Retirable is a mission-driven, New York-based fintech 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 that 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 traditional barriers to world-class retirement advice. We don't sell products, we build relationships. We don't push portfolios, we craft personalized roadmaps to financial freedom. This isn't just FinTech. This is about fundamentally reshaping how America retires—one person, one plan, one confident future at a time.

The Role

We are hiring our Head of Product to be a senior, hands-on operator who will own the product roadmap end-to-end. You will report directly to the CEO and partner closely with the CTO and engineering team to ship.

This is a player-coach role with the player dial turned all the way up. You will write the strategy, prototype the next feature, sit with engineering to ship it, and then write the launch post. You will build the team underneath you over time, but for now you are the team.

What You'll Own

Product strategy & roadmap. Define what we build, why, and in what order. Translate Retirable's mission into a sequenced set of bets that move retention, advisor leverage, and AUM.

AI in the core product. Lead the integration of AI across the client experience and the advisor / retirement / investment back office. Streamline the workflows our advisors run today, automate what shouldn't be human, and make every advisor more effective.

Engineering leverage. Help our engineers 2x their output without 2x'ing headcount. Bring AI-first development practices, prototyping tools, and tight feedback loops to the team.

Hands-on shipping. Bias toward working prototypes over PRDs wherever it makes sense.

How You Work

AI-first by default. You assume AI is part of the answer, not an add-on. You use it daily in your own workflow and you push the team to do the same.

Commercial instinct. You think about CAC, LTV, conversion, and unit economics as naturally as you think about UX.

Prototypes over PRDs. You'd rather show than tell. A working demo beats a 10-page spec, and you can produce either one when the situation calls for it.

High velocity. You optimize for shipping. You break work into small pieces, you ship something every week, and you iterate based on what users actually do.

Hands-on, not hands-off. You are still in the work. You write the spec, you draft the copy, you QA the build, you watch the user session.

What You Bring

5–10 years in product, ideally with at least one tour at an early-stage startup where you owned a meaningful surface end-to-end. Bonus points for fintech, wealth management, or anything advisor-adjacent.

Demonstrated AI fluency. You have shipped AI-powered features in production, not just prompted ChatGPT.

Strong design and engineering taste. You can sit with a designer and an engineer as a peer, not just a stakeholder.

Comfort with regulated environments. We operate as an SEC-registered investment advisor. You don't have to be a compliance expert, but you need to respect the guardrails and ship within them.

Nice to Have

Experience building tools used by financial advisors, RIAs, or any back-office operator.

A CFP, Series license, or genuine interest in personal finance and retirement.

Founder or founding-team experience.

A portfolio of side projects, prototypes, or products you've shipped on your own.

Why This Role

Direct line to the CEO and a real seat at the strategy table from day one.

A massive, underserved market — most retirees still don't have access to good advice, and AI is the unlock.

Greenfield: you will define the product function, the marketing function, and how AI shows up in both.

Leverage: every feature you ship reaches retirees who genuinely need it and advisors whose work you can make 10x better.

The Details

Location: On-site New York.

Compensation: $190K–$250K base + meaningful early-stage equity.

Reports to: CEO. Partners closely with the CTO.

Type: Full-time, individual contributor (for now — team-building comes next).

Junior Associate Financial Advisor

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

Apply Here

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.

Associate Financial Advisor

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

Apply Here

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.

Financial Advisor

Apply Here

Who We Are

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.

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 a Financial Advisor, you’ll:

• 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.
• What We’re Looking For
• 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.

What you bring

• Demonstrated 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.
• Schedule: Monday–Friday, 9am–6pm CST, with 2 Saturdays per month in place of a weekday. Less time chasing, more time advising.

Nice to Have

• Experience in the senior market or with retirement-stage clients.
• Series 65, Series 7 and Series 66, or CFP.
• Bilingual (Spanish)

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.
• Compensation: $65,000–$85,000 base plus quarterly performance bonus, with OTE of $75,000–$95,000. Early advisors 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.