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Drake & Associates

Client Development Specialist (Inside Sales)

20965 Crossroads Cir, Waukesha, WI 53186-4083

On-site · Full-time · $40k (as posted)

First seen by offpeak October 4, 2026

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Drake & Associates is a growing financial planning firm dedicated to helping clients achieve financial confidence through comprehensive planning and an exceptional client experience. As we continue to grow, we are seeking a Client Development Specialist who is passionate about serving clients, thrives in a fast-paced environment, and takes pride in delivering accurate, high-quality work.


About This Opportunity

The Client Development Specialist ("Dreamweaver") plays a key role in growing Drake & Associates by deepening relationships with our existing clients and creating opportunities for referrals, introductions, and continued engagement.


Working closely with our Financial Advisors, you'll proactively connect with clients following strategy meetings to reinforce the value of their financial plan, ensure an exceptional experience, and confidently ask for referrals when appropriate. This is a relationship-driven, inside sales position focused on deepening existing client relationships—not cold prospecting. Success in this role requires confidence making outbound calls, building rapport, and identifying opportunities to grow the firm's network through satisfied clients.


The ideal candidate is personable, goal-oriented, and enjoys building meaningful relationships over the phone and in person. You are comfortable initiating conversations, asking for referrals, and working toward measurable performance goals while delivering a high level of service that reflects the Drake brand.


How You'll Make an Impact


What We're Looking For


Desired Traits


Compensation Structure

This role includes a competitive base salary plus an uncapped commission structure designed to reward strong performance and meaningful results. Success will be measured by referral generation, client engagement, and contributions to the continued growth of the firm.

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