Vanta: Senior Software Engineer, Design Systems
April 17, 2026
Headquarters: San Francisco, California, United States
URL: http://lawnstarter.com
About LawnStarter
LawnStarter is the nation’s leading on-demand marketplace for lawn care and outdoor services, with over $100M in annual bookings. We connect homeowners with vetted local service professionals (Pros) who handle everything from weekly mowing to pool cleaning. We’re profitable, growing 30%+ YoY, and expanding beyond lawn care to become the one-stop shop for all outdoor home services.
About Pro Experience
Our marketplace runs on supply. We have 10,000+ active Pros across the country, and their engagement, quality, and retention directly determine whether we can capture demand and grow. Right now, the supply is fragile, roughly 60% of onboarded Pros never complete a first job, and we’re losing millions of dollars in annual revenue because we don’t have enough Pros in the right places.
The Pro Experience function exists to close that gap. This is the team that most deeply understands what Pros experience, what they need to succeed, and what makes them stay, and translates that understanding into communications, programs, and internal advocacy that move supply metrics.
The Role
You’ll own how LawnStarter communicates with Pros, across every touchpoint, across the full lifecycle, with a clear goal: more Pros succeeding on the platform.
Today, most Pros experience LawnStarter as a job board, work comes in, they do it, they get paid. You’ll change that. You’re building the communications experience that makes Pros feel like LawnStarter is invested in their success: a platform that helps them grow their business, get better at their craft, and earn more over time. That’s the brand you’re building, not for homeowners, but for the 10,000+ small business owners who power the marketplace.
This isn’t a traditional CRM role or a brand role. It’s supply-side product marketing. You’re designing the communications experience that keeps our supply base activated, informed, motivated, and growing. That means owning the strategy for Pro-facing communications across in-product messaging, community, help content, incentive programs, and internal Pro advocacy with execution support from cross-functional partners.
What makes this role different:
– The timing is right. We’re profitable and growing 30%+ YoY. Bettermode is our community, incentives, and training hub for Pros. And we’ve built Brain, an internal knowledge system powered by AI that accelerates how we research, build, and ship. The pieces are in place, what’s missing is the strategic and hard working owner who connects them into a coherent Pro experience.
– You’re building the infrastructure. There’s no documented Pro positioning statement, no messaging playbook to inherit. You’ll design the processes, not just run them.
– Your north star is supply, not engagement. Open rates and community posts are proxies. The real question is: are more Pros completing their first job? Are they active at 30, 60, 90 days? Are high-quality pros churning? Are they succeeding?
– You’ll be the internal voice of the Pro. Product, Ops, and Support will come to you when they need to understand how Pros will react to something. You’ll push back when the company is about to do something that will land wrong.
What You’ll Own
– In-product messaging: Partner with Product to design and maintain the system for Pro-facing in-app communications, communicating platform changes, incentives, and performance data at the right moments in the Pro journey.
– Community, upskilling & brand voice: Pro community building in Bettermode, which includes engagement strategy, content cadence, and the tone of voice for all Pro-facing communications. Pros are small business owners, not gig workers, the voice should reflect that. Define the vision for Pro Academy (training, upskilling, potential partnerships like Greenius); work with partners on content production and delivery.
– Pro help content: Strategy for the knowledge base, FAQs, and how-to content that let Pros find answers without contacting support. Work with PMs on help content for feature launches and platform changes. Measure success by deflection, not just views.
– Internal Pro advocacy: Own the Pro listening system, interviews, call reviews, Bettermode monitoring, support trend analysis, and route insights to product, ops, and support in ways that drive actual decisions.
– Gamification & incentive programs: Own how challenges, badges, and tier-based incentive programs are communicated to Pros across the full lifecycle, from early activation through long-term retention. Product and Data design the incentive structures; you ensure Pros understand, engage with, and are motivated by them.
Problems to Solve
60% of onboarded Pros never complete a first job.
They sign up, complete onboarding (often same-day), enter the Intro tier, and then disappear. The supply math is stark: of every 30 Pro leads acquired, only 1 becomes a valuable active Pro. This is the single biggest supply lever available, and it’s currently unowned.
