Remote Retirement Specialist Jobs
Remote Retirement Specialist jobs are in strong demand across the U.S., with remote-first financial services firms, insurance carriers, and distributed benefits-consulting teams actively hiring. Employers hiring remotely right now include Altigro Pension Services, TPA Company, and Transamerica. Scan the live roles below and apply to whichever ones fit.
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We are excited to speak to you about this opportunity. If you are interested in joining our growing team, please apply to this link directly.
Who we are
At Aquila, we invest in category-defining B2B/B2G software companies globally, acting as a thought-partner, striving for the success of our companies in the long term. We are a well-managed, profitable company that operates like a startup with the financial backing of a parent company. For our people, this means limitless possibilities.
We are unapologetically unique, pivoting to respond to the needs of the multiple markets we operate in. We have ambitious goals, and we are looking for genuine contributors with integrity, energy, flexibility, and loyalty. We are investing in building future leaders who can take an idea and make things happen.
About CalcAir
CalcAir, a Gemini Group company within Aquila, provides retirement plan administration software to third-party administrators and benefits professionals across the United States. With more than 50 years of industry experience, we help our customers manage complex retirement plans, navigate changing regulations, and deliver accurate, efficient administration services.
Who we need
Reporting to the Director of Customer Experience, we are hiring a Retirement Plan Administration Support Specialist. You will apply your knowledge of retirement plan administration to help customers resolve complex questions related to plan calculations, software functionality, and regulatory requirements. You will work closely with our development team to investigate issues, identify opportunities for improvement, and test software changes, helping ensure our solutions deliver accurate results and meet the needs of the retirement plan professionals who rely on them.
This is a fully remote role based anywhere in the United States. You will work an eight-hour shift within our customer support hours of 8:00 a.m. to 5:30 p.m. Central Time.
What’s in it for you
A new direction for your career. You will have the opportunity to bring your retirement plan administration expertise into a software company that serves the industry you know. You will build on your knowledge in a customer-facing role, developing new skills in software support, troubleshooting, and product functionality while helping retirement plan professionals make the most of the technology they rely on.
Broader exposure and impact. You will work with a diverse range of third-party administrators and benefits professionals across the United States, gaining insight into different approaches, challenges, and retirement plan requirements. You will expand your industry knowledge while helping customers solve complex problems and improve how they work. Through your collaboration with the development team, you will also have a voice in how our software evolves, sharing feedback and helping test improvements that benefit customers across the industry.
Career growth and opportunity. You will join a team where your industry knowledge is valued and where there are opportunities to develop your career in new directions. You will gain exposure to different aspects of the software business, with potential pathways into senior support, product, or other customer-facing roles. As part of Aquila's broader portfolio of software companies, you will also have access to a wider network of businesses and potential opportunities to grow your career over time.
As our new Retirement Plan Administration Support Specialist you will
Guide and support customers. You will respond to questions from retirement plan administrators and other industry professionals through phone, email, and our support ticketing system. You will help customers navigate software functionality, understand results, and work through issues involving their day-to-day administration activities. You will provide clear explanations and follow through on questions that require further investigation.
Solve complex administration questions. You will draw on your understanding of qualified retirement plans, including calculations, compliance testing, contributions, distributions, and regulatory requirements, to investigate customer questions. You will look beyond what the software displays to understand the underlying administration process, research unfamiliar scenarios, and determine the correct result.
Collaborate on software improvements. You will identify and document software issues, communicate bug reports and enhancement requests, and work with our development team to help resolve them. You will also bring your perspective as an experienced administrator to discussions about new features and changes driven by evolving legislation.
Test and validate changes. You will help test software fixes, new functionality, and regulatory updates before releasing them to customers. Using your knowledge of retirement plan rules and calculations, you will evaluate whether the software produces the expected results across different administration scenarios and provide feedback when further changes are needed.
Share knowledge with customers and colleagues. You will contribute to release notes, written resources, training materials, and webinars that explain software functionality, regulatory changes, and common administration questions. You will make complex information accessible and help customers get more from the software they use.
You bring
The retirement plan administration experience. You have hands-on experience administering U.S. qualified retirement plans and understand the processes, calculations, and compliance requirements involved. You know how administration tasks are performed, what results to expect, and how to investigate discrepancies. Your experience may come from a third-party administrator, insurance company, investment firm, or an organization that manages retirement plans internally.
The industry knowledge. You have a strong understanding of qualified retirement plans, including compliance testing, contributions, distributions, and plan documentation. You are familiar with ERISA and regulatory developments such as SECURE 2.0. You bring knowledge of defined contribution plans, and experience with defined benefit or cash balance plans is an asset. You know where to find reliable information when regulations change or unfamiliar questions arise.
The software experience. You have used retirement plan administration software in your work and understand how it supports calculations, compliance, and day-to-day administration. You may have experience with CalcAir, DATAIR,Relius, ASC, FT Williams, or similar platforms, including internally developed systems. You are comfortable working with spreadsheets to review calculations and validate results.
The analytical and problem-solving skills. You can work through complex questions, investigate unexpected results, and identify the source of an issue. You take a methodical approach to reviewing information, testing assumptions, and finding answers. You know when to involve others and can clearly explain what you have found and how to resolve it.
The customer focus and communication skills. You can explain complex retirement plan concepts and software functionality in a way that is clear and helpful to customers with different levels of knowledge. You listen carefully, ask thoughtful questions, and take ownership of resolving issues, keeping customers informed along the way. You are comfortable working independently and collaborating with support and development colleagues to find solutions.
