Full-Time

Senior Learning & Development Specialist

Posted on 9/5/2026

Gusto

Gusto

5,001-10,000 employees

Payroll, benefits, HR platform for SMEs

Compensation Overview

$91.1k - $136.5k/yr

+ Equity (RSUs)

Las Vegas, NV, USA + 4 more

More locations: San Francisco, CA, USA | New York, NY, USA | Phoenix, AZ, USA | Denver, CO, USA

Hybrid

Denver, San Francisco, and New York employees work in the office approximately 2–3 days per week.

Category
People & HR
Required Skills
LLM
Data Visualization
REST APIs
Data Analysis

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Requirements
  • At least 5 years of Learning and Development experience.
  • Ability to travel up to 50% of the time.
  • Proven experience designing, developing, and facilitating learning programs across multiple knowledge areas.
  • Strong coaching skills, including mentoring learners, participants, and junior team members.
  • Experience managing end-to-end learning programs, including cohort management and continuous improvement.
  • Strong stakeholder management skills and experience aligning learning initiatives with business goals.
  • Ability to analyze program outcomes and use insights for continuous enhancement.
  • Ability to manage multiple priorities effectively in a fast-paced environment.
  • Demonstrated experience designing, implementing, and evaluating artificial intelligence-enabled learning solutions.
  • Demonstrated experimentation with artificial intelligence applications in learning, communication, or content design.
  • Practical experience with modern artificial intelligence tools and workflows used in Learning and Development, including familiarity with large language models, prompt engineering, and application programming interfaces and integrations.
  • Familiarity with artificial intelligence tools supporting content creation, data analysis, or learner engagement.
  • Ability to prompt and fine-tune artificial intelligence tools to produce high-quality, relevant, and brand-aligned outputs.
  • Experience evaluating or implementing artificial intelligence-enabled learning platforms.
Responsibilities
  • Facilitate in-person, virtual, and hybrid learning sessions across at least six distinct and complex knowledge areas, tailoring delivery for audiences including mid-level and senior leadership participants.
  • Create inclusive and dynamic learning environments that challenge participants to apply critical-thinking and problem-solving skills in real-world scenarios.
  • Engage learners through interactive techniques, real-world examples, and structured activities that reinforce course content and objectives.
  • Provide real-time feedback and coaching to learners to enhance their understanding and skills development.
  • Design and facilitate sessions teaching Customer Experience teams to use artificial intelligence tools responsibly and effectively in daily workflows.
  • Use artificial-intelligence-assisted tools to enhance participation and personalization during live training.
  • Use insights from artificial-intelligence-driven learning platforms to tailor discussions, provide targeted feedback, and reinforce learning outcomes.
  • Lead comprehensive course design efforts and continuously improve learning materials and methods to meet evolving Customer Experience and business needs.
  • Own content development and serve as the final quality-control point for course content updates, ensuring learning materials align with strategic business goals.
  • Develop and manage communication strategies for learning initiatives, collaborating with leadership and cross-functional teams to secure alignment and stakeholder buy-in.
  • Integrate artificial-intelligence-enabled design approaches into curriculum development to improve personalization, scalability, and learner engagement.
  • Use artificial-intelligence-enabled authoring tools to prototype, script, and iterate on training materials.
  • Manage complex, high-visibility learning programs end to end, with accountability for program success, continuous improvement, and alignment with business outcomes.
  • Oversee multiple Customer Experience Academy cohorts simultaneously, ensuring efficient cohort management and providing strategic guidance on program implementation and learner success.
  • Monitor participant progress and engagement, proactively identifying and addressing barriers to success.
  • Drive program improvements using participant and stakeholder feedback to evolve learning offerings and maintain alignment with business goals.
  • Operationalize artificial intelligence tools to automate repetitive program-administration tasks where appropriate.
  • Implement artificial-intelligence-assisted project tracking, communication, and reporting tools to streamline coordination and status visibility.
  • Serve as a primary contact for high-level stakeholders and maintain strategic relationships to align learning programs with business priorities.
  • Collaborate with senior leadership and department heads to design learning initiatives supporting organizational growth and Customer Experience effectiveness.
  • Influence and negotiate with stakeholders at all levels, aligning learning objectives with business needs and representing the Customer Experience Learning and Development team in strategic discussions.
  • Use artificial-intelligence-supported data visualization and summary tools to synthesize stakeholder feedback and present actionable insights.
  • Communicate the value and limitations of artificial-intelligence-assisted solutions to stakeholders, ensuring transparency and alignment with organizational standards.
  • Own the learning data strategy for key programs, using data analysis to assess program effectiveness, identify trends, and provide strategic insights to leadership.
  • Track key performance indicators such as learner progress, program impact, and return on investment to optimize learning experiences.
  • Support team members in developing data-analysis skills and applying Kirkpatrick Model of Training Evaluation data.
  • Use artificial-intelligence-derived insights to personalize learning and measure artificial-intelligence-enabled program effectiveness.
  • Use artificial-intelligence-powered analytics dashboards to identify learning trends, skill gaps, and performance-support opportunities.
  • Translate artificial-intelligence-derived insights into actionable recommendations for program optimization.

