Choosing a new company can be complicated.

At Square Peg, we aim to
make the process seamless, memorable and exciting.

Why should you join us?

Small Business with Big Personality

Square Peg is a place where individuality and expression is celebrated. If you are looking for a place that allows you to be yourself, then look no further.

Meet the Pros

Working with top talent brings out the best in people. We have top experts from across the technology sector. If you want to be the best, then work with the best.

Work with a Purpose

We carefully curate our programs and projects to align with missions that provide long lasting and impactful solutions.

It’s a Journey — Not a Job

Life is movement, and our philosophy is to stay in constant motion—meeting you at every stage of your career journey. No matter If you are a new college grad, fresh out of the military, or an experienced industry professional — we have a career pathway for you.

Future Focused

At Square Peg, we take big bets to move our customers into the future with technology and innovation. If you have an idea for something new, bring it to the table and let’s talk it through. Our research and development (R&D) efforts are in full swing, and we are partnered with the latest and greatest technology vendors, academic institutions and research organizations to take your career into the future.

What sets us apart?

At Square Peg Technologies, we don’t just invest in innovation—we invest in people. We believe that when our team thrives, so does our mission. Here’s what sets us apart:

Top-Tier
Benefits

Enjoy premium healthcare coverage, generous PTO, and parental leave policies that truly support families.

Manager
Supported Growth

Whether you’re upskilling, changing directions, or aiming for leadership, your manager will back your ambitions with training support, tuition reimbursement, and internal opportunities.

Work-Life Balance
that Works

We respect your time. We have a culture that encourages unplugging to help you recharge and stay focused on what matters.

A Team That Feels
Like a Team

You won’t be just a number here. Our people-first culture means you’ll be part of a supportive, collaborative environment where your voice matters and your impact is real.

Real
Recognition

Your work won’t go unnoticed. We regularly celebrate milestones, wins, and contributions—big and small—because we believe appreciation fuels great performance.

More Than
Just a Career

You’ll build a meaningful, balanced, and rewarding work life. Join an award-winning workplace! We are a proud two-time recipient of the Washington Business Journal Best Places to Work award (2019 & 2024).

Exceptional Benefits That Truly Take Care of You

At Square Peg Technologies, we believe great work starts with people who feel valued, supported, and inspired. That’s why we offer one of the most competitive and comprehensive benefits packages in the industry—designed to support every part of your life, not just your work.

100% Company-Paid Health Coverage

We cover 100% of your Health, Dental, and Vision insurance—for you and your family.

Coverage When You Need It

Fully covered Short-Term Disability, Long-Term Disability, and Life Insurance—so you’re protected, no matter what.

Generous 401(k) Plan

100% company match up to a certain percentage of your salary to help you build your future.

Paid Time Off

Up to 5 weeks of time off—we know rest fuels your best work.

Career Development

Get reimbursed every two years for professional development—whether it’s a certification, course, or conference.

Technology Reimbursement

Keep up with the latest tech with our reimbursement every two years to upgrade your computer, mobile phone and other tech—so you can work your best, wherever you are.

Wellness Support

Your well-being is our priority. Our Employee Assistance Program offers you and your household 24/7 confidential access to short-term counseling, work-life specialists, and expert legal or financial guidance—all at no cost.

We care about your health. Get yearly reimbursements for gym memberships, fitness gear, and more to support your well-being.

Give Back with Company Support

We match your charitable contributions dollar for dollar, up to $1,000 annually—so your generosity goes even further.

Goal Setting & Career Coaching

We’re committed to your long-term growth. You’ll have yearly goal-setting sessions and ongoing manager support to help you thrive and advance in your career.

A Team That Enjoys the Community

From volunteer drives to company outings, and holiday celebrations, we believe in building community and having fun together.

At Square Peg, you’re not just an employee— you’re part of a company that truly invests in your future!

Trusted by the highest levels.

A continuing trusted partner for analytics

The team at Squarepeg continues to be a trusted partner for analytics and managing major implementation for our customers. I’ve recommended them for multiple data centric projects.

Regional Vice President

Tableau

Endless opportunities to explore and advance your career

Squarepeg provides excellent work life balance with top notch benefits. The management team really cares about their employees. The hiring process was wonderful and easily streamlined. There are endless opportunities to explore and advance your career at Squarepeg

Senior Data Analyst

Washington D.C.

We wouldn’t hesitate to recommend them

It’s refreshing to find a small business that punches above its weight. Square Peg is a shining example of how a team of passionate experts can deliver exceptional results. We wouldn’t hesitate to recommend them to any government agency looking to unlock the power of their data.