Remote Customer Success & Operations Associate – Financial Services Specialist for 401(k) Rollover Solutions

About Capitalize – Transforming the Way America Saves for Retirement

At Capitalize, we are on a mission to eliminate friction in the $20 trillion retirement‑savings market. Every year, more than 20 million Americans change jobs, triggering a 401(k) rollover — a process that is traditionally paper‑heavy, time‑consuming, and prone to costly mistakes. Our team of innovators, engineers, and financial experts has built a modern, digital platform that automates the entire rollover journey, giving people confidence that their retirement assets are protected and positioned for growth.

Since our inception, we have attracted $35 million in venture capital from premier investors such as RRE Ventures, Canapi Ventures, and Greycroft. Our groundbreaking technology has earned us a place on TIME’s 100 Best Inventions list and a spot among Forbes’ Top 50 Fintech Companies in the United States. While our growth is rapid, our core values remain constant: we put people first, we champion transparency, and we foster a culture where every voice matters.

Why This Role Matters – The Customer Success & Operations Associate Impact

Saving for retirement can feel overwhelming. Confusing paperwork, unfamiliar terminology, and tight deadlines often leave customers anxious. As a Customer Success & Operations Associate, you will be the trusted guide who demystifies the rollover process, ensuring each client feels supported from the moment they sign up until the final transfer is complete. Your insight will also travel directly to our product and engineering teams, shaping the roadmap for the next generation of financial tools.

Key Responsibilities – What You’ll Do Every Day

• Personalized Guidance: Walk customers through every step of the Capitalize rollover experience via live chat, email, and phone, translating complex financial concepts into clear, actionable advice.
• Financial Expertise Development: Become an internal subject‑matter expert on 401(k) plans, rollovers, IRAs, and related regulations, continuously updating your knowledge base.
• Institution Liaison: Communicate with banks, brokerage firms, and employers on behalf of customers to facilitate smooth transfers, resolve exceptions, and secure required documentation.
• Knowledge‑Base Stewardship: Author and maintain internal SOPs, FAQ articles, and troubleshooting guides that empower both teammates and customers to solve problems quickly.
• Customer Feedback Loop: Capture, synthesize, and deliver actionable feedback to product, design, and engineering teams, ensuring our platform evolves in lockstep with user needs.
• Cross‑Functional Collaboration: Partner with marketing, compliance, and risk teams to refine messaging, ensure regulatory adherence, and improve overall service quality.
• Metrics & Reporting: Track key performance indicators such as response time, resolution rate, Net Promoter Score (NPS), and churn, using data to drive continuous improvement.
• Flexibility & Coverage: Provide support during peak periods, including occasional extended hours, to guarantee a seamless customer experience.

Essential Qualifications – What We Require

• Minimum four (4) years of experience in a customer‑service, client‑success, or account‑management role, preferably within a financial‑services environment.
• Demonstrated familiarity with 401(k) plan structures, rollover mechanics, and IRA options; certification such as FINRA Series 6, 7, or equivalent is a strong plus.
• Exceptional written and verbal communication skills, with a proven ability to simplify complex financial jargon for a diverse audience.
• Proficiency with modern help‑desk platforms (e.g., Zendesk, Intercom) and CRM systems (e.g., Salesforce, HubSpot).
• Track record of using data to inform decisions—experience with analytics tools (e.g., Looker, Tableau) is beneficial.
• Self‑starter mindset capable of thriving in a fully remote environment; disciplined time management and strong organizational habits.
• Passion for financial empowerment and a genuine desire to help people secure their retirement futures.

Preferred Qualifications – What Sets You Apart

• Experience working at a fast‑growing startup or technology‑driven financial firm, where agility and iteration are everyday realities.
• Background in regulatory compliance (e.g., FINRA, SEC) or prior exposure to audit processes.
• Hands‑on familiarity with API‑based integrations between financial institutions and fintech platforms.
• Multilingual abilities that enable support for non‑English‑speaking customers.
• Demonstrated leadership in mentoring junior team members or leading process‑improvement initiatives.

Core Skills & Competencies – The DNA of Success

• Empathy & Active Listening: Ability to understand customer concerns deeply and respond with patience and reassurance.
• Analytical Problem‑Solving: Quickly diagnose issues, identify root causes, and devise effective solutions.
• Attention to Detail: Meticulous handling of sensitive financial data and documentation.
• Adaptability: Comfortable navigating an ever‑changing product landscape and regulatory environment.
• Collaboration: Strong team player who contributes ideas, shares knowledge, and builds relationships across functions.
• Technological Fluency: Facility with cloud‑based collaboration tools (Slack, Google Workspace, Notion) and a curiosity for emerging fintech trends.

Career Growth & Learning Opportunities

Capitalize invests heavily in the professional development of its people. As a Customer Success & Operations Associate, you will have access to a variety of growth pathways:

• Specialization Tracks: Transition into a senior client‑success manager, product analyst, or compliance officer role as you gain expertise.
• Mentorship Programs: Pair with senior leaders for guidance on career milestones, industry certifications, and leadership skills.
Continuous Education: Reimbursement for relevant courses (e.g., CFP, CFA, advanced FINRA certifications) and attendance at fintech conferences.
• Innovation Labs: Participate in cross‑functional hackathons that allow you to prototype new features or process improvements.
• Global Exposure: Opportunities to collaborate with our New York office, expanding your network and cultural competence.

Our Culture – A People‑First, Inclusive Environment

We believe that a thriving workplace is built on transparency, respect, and shared purpose. At Capitalize:

• Diversity & Inclusion: We actively recruit talent from varied backgrounds, fostering a culture where every perspective is valued.
• Open Communication: Regular all‑hands meetings, transparent OKRs, and a flat hierarchy ensure your voice is heard.
• Work‑Life Harmony: Remote‑first policy allows you to work from anywhere in the United States, with flexible scheduling to accommodate life’s demands.
• Well‑Being Support: Access to mental‑health resources, virtual fitness classes, and a generous paid‑time‑off policy.
• Celebration of Wins: From team‑wide shout‑outs to quarterly “Innovation Awards,” we recognize both individual and collective achievements.

Compensation, Perks & Benefits – What You’ll Receive

• Competitive Salary: Annual base pay ranging from $45,000 to $52,000, commensurate with experience and expertise.
• Equity Ownership: Stock options that align your success with the company’s growth trajectory.
• Comprehensive Health Coverage: Medical, dental, and vision plans with 100% of premiums covered for employees and 50% for dependents.
• Retirement Savings: 401(k) plan with company matching contributions to help you build your own financial future.
• Family Support: 12 weeks of fully‑paid parental leave, plus flexible return‑to‑work options.
• Professional Development Stipend: Annual budget for courses, certifications, or conferences of your choosing.
• Remote Work Allowance: Home‑office stipend for ergonomic furniture, high‑speed internet, and productivity tools.
• Team Building: Quarterly off‑site retreats, virtual happy hours, and community service days to strengthen bonds.

How to Apply – Join the Retirement Revolution

If you are excited about shaping the future of retirement savings and thrive in a fast‑paced, mission‑driven environment, we want to hear from you. Even if you don’t meet every single requirement, we encourage you to apply—diverse experiences and perspectives are what make us stronger.

Take the next step in your career and become a catalyst for financial confidence. Click the link below to submit your resume, cover letter, and any relevant certifications.

Apply Now – Become a Capitalize Customer Success Champion

We Encourage You to Apply!

Even if you feel you’re not a perfect match, we’d love to hear from you. Capitalize is always searching for passionate, talented individuals ready to contribute to a brighter, more secure retirement future for all Americans.