LawnStarter

Lead service delivery quality and trust, develop AI-powered support systems and evaluation frameworks for automated resolutions. | AI-native product manager with marketplace experience, technical fluency to partner with engineers, and strong system design and policy skills. | About LawnStarter LawnStarter is the nation's leading on-demand marketplace for lawn care and outdoor services, with over $100M in annual bookings. We're expanding beyond lawn care to become the one-stop shop for all home services — operating across three brands (LawnStarter, Lawn Love, Home Gnome) on a single shared platform. About Service Delivery at LawnStarter We make a promise on both sides of the marketplace: customers get a job done well, and Pros get paid fairly for doing it. Service delivery is everything that happens after a customer books — keeping that promise through completion, support, and the moments when things don't go to plan. This is the hard part of running a marketplace: we broker work we can't directly see, between two parties whose interests sometimes collide. Get it right and people stay for years. Get it wrong and you lose customers, Pros, or both. Trust is the product — and increasingly, the systems that protect it are AI-powered. The Role This is a broad Senior PM role on the quality, trust, and communication side of service delivery — setting the right expectations on both sides, steering Pros to deliver great work, resolving conflicting interests fairly, and making our AI-powered support genuinely good. You'll work on live, high-scale systems with a mandate to make them better. Service delivery is a big area with more than one PM in it. You'll work alongside them; your center of gravity is the trust between both sides of the marketplace. What makes this role different: It's a real area of impact, not a single feature. You'll shape strategy, policy, and the systems behind a whole slice of the post-booking experience — not optimize one screen. It's inherently two-sided. You work for customers and Pros at once, and you're often the one arbitrating between them. Pleasing one side at the other's expense is failure. AI is a core tool, not a side project. Support and outreach already run on AI. You'll push how far that goes — and build the evals that prove it's good before we trust it with more. Problems to Solve Getting expectations right before the work ever starts. Most service failures aren't bad work — they're mismatched expectations. The grass grew a tier past what was booked; "deep clean" meant something different to each side; the yard didn't match the photos. You'll make sure what's promised to the Pro matches what the customer actually expects, that those expectations are the right ones for the property and service, and that Pros are steered toward delivering great work. Every mismatch you prevent up front is a conflict you never have to resolve later. Arbitrating genuinely competing interests. A customer wants a date the Pro can't commit to. The grass is long enough to need a different price tier than booked. The job wasn't what the listing photos suggested. These aren't bad actors — both sides are right from where they sit, and the marketplace has to make a call. You'll build the policies and the (increasingly AI-assisted) decision systems that resolve these fairly and consistently at scale — and make the judgment call yourself when there's no clean answer. Making AI trustworthy enough to do more — which means evals. Customer-side AI already handles ~34% of support at roughly a penny per message, and Pro-side support is still to be built. Expanding either is gated on one hard, ongoing, technical thing: can we prove the AI resolved a case rather than just closed it? You'll own the eval systems — golden datasets, automated judges, regression detection, human-review sampling — that define what "good" means for an open-ended conversation, gate every change, and catch quality drift before a customer feels it. This is the deep, unglamorous work that makes a slick demo safe to scale. Messaging that connects both sides — and quietly protects the marketplace. The inbox is how 500K+ customers and 20K+ Pros coordinate across all three brands — and the record we lean on when something goes sideways. It also has to moderate: catching when a relationship is drifting off-platform (disintermediation) or a conversation is heating into conflict. You'll keep communication easy for the legitimate 99% while spotting the patterns that quietly cost us customers, Pros, and revenue. What Success Looks Like (Year 1) Expectations match on both sides: Pros know exactly what each job requires, customers get what they expected, and fewer jobs go sideways from misalignment in the first place. Competing interests resolve faster and more fairly: A clearer resolution model with measurable consistency — and more of these conflicts prevented up front by better expectation-setting. AI is provably good, and does more: An eval suite gates AI changes so no quality regression ships unseen — and on that foundation, higher resolution on customer support plus a first version of Pro-side AI support live. Messaging connects and protects: Measurable improvement in messaging reliability and engagement, plus working moderation that