Financial Services Military Transition Opportunity

Northwestern Mutual - Poughkeepsie; City of Poughkeepsie (NY); On-site; USD 65,000 - 95,000; Full time

Benefits offered by this job

Retirement

Dental insurance

Flexible schedule

Health insurance

Opportunity for advancement

Training & development

Vision insurance

Job summary

Northwestern Mutual – Poughkeepsie, NY is seeking mission-driven leaders to join a team that values disciplined service and mentorship. You’ll learn the financial planning business through structured training, with sponsorship for licenses and a path to building your own client relationships within a supportive team.

Ideal candidates are veterans, military spouses, or transitioning service members who want long-term careers.

Qualifications

• 4-year college degree required.
• Strong communication and relationship-building skills.
• Willingness to complete our Culture Index assessment as part of the interview process.

Responsibilities

• Training and mentorship to help you learn the business, similar in structure to the training pipelines you're used to
• Support working toward your required professional licenses (Series 6, 63, and state insurance licenses), with sponsorship provided
• A team environment that values structure, accountability, and looking out for one another
• Resources and guidance to help you build your own client relationships and practice
• The independence to build a business around your goals, strengths, and networks while still being part of a team
• Performance-based compensation with no ceiling on what you can earn

Skills

Strong communication

Relationship-building

Education

4-year college degree

Job description

Benefits:

• Retirement
• Dental insurance
• Flexible schedule
• Health insurance
• Opportunity for advancement
• Training & development
• Vision insurance

Your Mission Doesn't Have to End When Your Service Does

You are under pressure. You executed the mission, no matter what. You took care of your people. Those aren't just military values — they're exactly what it takes to build a career in financial services, and exactly what we're looking for.

At Northwestern Mutual – Poughkeepsie, NY, our mission is to build enduring relationships that inspire financial security. We take a holistic approach to insurance and investments to provide comprehensive financial planning, backed by a best-in-class advisor support platform and an experienced mentorship program. Whether you're actively transitioning out of service, a veteran years removed from the military, or a spouse who's supported a service member through the journey, you'll find a team here that understands discipline, service, and mission-focus — because it's built into who we are.

We're proud to support our local community through Alex's Lemonade Stand Foundation, The Children's Home of Poughkeepsie, and the Poughkeepsie Foodbank.

Want a look at our culture? Watch this VIDEO

Our Thriving Office Location

2515 South Road, 2nd Floor, Poughkeepsie, NY 12601

About Northwestern Mutual

Northwestern Mutual is a FORTUNE 500® company providing financial services to more than 5 million people. Founded in Wisconsin in 1857, it operates as a mutual company — accountable to policy owners, not Wall Street shareholders. The company provides insurance, investment, and financial planning solutions built around one goal: helping clients achieve real financial security. In 2024, FORTUNE® named Northwestern Mutual one of the "World's Most Admired Companies."

Why Veterans and Military Spouses Thrive Here

The skills that made you effective in uniform — leadership under pressure, discipline, mission-first thinking, and genuine care for the people around you — translate directly into building a financial planning practice. You already know how to earn trust, follow through, and adapt when the situation changes. What matters here isn't a finance background; it's your ability to lead, connect, and commit to the mission of protecting the people you serve.

Our team provides:

• Training and mentorship to help you learn the business, similar in structure to the training pipelines you're used to
• Support working toward your required professional licenses (Series 6, 63, and state insurance licenses), with sponsorship provided
• A team environment that values structure, accountability, and looking out for one another
• Resources and guidance to help you build your own client relationships and practice
• The independence to build a business around your goals, strengths, and networks while still being part of a team
• Performance-based compensation with no ceiling on what you can earn

Meet the Team:

Kevin Caccomo — Managing Director & Wealth Management Advisor, CFP®, ChFC®, CLU®, RICP®

With Northwestern Mutual since 2012, Kevin has built his career helping clients achieve financial security through personalized planning. He’s passionate about creating memories with his family, especially outdoor adventures and trips to Disney, and has a deep appreciation for travel.

James Wong — Financial Advisor/Growth & Development Director

James joined Northwestern Mutual in 2020. Before that, baseball shaped his life — from Little League through college ball at Post University and into professional baseball, followed by a role as Director of Baseball Operations and Head Coach for a youth sports organization in New York City. A husband and father, he's passionate about mentorship and leading by example, both on the field and off.

William Brammer — Financial Advisor/Growth & Development Director

Raised in the Hudson Valley, William discovered his path to financial planning during a senior seminar at SUNY New Paltz. He joined Northwestern Mutual's internship program in 2016 and became a full-time advisor in 2017. A former football team captain and coach, he later led the office's internship program and now serves as a Growth & Development Director for new advisors. Outside the office, he enjoys time with his wife, baby, and two dogs around Wappingers Falls.

Alyssa Marchinek — Director of Selection

Alyssa recently joined the team as Director of Selection, where she connects driven, relationship-focused people with meaningful career opportunities. Outside of work, she loves spending time with family and friends, cooking, planning game nights and dinner parties, and creating photo and video projects.

Johnny Crawford — Director of Selection

Johnny has served as Director of Selection at Northwestern Mutual for the past nine months, connecting talented individuals with rewarding career opportunities. He's licensed in Life, Accident, & Health Insurance with over three years of client service experience.

This Opportunity May Be a Strong Fit If You:

• Are veterans, transitioning service members, National Guard/Reserve members, or military spouses
• Value structure, mentorship, and mission-driven work
• Are you ready to lead again? This time, leading your own practice
• Want to build something long-term rather than simply fill a job

What You'll Need

• A 4-year college degree (required)
• Strong communication and relationship-building skills
• Willingness to complete our Culture Index assessment as part of the interview process

If you're ready to bring your leadership and discipline into a new mission, we'd love to start a conversation.

Northwestern Mutual is the marketing name for The Northwestern Mutual Life Insurance Company (NM) and its subsidiaries in Milwaukee, WI. Kevin Caccomo is a General Agent of NM and is not in legal partnership with NM, or its subsidiaries.