Software Engineer

Company: Five & Fly
Location: Denver , Colorado
Type: onsite
Posted: Aug 19, 2026
Views: 0
**SKILLBRIDGE to FULL-TIME EMPLOYMENT**

Ready to shape the future of AI infrastructure and build systems that power the most advanced unstructured data pipelines in the world? We’re building the backbone of generative AI—enabling federal agencies, defense organizations, and public sector partners to transform PDFs, HTML, Word docs, images, and more into high-performance data pipelines that scale securely and reliably.

Our tools already power mission-critical workloads for half of the Fortune 500, and our open-source package has been downloaded 36+ million times. Now, we’re entering our next chapter—bringing these same innovations to the US government—and we’re hiring a Software Engineer - Public Sector to help lead the charge.

If you’re energized by solving hard technical problems that truly matter—and you want to build solutions that empower agencies and support national missions—this is your moment.

Active SECRET clearance required
  • Own the technical vision for some of the most complex, high-impact systems powering federal and public sector data pipelines.
  • Drive architectural strategies that prioritize scale, performance, and security compliance.
  • Write production-ready code and lead projects that directly support mission-critical workloads.
  • Solve deep technical challenges like data orchestration at scale, secure data flow optimization, and AI-first infrastructure for sensitive workloads.
  • Align engineering, product, and go-to-market teams to deliver solutions that meet public sector compliance and security needs.
  • Guide architectural decisions that balance innovation with risk mitigation.

What We're Looking For

  • 5–9 years building software for US government or Department of Defense (DOD) networks.
  • Active SECRET clearance required; TS/SCI strongly preferred
  • Deep expertise in Python, distributed architectures, and AWS, Azure, or GCP.
  • Proven success leading mission-critical technical initiatives and mentoring engineering teams.
  • Passion for performance, reliability, and elegant, compliant solutions.
  • Unstructured values service and encourages veterans of the US military and civilian agencies to apply to this role.
  • Ability and willingness to travel up to 20%

Bonus Points

  • Experience with AI/ML systems, unstructured data, or real-time pipelines.
  • Familiarity with FedRAMP, IL5, or other compliance frameworks.
  • Expertise with Kubernetes, IaC, or scaling SaaS infrastructure.
  • Startup DNA—you thrive in fast-moving, high-impact environments.

Why You'll Love It Here

You'll be surrounded by smart, kind, low-ego people who genuinely enjoy building together. We invest in our team with company offsites, best-in-tech swag, and the tools you need to do your best work, wherever you're based.

We support you holistically, not just at work. From medical, dental, and vision coverage effective the 1st of the month following your start date, life and disability insurance, unlimited PTO, and flexible parental leave, to a 401(k) with company match, equity, a $500 work from home stipend, $70/month internet reimbursement, and team/company offsites throughout the year - we want you focused on building, growing, and staying energized for the long haul.

If you're excited about what we're building, we'd love to meet you.

Apply Now ♡ Save Job

About the Company

Name: Five & Fly
Location: New York
Website: https://fiveandfly.pinpointhq.com

If you’re looking for somewhere you can learn quickly, make a meaningful impact in a fast-paced business, and grow your career, you’re in the right place. Transition from the battlefield to the boardroom. You set yourself apart–you’ve built a career supporting and defending the Constitution. Not to mention your character. You’ve exhibit true faith, learning to lead in ways your civilian counterparts will never understand. And now, you are ready for something new. But you wonder, will you be able to find meaningful work outside of the military? Will a civilian employer value what you have to bring to the table? We’re here to make sure of it.

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