Tech Automation & Systems Manager — Insurance Agency (Chicago, IL)

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: TYPE OF WORK

Full Time

: SALARY

$9-$11 per hour

: HOURS PER WEEK

40

: DATE UPDATED

Mar 26, 2026

JOB OVERVIEW

**$9–$11/hour | Full-Time 40 hrs/week | Philippines Day Shift | 1099 Contractor**

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**THE COMPANY**

Weer Insurance Group is an independent commercial insurance agency based in Chicago, IL. We serve contractors, trucking companies, restaurants, and businesses across the Chicagoland metro and Wisconsin markets — approximately 4,400 active clients. You will work directly with the CEO, not a manager at an outsourcing firm.

---

**THE SCHEDULE**

Monday–Friday, 8:00 AM – 5:00 PM Philippines Time (PHT / GMT+8)
This is a Philippines DAY SHIFT. You work normal waking hours — no graveyard shift.

Work style: Async-first. You work independently while the CEO sleeps and deliver documented results he reviews each morning. Weekly live video check-in required.

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**IMPORTANT — READ BEFORE APPLYING**

This role requires exactly 40 hours per week tracked via Hubstaff with task-level logging. Hours are non-negotiable. If you are looking for flexible or part-time work, this is not the right fit.

Daily EOD summary required every day — completed work, blockers, and next day's plan with specific counts and dates. "In progress" is not an acceptable status update.

After any system change you made, you are responsible for verifying all connected systems still work before closing the task. Attention to detail is not optional in this role.

---

**OUR TECH STACK — YOU WILL WORK IN THESE SYSTEMS FROM DAY ONE**

Agency Management: EZLynx (AMS), AgencyZoom (CRM + pipeline automation)
Automation: Zapier, Cognito Forms, Webhooks

Email & DNS: Microsoft 365, GoDaddy, SPF/DKIM/DMARC, SendGrid (EZLynx infrastructure), MXToolbox
Social Media: SocialPilot, Canva
Communication: Microsoft Teams, LightSpeed VOIP
Time Tracking: Hubstaff (mandatory)
Document Automation: Adapt (carrier notices + non-payment workflows)
APIs: EZLynx open API (custom integration work)
Other: Tarmika (Commercial Insurnace Rater), Chrome Extension development (queued project)

---

**WHAT YOU WILL OWN**

Your mission: The CEO spends zero time troubleshooting tech issues. Automations run flawlessly. Leads never get lost.

Automation & Systems (40%)
— Build, test, and monitor Zapier workflows connecting EZLynx, AgencyZoom, and Cognito Forms
— Migrate and document automation logic so it can be maintained by others
— Eliminate manual data entry bottlenecks
— Verify all connected systems still function after every change you make

Pipeline & CRM Management (25%)
— Build and activate AgencyZoom pipeline automations for Commercial Lines and Personal Lines
— Manage lead list scrubbing, segmentation, and pipeline loading
— Track lead counts, pipeline movement, and automation errors daily

Email Deliverability & Campaigns (15%)
— Own SPF, DKIM, and DMARC configuration across all agency domains
— Monitor and optimize AgencyZoom email sequences — report open rates on a consistent schedule
— A/B test subject lines; diagnose and fix deliverability failures

Social Media (15%)
— Schedule 2–3 posts per week via SocialPilot (Facebook, LinkedIn, Instagram)
— Create graphics in Canva; maintain content calendar; track engagement monthly

Proactive Problem-Solving (5%)
— Spot inefficiencies and surface them with a proposed solution, not just a problem statement
— Flag blockers the same day they are discovered

---

**REQUIRED EXPERIENCE**

— 3+ years automation/CRM experience — Zapier, Make, or equivalent
— API integration and webhook experience — you can build custom connections, not just pre-built Zaps
— Email deliverability — you understand SPF/DKIM/DMARC and can diagnose why emails land in spam
— DNS management — you know what an A record, CNAME, and TXT record are and how they interact
— Strong written English — your daily summaries and client-facing automations must be professional
— Reliable infrastructure: 10+ Mbps internet, backup connection, UPS power backup

Preferred (not required):
— US insurance agency experience — EZLynx, AgencyZoom, AMS360, or Applied Epic
— Chrome Extension development
— GoHighLevel, HubSpot, or Salesforce automation experience

---

**COMPENSATION**

This is a 1099 independent contractor position. No benefits. Pay via Wise, bi-weekly.

Starting rate based on experience:
— Strong automation, no insurance experience: $9/hour ? $10 after 90 days ? $11 Year 1
— Automation + insurance agency experience: $10/hour ? $11 after 90 days ? $12 Year 1
— Senior expert + API/certifications: $11/hour ? $12 after 90 days ? $13 Year 1

Long-term path: $11–$13/hour Year 2–3 (automation team lead) | $13–$15/hour Year 4–5

Rate increases are tied to consistent 40-hour weeks, on-time deliverables, and measurable output — not tenure alone.

---

**HOW TO APPLY**

Email: ----------
Subject line: Tech Automation – [Your Name] – [Years Experience] – [Primary Platform]

Include all of the following:

1. PORTFOLIO (required)
3–5 automation workflows you have built. For each include: platform used, business problem solved, and measurable results (time saved, leads captured, error reduction).

2. ANSWER THESE 5 QUESTIONS

Q1: You update DNS records to fix an email deliverability issue and the agency website goes down. What happened and what is your step-by-step recovery process?

Q2: An AgencyZoom email sequence has a 3% open rate on Email 1 and 0% on Emails 2–5. Walk through your diagnosis and the first three changes you would make.

Q3: A Zapier workflow routing leads from a web form into a CRM stops firing. What are your first five troubleshooting steps?

Q4: The CEO asks you to automate follow-up for commercial prospects who haven't responded in 30 days. Describe the workflow you would build and how you would test it before activating on live leads.

Q5: Write a social media post for a commercial insurance agency targeting contractors in Illinois. Include post copy and a brief description of the Canva graphic you would pair with it.

3. ONE CASE STUDY (300–500 words)
Problem | Solution | Measurable Results

4. INFRASTRUCTURE CONFIRMATION
Internet speed and backup plan | Power backup (UPS or generator) | Available start date

5. TWO REFERENCES
Automation clients, managers, or direct collaborators

---

**INTERVIEW PROCESS (2–3 weeks)**

Step 1: Application review — portfolio and screening questions evaluated
Step 2: Technical interview (30 min) — live walkthrough of your portfolio
Step 3: Paid test project ($100, 8–10 hours) — real insurance automation scenario
Step 4: Reference check
Step 5: Offer

---

**WHAT MAKES A STRONG CANDIDATE**

— You can explain why an automation works, not just how to click through it
— You test everything connected to what you touched before you close a task
— You surface blockers the same day, not the next morning
— You measure your work in time saved and revenue impact, not features shipped
— You show up for 40 hours every week and your daily summaries prove it

---

Weer Insurance Group | Chicago, Illinois | ----------
Independent Contractor | We value automation expertise over insurance experience

SKILL REQUIREMENT

Marketing Automation Social Media Management DNS Management

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Tech Automation & Systems Manager — Insurance Agency (Chicago, IL)

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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