Attorney / Senior Associate - Trusts and Estates

Estate Planning Attorney Sophisticated HNW Work | High Growth Boutique | Real Origination Opportunity Chicago (Hybrid) Up to $200K Base + Bonus

I’m working closely with a rapidly growing Chicago boutique that is quietly becoming one of the most exciting platforms in the market for attorneys looking to combine high-quality work, strong earning potential, and genuine career progression.

• Sophisticated estate planning work (not basic wills)

• A firm where business development is genuinely rewarded

• A collaborative environment with no internal politics or silos

Why This Firm Stands Out

Serious Growth — Not Just Talk

• The firm has doubled in size and office space in recent years

• Continued expansion across corporate, real estate, and niche sectors

• Strong internal referrals = immediate cross-selling opportunities

Collaborative, “Givers Gain” Culture

• No silos — attorneys actively share work and clients

• Leadership is hands-off but highly supportive

• Hybrid model tailored to individuals (not one-size-fits-all)

A genuinely adult environment where you’re trusted to perform

High-Quality, Sophisticated Client Base

• Work with:

o Family-owned businesses; Entrepreneurs; High-net-worth individuals

• Exposure to complex estate planning strategies and tax-sensitive matters

Notable firm successes include:

• Appellate victory securing $700K+ in damages

• Significant fraud recovery judgments for business clients

Clear Path to Growth & Earnings

• Strong mentorship from recognised attorneys (including “40 Under 40” talent)

• Huge demand in estate planning = significant runway for growth

• 20% origination credit on new business

Described internally as: “shooting fish in a barrel” for building a book

The Role

This is a hands-on estate planning position with real responsibility:

• Draft sophisticated wills and trusts (full lifecycle estate planning)

• Handle high-net-worth client relationships directly

• Work across:

o Gift & estate tax (706 / 709 exposure)

o Probate matters

o Advanced planning strategies

What They’re Looking For

5+ years’ experience in estate planning

Strong drafting experience across wills, trusts, and estate structures

Exposure to gift/estate tax and probate

Compensation

Up to $200K base (DOE)

Bonus + 20% origination credit

Strong long-term earning potential

Interested?

For a confidential no obligation conversation please email your resume to View email address on click.appcast.io