Client Engagement Associate Jobs in Milwaukee, WI

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

• Conduct proactive outbound phone calls to existing clients following advisor meetings to strengthen relationships, reinforce the value of our services, and confidently ask for referrals and introductions.
  
• Build strong relationships with clients through personalized follow-up and ongoing communication that creates a memorable client experience.
• Consistently generate a minimum of three qualified referrals per week by confidently asking satisfied clients for introductions in a professional and natural manner.
• Identify opportunities to deepen client relationships by uncovering additional needs, outside assets, family members who may benefit from planning, and other opportunities to serve.
• Gather client testimonials and online reviews through thoughtful, well-timed outreach.
• Identify service concerns during client conversations, coordinate internal resolution, and partner with advisors to ensure a seamless client experience.
• Support the Marketing team in planning and executing client appreciation events, including invitations, confirmations, reminders, hospitality, and post-event follow-up.
• Execute client appreciation initiatives, including personalized gifts, milestone recognition, and other "wow" moments that strengthen client loyalty.
• Accurately document client conversations, referrals, opportunities, and follow-up activities in Salesforce and utilize ActiveCampaign to support ongoing communication.
• Partner closely with Advisors, Marketing, and Operations to ensure every client interaction strengthens relationships and supports the firm's continued growth.
  

What We're Looking For

• Bachelor's degree preferred.
• 2+ years of experience in inside sales, business development, account management, or another client-facing role that included sales responsibilities and outbound phone outreach required.
  
• Demonstrated experience making outbound calls to existing clients and/or prospective clients as part of a sales, relationship management, or business development role.
  
• Proven ability to build trust, influence conversations, and confidently ask for referrals or additional business.
• Strong verbal and written communication skills with a genuine passion for connecting with people.
• Naturally curious and skilled at uncovering opportunities through conversation.
• Highly organized with excellent follow-through and attention to detail.
• Comfortable working toward measurable performance goals and referral targets.
• Experience with Google Workspace.
• Salesforce, ActiveCampaign, or similar CRM experience preferred.
  

Desired Traits

• Client-focused with a strong sense of ownership.
• Organized, adaptable, and able to manage multiple priorities.
• Positive, dependable, and committed to continuous improvement.

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.