catches off-platform leakage and conflict early. Who You Are AI-native. You use AI daily in your own work, and you have real intuition for how to measure whether an AI experience is actually good — not just whether it shipped. You've built or owned evals, or you're hungry to, because you know that's what separates a trustworthy agent from a demo. This is unlikely to be a good fit if you treat LLM quality as a vibe check or as engineering's problem to figure out. Comfortable making two-sided calls. You can hold both the customer's and the Pro's interest in your head at once, and you're willing to make the call when they conflict — clearly, and with a rationale you'd defend to either side. This is unlikely to be a good fit if you're a people-pleaser who can't say no, or if you instinctively optimize for one side and forget the other exists. You design for the right outcome up front. You're not satisfied grading work after the fact — you'd rather get the expectations right at the start so the job goes well in the first place, for both the customer and the Pro. This is unlikely to be a good fit if you gravitate to measuring and auditing results over shaping them before they happen. A marketplace systems thinker. You see service delivery as a system of incentives, policies, and feedback loops — not a set of screens — and you design rules that hold up across edge cases and bad actors. This is unlikely to be a good fit if your instinct is to solve every problem with UI rather than incentives and policy. Data-informed. You live in the numbers that matter here — CSAT, resolution rate, eval scores, churn, deflection — and you know when the data is thin enough that a judgment call is needed. This is unlikely to be a good fit if you either ignore data or refuse to move without perfect information. Technically fluent. You partner with engineers on how AI and messaging systems work and give real feedback on design tradeoffs. You don't write production code, but you don't treat the systems as a black box either. This is unlikely to be a good fit if you need everything translated out of technical terms first. This Role Is NOT A support PM role. Support is one surface of a much broader product area. If you picture your days as managing a ticket queue or a help center, this isn't that. The internal-AI role. We have a separate PM driving AI adoption in internal tooling. This role is about AI in the user-facing service-delivery experience — customers and Pros, not internal teams. A greenfield 0→1 role. These systems are live and serving hundreds of thousands of people today. You'll improve and re-architect under real load, not build from a blank page. A single-audience role. You serve — and arbitrate between — both customers and Pros. If you only want to think about one side of the marketplace, the tension here will be uncomfortable. Base salary: $140,000 - $170,000 Equity: The systems you'll work on touch every customer and Pro — quality, trust, and retention all run through service delivery. We want you invested in the long-term outcome. Healthcare: Medical, dental, and vision Fully remote: Work from anywhere in the US. This role requires deep focus and close partnership with engineering and ops — we trust you to manage your environment. Flexible PTO: We Focus On Results LawnStarter provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, or genetics. We comply with applicable state and local laws governing nondiscrimination in employment.

As a Principal Software Engineer, you will lead projects end-to-end, collaborating on system architecture and technical strategy. You will also mentor engineers and contribute to both server-side and client-side development. | The ideal candidate should have experience as a principal engineer or lead full-stack engineer, with strong skills in software development. Familiarity with cloud services and a solid understanding of computer science concepts are essential. | Principal Software Engineer We’re currently hiring a Principal Software Engineer to join our growing remote team. Help Us Build the Future of Outdoor Services At LawnStarter, we’re transforming the $100B+ outdoor home services industry—making it easier for homeowners to book, manage, and enjoy services like lawn care, landscaping, and more. With $30M+ in venture funding and solid traction, we’re investing in the next generation of our platform—and we’re looking for a Principal Software Engineer to help drive it. 📹 See what we’re building 🌟 Why This Role Rocks Own What You Build – Lead projects end-to-end with full autonomy and real impact. Remote & Flexible – Work from anywhere and set your own hours. Build Meaningful Tech – Help shape the tools that thousands of homeowners and service pros rely on daily. Join at the Right Time – We have strong product-market fit and real momentum—you’ll help define what comes next. 💻 Our Tech Stack Languages & Frameworks: PHP (Laravel), JavaScript (React, React Native, Vue) Cloud Services: AWS (Lambda, ECS, EKS, Aurora, Redshift) Approach: We’re not fixated on specific languages. If you have strong engineering fundamentals and experience with any mainstream object-oriented language, we believe you can quickly learn and adapt to our tech stack. 