Gusto provides payroll, benefits, and HR services for small to mid-sized businesses through a cloud-based platform. It automates payroll processing, employee benefits enrollment (health insurance, retirement), and HR tasks in one place via a subscription model with tiered plans. By centralizing these functions, it helps businesses save time, stay compliant, and avoid maintaining a large in-house HR team. Its goal is to help SMEs run people operations more efficiently and support growth with easy-to-use, scalable software.

Company Size

5,001-10,000

Company Stage

Series E

Total Funding

$706.2M

Headquarters

San Francisco, California

Founded

2011

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Simplify Jobs

Simplify's Take

What believers are saying

  • Over 500,000 customers give Gusto dense SMB data and strong product feedback loops.
  • AI handled 50% of new code and 50% of support cases by 2026.
  • Small-business formation stayed near record highs in 2026, feeding payroll customer acquisition.

What critics are saying

  • Rippling and Deel keep winning larger customers with broader global and IT workflows.
  • March 2026 outage halted payroll, benefits, and HR for over two hours.
  • IPO delay traps employees in private liquidity while valuation stays flat near $9.3 billion.

What makes Gusto unique

  • Gusto crossed $1 billion revenue in May 2026 with cash-flow-positive operations.
  • Gusto Cofounder, launched in 2026, automates payroll, compliance, and approvals from context.
  • Guideline acquisition natively bundles 401(k) retirement administration into small-business payroll.

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Benefits

It’s a marathon, not a sprint: Employees celebrating 5 or 10 years at Gusto enjoy a month-long sabbatical to travel and relax after all their hard work.

Meals and conversations: Free meals, snacks, and drinks to keep us fueled, but more importantly: they bring people together and foster community.

Wellness for every body: We’re proud to offer inclusive health care such as hormone treatments, gender-affirming surgery, therapy, family planning, and more.

The time you need: Our flexible PTO policy means every employee is encouraged to take the time they need now to keep doing great work, long term.

Family-friendly benefits: Fertility treatments, primary and secondary parental leave, sleep coaching, house cleaning for new parents, and more.

Be well, be you: Get free, comprehensive medical, dental, and vision benefits, plus a monthly fitness stipend and mental health resources too.

Growth & Insights and Company News

Headcount

6 month growth

-5%

1 year growth

-5%

2 year growth

-3%
Built In SF
Aug 31st, 2026
Enterprise fintech platform Gusto recognized by CNBC.

