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.

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

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.

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.

Faster compliance turnarounds

Documented runbooks and immutable pipelines supported rapid responses to external auditors and cybersecurity insurance reviews.

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.

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.

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.