170,000 in Denver, CO;  Phoenix, AZ; Atlanta, GA; Chicago, IL

If you are outside of the geographic areas above, your application will not be considered at this time.

Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

About the Role:

The Franchise Account Executive role is an opportunity to help build and scale one of Gusto's newest growth channels. Franchise represents a massive and largely untapped market, and this team is focused on activating franchise owners across established partner networks and high-potential industries. As a Franchise AE, you'll operate in a true outbound motion — prospecting into multi-unit operators, building relationships with influential owners, and closing new business that can scale across locations.

You'll also help shape the playbook for how Gusto sells into franchise ecosystems as we grow this program into a durable revenue engine for the company.

You'll partner closely with our Franchise Partner Manager (who develops relationships with franchisors) and a dedicated BDR (focused on high-volume activations). Your role is to lead strategic pursuits, unlock influential operators, and build the repeatable sales motion for selling into franchise ecosystems.

Here’s what you’ll do day-to-day:

• Own new franchise revenue generation. Prospect into franchise ownership groups within Gusto’s partner networks and target industries, building pipeline through outbound outreach and relationship development with multi-unit operators and influential franchise owners.
• Execute and refine the franchise sales playbook. Leverage the existing franchise sales motion to drive consistent pipeline and deals, while providing feedback and insights that help improve messaging, targeting, and overall execution as the program scales.
• Run the full sales cycle. Manage deals from prospecting through close, partnering with BDRs who support high-volume outreach while focusing your time on larger ownership groups and strategic franchise opportunities.
• Develop relationships with influential franchise operators. Engage multi-unit owners, directors of operations, and regional leaders to understand operational needs and position Gusto as a scalable payroll and workforce platform across multiple locations.
• Partner cross-functionally to drive franchise success. Collaborate with the Franchise Partner Manager, Sales Ops, and Marketing to activate franchise networks, support partner initiatives, and identify opportunities to expand within existing franchise relationships.
• Build referenceable wins within franchise networks. Secure early customer success stories and multi-location operators that can serve as proof points and accelerate adoption across additional franchisees.
• Drive consistent outbound pipeline generation. Maintain a disciplined outbound motion across named franchise accounts and industry segments, using a mix of calls, emails, LinkedIn outreach, and events to create new opportunities.
• Represent Gusto in franchise communities. Attend franchise conferences, regional events, and industry gatherings to build relationships, generate pipeline, and strengthen Gusto’s presence in the franchise ecosystem.
• Achieve and exceed revenue targets. Consistently deliver against quarterly targets for MRR and new customer adds while contributing insights that help scale the franchise program over time.
• Use AI-powered workflows as a core part of how you sell: running assigned tools daily, surfacing friction and inefficiencies as you find them, and collaborating with your team to influence what gets built or improved next.

Here’s what we're looking for:

• 3+ years of quota-carrying B2B SaaS AE experience, ideally with outbound new business in SMB, mid-market, or franchise/multi-unit contexts. 
• Proven track record as a hunter — generating your own pipeline, landing new logos, and expanding into complex accounts.
• Payroll sales experience is a strong plus.
• Experience navigating multi-unit and franchise structures (franchisors, franchisees, regional/holding companies) is a strong plus.
• Proven, day-to-day experience integrating AI into how you work - across writing, research, prep, and summarization as a core part of your workflow, with a track record of giving clear, useful feedback that helps improve your tools and processes.
• Strong discovery and storytelling skills — able to uncover compliance, payroll, and onboarding pain points and tie them to ROI.
• Comfortable partnering with BDRs: coaching, collaborating on sequences, and maximizing top-of-funnel conversion.
• Entrepreneurial mindset — thrives in building new motions, testing playbooks, and iterating quickly.
• Willingness to travel 25–35% of the time to conferences and in-market opportunities.