Enterprise fintech platform Gusto recognized by CNBC. The company was also considered one of the best small business payroll software solutions by Inc. Published on Aug. 31, 2026 Rose Velazquez Gusto, a software company helping businesses streamline payroll, benefits and other HR processes, was recently featured on CNBC's 2026 list of the world's top fintech companies. Gusto was listed under the enterprise fintech category, which highlights companies that serve financial institutions and businesses and are critical for how modern financial services operate. CNBC used a rating system established by Statista to determine its ranking, combining evaluations of key performance indicators and original research. In total, CNBC examined 3,500 businesses and more than 25,000 data points. Its final list features 500 organizations spanning over 50 countries and territories. Gusto serves more than 500,000 businesses across the U.S. and processes tens of billions of dollars of payroll annually. It also supports administration of employee benefits including health insurance and 401(k) accounts while working to help companies enhance their workplace experiences. Alongside its feature on CNBC's list, Gusto was recently recognized by Inc. as one of the best payroll software platforms for small businesses.

Secret Milano
Aug 26th, 2026
Rich fiordilatte, crunchy crumble, rum, and raisins: Casa Manfredi's legendary maritozzo becomes an ice cream in Milan for just 14 days.

Rich fiordilatte, crunchy crumble, rum, and raisins: Casa Manfredi's legendary maritozzo becomes an ice cream in Milan for just 14 days. From September 7 to 20, 2026 - and then again in November for Maritozzo Day - Gusto 17's stores in Milan will feature "Maritozzo 17," a limited-edition flavor born from the collaboration between Giorgia Proia's Roman pastry shop and the Milanese artisanal gelato brand. August 26, 2026 A leavened pastry that symbolizes contemporary pastry-making, transformed into gelato without losing its identity. This is the concept behind Maritozzo 17, the limited edition born from the collaboration between Casa Manfredi - the signature pastry shop founded in Rome in 2015 by pastry chef Giorgia Proia and her partner Daniele Antonelli - and Gusto 17, a Milan-based premium artisanal gelato brand. Two time periods, two Milanese stores. The flavor will be available during two distinct periods: from September 7 to 20, 2026, and, in celebration of Maritozzo Day, from November 23 to December 6, 2026. The participating locations are the two Gusto 17 stores in Milan, at Via Luigi Cagnola 10 and Via Savona 17, as well as the Salerno location at Piazza Portanova 36. The flavor will be available in cones, cups, and tubs. Anatomy of a flavor. Maritozzo 17 is built around a fiordilatte with a richer texture than usual, enriched with a maritozzo crumble that recreates its textural quality, and finished with rum and raisins - the signature ingredients of Giorgia Proia's original dessert. The stated goal is not a faithful reproduction, but rather a translation of the pastry's identity into the language of gelato: the same textures, the same aromas, a different format. "The goal wasn't to replicate a dessert, but to translate its identity into the language of gelato," explained Vincenzo Fiorillo, co-founder of Gusto 17. Giorgia Proia emphasized that the collaboration is an expression of the creativity and passion that have driven the Casa Manfredi project since its opening. Casa Manfredi: from the capital to Milan. Founded in 2015 on Viale Aventino in Rome, Casa Manfredi is now a recognizable icon of contemporary Italian pastry. Giorgia Proia, an architect by training, honed her craft alongside masters such as Gianluca Fusto, Rolando Morandin, and Antonio Bachour, developing an approach centered on ingredients and artisanal precision. In 2023, Casa Manfredi opened a second location inside the Teatro di Roma, at Via dei Conciatori 5. With Maritozzo 17, the Roman project makes its debut in Milan through a partnership with one of the city's leading gelato brands.

TechRseries
Aug 12th, 2026
Clair reaches $100M revenue run rate in under two years.

