Senior Financial Advisor

Retirable is a mission-driven 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 aged 55+ heading 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.

About the role

You will join as a senior, experienced member of our new Milwaukee office. As a leader on the team, you'll bring seasoned client-facing judgment to the group, model best practices for newer advisors, and help instill our values in the growing Midwest hub. This role sits on the front lines, helping clients and prospects navigate the transition into retirement with peace of mind.

Responsibilities

• Conduct financial planning consultations with warm inbound prospects who’ve requested a consultation.
• Build personalized retirement plans covering Social Security, withdrawal strategy, tax efficiency, and longevity risk.
• Guide new clients through onboarding and account funding.
• Maintain ongoing relationships with the clients you onboard, conducting reviews and adjusting plans as life changes.
• Partner with product, marketing, and operations to surface what you’re hearing from clients.

Requirements

We’re looking for a fiduciary advisor with genuine sales ability, someone who can build trust quickly, understand clients' needs, and motivate them to take control of their financial lives.

• 3 to 5 years client-facing financial planning experience.
• You can close. You can guide a discovery call to a clear recommendation, handle objections honestly, and convert qualified prospects into long-term clients without high-pressure tactics.
• You see the fiduciary standard as the only framework under which retirement advice makes sense.
• You’re genuinely interested in retirement planning as a domain: Social Security claiming, sequence-of-returns risk, Roth conversions, Medicare interactions.
• You’re comfortable in a role that’s still being built. Processes will change, tools will evolve, and you’ll have direct input into both.

Nice to Have

• Experience in the senior market or with retirement-stage clients.
• Series 65, Series 7 and Series 66, or CFP.
• Prior experience informally mentoring or supporting less experienced advisors.
• Bilingual (Spanish).

Benefits

• 401(k) with match.
• Medical, dental, and vision coverage.
• Generous PTO and parental leave.
• CE/licensing budget that covers continuing education and license renewals.

Pay

$75,000–$95,000 base plus quarterly performance bonus, with OTE of $95,000–$115,000. Early advisors also receive an equity grant.

Schedule

Monday–Friday, 9am–6pm CST, with 2 Saturdays per month in place of a weekday.

Why Join Retirable

• Work that compounds. Every client you bring on is someone who would otherwise retire without professional advice.
• A real path forward. Early advisors grow into senior advisor, team lead, and specialist roles as the firm scales. We promote from within and invest in the credentials (CFP, ChFC, RICP) that get you there.
• Tools that respect your time. Our internal platform handles plan generation, account opening, and ongoing client tracking so you spend your day in conversations, not spreadsheets and CRM workflows.
• Mentorship from leaders who’ve scaled fintech advisor teams from zero.