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:

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

We're looking for our new Head of Accountant Community to build and scale Gusto's brand presence and community with the accountant audience.

This is a highly visible, strategic role responsible for representing Gusto externally to accountants through thought leadership, community programs, events, and partnerships. You'll create the connective tissue between brand, community, and growth—driving firm recruitment, activation, and long-term engagement while strengthening Gusto's reputation as the small business partner accountants trust and advocate for.

About the Team

This role is part of the go-to-market team responsible for driving pipeline and fueling growth across indirect channels. We combine creativity, data-driven insights, and cross-functional collaboration to design campaigns that reach, engage, and convert the right audiences at scale. Together, we've helped Gusto grow to serve thousands of accounting partners nationwide, and we're just getting started.

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

● Build and lead Gusto's accountant community strategy, defining how we show up consistently and credibly across owned, earned, and experiential channels.

● Represent Gusto externally to the accountant audience through thought leadership, speaking opportunities, events, community programs, and industry partnerships.

● Develop and scale community programs and experiences (virtual and in-person) that foster connection, education, and advocacy among accounting firms.

● Own and evolve Gusto's accountant-facing thought leadership strategy, partnering with content, comms, and product marketing to create narratives that build trust and authority.

● Partner closely with product, marketing, and sales teams to ensure community efforts translate into firm recruitment, activation, and engagement.

● Design and execute events and sponsorship strategies (e.g., conferences, field events, roundtables, meetups) that strengthen brand affinity and accelerate funnel impact.

● Collaborate with PR, comms, and social teams to amplify community voices and elevate Gusto's presence in the broader accounting ecosystem.

● Establish feedback loops with accountants to surface insights that inform product positioning, messaging, and partner experience.

● Define and track success metrics across accountant community health, including awareness, sentiment, engagement, and top-of-funnel performance.

● Manage budgets, vendors, and external partners to deliver high-quality programs efficiently and at scale.

Here's what we're looking for

● 7–10 years of experience in community marketing, ideally within partner- or relationship-driven industries.

● Proven experience building and scaling communities or external-facing programs that drive trust, engagement, and long-term growth.

● Strong track record of representing a brand externally through events, speaking, partnerships, or thought leadership.

● Experience developing integrated programs that connect brand and community efforts to measurable business outcomes.

● Excellent storytelling and communication skills, with the ability to craft compelling narratives for senior, professional audiences.

● Strong cross-functional collaborator who can influence without authority and partner closely with sales, product marketing, comms, and leadership.

● Data-informed mindset with experience defining and measuring success across brand, engagement, and funnel metrics.

● AI fluency: Ability to use AI tools (e.g., ChatGPT, Glean) to improve efficiency in content creation, personalization, and insight generation, with strong judgment about when to apply AI vs. human expertise in community building.

● Comfort operating in a fast-paced, ambiguous environment while building something net-new from the ground up.

● Bonus: experience marketing to accountants, professional services firms, or other referral-based ecosystems.

Compensation

Our cash compensation amount for this role is $152,655/yr to $190,000/yr in Denver, Phoenix/Scottsdale, Las Vegas, Chicago, and Atlanta; $180,000/yr to $225,000/yr for San Francisco & New York, and CAD $147,000 to $180,000/yr for Toronto. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

#LI-HYBRID

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.

About the Role

The Revenue Operations team at Gusto is a full-stack team responsible for data, analytics, and operational excellence in pursuit of scaling our revenue growth. The Go-To-Market Analytics team is one functional area, responsible for defining and owning the metrics for scaling our Sales teams. 

Gusto is looking for a Revenue Analytics Engineer to build and maintain foundational data infrastructure that is crucial to growing and scaling our Sales efforts. In this role, you will partner with our GTM analysts to scope and deliver data products for an audience ranging from company and revenue leadership to operational and frontline sales. In doing so, you will own significant portions of our sales data from end-to-end, focusing on the transformation, design, and visualization workflows. In addition, you will establish best practices for systems design and workflows to maximize usefulness of AI at scale. 

This role will report to the Head of Go-To-Market analytics, and partner closely with Data Science, Data Platform, and Business Technology teams. 