🌱 What You’ll Do As a Principal Software Engineer, you’ll work closely with the Software Architect and other engineers to: Collaborate on designing and implementing system architecture, technical strategy, and engineering standards. Lead technical initiatives across teams, ensuring alignment with architectural direction and goals. Build and maintain platform-level components, services, and libraries that enhance engineering efficiency and system maintainability. Mentor engineers through code reviews, pair programming, and hands-on guidance. Contribute directly to both server-side and client-side development across the entire stack. Write and review technical design documents, system diagrams, and reference implementations. Evaluate and implement new tools, frameworks, and best practices to continuously improve our platform. Enhance observability, performance, scalability, and security throughout our system. Share knowledge and insights to foster team growth and improvement. 🔍 What We’re Looking For We’re looking for someone who is: Experienced: A principal engineer, lead full-stack engineer, or someone with relevant experience in similar roles. Highly skilled in both server-side and client-side software development. Technically Proficient: Familiar with cloud development (AWS, Google Cloud, Microsoft Azure). Experienced with Test Driven Development (TDD), RESTful APIs, React, MVC frameworks, and security concerns (e.g., XSS attacks). Fundamentally Strong in Computer Science Concepts: You can explain concepts like Big O notation, pointers, composition vs. inheritance, and data structures such as arrays, sets, and linked lists. Database-Savvy: Proficient in SQL and NoSQL databases, and understand operations like CRUD, indexes, and joins. Cloud Infrastructure Expert: Comfortable working with cloud infrastructure (e.g., AWS Lambda, ECS, EKS, Aurora) and utilizing Infrastructure as Code (IAC). Customer-Centric: Passionate about clean code and building customer-driven solutions with a focus on quality and reliability. All team members at LawnStater are expected to embody our core values which are: Be data-driven, Get shit done, People are critical, Challenge the status quo, Be scrappy, and Be the Customer. Salary Range: 130K-180K USD annually Healthcare benefits: Medical, dental, and vision Fully remote position: Work remotely from anywhere you want. Unlimited PTO: We focus on results. Take the time you need to recharge or enjoy life, work hard when you are back. Disclaimer LawnStarter provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, or genetics. In addition to federal law requirements, LawnStarter complies with applicable state and local laws governing nondiscrimination in employment in every location in which the company has facilities. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, transfer, leaves of absence, compensation, and training. LawnStarter expressly prohibits any form of workplace harassment based on race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, genetic information, disability, or veteran status. Improper interference with the ability of LawnStarter’s employees to perform their job duties may result in discipline up to and including discharge. LawnStarter is building the future of outdoor home services. Want to help us shape it? Apply now and let’s grow together.

Monitor and evaluate customer service interactions, provide feedback, develop QA documentation, and collaborate to improve service quality. | Entry-level QA role requiring good attendance, no active warnings, and ability to work standard business hours with no prior QA experience required. | We are seeking an Operations Quality Assurance Specialist to join our team. In this role, you will be instrumental in conducting quality assessments, resolving issues, and maintaining our high operational standards. This position is a unique opportunity to make a significant impact in a crucial phase of our team's development. What you'll be doing: LawnStarter is seeking an Internal Quality Assurance Specialist to join our team. In this role, you will be responsible for monitoring and evaluating the quality of customer service interactions and ensuring compliance with company policies and procedures. You will play a crucial role in driving continuous improvement in the quality of service provided to our customers. Responsibilities: Conduct internal evaluations of client interactions and provide feedback to team members Identify areas of improvement and work with the team to develop and implement solutions Develop and maintain quality assurance documentation and procedures Collaborate with cross-functional teams to ensure consistency in service quality Stay updated on industry standards and best practices in quality assurance Must be in T3 and above. Must currently meet or exceed QA standards. Must not have any active written warnings. Must have excellent attendance. Open to all locations. Must be able to work Monday - Friday, 8 am - 5 pm Central Time. Prior experience in quality assurance is beneficial but not required. Please check with your manager regarding your eligibility for this role. Join us to experience a supportive team environment with opportunities for professional development and a chance to contribute significantly to key projects and initiatives.