I’m helping Windy City HVAC Repair find a top candidate to join their team full-time for the role of Chief of Staff .
You’ll build and scale two companies, driving their future as Chief of Staff.
Compensation : USD 10 - 12 / hour
- Bonuses (up to 20% of base compensation)
Location :
Remote (specific timezones)
Mission of Windy City HVAC Repair
"At Windy City HVAC Repair, our mission is to restore trust and quality in Chicago’s heating and air conditioning services. We are committed to delivering transparent, skillful, and dependable solutions that keep your home comfortable year-round."
What makes you a strong candidate
You are an expert in Team building, Operations management.You are proficient in Training, Scheduling, Meeting management, Interviewing, Hiring.English - Fully fluentResponsibilities and more
Chief of Staff to the CEO – HVAC & Property Management
Pay : $10.00-$12.00 per hour + Bonuses | Full-time | Remote
We're scaling two fast-growing companies – HVAC and property management – and need an ultra-high performer who thinks three steps ahead and executes without being asked.
Here's the reality : You'll jump between both companies daily. One minute you're scheduling HVAC jobs, the next you're hiring for property management, then pivoting to execute a marketing campaign. You need to move fast, switch contexts seamlessly, and deliver exceptional quality on everything you touch.
This is for someone relentless – who wants to grow alongside a founder building multiple businesses over the next decade.
What You’ll Actually Do
Multi-Company Operations (You'll Work Across Both Businesses)Jump into whichever company needs you most – HVAC operations one day, property management growth the next (communicate and coordinate with a staff of 20+ team members)Short-term priority : Run day-to-day operations and scheduling for the HVAC business until we hire a dedicated AdminHandle whatever special projects or urgent needs arise – extreme flexibility requiredHiring & Team Building
Own the hiring process for both companies – sourcing, screening, interviewing, and onboardingConduct interviews confidently and assess talent effectivelyBuild and scale teams as we growStrategic Execution
Own and execute our marketing roadmap (email campaigns, newsletters, LinkedIn / email outreach)(not a deal breaker)Build and optimize systems in Zapier, Notion, Aptly, Jobber, ServiceTitanTake delegated projects and drive them to completion independentlyOperations & Marketing
Tame the chaos : inbox management, calendar optimization, document flowRun meetings, set agendas, drive accountabilityDesign high-quality content in Canva for social media and campaigns (not a deal breaker)Create SOPs and training materials (Loom, Notion, ChatGPT)You're the One If You :
Must-Haves (Non-Negotiable)
5+ years as a Director of Ops / Ops leader or EA supporting founders or executivesNative or near-native English fluency (written and verbal) – you communicate with precision and clarityProactive by nature – you don't wait to be told what to doMarketing background (basics) – you know Canva, email marketing, and social media inside-outProven hiring experience – comfortable interviewing and selecting candidatesTimezone compatibility – within 4 hours of CSTFast-paced operator with ability to pivot instantly – you adapt on the fly without missing a beatThe Intangibles We're Looking For
Extreme detail orientation – your work is consistently high-quality and polishedTrusted executor – when something's handed to you, it gets done right without supervisionWilling to do whatever the job calls for – some days it's strategy, some days it's HVAC schedulingLoyalty and commitment – you're looking for a long-term home, not a stepping stoneExtreme ownership – when something needs doing, you make it happenResourcefulness – you figure it out, even when you don't know how yetWhy This Opportunity?
Career trajectory, not just a job – grow into COO, Operations Manager, Marketing Director, or whatever you're capable ofTrue ownership – you'll have real impact across two growing companiesFully remote with semi-flexible hours (outcomes >hours logged)
Generous PTO + paid holidays + annual team trip#J-18808-Ljbffr