Here’s what you’ll do day-to-day:

• Establish relationships with internal stakeholders to determine business needs, scoping and delivering solutions through data products
• Design, build, and maintain data pipelines and dashboards to automate “keep the lights on” work out of manually-managed processes
• Build a data foundation by incorporating business logic into raw data tables, laying the groundwork to enable value-add insights
• Create a dynamic reporting environment based on stakeholder needs
• Identify data discrepancies and set best practices for data logic to create a clean and well-documented environment
• Collaborate with broader data organization as steward to the definition and process management of core Gusto metrics

Here’s what we're looking for:

• Education or work experience in Engineering or Computer Science, or a related technical field 
• 7+ years of experience in an analytics engineering, business intelligence, or technical data analytics role
• Experience with SQL and ETL optimization techniques, especially within cloud-based data warehouses like Redshift, Snowflake, etc.
• Command-line experience and familiarity with version control collaboration tools (git)
• Experience with data pipeline management technologies with dependency checking, such as Airflow, as well as schema design and data modeling tools (dbt)
• Experience with data visualization technologies, e.g., Tableau, Looker, Sigma, Mode, Hex
• Experience with Python and data ingestion tools
• Ability to problem-solve open-ended problems and project manage dependencies and timelines to optimal outcomes
• Ability to demonstrate tools, business intuition, and attention to detail for data validation and QA 

Our cash compensation amount for this role is targeted at $138,000-156,000 in Denver & most remote locations, and $168,000-189,000 in New York & 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.

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:

We're looking for a Senior Field Event Marketing Manager to bring Gusto to life through bold, memorable events and experiences.

This is a highly visible, strategic role responsible for designing, producing, and optimizing event marketing programs—from trade shows and industry conferences to Gusto-owned activations and experiences. You'll plan, execute, and optimize event marketing campaigns as part of a cross-functional go-to-market team, turning strategy into on-the-ground execution that builds brand affinity and pipeline.

About the Team:

This role is part of the go-to-market team responsible for driving pipeline and fueling growth across Gusto's channels. We combine creativity, data-driven insights, and cross-functional collaboration to design campaigns that reach, engage, and convert the right audiences at scale. Together, we've helped Gusto grow to serve hundreds of thousands of customers nationwide, and we're just getting started.

Here’s what you’ll do day-to-day:

• Collaborate with cross-functional stakeholders and leadership to set goals, develop event strategies, execute plans, and evaluate performance to drive continuous improvement over time.
• Build and manage end-to-end event campaign programs including scopes of work, resource plans, budgets, contracts, and timelines—keeping everything on track and on budget.
• Leverage a deep understanding of Gusto's internal and external market positioning and target audiences to inform event decisions, from format and venue selection to messaging and audience targeting.
• Design and produce a range of event types—from large-scale owned events (500+ attendees) to trade show activations, field events, and intimate customer experiences—that strengthen brand affinity and accelerate funnel impact.
• Build strong relationships with external partners including industry and show organizers, agencies, and vendors, negotiating favorable terms and ensuring seamless delivery.
• Assemble the right internal and external resources for each opportunity, fostering collaboration and creative excellence with Gusto's creative teams, agencies, and production partners.
• Maintain accuracy and accountability of event budgets, evaluate results against goals, deliver wrap-up reports, and make recommendations to senior leadership for Event Marketing.
• Build upon and advocate for the event marketing and production craft and vision at Gusto—championing breakthrough experience design, emerging event technology, and innovative production approaches.
• Leverage AI tools and technologies to enhance event marketing workflows—from audience analysis and content personalization to post-event reporting and campaign optimization—driving efficiency and deeper insights across the event lifecycle.

Here’s what we're looking for:

• 7–10 years of experience in event marketing and production, with a proven track record of producing a wide range of events (trade shows, activations, conferences, owned events for 500+ attendees, and white-glove experiences) across varying levels of complexity, scale, and design.
• A passion for event marketing and production with a willingness to roll up your sleeves and get hands-on in execution—you move effortlessly between big-picture strategy and intricate operational details.
• Strong project management and communication skills with a proven ability to manage multiple stakeholders at all levels and across different geographies, keeping complex programs running on time and on budget.
• Experience managing and collaborating with internal creative teams and external agencies, driving alignment and excellence in production delivery.
• Passionate and knowledgeable about breakthrough experience design and emerging event technology, always looking for new ways to elevate the craft.
• A natural cross-functional collaborator who thrives on building and maintaining relationships across the organization to drive results.
• An intellectually curious self-starter who isn't afraid to ask questions and uses answers to bring clarity and direction to the broader team.
• AI fluency and a willingness to integrate AI-powered tools into your workflow to work smarter and unlock new possibilities.
• Comfort operating in a fast-paced, ambiguous environment while building scalable programs and processes.
• Note: this role requires frequent travel throughout North America.

