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Salary: USD 80,000 - 120,000 / annual
Sira is a workforce management platform for deskless teams (security, cleaning, field operations), handling scheduling, timesheets, payroll, HR, compliance, and invoicing. The company is YC S25-backed and currently has 4,500 workers clocking in daily. The founder previously worked at Intuit on QuickBooks Time and Payroll.
This is a founding-stage customer success and product role that merges two functions into one. The core thesis: the person taking customer calls and running implementations knows more about what to build than anyone in a roadmap meeting. AI enables one person to own both ends of this loop.
You will own the full customer lifecycle: run implementations end-to-end (kickoff, data migration, configuration, training, go-live) for customers like 300-person security companies migrating off legacy systems like ADP. You'll pick up the phone for operational issues—some training, some real bugs—and triage quickly. You'll work directly with the CTO and engineering, bringing evidence-based product recommendations backed by customer feedback, frequency data, and business impact. You'll build your own leverage using AI tools (Claude, etc.) to automate manual work that would normally require a team.
You should have real energy for both customer interaction and product thinking. You enjoy long calls with operations managers and genuinely like people—not just stakeholder management. You're fluent with AI daily (not just familiar with ChatGPT); ideally you've built things with it. You're technical enough to dig through CSVs, debug payroll imports, write bug reports engineers respect, and ask smart questions about data models—but you don't need to write production code. You want ownership over a queue: if an account is at risk, you fix it; if a process is broken, you rewrite it.
You'll work directly with the founder Nathan and CTO Antonio every day, inheriting a function the founder built rather than one outsourced from the start. You'll see the full arc from early customers to scale and shape the product along the way.
