Estate Planning & Probate Associate

Attorney - Estate Planning, Probate & Trust Administration Associate | The Heartland Law Firm | Chicagoland, ILJob Type: Full-Time | In-Office | Hybrid After 6 monthsLicense Required: Active Illinois Bar Admission Who We AreThe Heartland Law Firm is a busy estate planning, probate, trust administration, and elder law practice built around one core belief: that every client deserves to be moved forward with care, precision, and follow-through at every single interaction.We are a team of ten in-office professionals "” and a broader virtual team "” who show up every day to serve families through some of the most significant moments of their lives. We are organized, process-driven, and deeply people-focused. We have built something worth being proud of, and we are looking for someone who wants to be part of building it further.A Note On How We Hire "” And Why We Call This An ApprenticeshipWe want to be direct with you about something, because we think it matters.We do not call this an apprenticeship because we have any doubt about your legal ability. If we hire you, we trust that you can do the legal work. That is not what this stage is about.We call it an apprenticeship because we believe the most important things you will learn here cannot be found in a law school classroom or measured by your bar score. They are:How we serve clients "” with follow-through, warmth, and relentless attention to detailHow our processes work "” and how to execute them with precision across a high volume of active mattersHow our team functions "” the culture, the dynamics, the unspoken standards we hold each other toHow to become more valuable to clients and teammates with every passing monthFrom day one, you will carry real cases. You will speak directly with clients. You will have genuine autonomy and responsibility. This is a full Associate role in every meaningful sense.What makes it an apprenticeship is the orientation "” you arrive ready to learn the how of this place, not just perform the what. You come in with curiosity, humility, and a hunger to grow into the fullest version of what this role can become.We don't call it a probationary period. We don't frame it as entry-level. We call it the Apprentice Stage "” because that's what it actually is, and because we believe the right person will hear that and feel excited, not diminished.If that lands well with you, keep reading.Is This You?The attorney who will thrive here is not necessarily the one with the most credentials or the sharpest legal argument.It's the one who picks up the phoneIt's the one who feels it personally when a task slips, when a client doesn't hear back, when a file stalls. It's the one who walks into a room of ten people and immediately asks "how can I make this team better today?" "” not "how do I stand out?"You lead with your heart as much as your mind. You are energized by process, not burdened by it. You understand that serving people well is a team sport, and you bring energy that lifts the room rather than draining it.If that describes you, we want to meet you.This Role Is NOT The Right Fit If You:Prefer minimal client contact or slow-paced, research-heavy workStruggle to follow detailed processes consistently across a high volume of filesWork best as an independent operator rather than as a contributing team memberLead with ego over empathy in professional relationshipsDefault to email when a phone call would serve the client betterArrive believing the culture needs to adapt to you, rather than the other way aroundWhat Your Days Actually Look LikeProactively contact clients and move their matters forward "” you initiate, you follow up, you close the loopManage a high volume of active files simultaneously with precision and careTrack and complete dozens of tasks per week across multiple concurrent casesDraft estate planning documents "” wills, trusts, powers of attorneyPrepare and file court documents in Illinois probate courtsCommunicate with clients, opposing counsel, and courts with professionalism and warmthLearn and consistently use Clio and our internal practice management systemsContribute actively to team culture "” in attitude, in accountability, and in how you show up every dayParticipate in structured mentorship and grow into increasing independence and responsibilityQualificationsJuris Doctor (JD) requiredActive Illinois Bar License (required or pending admission)0-3 years of legal experience preferredHighly organized with exceptional attention to detailComfortable managing high volume and competing priorities without dropping the ballStrong communicator "” in writing, on the phone, and in personTech-comfortable and willing to learn legal practice management softwareGenuine interest in estate planning, probate, elder law, and family-focused legal workPreferred AttributesYou pick up the phone rather than defaulting to emailYou genuinely welcome feedback and adjust quickly "” not defensivelyYou lose sleep when something falls through the cracksYou are driven by client outcomes, not just task completionYou read team dynamics and actively contribute to a positive cultureYou are excited about being part of building something "” for clients, for the team, and for yourselfWhat We OfferA true mentorship relationship with experienced attorneys "” not just supervisionReal client-facing responsibility and autonomy from the startA defined growth path with salary review and advancement within the first yearA collaborative in-office culture where your contribution is seen, valued, and recognizedA team that genuinely cares about the work and about each otherBroad exposure across probate, trust administration, estate planning, and elder lawWork EnvironmentThis is a full-time, in-office position. In-person presence is essential "” not just for learning, but because our culture and our clients depend on it. Hybrid arrangements may be considered after an established tenure for the right candidate.Schedule: Monday-FridayHow to ApplyPlease submit the following to HelpDesk@ResumeCover letter addressing two things:Describe the legal career you are trying to build and what specifically about this posting resonates with that visionTell us about a time you managed multiple competing priorities under pressure "” and how you made sure nothing fell through the cracksApplications without a cover letter will not be considered. We read every one.

Created: 2026-05-09