Legal Jobs in Chicago, IL (Now Hiring) — 953 open — Page 7

About Us

Legora is redefining how legal work gets done. Not built for lawyers, built with them. We work alongside the world’s best legal teams, who expect excellence, precision, and speed, and we hold ourselves to the same bar.

Our AI-native workspace lets legal professionals move faster, think more clearly, and operate with sharper precision. By analysing thousands of documents in minutes and powering end-to-end workflows, we cut through complexity, teams can focus on what matters: judgment, strategy, and outcomes.

1,000+ customers across 50+ countries trust us, including Cleary Gottlieb, Goodwin, Linklaters, White & Case, Dentons, and Barclays. We’ve scaled to $100M+ in ARR, with teams across Europe, North America and APAC, and continue to expand through acquisitions including Qura, Walter AI and Graceview.

We partner with world-class performers: including Aaron Judge and the New York Yankees, Ludvig Åberg (and his caddie), and campaigns featuring Jude Law.

Joining Legora means three things.

• We lean in: ownership over titles, outcomes over intentions.

• We fight for excellence: high standards, direct, ego-free feedback.

• We grow together: as a team and with our customers.

Mission before ego. Everyone contributes. No one coasts.

If you’re driven by impact, pace, and raising the bar. This is the place.

About the Role

The way legal work gets done is changing, and Engagement is at the center of that transformation. We're looking for an experienced, strategic Engagement Director to build and lead a multi-layered team within our growing Engagement org that helps the world's top law firms and corporations fundamentally change the way they work with Legora.

This is a role for someone who has led change inside large, complex organizations and built and scaled the teams — and the leaders — that deliver it, and knows that real transformation is designed and managed. You will own the adoption and long-term success of an entire vertical (e.g., Enterprise Firms, East or Mid-Market Corps, West) — leading a team of Engagement Associates, Managers, and Senior Managers who build the relationships and define the outcomes, while you reserve yourself for the most strategic accounts and C-suite relationships as the senior strategic advisor who ensures Legora becomes an embedded part of how legal teams operate.

At the heart of the role is defining the engagement model for your vertical and building the frameworks and standards your team uses to design each client's adoption playbook and deliver multi-year change-management programs that transform how they work. Across the portfolios in your vertical you'll set the bar for how a tailored roadmap is built, how initiatives are sequenced from initial rollout through firm-wide scaled adoption, how measurable outcomes and ROI are defined, and how the program evolves as new AI capabilities and use cases emerge.

You will be critical as we continue to build a best-in-class adoption program at Legora, partnering with Leadership to scale the teams, leaders, and standards that help clients realize measurable ROI, expand successful use cases and transform the way their teams work.

What You’ll Do

You'll lead the post-sale customer experience for a vertical (e.g., Enterprise Firms, East or Enterprise Corporates, East) — owning onboarding, adoption and long-term value realization across every account in it, through the teams and leaders you build. Specifically, you will:

• Define the engagement model for your vertical, setting the standard for how your team designs each client's adoption playbook: the tailored change-management approach, stakeholder map and target outcomes for how that customer adopts Legora and transforms the way they work.

• Build the operating rhythms — portfolio and pipeline reviews, health inspection, coaching cadences — that keep the team executing against those playbooks at scale, sequencing initiatives from initial rollout to firm-wide scaled adoption and adapting as clients' needs and Legora's capabilities evolve.

• Coach the team — including other people managers — to act as strategic advisors who deeply understand client goals and legal workflows, reserving yourself for the most strategic accounts and C-suite relationships, to engage executive sponsors, surface high-impact opportunities, and guide clients toward maximum value from Legora.

• Set the standard for how the team drives sustained value through a structured operating cadence: success plans, enablement, stakeholder check-ins, training and value reviews — turning what works across portfolios into repeatable, scalable motions the whole vertical adopts.

• Partner with Leadership and orchestrate engagement from cross-functional teams across your vertical to accelerate client success (GTM, Product, Legal Engineering, Engineering, Marketing, Support), maintaining end-to-end context across your portfolio and shaping how Legora delivers value.

• Partner with GTM leadership on key commercial moments across the vertical to ensure seamless handoffs, continuity, and a great customer experience, and to identify and realize expansion opportunities — coaching the team to lead these conversations and stepping in on the most complex or strategic renewals and expansions.

• Translate vertical-level feedback into action by collaborating closely with Leadership, Product, Engineering, and Marketing to shape roadmap, positioning, and enablement.

What You Bring

You care deeply about customer outcomes and you know that transformation has to be designed and led — and that scaling it across a vertical takes a high-performing team and the leaders to run it. You're proactive, strategic and comfortable steering demanding, senior stakeholders and executive sponsors through significant change. You take pride in being the reason customers — and the teams behind them — adopt, grow and succeed.

We're looking for:

• A consulting or transformation background, with a demonstrated track record of designing and delivering change-management programs inside large, complex organizations — and building and leading the teams — and leaders — that deliver them at scale.

• Experience building the standards and operating rhythms that scale tailored, client-level transformation roadmaps and adoption plans across a vertical and steering them to measurable outcomes.

• 10+ years in management consulting, customer success, account management, or a related field, with 5+ years managing client-facing teams — including other managers and team leads — ideally with exposure to high-growth B2B SaaS or Legal Tech.

• A track record of owning adoption, retention, and satisfaction across a vertical of enterprise clients and senior stakeholders — and of developing the people and leaders who deliver those outcomes.

• Experience working with legal, compliance, or other regulated and complex industries or the ability to learn a complex domain exceptionally fast.

• Strong operational discipline; you build inspection frameworks and run tight rhythms that keep multi-workstream initiatives moving across multiple teams and your clients confident.

• Excellent communication skills and strong executive presence — written, verbal, and interpersonal. You are trusted in the boardroom with C-suite and legal leaders, coach your team and leaders through them, and roll up your sleeves with hands-on teams.

• High EQ: you know when to listen, when to advise, when to coach and when to act — and when to step in versus let your team and leaders lead.

• A love of fast-paced, early-stage environments where you build the playbook, the team and the function, not just build for yourself.

• Deep data fluency; you read portfolio metrics and account health with rigor and use them to drive decisions across the vertical.

What's In It For You

• Global collaboration: Partner with teams and clients domestic and internationally.

• Competitive package: Comprehensive salary, benefits, and tools for success.

• Meaningful work: Your efforts shape how thousands of lawyers use AI daily.

• In-person environment: West Loop office designed for ambitious builders and company provided lunch daily.

• Benefits & Perks: We invest in our people with a comprehensive, thoughtfully designed benefits package:
  Medical, Dental & Vision

  • Multiple medical plan options through Aetna and Kaiser Permanente

  • HSA or Healthcare FSA (based on plan selection)

  • Dental plans via MetLife

  • Vision plans via Vision Care

  Family Support

  • Generous parental leave

  • Free access to Maven Clinic

  • Dependent Care FSA

  • Free One Medical membership for employees and dependents

  Additional Perks

  • Pre-tax commuter benefits

  • Life Insurance + STD/LTD

  • 401(K) with generous company match

  • Unlimited PTO

  • Robust voluntary benefits, including identity protection (via Aura), legal coverage via MetLife, pet savings programs, and more

Legora is an Equal Opportunity Employer

At Legora, we believe great teams are built on diversity of thought and experience. We’re proud to be an equal opportunity employer and committed to creating an inclusive, high-performance culture where everyone can do their best work. We welcome people of all backgrounds and don’t discriminate based on race, color, religion, national origin, gender, gender identity or expression, sexual orientation, age, disability, veteran status, or any other characteristic protected by law.