About the role
What we're looking for:
We need someone with 1-5 years of experience in customer success or onboarding who is AI-native, scrappy, and passionate about helping customers succeed. You should be comfortable picking up the phone, running screen shares, and solving problems on the fly for deskless teams (security guards, cleaning crews, field service). Bonus points if you've worked at a payroll, HR, or scheduling software company like Paycom, Gusto, or ADP.
What you'll do:
- Own the full customer onboarding lifecycle — run kickoff calls, coordinate data migration with our offshore team, and guide customers through go-live over 3-week implementation cycles
- Be the voice customers count on — answer inbound calls from admins and employees, resolve issues quickly, and ensure no one is left waiting
- Run 4-5 scheduled onboarding and support calls per day, plus handle 7-8 ad hoc inbound calls from employees needing help
- Use Claude and AI tools to solve customer problems fast — reformatting documents, updating spreadsheets, generating reports, and unblocking workflows
- Work directly with the founders and CTO to escalate technical issues and provide product feedback based on what you hear from customers daily
- Write short help articles and setup guides that save the next customer the same question
About Sira
Sira is the all-in-one workforce management platform for deskless teams. Security guard companies, commercial cleaning crews, and field service businesses run their scheduling, timesheets, payroll, HR, and compliance on Sira. We're a Y Combinator (S25) company in San Francisco, growing fast because our customers love the product.
Founded by the former leader of Intuit's $1.2 billion QuickBooks time tracking and payroll app — a product that paid one out of every 10 employees in the US — Sira was born from the belief that AI could fundamentally transform how hourly workforce management works. When the opportunity to rebuild from scratch presented itself, the founders quit their jobs and started building about a year and a half ago.
Sira automates time tracking, scheduling, and payroll for companies with 50 to 1,000 employees using intelligent agents. The mission is to cut admin work, stay compliant, and boost team productivity 24/7 — while maintaining a human-first philosophy where real people pick up the phone when customers need help.
The culture is scrappy, fast-moving, and founder-led. Every team member works closely with the founders, and customer conversations directly shape what gets built next. Sira values hunger, passion for the customer, and a willingness to use modern AI tools to solve problems creatively.
Required skills
Other roles at Sira
Job details
Salary
$95,000 - $135,000
Location
San Francisco, United States
Experience
1+ years
Funding
Total raised
$3.4M
Last stage
Seed
Investors
What happens next.
No applications, no recruiter spam. Just the intro.
Confirm the fit
A few questions to make sure this role is the right shape for you. Two minutes.
I pitch you to the company
I write the intro, send it to the founder, and handle the back-and-forth.
A meeting lands on your calendar
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.