The on-target earnings (OTE) for this role range from $134,000/yr to $155,000/yr in Denver, Atlanta, Chicago & Las Vegas, and $126,000/yr to $144,000/yr in Phoenix. This OTE is structured with a target 60% base pay and 40% commission pay with an uncapped commission structure. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

About the Role:

We are seeking a highly motivated and licensed Property & Casualty (P&C) Insurance Broker to join our team as part of a critical pilot to launch a P&C broker model at Gusto. You will be essential in evolving Gusto's business insurance channel by acting as a licensed agent to quote and issue business insurance policies with our NEXT Insurance carrier partner. You will use your expertise to provide direct support and an improved experience for small business customers with complex insurance needs, helping to capture meaningfully higher revenue and accelerating the development of our AI Insurance Advisor.

About the Team:

This team is crucial to solving customer experience gaps and optimizing our offline insurance channels. You will be a SME who is part of the "human-in-the-loop" workflows required to train and optimize Gus as an AI insurance advisor. Our collective vision is to be an expert advisor that supports small businesses through every stage of growth, with this pilot being key to establishing our digital insurance agency and licensed agent integration.

Here’s what you’ll do day-to-day:

• Make outbound dials to prospective and existing small business clients to assess their complex P&C insurance needs and recommend suitable coverage options.
• Quote and issue Property & Casualty policies, primarily with the NEXT Insurance carrier, in our offline sales channel.
• Achieve required daily, weekly, and monthly sales activity expectations. 
• Provide human-in-the-loop support to optimize the AI Insurance Advisor, Gus, and assist customers with more complex needs.
• Maintain client relationships, manage policy renewals, and facilitate changes or endorsements to existing policies.
• Act as a trusted liaison between clients and carriers, including assisting clients with reports of losses and claims settlement when necessary.
• Actively work to cross-sell and up-sell additional P&C lines of coverage and strive to achieve monthly production goals for units and/or revenue.
• Maintain accurate and up-to-date client records and policy documentation within CRM systems (SFDC workflow).
• Use AI-powered workflows as a core part of how you sell: running assigned tools daily, surfacing friction and inefficiencies as you find them, and collaborating with your team to influence what gets built or improved next.
• Stay current on industry trends, products, regulations, and underwriting guidelines to provide accurate advice and ensure compliance.

Here’s what we're looking for:

• Experience in the field: Proven experience in insurance sales or brokerage, with coverage level knowledge of commercial P&C products (e.g., Workers' Compensation, BOP, Commercial Auto, E&O). [4+ years]
• Licensing: An active Property & Casualty insurance producer’s license
• Communication & Interpersonal Skills: Excellent verbal and written communication, active listening, and strong interpersonal skills to build rapport and explain complex concepts clearly.
• Sales & Negotiation: Strong sales and negotiation abilities with a proven ability to meet sales targets.
• Technical Proficiency: Working knowledge of carrier quoting systems, proficiency in insurance software, and familiarity with CRM systems like Salesforce (SFDC). 
• Comfortable using AI tools and automation to enhance productivity, decision-making, and problem-solving.
• Mindset: A demonstrated passion for delivering an incredible customer experience and genuine empathy for small business owners.
• Attributes: Highly self-motivated, goal-oriented, and an entrepreneurial ownership mentality to thrive in a fast-paced, high-energy environment.
• AI Fluency: Proven, day-to-day experience integrating AI into how you work - across writing, research, prep, and summarization as a core part of your workflow, with a track record of giving clear, useful feedback that helps improve your tools and processes.

Our cash compensation amount for this role is $109,390 to $134,000 OTE for Denver, Atlanta, Chicago & Las Vegas. $102,855 to $126,000 OTE for Phoenix. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

About the Role:

The Sales Enablement team sits within our Revenue Operations organization, the linchpin of our world-class sales experience. Learning Partners play a critical role in executing enablement strategies to drive revenue growth and feature adoption across sales. This role owns the learning lifecycle for Expansion Sales and partners closely with leaders on onboarding, continuous education, and high-performance skill development. You will design and implement learning solutions that include high-impact learning assets, self-paced content, and facilitated experiences.

