HighSide Secure Collaboration Case Study

HighSide delivers a zero-trust communications platform used by federal agencies and highly regulated enterprises to protect critical data. They asked Siblings Software to extend their core engineering team with DevOps and Python specialists who could accelerate customer-facing features without compromising on security or compliance.

Engagement

24+ months

Continuous collaboration since 2022.

Team

DevOps + Python

Specialists embedded in HighSide’s secure product squads.

Stack

Python · JS · AWS

Kubernetes, Docker, Terraform, serverless analytics.

Highlights

38% faster releases

Measured after introducing automated delivery pipelines.

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A Security-First Platform That Needed More Velocity

HighSide's platform gives distributed teams a workspace to exchange classified documents, coordinate incidents, and manage identity-sensitive workflows. Growth in government and financial services brought an unprecedented roadmap: hardware-backed key management, secure desktop sync, and analytics for auditors. Their in-house engineers were focused on new capabilities, leaving little bandwidth to harden infrastructure and streamline releases.

By bringing in Siblings Software, HighSide gained rapid access to screened senior talent in DevOps and Python engineering—without delaying compliance commitments or spinning up lengthy hiring processes. Our team joined daily stand-ups, committed to existing repositories, and worked within HighSide's zero-trust protocols from the first sprint.

The Challenge: Scaling Security Without Slowing Innovation

When HighSide approached us in early 2022, they faced a classic engineering dilemma: their product team was shipping features that federal agencies and Fortune 500 companies needed, but their infrastructure couldn't keep pace. Manual deployment processes meant releases took five days from code commit to production. Their Kubernetes clusters across US, EU, and GovCloud regions were drifting out of sync, creating compliance risks. And their Python-based desktop sync client needed cross-platform packaging improvements to support Windows, macOS, and Linux—all while maintaining FIPS 140-2 compliance.

The stakes were high. HighSide's customers include federal agencies handling classified information, financial institutions processing sensitive transactions, and healthcare organizations managing protected health data. Every deployment needed to pass security audits, maintain zero-downtime SLAs, and preserve audit trails for compliance officers. Their existing team of talented engineers understood the product deeply, but they were stretched thin between feature development and infrastructure maintenance.

Our Approach: Embedded Expertise with Zero Disruption

We didn't replace HighSide's team—we extended it. Within two weeks of contract signing, we embedded a senior DevOps engineer and a Python specialist directly into HighSide's product squads. These weren't consultants working in isolation; they joined daily stand-ups, participated in sprint planning, and committed code to the same repositories HighSide's internal engineers used. From day one, they worked within HighSide's zero-trust security model, using the same access controls, encryption standards, and audit logging that protected the platform.

The DevOps engineer focused on rebuilding CI/CD pipelines using GitHub Actions, implementing infrastructure-as-code with Terraform, and establishing Kubernetes GitOps workflows with ArgoCD. Meanwhile, the Python specialist collaborated with HighSide's desktop team to improve cross-platform packaging, enhance the secure sync client's reliability, and implement automated testing for Windows, macOS, and Linux builds.

Project Goals

Automate a FIPS-compliant CI/CD workflow capable of promoting builds across FedRAMP workloads.
Scale multi-tenant infrastructure while containing infrastructure-as-code drift across regions.
Ship new desktop collaboration features without interrupting existing enterprise customers.
Strengthen monitoring and incident response readiness for highly sensitive deployments.

How We Partnered

Embedded a senior DevOps engineer to rebuild pipelines with GitHub Actions, Terraform, and Kubernetes GitOps.
Assigned a Python specialist to co-own the secure desktop sync client and cross-platform packaging.
Co-created runbooks and tabletop exercises with HighSide’s security officers to meet audit expectations.
Provided ongoing DevOps and infrastructure support via our outsource development team model.

Results That Mattered

Over 24 months of continuous collaboration, the improvements we delivered weren't just technical—they transformed how HighSide's engineering organization operated. Here's what changed:

Release cycle shortened by 38%

Automated testing matrices and container promotions cut manual handoffs from five days to three, enabling HighSide to respond faster to client feature requests. We implemented parallel test execution across multiple environments, automated security scanning with Snyk and Trivy, and created blue-green deployment strategies that eliminated downtime during releases.

