Senior Staff Software Engineer – Onboarding, Activation

Jobtailor; San Francisco (CA); On-site; USD 180,000 - 240,000; Full time

Job summary

Jobtailor is seeking a Senior Software Engineer to own onboarding experiences end to end, leveraging AI/LLM to accelerate customer activation. You will collaborate with Product, Design, and Data to validate hypotheses, ship incremental improvements, and mentor the team toward high-quality, scalable solutions.

Lead the design of reusable onboarding components, prototype new 0-to-1 experiences, and drive ownership and execution in a fast-moving environment.

Qualifications

• 10+ years of software engineering experience and shipping customer-facing products at scale.
• Product-minded engineering approach focused on customer problems and meaningful metrics.
• Ability to operate independently across product, design, and data partnerships.
• Demonstrated ability to move fast and execute with high quality.
• Experience applying AI/LLM capabilities to real product problems.
• Habit of using AI tools to work more effectively.
• Founder mindset with ownership, ambiguity tolerance, greenfield problem solving.
• Track record of technical leadership, mentorship, and setting engineering standards.
• Strong full-stack fundamentals across front end, back end, and data.

Responsibilities

• Own meaningful slices of signup-to-activation end to end, from data model to UI.
• Ship measurable improvements to onboarding speed and reliability for new customers.
• Invent and prototype net-new, 0-to-1 AI-powered onboarding experiences.
• Partner with Product, Design, and Data to frame problems and validate hypotheses with customers.
• Identify where AI removes customer effort and embed those experiences in onboarding flow.
• Design modular, reusable onboarding building blocks for new entry points into the product.
• Provide technical direction through high-quality code, reviews, and mentoring.
• Make sharp scoping decisions, ship simple versions, and iterate based on results.

Skills

Years of experience

AI/LLM in products

Technical leadership

Full-stack development

Product-minded engineering

Job description

• Own meaningful slices of the signup-to-activation experience end to end, from data model to UI
• Ship measurable improvements to how quickly and reliably new customers get up and running
• Invent and prototype net-new, 0-to-1 AI-powered onboarding experiences
• Partner with Product, Design, and Data to frame problems, form hypotheses, and validate them with real customers
• Identify where AI removes customer effort and build those experiences into the onboarding flow
• Design modular, reusable onboarding building blocks for new entry points into Gusto
• Provide technical direction through high-quality code, reviews, and mentoring
• Make sharp scoping decisions, ship simple versions, and iterate based on results

Requirements

• 10+ years of software engineering experience, including building and shipping customer-facing products at scale
• Product-minded engineering approach focused on customer problems and meaningful metrics
• Ability to operate independently across product, design, and data partnerships
• Demonstrated ability to move fast and execute with high quality
• Experience applying AI/LLM capabilities to real product problems
• Habit of using AI tools to work more effectively
• Founder mindset, high ownership, comfort with ambiguity and greenfield problems, and bias toward action and outcomes
• Track record of technical leadership, mentorship, and setting engineering standards
• Strong full-stack fundamentals across front end, back end, and data

Core Competencies

Demonstrates extensive experience in software engineering with a focus on building customer-facing products, applying AI/LLM capabilities, and leading technical direction. Emphasizes a product-minded approach, strong full-stack fundamentals, and the ability to collaborate effectively across teams.

Highest-signal resume keywords

• 10+ Years Software Engineering Experience
• AI/LLM Application in Products
• Technical Leadership and Mentorship
• Full-Stack Development
• Product-Minded Engineering Approach

Hard Skills

• Software Engineering
• Full-Stack Development
• AI/LLM Capabilities
• Data Modeling
• UI Design
• Code Reviews
• Prototyping
• Customer-Facing Product Development
• Modular Design
• High-Quality Code

Soft Skills

• Ownership
• Comfort with Ambiguity
• Bias Toward Action
• Collaboration
• Problem-Solving

Industry Keywords

• Onboarding Experience
• Customer Activation
• Product Design
• Data Partnerships
• Engineering Standards