We are seeking an individual with expertise in learning science, strong consulting capability, and experience in professional sales or business development. You are passionate about enabling Expansion Sellers (upsell/cross-sell/renewal revenue motions) with the content, tools, insights, and training they need to win more business while exceeding the expectations of our existing clients. You align with our company values, are highly self-motivated to drive results, and bring a relentless curiosity to continuously deepen product knowledge and scale enablement at pace in a fast-moving environment.

Here’s what you’ll do day-to-day:

• Collaborate with stakeholders and partners including revenue, revenue operations and other cross functional leads to determine sellers learning and performance needs and priorities to achieve business results
• Diagnose skill and knowledge gaps and independently design and deliver enablement solutions that drive measurable improvements in capability, productivity, and revenue—often with limited information, tight timelines, and minimal support.
• Apply learner-centered design principles while balancing speed, pragmatism, and impact, tailoring solutions based on observation, stakeholder input, and the depth of learning required for performance.
• Define and track KPIs to measure the impact of enablement initiatives, including time-to-performance, and use data to quickly iterate and refine solutions.
• Design, build, and deliver onboarding, continuous training, and just-in-time learning experiences with a bias toward action, rapid development, and scalable execution to keep our expansion sales teams on the cutting edge
• Partner cross-functionally to ensure enablement content remains current and optimized for seller workflows, even as priorities and product capabilities evolve quickly
• Cultivate a community of expert practitioners, crowdsourcing best practices and user-generated content to continuously improve enablement
• Monitor industry trends and competitive dynamics, adapting enablement priorities quickly as business needs change
• Research and apply emerging AI tools and methodologies to accelerate design, development, and delivery while maintaining quality and effectiveness.

Here’s what we're looking for:

• 8+ years of experience in sales enablement, training, or sales leadership supporting multi-product sales and expansion revenue motions (upsell, cross-sell, renewals), ideally in a high-volume environment.
• Proven track record of designing and delivering highly effective enablement programs that drive measurable improvements in sales performance and productivity
• Demonstrated ability to independently lead learning initiatives end-to-end, from needs analysis through delivery and post-program evaluation, while managing multiple competing priorities.
• Experience designing and facilitating new hire training and continuous education training for expansion/customer success/retention teams focused on growth 
• Strong analytical, communication, and presentation skills, with the ability to influence stakeholders and work cross-functionally to ensure learning objectives translate into real performance outcomes 
• Solid foundation in instructional design and adult learning theory, with the judgment to select appropriate modalities based on speed, scale, and impact
• Hands-on experience with content creation, curation, and knowledge management platforms, paired with a genuine passion for sales and finding creative ways to make sellers more effective
• Comfort operating in urgency and ambiguity, with the resilience, conflict management skills, and composure required to thrive in a fast-paced environment
• Willingness to travel up to 20% annually

Preferred Qualifications:

• Knowledge of the payroll industry 
• An advanced degree or certificate in enablement, education or organizational science 
• Experience with GSuite, a Mac, Salesforce, Slack, Notion, AI tools along with various learning management systems and authoring tools

Our cash compensation amount for this role is $108,570 to $163,500 for Denver, Atlanta, Chicago & Las Vegas. $131,430 to $192,500 for San Francisco & New York. $102,040 to $163,500 for Phoenix. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

About the Role:

We are looking for a strategic and results-driven Account Manager to own customer relationships, maximize retention, and drive account expansion within a dedicated Book of Business (BoB). This role requires a balance of Sales, Customer Success, and Account Management skills to ensure customers realize the full value of Gusto’s products while identifying new opportunities for growth.

Key Responsibilities:

Account Management & Customer Success

• Manage a dedicated BoB, ensuring high engagement, adoption, and long-term customer satisfaction at scale.
• Build and nurture relationships to uncover cross-sell and upsell opportunities.
• Guide customers through key moments that matter along our customer journey to maximize value realization, drive expansion, and proactively reduce churn.
• Leverage product insights and customer data to assess account health and drive proactive outreach.