High availability across regions

Kubernetes cluster baselines and Terraform modules ensured US, EU, and GovCloud environments remained in lockstep, improving SLA adherence for security-conscious customers. We reduced configuration drift from 15% to less than 2% across all regions, and implemented automated health checks that reduced mean time to recovery (MTTR) by 45%.

Faster compliance turnarounds

Documented runbooks and immutable pipelines supported rapid responses to external auditors and cybersecurity insurance reviews. We created comprehensive documentation covering deployment procedures, incident response protocols, and security controls that reduced audit preparation time from weeks to days.

Deep product collaboration

Our engineers co-led backlog refinement, mentored junior staff, and sustained a transparent cadence that the HighSide leadership team praised for clarity. We established architecture decision records (ADRs), implemented code review best practices, and created knowledge-sharing sessions that helped HighSide's team grow their DevOps capabilities.

Technical Achievements in Detail

Beyond the headline metrics, we delivered concrete technical improvements that made HighSide's platform more reliable, secure, and maintainable:

CI/CD Pipeline Transformation: Replaced manual deployment scripts with automated GitHub Actions workflows that run comprehensive test suites, security scans, and compliance checks. The pipeline now supports automated promotion from development to staging to production across FedRAMP-authorized environments, with manual approval gates for production deployments.
Infrastructure as Code Standardization: Created reusable Terraform modules for Kubernetes clusters, load balancers, and networking components across AWS regions. This eliminated configuration drift and enabled HighSide to spin up new environments in hours instead of days.
Cross-Platform Desktop Client Improvements: Enhanced the Python-based desktop sync client with automated build pipelines for Windows, macOS, and Linux. Implemented code signing for Windows and macOS, automated security updates, and improved error handling that reduced support tickets by 30%.
Observability and Monitoring: Implemented comprehensive monitoring using Prometheus, Grafana, and ELK stack. Created custom dashboards for application performance, infrastructure health, and security events. Set up alerting that reduced mean time to detection (MTTD) for incidents by 60%.
Security Hardening: Automated security scanning in CI/CD pipelines, implemented least-privilege access controls, and created runbooks for incident response. Conducted regular security reviews and penetration testing that helped HighSide maintain their compliance certifications.

Why HighSide Chose Siblings Software

HighSide's engineering leadership emphasized the immediate impact of embedding our specialists: sprint commitments stayed on track, delivery pipelines became predictable, and product managers regained focus on customer-facing work instead of firefighting releases.

Our blended nearshore team aligned with HighSide's time zone, preserved budget predictability, and complemented their existing talent with specialists in Python development outsourcing and secure cloud operations.

What Made This Partnership Work

From the first week, our engineers demonstrated they weren't just contractors—they were true team members. They participated in architecture discussions, challenged assumptions when appropriate, and contributed ideas that improved HighSide's platform. The DevOps engineer we embedded didn't just implement CI/CD pipelines; they mentored HighSide's junior engineers, documented best practices, and created reusable patterns that the team continues to use today.

The Python specialist we assigned didn't just fix bugs in the desktop client; they refactored critical components, improved test coverage from 45% to 78%, and created automated packaging pipelines that reduced release preparation time by 70%. Both engineers became trusted members of HighSide's engineering organization, participating in code reviews, design discussions, and even helping interview new candidates.

Time zone alignment was crucial. Our nearshore team worked in overlapping hours with HighSide's US-based team, enabling real-time collaboration during critical moments. When incidents occurred, our engineers were available to help troubleshoot. When sprint planning happened, they were present to contribute. This wasn't an offshore team working in isolation—it was a true extension of HighSide's engineering capabilities.

Resources & Further Reading

Secure collaboration overview by HighSide – context on the product vision we support.
AWS Security Blog – the best practices that shaped our infrastructure decisions.
CISA Zero Trust Maturity Model – standards referenced when designing HighSide’s deployment guardrails.