About the role

You'll be the second operator at Paragon. Your hiring manager and partner is our Head of Strategy & Operations, who's spent four years building this function from scratch and wants a partner to extend it. You'll have line-of-sight into every function of the company: people, legal, finance, compliance, recruiting, vendors, IT, and more. Within twelve months, you'll know how Paragon operationally runs better than almost anyone here.

It's a real operator role. Half of it is queue work: payroll, onboarding, benefits questions, vendor renewals, expense triage. You'll find satisfaction in systems that run smoothly and details done right.

The other half is building. Paragon is AI-native by default - we already have a working bench of internal automations, and you'll extend it. You'll build automations alongside doing the work, with the Head of Ops as a design partner.

What you'll own

You'll be close to the actual operating system of the company. The work is detailed, cross-functional, and very visible when it goes wrong. The goal is to keep the basics running cleanly while steadily making the system better.

Employee operations

• Run the details behind onboarding, offboarding, access, benefits questions, leave logistics, and employee changes

• Keep payroll, benefits, and people data accurate

• Turn repeated questions into docs, checklists, and lightweight self-serve resources

Compliance operations

• Keep the weekly compliance work moving: platform issues, security requests, evidence collection, access reviews, and follow-ups

• Translate audit asks into practical next steps for Engineering, Ops, and other owners

• Keep enough context documented that someone else can understand what happened without digging through five systems

Vendors, contracts, and tools

• Keep renewals, signing workflows, vendor accounts, and contract next steps organized

• Route agreements through the right review, approval, and signature path

• Catch the small problems early: stale seats, unclear owners, bad vendor answers, upcoming renewals, and spend that needs a decision

Recruiting support

• Keep scheduling, ATS hygiene, debriefs, and candidate communication moving

• Help hiring managers run a tight process

• Once ramped, help with first-round screens, outbounding, and candidate follow-through where it makes sense

Finance ops

• Help keep expenses, reimbursements, invoices, cards, and spend review clean

• Work the queues and leave a clear trail behind decisions

• Make recurring finance work easy to inspect instead of dependent on memory

Office + leadership rhythm

• Own the basic LA office logistics: visitors, parking, mail, packages, supplies, and light facilities needs

• Support All Hands, leadership meetings, monthly reporting, planning cycles, OKR follow-ups, and cross-functional action items

• Make loose ends visible so important commitments do not disappear

Automations and agents

• Notice the repeatable work while you are doing it

• Help turn the right candidates into agents, scripts, automations, or better workflows

• Keep judgment manual where it matters, and automate the parts that are repetitive, brittle, or easy to miss

A day in the life

8:45-9:15 — Check the queues

• Scan Slack, email, HR tickets, recruiting coordination, vendor messages, access requests, expenses, and signing workflows

• Separate what is actually urgent from what can be batched

• Flag anything the Head of Operations needs to know early

9:15-10:15 — Clear blockers

• Answer time-sensitive employee questions

• Move onboarding, access, benefits, leave, or offboarding items forward

• Confirm candidate scheduling, debrief logistics, or ATS follow-ups

10:15-11:30 — Work the recurring ops checklist

• Push forward whatever is live that week: payroll, benefits, compliance, vendors, recruiting, finance, or office

• Follow up with owners when something is stuck or unclear

• Update the tracker, ticket, checklist, or source-of-truth doc as you go

11:30-12:00 — Vendor / contract / finance queue

• Check signing workflows, renewals, vendor admin asks, invoices, reimbursements, and card issues

• Route anything that needs legal, finance, or Head of Operations approval

• Leave notes that make the current state obvious

12:00-1:00 — Lunch / office reset

• Handle small office items if needed: visitors, packages, mail, supplies, parking, or facilities details

• Reset before the afternoon block

1:00-2:00 — Clean up one system

• Update an SOP, improve a checklist, reconcile a messy queue, prep an access review, clean up expense memos, or organize a renewal calendar

• Look for the repeatable pattern: what should be documented, templated, automated, or delegated next time?

2:00-2:30 — Sync or async update

• Review priorities, escalations, approvals, and judgment calls with the Head of Operations

• Share what changed, what is blocked, and what you recommend

• Decide where the next focused block should go

2:30-3:45 — Build or improve an automation

• Turn a recurring workflow into a first draft of an agent, script, automation, or structured process

• Test it against the real workflow it is meant to improve

• Document when to use it and where human review is still required

3:45-4:30 — Close loops

• Respond to open employee, candidate, vendor, HR, finance, or engineering threads

• Move tickets and trackers to their real current state

• Make sure no one is waiting because the next step is unclear

4:30-5:00 — Leave tomorrow cleaner

• Send a short end-of-day or end-of-week update when useful

• Capture tomorrow's follow-ups

• Leave the queues cleaner than you found them

Weekly / biweekly rhythms

• Compliance digest and expense queue review

• Payroll and 401(k) review cycles

• Vendor renewal and signing queue review

• Recruiting coordination and debrief support when roles are active

• 1:1s with the Head of Operations to review priorities, escalations, and automation opportunities

The best version of this role is not someone who merely keeps up with the work. It is someone who turns messy recurring operations into cleaner systems.

You're a strong fit if you

• Have 1-3 years of operations / HR coordinator / EA / BizOps experience at a startup

• Have hands-on PEO or EOR experience (Deel, Rippling, Justworks, or similar)

• Have touched at least one compliance platform (Secureframe, Vanta, Drata, or similar)

• Are a daily Claude / ChatGPT / Cursor user; have shipped at least one automation (Zapier, n8n, Make, Apps Script, custom script - any tool, any complexity)

• Have written at least one SOP, runbook, or process doc that someone else used

• Are fluent with the standard SaaS ops stack (HRIS, ATS, expense cards, MDM, e-signature, knowledge tools); willing to learn whatever's in front of you

• Default to documenting and systematizing rather than memorizing

• Have judgment about what to escalate vs. handle

• Write clearly and patiently in vendor and employee threads

• Operate well without close supervision

Bonus

• Built or contributed to internal tools / agents at a previous job

• Familiarity with Claude Code, Cursor, n8n, Make, Retool

• State leave law knowledge (CA PFL, WA PFML, NY PFL)

• Experience scaling onboarding through 50 to 100 employees

• SOC 2 / ISO 27001 / HIPAA evidence-gathering experience

• Budget tracking or light variance analysis experience

Compensation Range: $70K - $85K