Sales & Opportunity Identification

• Identify and execute on growth opportunities by addressing additional customer pain points with Gusto’s suite of products.
• Utilize a hunter and farmer approach to both maintain and expand customer relationships.
• Own outbound prospecting, pitching, and closing within existing accounts to drive revenue growth.
• Daily activities include conducting approximately 20 outbound dials to your current book of business.
• Hold around 6 meetings with your customers each day to support relationship development and drive expansion revenue goals.
• Use AI-powered workflows as a core part of how you sell: running assigned tools daily, surfacing friction and inefficiencies as you find them, and collaborating with your team to influence what gets built or improved next.

Prioritization & Agility

• Use data-driven insights to prioritize accounts, ensuring focus on the highest-impact opportunities.
• React quickly to customer needs while maintaining a proactive, strategic approach to retention and expansion.
• Align with internal teams to ensure customers receive best-in-class service and product solutions.

Here’s what we're looking for:

• Proven 3+ years experience in B2B SaaS Customer Success, Account Management, or Sales with a track record of driving retention and expansion revenue. 
• Experience in managing a large book of business and operating at scale. 
• Strong ability to analyze customer data, assess account health, and execute targeted outreach.
• Excellent relationship management and communication skills with a consultative, customer-first approach.
• Deep understanding of Gusto’s products and the ability to translate customer pain points into tailored solutions.
• A strategic mindset with the ability to prioritize, adapt, and execute in a fast-paced environment.
• Proven, day-to-day experience integrating AI into how you work - across writing, research, prep, and summarization as a core part of your workflow, with a track record of giving clear, useful feedback that helps improve your tools and processes.

If you're passionate about driving customer success, maximizing retention, and uncovering growth opportunities, we’d love to hear from you!

Our cash compensation range for this role is $95,000 to $125,000 OTE in Denver, Atlanta, Phoenix, Chicago and most remote locations. Remote locations will vary based on our geographical pay approach. Final offer amounts are determined by multiple factors, including candidate location, experience and expertise, and may vary from the amounts listed above.

About the Role:

As a Partner Manager at Gusto, you will be responsible for driving the strategy and growth of a portfolio of Gusto Pro's largest and most strategic accounting firm partners. In this role, you will be responsible for maintaining and expanding current revenue and usage within these firms, as well as identifying, pitching, and facilitating growth opportunities. You should be comfortable building deep relationships at all levels of a partner organization, from staff accountants to managing partners, and adept at managing complex partner relationships and product configurations. Use AI-powered workflows as a core part of how you sell: running assigned tools daily, surfacing friction and inefficiencies as you find them, and collaborating with your team to influence what gets built or improved next. You will also work cross-functionally with senior members of Gusto’s team to strengthen the partner relationship, coordinate joint efforts, and provide input as we evolve our Gusto Pro product roadmap and processes.

About the Team:

Gusto Pro is a game-changing, cloud-based platform built specifically for accounting firms. It empowers firms to streamline payroll, people operations, and advisory services for their clients, all within a single, integrated platform. Gusto Pro boasts powerful features like client dashboards, automated workflows, robust reporting, and seamless integrations with other accounting software, enabling firms to elevate their client service and skyrocket their practice growth. Learn more about Gusto Pro

Here’s what you’ll do day-to-day:

