Junior Associate Financial Advisor

Milwaukee, WI · Hybrid (3 days in-office) · $45,000 – $55,000

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Who We Are

Retirable is a mission-driven, venture-backed fintech headquartered in New York with a growing advisor hub in Milwaukee that helps everyday Americans retire with financial confidence. Through professional retirement advice, wealth management, and banking, we’re the bridge between where Americans are today and the confident, well-funded retirement they deserve.

The problem is staggering: 12,000 Americans retire each day and less than a quarter have ever seen a financial planning professional. That’s millions of hardworking Americans headed toward retirement underfunded, underprepared, and unnecessarily stressed.

At Retirable, we’re tearing down the traditional barriers to world-class retirement advice. We’re a fee-based fiduciary RIA, which means our advisors are paid to give the right advice, not to hit product quotas. We craft personalized retirement roadmaps that put clients first, because that’s the only model that works when the stakes are someone’s life savings.

The Opportunity

You will join as a foundational member of our new Milwaukee office. As an early team member, you will help build the culture alongside the leadership team and instill our values in the growing Midwest hub.

As a Junior Associate Financial Advisor, you’ll be learning one of the most important conversations in financial services, the first one a prospective client has with Retirable. That conversation sets the tone for everything that follows, and you’ll have the coaching, call review, and team support to get it right.
This is a structured entry point into retirement planning for someone who is motivated by mission, eager to develop real financial services skills, and ready to grow into the Associate Financial Advisor role. No license is required at hire. We’ll support you in getting there.

In this role, you’ll:

• Conduct introductory qualification calls with individuals approaching or in retirement, learning to build trust quickly and understand each prospect’s goals, timeline, income needs, assets, and planning gaps.
• Develop your ability to identify whether a prospect is a strong fit for Retirable’s advisory services and guide qualified ones toward a Financial Advisor consultation with clear expectations set.
• Learn to educate prospects on how Retirable helps with retirement income, Social Security, investment strategy, and long-term planning in plain, approachable language.
• Handle common objections with the support of established scripts, coaching, and regular call review, building toward independent, consultative judgment over time.
• Build strong CRM habits and compliance discipline from day one, contributing to a seamless experience from first call to advisor relationship.

What We’re Looking For

We’re looking for someone at the start of their financial services career who is energized by meaningful conversations, motivated by helping people navigate important decisions, and ready to be coached into a consultative approach to retirement planning. Prior financial services experience is a plus but not required. What matters most is attitude, curiosity, and the communication skills to connect with people navigating real financial anxiety.

• Strong verbal communication and a natural phone presence. You’re comfortable talking with people, asking thoughtful questions, and listening as carefully as you speak.
• Empathy and emotional intelligence, particularly in conversations with older adults and pre-retirees who may be anxious about their financial futures.
• A consultative instinct. You’re interested in understanding someone’s situation before jumping to a solution, and you’re not drawn to high-pressure sales tactics.
• Coachable and eager to improve through feedback, call review, and practice. You see every conversation as a chance to get better.
• Schedule: Monday–Friday, 10am–7pm CST. Less time chasing, more time in real conversations.

Nice to Have:

• Prior experience in sales, customer service, financial services, or a client-facing role.
• Interest in retirement planning topics such as Social Security, Medicare, or income planning.
• Bilingual (Spanish).

Why Join Retirable

• Compensation: $42,000–$47,000 base plus monthly performance incentive, with total earnings of $45,000–$55,000. Early team members also receive an equity grant.
• A real path forward. This role is a deliberate on-ramp to the Associate Financial Advisor role. We’ll sponsor your Series 65, invest in your development, and promote from within as you demonstrate the judgment and skills to take on more.
• Work that compounds. Every prospect you qualify is someone who would otherwise navigate retirement without professional guidance.
• Tools that respect your time. Our internal platform handles scheduling, documentation, and client tracking so you spend your day in conversations, not administrative work.
• Mentorship from Associate Financial Advisors, Financial Advisors, and leaders who’ve built and scaled fintech advisory teams from zero.
• Full benefits: 401(k) with match, medical/dental/vision, generous PTO, parental leave, and a CE/licensing budget that covers your Series 65 and future renewals.

Retirable is an equal opportunity employer. We value inclusion and do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.