Compensation

Our cash compensation amount for this role is $152,655/yr to $190,000/yr in Denver, Phoenix/Scottsdale, Las Vegas, and Atlanta, and $180,000/yr to $225,000/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:

We're looking for a Senior Sales Compensation Analyst to join our Revenue Operations team. As a senior individual contributor, you will serve as a hands-on operator, subject matter expert, and strategic partner to our sales organization — owning end-to-end compensation administration while independently shaping the compensation programs and operational frameworks that drive Gusto's growth.

This is a high-visibility role at the intersection of Sales, Finance, and Revenue Operations. You'll bring deep expertise in sales compensation administration, advanced analytical capabilities, and a track record of building scalable programs that are fair, accurate, and motivating. You'll operate with a high degree of autonomy alongside the Head of Sales Compensation — driving plan administration, contributing to plan design for assigned segments, and setting the operational and analytical standard for the team. You'll leverage AI tools to push the boundaries of what our team can deliver.

About the Team:

The Sales Compensation team at Gusto sits within the Revenue Operations organization and serves as the backbone of how Gusto's sales force is motivated, rewarded, and aligned to company growth. We are a small, high-impact team with outsized visibility — our work touches every quota-carrying role across the company and directly influences how Gusto attracts, retains, and drives performance from top sales talent.

Here’s what you’ll do day-to-day:

• Own sales compensation administration for assigned teams — execute accurate, on-time commission calculations, payment processing, crediting, draws, clawbacks, and dispute resolution each pay cycle; Serve as the team's Xactly platform owner and subject matter expert, defining configuration standards, driving platform decisions, and maintaining data integrity across plan setup, participant management, and workflow automation 
• Own monthly reporting & analytics for assigned segments — deliver attainment summaries and payout forecasts to Sales, Finance/Accounting, and Rev Ops; maintain KPI dashboards and perform ad hoc analysis on performance trends and budget adherence.
• Contribute to plan design for assigned segments — Support and, where designated, independently own compensation plan inputs for assigned sales segments, including rate validation, accelerator analysis, and rules of engagement; build financial models and scenario analyses that inform quota-setting and plan design decisions; connect compensation mechanics to broader outcomes across Finance, HR, and Sales Strategy
• Define and improve processes and compliance — document and continuously improve comp processes; maintain adherence to internal compliance standards and accounting rules; ensure role changes, new hires, and terminations are reflected accurately across Xactly and downstream systems
• Lead assigned cross-functional initiatives - Drive projects spanning Sales, Finance, HR, and Rev Ops; use data and structured analysis to influence stakeholders and build alignment across functions
• Leverage AI to elevate comp operations — actively incorporate AI tools to automate repetitive tasks, accelerate reporting, and surface insights; partner with the Head of Sales Compensation to identify and scale AI-driven improvements across the team 

Here’s what we're looking for:

• 8+ years of hands-on sales compensation administration experience with demonstrated end-to-end ownership of commission processes in a high-growth environment 
• Experience in full-cycle comp administration — calculations, crediting, draws, clawbacks, and dispute resolution. 
• Xactly platform expertise - intermediate-to-advanced admin required (certification preferred); proven ability to own system configuration, data integrity, and workflow design; Salesforce and Tableau/Looker/Power BI proficiency; other ICM platforms a plus
• Advanced analytical skills - compensation modeling, scenario analysis, and reporting; solid understanding of quota-setting methodologies, GTM motions, and sales roles (AE, AM, SDR, overlay) 
• Cross-functional influence — track record of leading initiatives and driving alignment across Sales, Finance, HR, and Operations without direct authority  
• AI competency — actively uses AI tools to automate tasks, accelerate analysis, and improve accuracy with a habit of exploring and applying new tools practically 
• Attributes — detail-oriented, proactive, and highly organized; clear communicator who can simplify complex comp mechanics for reps, managers, and cross-functional partners
• Bachelor's degree in Finance, Business, Mathematics, or related field — or equivalent experience

Our cash compensation amount for this role is $113,880 to $139,500 for Denver, Atlanta & Las Vegas. $138,365 to $169,500 for San Francisco & New York. $106,940 to $131,000 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.