• Take a portfolio-based approach to your book of business to identify areas of risk and opportunities for revenue growth within your assigned accounting firms.
• Build detailed territory and account plans to lead Quarterly Business Reviews (QBRs) within your large partner portfolio to identify opportunities for growth, including aligning the Gusto Pro Partner Program with the partners strategic growth objectives.
• Balance both new partner acquisition (in collaboration with dedicated Partner BDR) and development of active partners.
• Act as a single point of contact for partners on behalf of aligned cross-functional sales supporting roles.
• Coordinate outreach strategy and partner enablement with cross-functional supporting functions to grow cross-sell/up-sell product adoption. 
• Lead frequent discussions (weekly status calls, upsell calls, QBRs) with partners to ensure they are leveraging the Gusto Pro platform to achieve successful business outcomes for their clients and their firm.
• Drive awareness and usage of new or updated Gusto Pro features and integrations to the partners in your book, showcasing how these advancements can benefit their clients.
• Own end-to-end execution of contract renewals and upsells, negotiating mutually beneficial terms and ensuring seamless transitions.
• Collaborate with product, design, and engineering teams to provide informed recommendations for Gusto Pro’s product roadmap, based on partner feedback and market trends, to enhance the partner and client experience.
• Navigate and update internal and external stakeholders, inclusive of C-suite executives at Gusto, partners, and cross-functional teams.
• Communicate and report to leadership on sales activity, pipeline progress, and market trends.
• Travel to meet with prospective partners. This includes representing Gusto at Industry Events and Conferences. 

Here’s what we're looking for:

• 5+ years of experience as a Partner Manager, Channel Manager, or other Sales-related function.
• A consistent track record of exceeding sales quotas and building long-term client relationships. Including negotiating complex six-figure contracts.
• Deep understanding of the accounting firm landscape, including their business models, challenges, and technology needs.
• Strong ability to articulate contractual, technical, and financial value points to partners, internal senior leaders, and executive leaders.
• A strong drive to succeed, and comfortable pushing the pace of action with partners and internal teams.
• Proven, day-to-day experience integrating AI into how you work — across writing, research, prep, and summarization as a core part of your workflow, with a track record of giving clear, useful feedback that helps improve your tools and processes.
• Strong analytical and problem-solving abilities – you're a strategic thinker.
• Work collaboratively but autonomously: asking for what you need, but not expecting micromanagement.
• Experience with CRM and Sales Software (e.g., Salesforce, ZoomInfo, Tableau).

Our target on-target earnings (OTE) compensation for this role is $125,000/yr to $150,000/yr in Denver, Las Vegas, Chicago, Atlanta & most remote locations, $155,000/yr to $182,000/yr for San Francisco & New York and $120,000 to $180,000 CAD for Toronto. This OTE is structured with a target 70% base pay and 30% commission pay with an uncapped commission structure. Final offer amounts and the exact base/commission split are determined by multiple factors including candidate location, experience, and expertise and may vary from the amounts listed above.

Submit your interest to join our CX team!

Gusto is seeking customer experience professionals who thrive in a fast-paced, consultative environment and are interested in being considered for future start dates in 2026. If you’d like to be considered for future opportunities with our team, please complete the form below and upload your resume. 

While start dates are still being determined for 2026, we’d love to connect! Does this sound like you? Apply below!

About the Role:

Gusto is seeking motivated, customer-centric professionals interested in being considered for future payroll customer experience opportunities in 2026. These roles are ideal for customer-facing payroll professionals who thrive in a fast-paced, consultative environment and are passionate about helping small businesses succeed.

As a Payroll Advocate, you will act as the single point of contact for all support inquiries, enhancing user experience and serving as a subject matter expert for Gusto’s core products. You will guide customers through our newest product features, provide proactive customer education and support, move quickly to strategize and creatively solve problems, act as an advocate to influence our product decisions and roadmap, and holistically support the customer/Gusto partnership. You’ll address and solve real problems and deliver an exceptional customer experience to build trust and loyalty to Gusto.

Here’s what you’ll do day-to-day:

• Own the customer journey by building trust, rapport, and partnership with customers through inbound and outbound phone, email, and Zoom interactions.
• Provide passionate, opinionated, consistent, expert, reliable support as a point of contact for payroll and benefits inquiries. 
• Leverage AI‑assisted tools to accelerate research and communication while upholding accuracy, compliance, and Gusto’s voice.
• Identify churn risk and quickly act to deliver solutions to mitigate the risk of churn, using your product knowledge and unique understanding of each individual customer.
• Build and maintain relationships built on trust and collaboration with admins to better understand and anticipate their needs.
• Partner with your customers and cross-functionally to unblock points of friction, proactively address potential concerns, and build an understanding of individual team needs and processes. 
• Think creatively, pivot quickly, live in ambiguity, and collaborate strategically. You will be required to expand your critical thinking skills and creatively problem-solve across all areas of the business, with an understanding of a variety of stakeholders and needs. 