Clair reaches $100M revenue run rate in under two years. The rapid growth is fueled by $2 billion in wage advance volume run rate, 500,000 monthly active users, and over 300,000 active businesses on the platform. Clair, the embedded earned wage access infrastructure powering payroll and workforce platforms, announced it has crossed $100 million in revenue run rate in under two years. Clair also turned cashflow positive earlier this year. These milestones come as Clair hits record highs across its platform, with $2 billion in wage advance volume run rate, 500,000 monthly active users, and over 300,000 active businesses. This growth underscores the scale of the financial problem Clair was built to solve: U.S. employers currently hold $500 billion in unpaid, earned wages. By embedding directly into partner platforms, including Gusto and QuickBooks, Clair unlocks that money for Americans when they need it most. These milestones show that work is accelerating as inflation and rising costs are making unexpected bills untenable for many American workers. "For centuries, the rule of labor was set in stone: work today, get paid weeks later," said Clair CEO Nico Simko. "We are rewriting that rule and betting that payroll and workforce apps will lead the democratization of faster access to wages. I am incredibly proud to achieve these milestones and see this vision operating at a massive scale." Clair is also expanding beyond earned wage access. The company unveiled two new products designed to help consumers pay their bills, build their credit, and save on fees. Bill Assist helps individuals keep track of their bills to help avoid overdraft or late fees, and Credit Builder provides individuals with a new path to build their credit score with every paycheck. Clair continues to work toward its mission to make America's workforce financially free by providing seamless, transparent, and fair access to financial services connected to the workplace. [To share your insights with us, please write to [email protected]]

Pilotstack
Jul 16th, 2026
Building an HR tech stack for 2026.

Building an HR tech stack for 2026. HR & People HR tech payroll From payroll and benefits to recruiting and performance management, the right HR tech stack saves hours of manual work each week. Here is how to evaluate and assemble the right combination of tools for your team size. Reading Time HR & People The HR technology landscape has matured significantly over the past three years. The era of spreadsheets and email-driven processes is ending for any company that values accuracy and compliance. In 2026, the question is not whether to adopt HR software - it is which combination of tools creates the most efficient workflow for your specific team size, geographic footprint, and growth trajectory. ## The Core HRIS Layer Every HR tech stack starts with a core HRIS to store employee records, manage organizational structure, and track employment lifecycle events. For companies under 50 employees, Gusto provides the most streamlined experience by bundling HRIS, payroll, and benefits into a single platform. The trade-off is that Gusto's HR features are shallower than dedicated HRIS platforms - its performance management module covers the basics but lacks the depth needed for companies with formal career laddering and 360-review processes. BambooHR remains the strongest standalone HRIS in the 50-200 employee range, offering deeper HR functionality around time-off policies, document management, and reporting, but requiring a separate payroll provider. Rippling has emerged as a strong third option for companies that want unified IT and HR administration - its device management and app provisioning features are unique in the market, though its HR depth does not yet match BambooHR. ## Payroll Processing Payroll accuracy is non-negotiable, and the payroll module you choose often determines the rest of your HR stack. If you use Gusto as your all-in-one platform, payroll is included and handles auto tax filing, multi-state withholding, and year-end W-2 processing with a tax penalty guarantee. If you use BambooHR as your HRIS, you will integrate with a dedicated payroll provider like Gusto or ADP. The integration between BambooHR and Gusto is mature, syncing employee records and time-off balances bidirectionally, but payroll journal entries still flow one direction into your accounting software. Companies with 100+ employees across 10+ states should evaluate ADP or Paychex for their broader tax compliance coverage and dedicated support teams - both handle edge cases like garnishments, local tax jurisdictions, and multi-entity payroll structures that all-in-one platforms may not support reliably. ## Recruiting and Applicant Tracking The recruiting layer of your HR stack needs to connect job postings, candidate pipelines, and onboarding. For companies hiring 5-20 people per year, t ## Performance Management Performance management is the most commonly deferred HR function, but investing in it early prevents the painful retroactive evaluations that companies face when they first need to make promotion or termination decisions with no documentation. For teams under 50 people, simple quarterly check-in templates in your core HRIS are usually sufficient. As teams grow beyond 50, dedicated performance management tools like Lattice or 15Five provide structured goal tracking, manager feedback calibration, and engagement survey capabilities that most all-in-one HR platforms lack. Lattice integrates directly with BambooHR and Gusto, pulling employee data and org structure to keep performance records aligned with the core HRIS. ## Compliance and Security HR data is among the most sensitive information your company holds. Every platform in your HR stack should support SOC 2 Type II certification, annual penetration testing, and role-based access controls that restrict payroll and personal information to authorized administrators only. Configure SCIM provisioning through your identity provider so that employee access to HR tools is automatically granted on hire date and revoked on termination date - manual deprovisioning is the leading cause of HR data exposure in growing companies. Run a quarterly access audit across all HR tools to verify that former employees, contractors whose engagements have ended, and interns whose terms have expired no longer have active accounts. ## Building Your Stack by Company Size The right HR tech stack depends on where your company is today and where it will be in 24 months. Companies under 25 employees should start with Gusto as an all-in-one: you get payroll, benefits, basic HRIS, and time tracking in one platform for predictable per-employee pricing. At 25-75 employees, add BambooHR or Rippling as a dedicated HRIS layer if Gusto's HR features feel limiting, and consider a lightweight ATS if you are hiring regularly. At 75-200 employees, evaluate a dedicated performance management tool like Lattice, upgrade your ATS to Greenhouse or Lever if recruiting volume demands it, and ensure your payroll provider supports all states where you have employees. Beyond 200 employees, enterprise HR suites like Workday or SAP SuccessFactors become worth evaluating, though the migration cost and implementation timeline (typically 6-12 months) means you should only make that jump when your current stack creates measurable friction in reporting, compliance, or employee experience. Key Takeaways * 1In-depth analysis of hr & people tools and trends * 2Practical recommendations for hr tech and payroll * 3Based on real testing and expert evaluation by PilotStack Team PilotStack Team is a software expert at PilotStack, specializing in hr & people tools and technology evaluation. Published July 16, 2026

