Help Scout · 1 month ago
Sr. Product Engineer
United States
Full-time
Remote
Senior Level
$162K/yr - $196K/yrHelp Scout builds software for relationship businesses, focusing on outstanding customer service. They are seeking a Sr. Product Engineer to develop AI-powered customer-facing features and ensure a seamless user experience across the full stack.
Customer ServiceSoftwareTechnical Support
No H1B
Responsibilities
Ship customer-facing AI features across the full stack. Build the experience and what's behind it — LLM-backed flows, retrieval (RAG) and embeddings, and agentic tool-calling — through to a fast, accessible, well-crafted UI. Most engineers here have a strength; yours leans frontend, and you take initiative across every layer
Treat AI output as something you verify, not assume. Build evaluations, guardrails, and monitoring into AI features so quality is measurable and holds up in production. Know when to trust a model's output and when to push back — and design the system so the product degrades gracefully when a model or provider misbehaves
Sweat the front-end craft. The interface is where AI either earns or loses customer trust. You care about responsiveness, streaming/loading states, accessibility, and the small details that make an assistive feature feel reliable rather than gimmicky
Stay close to customers. Join customer calls when more context is needed to design the right solution, participate in a support escalation rotation, and watch session recordings on the features you own. Bring that signal back into the work
Own outcomes, not just output. Before a project starts, you and a PM agree on a specific outcome metric the work is trying to move. You instrument it, and after it ships you're watching the dashboard and talking to customers — deciding what to do next, not just closing a Linear issue
Co-author the solution. PMs own strategy and sequencing; you bring the judgment and craft for how solutions actually get built, and you'll often shape the product thinking too. The best work happens when engineers, designers, and PMs support each other
Own production readiness from the start. Automation, reliability, monitoring, alerting, and logging aren't afterthoughts — they're part of how you ship. The work continues after merge
Use AI tools every day as part of your craft. We expect fluency with Cursor, Claude Code, or similar. If you saw a way to make the team's AI workflow better tomorrow, you'd say so
Help us hire. From time to time, partner with our Talent team to interview future teammates — one of the highest-leverage things any engineer here does
Qualification
Required
Strong, full-stack-capable engineer with a frontend center of gravity
Substantial JavaScript/TypeScript and React experience
Real front-end craft
Initiative across the stack and ship end-to-end without waiting for someone to own the other half
Built real things with LLMs — not just prototypes
Comfortable with retrieval (RAG), embeddings, prompt/context engineering, and agentic/tool-calling patterns
Point of view on what makes AI features actually reliable in production
High bar for AI quality
Think in terms of evaluation, verification, and guardrails
Measure whether an AI feature works rather than assuming it does
Genuinely fluent with AI coding tools and treat them as part of your craft
Move fast without sacrificing judgment
Customer-fluent
Actively seek out customer signal
Own outcomes
Measure work by whether it landed
Comfortable saying 'this didn't move what we hoped, here's what we want to try next.'
Take real ownership of the full development lifecycle
Automation, reliability, resilience, monitoring, alerting, and logging built in from the start
Communicate clearly in writing and in conversation
Give and receive direct feedback
See code review and pairing as real chances to teach and learn
Preferred
Experience making LLM features production-grade: latency/cost tuning, fallbacks and circuit breakers across providers, moderation/safety, and handling sensitive data responsibly
Familiarity with evaluation/observability tooling for AI (LLM-as-judge, test sets, tracing) and the discipline of building representative eval sets
Design sensibility — comfort partnering closely with designers and elevating the craft of an interface, not just implementing a spec
Experience in customer support, productivity, or other tools where trust and reliability are the product
Benefits
Competitive salary and an internal, transparent salary formula based on market data
Flexible time off – you choose the holidays and vacations that make sense for you
12 weeks of fully paid parental leave for all new parents, including adoption and foster care
A home office stipend to help you get set up and productive
A co-working stipend up to $300 a month if you choose to work out of your house
A yearly professional development stipend of $1,800 to help you grow in your craft
If you’re in the U.S. or Canada, we offer top tier health insurance for you and your dependents.
Company
Help Scout
Help Scout develops help desk software for business.
Founded in 2011
51-200 employees
Funding
Current Stage
Growth StageTotal Funding
$27.98MKey Investors
Lead Edge CapitalFoundry Group
2021-01-31Series B· $15M
2017-02-07Series B· $6.18M
2015-03-18Series A· $6M
Leadership Team
Denny Swindle
Co-Founder & CTO
Shawna Fisher
Chief Operating Officer
Recent News
2026-04-15
2025-09-19
Company data provided by crunchbase