Director, Assistant General Counsel – Mergers & Acquisitions and Strategic Transactions

Allstate • Chicago, IL

4d • Hybrid

About The Position

The Director, Assistant General Counsel – Mergers & Acquisitions and Strategic Transactions provides strategic legal leadership on the company’s acquisitions, divestitures, investments, venture capital initiatives, and other highly complex, strategic, or sensitive business transactions. Acting as a trusted advisor to senior executives and business partners, this role shapes transaction and business strategy, evaluates legal and commercial risks, and leads matters from inception through execution and post-closing matters. This position requires deep transactional expertise with strong business acumen, executive-level communication skills, and people leadership. The Director significantly influences the future strategy of the Law & Regulation function and supported business areas by developing innovative, practical solutions that enable the enterprise to deliver services, manage risk, and achieve growth objectives. As a Director/Officer, you won’t just deliver results – you drive our culture and shared purpose. At Allstate, we value in person connected experiences not just with your team but also other Allstaters. This may require travel within your local area or to one of our offices on a regular basis.

Requirements

• Juris Doctor (J.D.) from an accredited law school and active bar membership in at least one U.S. jurisdiction.
• Bachelor’s degree (required).
• 10+ years of experience, combining top-tier law firm and in-house experience, with significant responsibility for complex M&A and strategic transactions, preferably within a large, publicly traded company.
• Demonstrated experience leading transactions throughout the full lifecycle with clear ownership and accountability.
• Proven ability to advise senior management and executives on strategic, high-impact matters.
• People leadership experience, including managing and developing legal teams.
• Strategic thinker with strong business and transactional judgment
• Execution-oriented leader who delivers results
• Trusted advisor with executive presence
• Collaborative partner and clear communicator
• Ability to operate effectively in a fast-paced, matrixed, public-company environment

Responsibilities

• Lead all phases of domestic and cross-border M&A and strategic transactions end-to-end, including transaction structuring, indications of interest, letters of intent, due diligence, definitive agreements, regulatory approvals, closing mechanics, and post-closing matters such as transition services, earnouts, and indemnification administration.
• Serve as the primary legal advisor on acquisitions, divestitures, joint ventures, minority investments, venture capital transactions, and other strategic initiatives.
• Advise senior executives and business leaders on transaction strategy, legal and commercial risks, value tradeoffs, and structuring alternatives, translating complex legal issues into clear, business-focused recommendations.
• Evaluate legal risk in the context of enterprise risk appetite, deal economics, and strategic priorities, providing practical guidance that enables timely and disciplined execution.
• Drive execution across multiple parallel workstreams, anticipating issues, resolving obstacles, and maintaining deal momentum under tight timelines.
• Provide legal advice and counsel on highly complex, strategic, or sensitive business transactions beyond M&A, including marketing, real estate, and other strategic agreements that support growth and enterprise priorities.
• Draft, review, and negotiate sophisticated agreements and related documentation.
• Collaborate closely with finance, accounting, tax, HR, regulatory, compliance, and business stakeholders to align legal strategy with operational and commercial objectives.
• Monitor and analyze new laws, regulations, and case law; proactively advise business partners on emerging legal issues and risks and their impact on the business.
• Influence the future strategy and direction of the Law & Regulation function and supported business areas through authoritative legal advice and consultation.
• Develop and implement best practices, frameworks, and process improvements to enhance transaction execution, risk management, and compliance.
• Ensure disciplined and cost-effective engagement of outside counsel.
• Select, engage, and manage external legal advisors, including defining scope, staffing models, budgets, and performance expectations.
• Balance insourcing and outsourcing to maximize efficiency, quality, and consistency of legal work product.
• Provide direction, coaching, performance feedback, and final review and approval for the work of attorneys and paraprofessionals supporting M&A and business transactions.
• Hire, develop, and mentor talent, strengthening transactional capabilities across the legal organization and supporting long-term succession planning.
• Lead meetings with senior management and other key stakeholders.
• Manage departmental resources, including budget oversight and performance management.

Benefits

• Comprehensive technology setup, including a laptop, monitors, headset, keyboard, and mouse.
• Monthly connectivity reimbursement for employees eligible to work from home.
• Dedicated, private workspace free from distractions, along with appropriate desk and seating (when working from home).
• Reliable internet with minimum speeds of 50 MB download and 5 MB upload (when working from home).

What This Job Offers

• Job Type: Full-time
• Career Level: Director