TechRseries
Jun 3rd, 2026
Gusto launches Cofounder, an AI teammate purpose-built for small business.

Gusto launches Cofounder, an AI teammate purpose-built for small business. Cofounder is one of the first agentic interfaces for small businesses that knows a business' team, payroll, compliance tasks and more before even getting started. Gusto, the leading partner for small businesses, announced the launch of Gusto Cofounder, an AI teammate built specifically for small business owners. Unlike general-purpose AI tools that start from a blank slate, Cofounder launches with context from Gusto and customer-authorized connected tools, including a business's team, payroll schedule, benefits, and Gusto compliance calendar, and can immediately start taking action on behalf of small businesses. The launch comes as America's entrepreneurship boom accelerates. New business applications are running above 500,000 a month, near record highs. According to Gusto's 2026 New Business Formation Report, 60% of new business owners used AI to help launch their business in 2025 - double the rate from just two years ago. Half said AI made the process significantly faster or less expensive. "Small business owners are some of the most resourceful people in the world, but they're consistently stretched too thin," said Eddie Kim, Co-founder and Head of Technology at Gusto. "For most, running payroll isn't the hard part - it's everything they have to do ahead of running it. Pulling data from other systems, manipulating spreadsheets, chasing down missing inputs - the 'work before the work.' It's one of the most hidden burdens of running a business and Gusto Cofounder was built to take that off their plates entirely." Cofounder is designed to handle the operational work that consumes small business owners' time like running payroll, helping flag compliance risks, chasing missing timesheets, and surfacing staffing conflicts before they become issues. Owners can direct Cofounder through natural conversation via SMS, Slack, or the web with prompts like: * "Run payroll for this Friday and flag anything that needs my approval before it submits." * "Generate a weekly labor cost report by department and send it to me every Monday morning." * "Send me an approval request for any team expense over $25 before it gets processed." * "Flag any time-off requests that overlap with payroll deadlines or leave the team short-staffed." Cofounder also monitors businesses proactively, with more than 20 pre-built automations covering onboarding, payroll, expense approvals, and compliance tasks - patterns learned from the over 500,000 small businesses using the Gusto platform. "Cofounder allows you to interact with Gusto in a real human way. It feels like you're talking to a person. It's doing all of the Gusto things behind the scenes for me." - David Levin, CEO, Angry Sam Productions Gusto Cofounder integrates with Google Workspace, Notion, Slack, and other tools small businesses already use. Guardrails keep humans in control of key decisions while Cofounder handles the routine and flags exceptions. [To share your insights with us, please write to [email protected]]