Associate Financial Advisor

Milwaukee, WI · Hybrid (3 days in-office) · $55,000 – $65,000

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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. This role sits on the front lines, helping clients and prospects navigate the transition into a retirement with peace of mind.

As an Associate Financial Advisor, you’re often the first live conversation a prospective client has with Retirable. You’re the person who makes them feel heard, assesses whether we can help, and guides the right ones toward a consultation with one of our Financial Advisors. That conversation sets the tone for everything that follows.
In this role, you’ll:

• Conduct introductory qualification calls with individuals approaching or in retirement, building trust quickly and understanding each prospect’s goals, timeline, income needs, assets, and planning gaps.
• Identify whether a prospect is a strong fit for Retirable’s advisory services and guide qualified ones toward a Financial Advisor consultation, setting clear expectations and helping them prepare for the meeting.
• Educate prospects on how Retirable helps with retirement income, Social Security, investment strategy, and long-term planning, without delivering a full financial plan.
• Handle objections and uncertainty with empathy and confidence, knowing when to move forward and when a prospect isn’t the right fit.
• Keep accurate records in our CRM, follow compliance procedures consistently, and contribute to a seamless experience from first call to advisor relationship.

What We’re Looking For

We’re looking for someone energized by helping people make important financial decisions: someone who balances empathy with commercial judgment, brings genuine curiosity to retirement planning topics like Social Security, income planning, and Medicare, and approaches every conversation with a fiduciary mindset even before they’re the one delivering the advice.

• Experience in sales, client service, financial services, insurance, or a related consultative role.
• Strong verbal communication and a polished phone presence. You explain complex topics in plain, approachable language and listen as well as you talk.
• High emotional intelligence, particularly with older adults and pre-retirees navigating real financial anxiety. Consultative rather than transactional, comfortable handling objections without being pushy.
• Sound judgment in qualifying prospects, strong CRM discipline, and consistent follow-through on documentation and process.
• Schedule: Monday–Friday, 10am–7pm CST. Less time chasing, more time in real conversations.

Nice to Have:

• Series 65 license.
• Prior experience in financial services or retirement planning.
• Bilingual (Spanish).

Why Join Retirable

• Work that compounds. Every prospect you qualify is someone who would otherwise navigate retirement without professional guidance.
• A real path forward. This role is a deliberate on-ramp to the Financial Advisor role. We invest in the credentials (Series 65, CFP) that get you there, and we promote from within as the firm scales.
• 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 Financial Advisors and leaders who’ve built and scaled fintech advisory teams from zero.
• Compensation: $50,000–$55,000 base plus monthly performance incentive, with OTE of $55,000–$65,000. Early team members also receive an equity grant.
• Full benefits: 401(k) with match, medical/dental/vision, generous PTO, parental leave, and a CE/licensing budget that covers continuing education and license 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.