Chicago Middle Market Resident Sales Director, Team Leader

Aon Corporation•Chicago, IL

5d•Hybrid

About The Position

Aon is seeking a Chicago Middle Market Resident Sales Director, Team Leader to help clients make better risk and people decisions. This role involves leading, coaching, and enabling a team of producers to identify, develop, and win new opportunities. As part of an industry-leading team, this role empowers results for middle market clients by delivering practical, insight-led, and measurable solutions within our sales organization. You will report directly to the Chicago Resident Sales Director and will have direct reports in the Chicago office, with a primary focus on developing producers and revenue opportunities across the middle market segment.

Requirements

Minimum 10 years of sales leadership experience in the property and casualty industry, with shown success leading middle market-focused producers, client development strategies, and new business.
Confirmed collaboration skills to effectively lead new business teams in pursuit of targeted middle market prospects and existing-client whitespace opportunities.
Strong negotiation skills.
Exceptional oral presentation skills and ability to clearly articulate sophisticated messages in written form.
Track record of personally initiating, advancing, and closing consultative middle market sales involving multiple stakeholders, risk issues, and Aon solution partners.
Consistent achievement of assigned business goals.
Active execution in the development and maintenance of a productive sales and marketing culture.
Bachelor’s degree or equivalent, with Sales, Risk and Insurance Management, Business, Finance, or related curriculum preferred.

Responsibilities

Achieve or exceed the office’s quarterly and annual new business revenue goals, specifically with respect to mid sized risk capital objectives.
Lead the development and execution of go-to-market plans for direct reports, and other revenue-producing colleagues, with clear focus on middle market segmentation, target account selection, prospecting, and measurable sales goals.
Consistently meet or exceed personal production sales targets, with focus on middle market clients.
Recruit, train, mentor, and enable success for producers focused on the middle market; be viewed as a trusted mentor and connector for that producer group in the market.
Build and maintain a sales‑focused culture that prioritizes consistent pipeline creation, cross‑solution collaboration, referral development, and practical client engagement.
Support the execution of the National Sales and Marketing platform and initiatives.
Mentor, develop, problem-solve, and strategize with producers, Account Executives, broking leaders, and solution line partners to build, advance, and close specific middle market revenue opportunities, including both new logo pursuits and whitespace opportunities with existing clients.
Educate producers, Account Executives, broking leaders, and solution line partners on new products, approaches, services, and Aon capabilities, with practical guidance on middle market client applicability, buying triggers, value messaging, and recommended client and prospect dialogue.
Work with risk leaders to ensure clients and prospects receive regular written communication applicable to their business(es), exposures and needs.
Build, tailor, and implement targeted email campaigns, mailings, seminars, webinars, roundtables, and forums that are relevant to middle market buyers and aligned to the priority industries, key influencers, and new business goals.
Proactively and consistently communicate and meet with clients, prospects, insurers, centers of influence, and competitors to maintain current knowledge of local market dynamics, buying trends, carrier appetite, and talent.
Maintain an accurate and current middle market pipeline, including targeted prospects, next-best opportunities, stage progression, close probability, and expected revenue, to support confident forecasting and significant sales metric analysis.
Supervise and assess ongoing new business results and related pipeline activity across middle market producers, and revenue-producing colleagues, promptly anticipating and addressing negative variances, stalled opportunities, activity gaps, and coaching needs.
Maintain a fair marketplace in terms of prospect allocation across the office and firm’s resources and follow protocols for pipeline documentation and production credit disputes.
Recruit and present your recommendation and business plan for the business development personnel, producer profiles, Account Executive support, and specialist resources needed to grow this segment in the area(s).
Onboard business developers with a clear understanding of their role, target market, middle market value proposition, referral expectations, activity standards, sales goals, and use of Aon Connect, Aon’s local, national, and global resources, and supporting systems.
Identify and champion key influencers (accounting, legal, financial, private equity, banking, associations, and broader business community) to create collaboration and referral opportunities.
Ensure Aon deepens relationships with priority clients by identifying unmet risk capital, health, wealth, and human capital needs where we can deliver relevant, integrated solutions.
Communicate innovative approaches, best practices, market insights, carrier trends, competitor intelligence, and repeatable sales plays that help Aon win more consistently.