Chicago - Career Development Advisor

Winston Taylor LLP; Chicago (IL); On-site; USD 145,000 - 190,000; Full time

Benefits offered by this job

Comprehensive benefits

Job summary

Winston Taylor LLP seeks a Career Development Advisor to support mid-level and senior attorneys in litigation, focusing on lateral associates and retention across the firm.

The CDA reports to the Director of Attorney Development & Advancement and works with department chairs, practice leaders, and HR to implement talent strategies and development initiatives while driving partnerships and career transitions.

Qualifications

• Bachelor’s degree and J.D. required.
• 5+ years of legal practice in a large firm preferred, litigation experience helpful.
• Ability and willingness to travel as needed.

Responsibilities

• Advise mid-level and senior associates in Litigation on career development.
• Collaborate on lateral associate career initiatives with Recruiting and Practice Operations.
• Develop and lead programs to support associate growth and progression to partnership.

Skills

Travel willingness

Client service

Communication skills

Project management

Relationship building

Education

Bachelor’s degree

J.D.

Tools

Microsoft Office

Job description

About Us

At Winston Taylor, we set the standard, together. Winston Taylor is a transatlantic law firm built for the businesses, people, and markets driving capital and innovation. Here, you're in the room. In the action. Sleeves rolled up. You'll work with leading clients. Disruptors. Fast-growth companies. And help them to stay one step ahead of the moment and make critical decisions that shape their future. We're present in the U.S., U.K., Europe, Latin America, and the Middle East, combining the scale and speed that clients demand. You'll be trusted with real responsibility from the outset and build experience through hands‑on work. We take your progression personally. We provide the platform. You shape the work around your goals and aspirations. Step into the moments that matter. Join Winston Taylor.

Position Summary

The Career Development Advisor (“CDA”) is a broad-based position operating at the centre of Winston’s personalised and holistic approach to attorney talent development. The CDA is primarily responsible for helping mid‑level and senior attorneys in the Litigation Department to develop and thrive in successful careers, with an expanded focus on lateral associates and retention across the firm. Reporting to the Director of Attorney Development & Advancement, the position works with leaders and professionals across the firm including Department Co‑Chairs, Practice Group Leaders, the Practice Operations teams, and other members of the Talent team, Opportunity & Inclusion team, and Business Development team. The CDA champions Winston’s culture and supports execution of the firm’s Talent strategy by ensuring mid‑level and senior attorneys and lateral associates have the knowledge, skills, and support to perform their roles successfully and advance along their chosen career paths.

Position Responsibilities

• Advisor to mid‑level and senior associates in the Litigation Department. Regularly meets with mid‑level and senior litigation associates as a trusted advisor on their career development.
• Works closely with the Director of Attorney Development & Advancement on lateral associate career development initiatives across the firm (both transactions and litigation) including partnering with Attorney Recruiting and Integration team and Practice Operations team to support lateral associate success.
• Supports high‑potential talent identification and related initiatives, expanding beyond general career development to proactively identify, track, and advocate for attorneys demonstrating exceptional potential for leadership and client development.
• Develop programmes and initiatives that support associate career growth and development at the mid and senior levels. Leads the existing Litigation Senior Preview programme, where sixth‑year associates meet with their Practice Group Leaders for a wide‑ranging discussion about career goals and development.
• Supports the firm’s Path to Partner programme by working closely with relevant stakeholders to provide support, guidance, and programming, for associates on the partnership track. Helps potential candidates for partnership understand the firm’s business needs and build a strong business case for partnership.
• Supports and develops initiatives related to attorney career transitions for mid‑level and senior associates, including: (a) partnering with the firm’s alumni programme to offer programming related to in‑house career opportunities; and (b) developing resources and events that provide support for those considering non‑partnership career paths.
• Works closely with the Director of Practice Operations, Practice Operations managers, Assignment partners, and Practice Group Leaders on cultivating the talent pipeline and staffing to meet client needs and with an eye toward department utilisation objectives, experience, and individual attorney development goals.
• Assists mid‑level and senior attorneys in tracking their professional development and legal skills in relation to the Winston Development Framework and Litigation practice group milestones and benchmarks.
• Works with the Director of Attorney Development & Advancement to support mid‑level and senior associates in achieving developmental goals and experience in areas for focus as identified in the annual evaluation process and assists in translating feedback into actionable goals.
• Collaborates with HR, Attorney Recruiting, Opportunity & Inclusion teams on attorney retention programmes; proposes and contributes to creative retention strategies that are tailored to individual attorneys’ career objectives.
• Works closely with the Opportunity & Inclusion team to ensure equitable access to and distribution of client opportunities and to support the firm’s strategic objectives in developing and retaining a diverse talent pool and pipeline.
• Identifies trends to provide input to the Learning & Development team that will enhance training programmes and initiatives, with a particular focus on the developmental needs of mid‑level and senior associates.
• Keeps apprised of all applicable development initiatives, programmes, and firm resources to advise associates on how to leverage them to advance their careers.
• Identifies relevant trends and information related to recruiting, retention, talent development, and morale and regularly communicates with firm leadership and department heads about how to address them.
• Supports mid‑level and senior attorneys in career planning through key career inflection points, including when leaving or returning from leaves of absence, navigating flexible hours arrangements, and preparing for the Path to Partnership process.
• Other projects as needed.

Experience, Skills, And Qualifications

• Bachelor’s degree and J.D. required.
• 7+ years of experience in professional development or coaching at a law firm and/or career advisory role in academia or a professional services firm required.
• Ability and willingness to travel as needed to support business objectives required.
• Must live within a commutable distance to a firm office with the ability to come into the office 3‑4 days per week.
• 5+ years of legal practice in a large law firm strongly preferred. Litigation practice experience preferred.
• Strong client service focus with the ability to influence and guide others in a complex, matrixed organisation.
• Strong business acumen and understanding of law firm operations, including partnership economics and governance.
• Excellent judgement and discretion with respect to confidential information, particularly regarding partnership‑track matters and high‑potential talent assessments.
• Demonstrated experience managing litigation professional development programmes, including designing and leading structured evaluation or preview processes.
• Ability to establish credibility and build strong relationships at all levels of the firm across practices and geographies, particularly with Litigation Department Chairs, Practice Group Leaders, and administrative leaders.
• Experience leading cross‑functional programmes and initiatives that require coordination across multiple firm departments and stakeholders.
• Comfort and confidence engaging directly with senior firm leadership on sensitive talent matters, including partnership candidacy and career transitions.
• Outstanding interpersonal skills and innovative problem‑solving capabilities.
• Outstanding writing and verbal communication and excellent presentation skills. Ability to effectively tailor communications for different stakeholders.
• Tech savvy with solid Microsoft Office skills or ability to quickly learn.
• Extremely detail‑oriented, strong organisational, analytical, and excellent project management skills, including ability to prioritise work in a dynamic environment to meet deadlines.

Benefits

Winston offers comprehensive benefits that provide a full spectrum of coverage and support for our full‑time employees and their families. Additional information about benefits and rewards can be found here .

Salary

Illinois applicants only: The target annual salary range for this role is currently $145,000-$190,000 based on a regular, full‑time schedule. The amount of compensation offered will be determined by several factors, including but not limited to experience, qualifications, market data and internal equity. Total compensation includes a comprehensive healthcare benefits package, yearly retirement contribution, and may include an annual discretionary merit bonus.

We are an equal opportunity employer and welcome applicants from all backgrounds and experiences.