Client Relationship Specialist

Drake & Associates, LLC; Milwaukee (WI); On-site; USD 50,000 - 70,000; Full time

Job summary

Drake & Associates, LLC in Milwaukee, Wisconsin, is seeking a Client Success Specialist to enhance client relationships after meetings with Financial Advisors. This role emphasizes follow-ups and exceptional service to ensure client satisfaction and generate referrals.

The ideal candidate has at least 2 years of experience in a client-facing role, excellent communication skills, and is proficient with Google Suite and Salesforce. With competitive base salary and commission structure, this role promises rewarding contributions to our team.

Qualifications

• 2+ years of experience in client success or a related role.
• Comfortable with verbal and written communication.
• Diligent in managing client follow-ups and events.

Responsibilities

• Follow up with clients post-advisor meetings to reinforce value.
• Obtain referrals confidently, three per week.
• Manage client reviews and timing for outreach effectively.

Skills

Client relationship management

Excellent communication skills

Detail-oriented and organized

Proficient with Google Suite

Tools

Salesforce

ActiveCampaign

Job description

Drake & Associates is an independent financial planning firm dedicated to helping families retire with confidence and clarity. We are known for our integrity, education-first approach, and commitment to delivering an exceptional client experience.

Our culture is built on core values including Ultimate Client Experience, Extreme Ownership, Entrepreneurial Spirit, and Respect the Family. We believe in doing the right thing, supporting one another, and taking pride in the impact we make every day.

About This Opportunity

The Client Success Specialist (”Dreamweaver”) is responsible for strengthening relationships with existing clients after they meet with a Financial Advisor. This role does not involve selling, prospecting, or cold outreach. Instead, you will focus on thoughtful follow-up, personalized communication, and exceptional service that reinforces value, clarifies next steps, and creates memorable “wow” moments. Your primary objective is to generate consistent referrals by delivering an outstanding post-meeting experience that builds trust and enthusiasm.

How You\'ll Make an Impact

• Follow up with clients after advisor strategy meetings via phone and/or in-person touchpoints to reinforce value, confirm next steps, and ensure an outstanding experience
• Confidently and consistently obtain referrals (3 per week) in a manner that is professional, natural, and aligned with the Drake brand
• Gather and manage client reviews, including timing outreach appropriately, following up, and tracking progress through completion
• Identify service opportunities or concerns during follow-ups, coordinate internal resolution, and escalate when necessary to protect the client experience
• Support the Marketing team in the planning and execution of client events (invitations, confirmations, reminders, hospitality/logistics, and post-event follow-up)
• Execute client “wow” initiatives, including personalized gifts and surprise-and-delight moments tied to milestones, anniversaries, and key client moments
• Track all client outreach, outcomes, and next steps accurately in Salesforce, leveraging ActiveCampaign to support consistent communication workflows
• Maintain awareness of upcoming events, campaigns, client milestones, and marketing initiatives to align follow-ups, gifting, and outreach with the broader client experience strategy

What We\'re Looking For

• 2+ years of experience in client success, relationship management, hospitality-level service, marketing support, or a client-facing role in a professional services environment (financial services a plus)
• Excellent communication skills; both verbal and written (comfortable on phone and in-person)
• Exceptionally detail-oriented and highly organized; able to manage multiple client follow-ups, events, and initiatives without missing steps
• Proficient with Google Suite
• Experience with Salesforce and/or ActiveCampaign preferred (or similar CRM/marketing automation tools), but not required

Compensation Structure

This role provides a base salary along with a highly competitive commission structure that rewards strong performance, meaningful results, and contributions to our shared success.