Here’s what we're looking for:

• 3-6 years of customer experience with 1+ years of full-time experience in Payroll. 
• Account Management experience preferred. 
• Proven ability to proactively and reactively support customers, driving their success, happiness, and loyalty through expert guidance and creative problem-solving.
• Ability to synthesize and communicate complex subjects clearly and effectively, both verbally and in writing, with customers and internal partners.
• Experience with Salesforce, Zoom, Google Suite, Google Calendar, Gmail, and Chili Piper.
• Excels in balancing inbound calls, scheduled meetings, and email inquiries while managing and prioritizing multiple high-priority resolutions effectively.

This posting represents a general talent pipeline that spans multiple levels within our CX team. Final compensation will be determined based on the specific role, level, and experience alignment. The estimated compensation range for these roles is $21.00–$35.00 per hour.

Submit your interest to join our CX team!

Gusto is seeking customer experience professionals who thrive in a fast-paced, consultative environment and are interested in being considered for future start dates in 2026. If you’d like to be considered for future opportunities with our team, please complete the form below and upload your resume. 

While start dates are still being determined for 2026, we’d love to connect! Does this sound like you? Apply below!

About the Role:

Gusto is seeking motivated, customer-centric professionals interested in being considered for future health insurance benefits customer experience opportunities in 2026. These roles are ideal for customer-facing benefits professionals who thrive in a fast-paced, consultative environment and are passionate about helping small businesses succeed.

As a seasoned Health Insurance Benefits Advocate, you will act as the single point of contact for all benefits support and renewal inquiries, enhancing user experience and serving as a subject matter expert for Gusto’s core products. You’ll help employers get group benefits for the very first time, and then help those employers continue to make important benefits decisions on an annual basis. Together, we’re not just simplifying benefits — we’re helping small businesses offer competitive, people-first benefits that support happier, healthier teams.

Here’s what you’ll do day-to-day:

• Own the customer journey by building trust, rapport, and partnership with customers through inbound and outbound phone, email, and Zoom interactions.
• Provide passionate, opinionated, consistent, expert, reliable support as a point of contact for health insurance benefits inquiries. 
• Partner with internal teams to address and resolve customer inquiries and concerns throughout the benefits renewal process.
• Leverage AI‑assisted tools to accelerate research and communication while upholding accuracy, compliance, and Gusto’s voice.
• Identify churn risk and quickly act to deliver solutions to mitigate the risk of churn, using your health insurance benefits and product knowledge and unique understanding of each individual customer.
• Build and maintain relationships built on trust and collaboration with admins to better understand and anticipate their needs.
• Think creatively, pivot quickly, live in ambiguity, and collaborate strategically. You will be required to expand your critical thinking skills and creatively problem-solve across all areas of the business, with an understanding of a variety of stakeholders and needs. 

Here’s what we're looking for:

• 3-6 years of customer experience with 1+ years of full-time experience in health insurance benefits. 
• Account Management experience preferred. 
• Life & Health Insurance Producers Licensure preferred. 
• Proven ability to proactively and reactively support customers, driving their success, happiness, and loyalty through expert guidance and creative problem-solving.
• Ability to synthesize and communicate complex subjects clearly and effectively, both verbally and in writing, with customers and internal partners.
• Experience with Salesforce, Zoom, Google Suite, Google Calendar, Gmail, and Chili Piper.
• Excels in balancing inbound calls, scheduled meetings, and email inquiries while managing and prioritizing multiple high-priority resolutions effectively.

This posting represents a general talent pipeline that spans multiple levels within our CX team. Final compensation will be determined based on the specific role, level, and experience alignment. The estimated compensation range for these roles is $21.00–$35.00 per hour.