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Remote People Insight Jobs in Chicago, IL (NOW HIRING)

GTM Strategy & Operations Manager

Chicago, IL · On-site +1

$132K - $206K/yr

Over 1.5 million customers and more than a billion people in over 180 countries use Docusign ... You will be responsible for helping to build supporting analysis and insights that define our GTM ...

Translate complex analytical outputs into clear, practical insights for agronomy, field, and ... Familiarity with precision agriculture data sources (e.g., remote sensing, IoT sensors, field ...

Senior Associate, Tax Compliance & Reporting

Chicago, IL · On-site +1

$84K - $104K/yr

... insights, and consulting company; we shape the brands of tomorrow by better understanding people ... United States - EST or CST (Remote) We are looking for an experienced tax senior to assist our ...

Over 1.5 million customers and more than a billion people in over 180 countries use Docusign ... Provide the C-suite and GTM leadership with deep, actionable insights regarding key drivers of ...

Paid Search Strategist (REMOTE)

Chicago, IL · Remote

$84K - $97K/yr

About Blue Wheel Blue Wheel is a digital performance marketing agency that helps brands connect the people, platforms, and insights that drive growth across modern commerce. With more than 100 team ...

Paid Search Strategist (REMOTE)

Chicago, IL · Remote

$83K - $96K/yr

About Blue Wheel Blue Wheel is a digital performance marketing agency that helps brands connect the people, platforms, and insights that drive growth across modern commerce. With more than 100 team ...

Paid Search Strategist (REMOTE)

Chicago, IL · On-site +1

$84K - $97K/yr

About Blue Wheel Blue Wheel is a digital performance marketing agency that helps brands connect the people, platforms, and insights that drive growth across modern commerce. With more than 100 team ...

Senior Manager, Brand

Chicago, IL · On-site +1

$125K - $140K/yr

But toasty sandwiches are only as good as the people behind them. And yeah, we've got the best ... Key responsibilities include building and stewarding an insights-led annual marketing calendar ...

Senior Manager, Brand

Chicago, IL · Remote

$125K - $140K/yr

But toasty sandwiches are only as good as the people behind them. And yeah, we've got the best ... Key responsibilities include building and stewarding an insights-led annual marketing calendar ...

Showing results 41-60

Remote People Insight information

What are the most commonly searched types of People Insight jobs in Chicago, IL? The most popular types of People Insight jobs in Chicago, IL are:
Infographic showing various Remote People Insight job openings in Chicago, IL as of August 2026, with employment types broken down into 77% Full Time, 20% Part Time, and 3% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution.

Trust & Estate Tax Senior Manager/Director

Levelociti

Chicago, IL • Remote

$170K - $260K/yr

Full-time

Retirement, PTO

Re-posted 26 days ago


Job description


Position: Fully Remote Senior Tax Manager / Tax Director - Gift, Estate, Trust

Location: Remote (U.S.-based)

Compensation: Competitive salary ($170k–$260k+)

Bonuses: Generous annual performance bonuses

Benefits Include:

  • 401(k) with 5% match
  • Unlimited PTO + Summer Fridays off
  • Reduced busy season hours (average 50–55 per week)

About Us:

We're a progressive, nationwide firm headquartered in Chicago with offices across the country. Our focus is on delivering top-tier tax services while maintaining a people-first, remote-forward culture. We offer strong compensation packages, equity opportunities, and a real commitment to work-life balance.

Role Overview:

In this leadership role, you’ll manage a diverse client portfolio, guide a team of tax professionals, and take ownership of tax planning and compliance projects across various industries focusing on HNW,. Gift, Estate, Trust, including real estate, tech, construction, professional services, and more. You’ll collaborate closely with clients and senior leadership to deliver strategic insights and value.

Core Responsibilities:

  • Manage and deliver timely, high-quality tax services to a range of clients
  • Lead and mentor a team of tax professionals
  • Review complex tax filings, Gift, Estate, Trust, S Corps, C Corps, Partnerships, Individuals.
  • Develop and implement strategic tax planning initiatives
  • Keep up with tax law updates and apply them effectively
  • Foster strong client relationships and contribute to firm-wide strategy

Qualifications:

  • Bachelor’s in Accounting, Finance, or related field (CPA preferred)
  • 5+ years of tax experience, with at least 2 years in a leadership role
  • Strong technical expertise across entity types and individual taxation
  • Excellent leadership and communication skills
  • Able to manage multiple priorities in a remote, fast-paced environment

Why Join Us?

  • Highly competitive pay and bonus structure
  • Emphasis on flexible work schedule, 100% Remote
  • Open PTO Policy and summer schedule perks
  • Supportive, collaborative team culture

If you're a high-performing tax professional looking for a new challenge with real growth potential, we’d love to connect.


Send me your resume today for immediate consideration!