The curiosity to keep learning. You are interested in technology and how software can improve retirement plan administration. You are open to learning new software, contributing to product testing, and exploring ways to improve customer support. Familiarity with ticketing systems such as TeamSupport is an asset, as are industry designations such as QKA, QPA, APA, or ERPA, although these are not required.
Why join?
CalcAir and Aquila are part of Constellation Software Inc., one of Canada's largest and most successful software companies and its most successful technology stock over the last 10 years [TSE: CSU].
Our entrepreneurial culture, lean environment, and people come together to form a dynamic organization where purpose drives our growth. This is a place where high performance and hard work are rewarded, where leaders are grown, and where the best ideas win. With the autonomy to be creative and curious, we collaborate and iterate to achieve real impact in the communities we support.
We spend our days asking questions and challenging the status quo, manipulating our structure, roles, and internal operations in order to stay ahead in a competitive landscape.
If you share our growth mindset, relationship-focused approach, and high moral fibre, you will thrive at Aquila.
Apply now.
Diversity and inclusion are not mere words on paper to us. We welcome and appreciate candidates with a range of backgrounds and experiences. If you have 70% of the qualifications we are looking for and want to play an integral role in changing an industry, apply to express your interest.
What you can expect from our interview process:
A virtual interview with a Talent Advisor to discuss your interest in joining the company and in the role. The conversation will be recorded using BrightHire, an AI-powered video interview tool. More details will be shared when you are invited to interview.
A virtual interview with the Director of Customer Experience to explore your retirement plan administration experience, knowledge of regulations and calculations, familiarity with industry software, and approach to investigating and resolving customer questions.
A virtual interview with a senior member of the Customer Support team to further discuss your practical experience, approach to customer support, and how you would contribute to software testing and continuous improvement.
A final virtual interview with the General Manager to learn more about CalcAir, discuss your interest in the opportunity, and explore how your experience and career aspirations align with the direction of the business.
We promote equal employment opportunities for all. We do not discriminate on the basis of race, religion, color, sex, gender identity, sexual orientation, age, disability, national origin, veteran status, marital status or any other basis covered by appropriate law. All employment decisions are made based on qualifications, merit, and business needs. We welcome and encourage applications from people with disabilities and accommodations are available on request.
We use AI-powered tools to support aspects of our recruitment process, including interview recording, transcription, and note-taking. These tools help our recruitment team document conversations and maintain a consistent interview process. All candidate evaluations and hiring decisions are made by people, not AI.
We are excited to speak to you about this opportunity. If you are interested in joining our growing team, please apply to this link directly.
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Find JobsRemote Retirement Specialist Job Market
Who's Hiring
What Employers Look For
The qualifications that appear most often in remote retirement specialist jobs.
- Bachelor's degree in finance, business, or a related field
- Experience administering 401(k), 403(b), or defined benefit plans
- FINRA Series 65 or Series 7 license or willingness to obtain
- Knowledge of ERISA regulations and IRS retirement plan rules
- Proficiency with retirement plan recordkeeping or administration software
- Strong client communication and financial counseling skills
Tips for Your Remote Retirement Specialist Job Search
Apply early to remote roles that fit
Migrate Mate lists remote retirement specialist openings from across the U.S. in one place, so you can find roles that match your background and apply directly. Remote postings at financial services firms and benefits consultancies often close fast once a qualified applicant pool forms.
Show async communication skills upfront
Remote retirement specialist employers want proof you can explain plan design, compliance deadlines, and distribution rules clearly in writing. Include a sample client memo, compliance summary, or participant communication in your application materials to demonstrate that skill before the interview.
Highlight plan administration software proficiency
Remote roles depend on shared platforms like Relius, PensionPro, or similar recordkeeping and workflow tools. Name the systems you've used and what you accomplished in them. Employers screening remote candidates use this to gauge how quickly you'll contribute without in-person training.
Prepare for structured remote interviews
Remote retirement specialist interviews often include scenario questions on ERISA compliance, participant eligibility, or plan correction procedures answered entirely over video. Practice delivering precise, well-organized answers without visual aids, since your verbal clarity signals how you'll handle client and sponsor conversations remotely.
Remote Retirement Specialist Jobs: Frequently Asked Questions
How do I get a remote retirement specialist job?
Target companies that have already built distributed teams, particularly remote-first financial services firms, insurance companies, and benefits consultancies. Remote employers screen hard for self-direction, clear written communication, and the ability to explain complex retirement concepts, like plan design or distribution rules, through email and documentation rather than in-person conversation. Demonstrating that you can manage a client caseload or compliance calendar without direct supervision gives you a real edge.
Which companies hire remote retirement specialists?
Companies hiring remote retirement specialists right now include Altigro Pension Services, TPA Company, and Transamerica, based on current remote listings on Migrate Mate as of November 2026. These tend to be remote-first financial services firms, national insurance carriers, and distributed benefits-consulting organizations that serve employer plan sponsors or individual retirement clients across multiple states.
Can you get a remote retirement specialist job with no experience?
Yes, but remote entry-level retirement specialist roles are harder to land because employers expect you to work independently from day one with minimal oversight. Remote-first financial services firms and insurance companies do hire entry-level candidates who hold relevant credentials, like a CEBS designation or coursework in plan administration, and can show strong written communication and comfort with plan management software through projects, internships, or coursework portfolios.
Do you need a degree for remote retirement specialist jobs?
Not always. Many remote employers weigh demonstrated knowledge of retirement plan regulations, hands-on experience with 401(k) or defined-benefit plan administration, and industry credentials alongside or instead of a four-year degree. Candidates who can show concrete results, such as plan compliance records or participant education initiatives, often compete effectively even without a traditional degree.
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