Sira

AI Native Rippling for Deskless Workers

We think customer success and product are becoming the same job.

The person who hears the customer, who takes the call when a scheduler can't get a guard clocked in, who sits with an operations manager during go-live, that person knows more about what we should build than anyone in a roadmap meeting. AI makes it possible for one person to hold both ends of that loop. So we're hiring for it as one role.

About Sira

Sira is workforce management for deskless teams. Scheduling, timesheets, payroll, HR, compliance, and invoicing in one place. Our customers are security guard companies and commercial cleaning businesses running 50 to 300+ people in the field, and most of them are coming off a mess of ADP, Connecteam, spreadsheets, and paper.

We're YC S25, based in SF. Today 4,500 workers clock in on Sira. I was at Intuit before this working on QuickBooks Time and Payroll, so I know exactly how painful this software usually is. We're building the version that isn't.

Why this role exists

I've taken every customer call myself since day one. Every implementation, every go-live, every 7am "the app won't let my guard clock in" call. It's the reason the product is good. It's also the reason I can't keep doing it alone.

We're adding customers faster than I can personally onboard them. So I'm hiring the person who takes this over and does it better than I did, with AI doing the work that used to take a team.

What you'll do

• Get deployed into our customers. Run implementations end to end: kickoff, data migration, configuration, training, go-live. A 300 guard company with 24 sites moving off ADP is a normal project here.
• Pick up the phone. Schedulers, dispatchers, and guards call when something isn't working. Some of it is training, some of it is a real bug, and you'll know the difference fast.
• Work directly with our CTO and engineering on what we build next. You'll bring the evidence, not opinions. What you heard, from who, how often, and what it's costing them.
• Build your own leverage with AI. You should already be living in Claude or something like it. Writing your own prompts, spinning up your own tools, automating the parts of your job that shouldn't be manual. We want someone who runs a function that would normally take four people.

Who you are

You have real energy. You like a day that starts with a customer escalation and ends with a product spec. You move fast and you follow through.

You actually like people. Not "good with stakeholders." You enjoy a 45 minute call with a 60 year old operations manager who has run his security company on paper for 20 years. That call is the job, and the best version of this hire is genuinely excited for it.

You're fluent with AI. Not "familiar with ChatGPT." You use it daily and you've built things with it. Tell us what you've built.

You're technical enough to be dangerous. You can dig through a CSV, figure out why a payroll import broke, write a bug report an engineer respects, and ask a smart question about the data model. You don't need to write production code.

You want ownership more than a queue. If an account is at risk, you go fix it. If a process is broken, you rewrite it.

What you get

You're inheriting a function the founder built, not one that was outsourced from the start. Direct work with me and our CTO Antonio every day. Real ownership from week one. You'll see the full arc of a company going from early customers to real scale, and you'll have shaped the product by the end of it.

1. Intro call with Nathan (founder), 30 minutes
We'll talk about your background, what we're building, and what you've been using AI to do lately. Come with questions.

2. Paid working session, half day
A real slice of the job. You'll get an actual customer scenario, a messy data export, and a set of support transcripts. Build the implementation plan, flag what's broken, and write the product recommendation you'd bring to our CTO. Use whatever AI tools you want. We'd be surprised if you didn't.

Then we'll do two things live: you present it back to me, and we run a mock customer call where I play a frustrated operations manager at a 200 guard company and you take the call. We pay for your time either way.

3. Dinner with Nathan and Antonio
The last step is dinner, not an interview. We'll talk about how you'd work with engineering, how you'd build this function from scratch, and what you want out of the next few years. You should be deciding on us as much as we're deciding on you. Reference checks run in parallel.

Three steps, and we move fast. Expect a decision within 10 days of your first call, and you'll hear from us after every stage either way, including a no.