Pro communications are fragmented.
In-product messaging, email sequences, Bettermode posts, and help articles are managed across three different teams with no unified voice or strategy. Pros get inconsistent signals about how the platform works, what they should do next, and what the rules are. That inconsistency erodes trust.
Pro feedback doesn’t flow back to decisions.
We hear from Pros constantly, through support tickets, community posts, NPS surveys, direct calls. But there’s no systematic process for capturing, synthesizing, and routing those insights to decision-makers.
High-value Pros eventually build their own businesses, and we lose them.
Our best Pros reach the highest tiers, build strong customer relationships, and develop recurring revenue. At some point, the calculus shifts: they have enough of their own customers that the platform’s value proposition needs to be actively reinforced. Right now, no one owns the communications that make the case for why high-performing Pros should stay and grow with us. This is the hardest retention problem in the role, and it starts with understanding what these Pros actually need to hear.
What Success Looks Like (Year 1)
– More onboarded Pros complete their first job Significant improvement (5+ percentage points) in 30-day activation rate.
– Pros sentiment is measurably improving. You’ve established the baseline and can show the trend.
Requirements
Who You Are
You’ve developed genuine expertise on a supply-side or creator-side user segment by listening directly. Not from dashboards, from conversations, call reviews, community participation, and direct contact. You can name something specific you learned that surprised you and used it to change something internally. This is the most important thing you’ll bring to this role. This is unlikely to be a good fit if your “user expertise” is primarily quantitative, data matters, but this role requires knowing things that don’t show up in a funnel.
You write for real people, not for corporate approval. Your Pro-facing copy is clear, warm, and direct, not full of platform jargon or hollow encouragement. You know the difference between a message that earns attention and one that gets scrolled past, and you have examples you’re proud of. This is unlikely to be a good fit if your writing background is primarily internal documents, executive summaries, or B2B content.
You connect communications to outcomes. You don’t measure success by sends or opens, you ask whether behavior changed. You can trace a message or sequence back to a supply outcome, or explain why you can’t yet and what you’d need to measure it. This is unlikely to be a good fit if your analytics stop at engagement metrics.
You influence without authority. Your impact runs through Product, Ops, and Support, teams you don’t control. You’re comfortable building the case, presenting the data, and making it easy for partners to say yes. You’ve changed how a team made a decision by surfacing insights they didn’t have. This is unlikely to be a good fit if you need direct control over execution to feel accountable for outcomes.
You build from scratch. No playbook, no existing systems, no defined lanes. You’ll design the processes, not just run them. That’s energizing to you, not stressful. This is unlikely to be a good fit if you thrive in mature, well-documented environments with established workflows.
AI-native. You’ve used AI tools to scale content creation, synthesize qualitative feedback, or automate communications workflows, and you can show the output. You experiment and iterate, not just prompt. This is unlikely to be a good fit if you treat AI as a novelty or use it only for the occasional first draft.
This Role Is NOT
– A CRM execution role. Lifecycle comms are part of the picture, but you’re also owning in-product messaging, community, help content, gamification, and internal advocacy. Pure email/SMS management is a fraction of the job.
– A homeowner marketing role. This is supply-side. You’re communicating with Pros, not customers. If your experience is primarily consumer acquisition or B2C retention, you’d be switching contexts significantly.
– A product management role. You’ll partner with Product and influence the Pro App roadmap through data and advocacy, but you don’t own it.
– A people management role. This is a senior IC position. Broad scope and cross-functional influence, but no direct reports.
Benefits
– Base salary: $120k-$150k
– Equity: Stock options, Pro supply is one of the most critical levers in the business, and the person who owns how we communicate with that supply is investing in company value directly
– Healthcare: Medical, dental, and vision coverage
– Location: Fully remote (US-based), this role requires deep qualitative work, direct Pro listening, and async cross-functional collaboration; remote works because outputs are measured, not hours
– PTO: Flexible time off policy
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.
To apply: https://weworkremotely.com/remote-jobs/lawnstarter-senior-product-marketing-manager-pro-experience
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