StartPlaying

StartPlaying is the marketplace that turns passionate Game Masters (GM) into professional storytellers. We connect players looking for tabletop RPG sessions with GMs who run them, whether that's Dungeons & Dragons, Call of Cthulhu, or hundreds of other systems.

Tabletop roleplaying games aren't a niche hobby anymore. Millions of people play every week, and a growing number of GMs are turning their skill at running games into real income. We built the platform that makes that possible: booking, payments, scheduling, and discovery, all in one place.

Since 2020, GMs on StartPlaying have earned more than $75 million doing it. Our team is built of those passionate about building community, gaming, and creators. One of our founders was even among the first Pro Dungeon Masters.

About the Role

You'll own all email marketing for StartPlaying, across both our player and Game Master user bases. That covers lifecycle email (onboarding new users, activating signups who haven't booked or listed, winning back lapsed users) and marketing campaigns (convention promos, partner activations, event pushes, seasonal campaigns) and transactional emails.

You'll edit existing pipelines, write, scope, build, and test end-to-end: strategy, copy, segmentation, and performance tracking. You'll also pick up occasional landing page copy for campaigns and recruitment pages.

This is a role for someone who wants to set the point of view on how a modern lifecycle program should run, then go build it. We're looking for someone who will define what best practice looks like here rather than inherit it from a previous playbook.

The scope here is bigger than the hours by design. We expect you to come in, assess what will move retention and lifetime value fastest, and tell us what the priorities should be. Budgeting your own time against the contracted hours and sequencing the work accordingly is part of the job.

Structure: Part-time contract, roughly 80 hours per month (about 18 to 20 hours per week). Fully remote.

What You'll Own

• Lifecycle flows for players and GMs: onboarding, activation, reactivation, and everything in between
• Marketing and campaign emails for events, conventions, and partner activations
• Channel strategy and end-to-end campaign execution, including building, QA, launch, measurement, and optimization
• Ongoing testing and optimization across subject lines, send timing, and segmentation
• Light landing page copywriting as needed for campaigns and recruitment

Requirements

• 4+ years driving toward growth goals under set targets and timelines in a lifecycle or CRM role
• Hands-on http://Customer.io experience
• B2C experience
• Robust experience working with customer and user event data, and marrying it to well-designed, targeted campaigns
• Understanding of hypothesis-driven A/B, MVT, and holdout testing, with the ability to analyze results and pull out learnings that inform future tests
• Strong instincts for direct response creative, and a framework for adjusting based on experimentation
• Strategic thinker able to break down and organize problems, assess opportunity areas, and develop big ideas and priorities to move the business forward
• Comfortable working across two distinct user personas with different motivations
• Able to juggle always-on lifecycle flows alongside one-off event and campaign sends
• Strong writing, editing, and communication skills
• Highly organized and self-motivated, with a track record of scoping and prioritizing your own work against a fixed number of hours

Nice to Have

• Strong domain understanding of D&D and TTRPGs
• Experience standing up a lifecycle program from scratch rather than maintaining an existing one
• Marketplace or two-sided platform experience

What It's Like to Work Here

We're a small, mostly remote team of nerds, builders, and play enthusiasts. We optimize for thoughtful output and real impact.

You'll be part of a culture where:

• Everyone has a seat at the table, and your ideas can shape the company.
• We make data-driven decisions based on analytics and user needs.
• We strive to create the best solutions possible by embracing great ideas and encouraging one another along the way.
• We don't take ourselves too seriously and believe that happy employees do their best work.
• We love building cool shit and are passionate about delighting our users.
• We tackle challenging problems when necessary and celebrate innovative ideas to avoid them entirely.
• We cultivate an environment that encourages and enables people to learn, take on new challenges, and consistently own more impactful projects.

Our Values

• Growth Mindset: We're always evolving, learning, and improving.
• Collaboration: Great ideas come from shared perspectives.
• Passion: We are deeply committed to our mission and our craft.
• Relentless Resourcefulness: We are undaunted by problems and relentlessly work to find solutions to them.

StartPlaying is a safe space, and we value diversity. We are an equal opportunity employer: we do not discriminate based on race, religion, color, national origin, sex, sexual orientation, age, marital status, veteran status, or disability status. We think this should be a given, but are explicitly stating it anyway.