Rebuilding a security product through acquisition

Context

Security is a growing accountability for IT providers

Security services had become one of the fastest-growing revenue categories in managed services. Microsoft provides the frameworks and data; the challenge is accessing it across dozens of client tenants and turning it into something actionable. SaaS Security gave providers the tools to do that at scale.

One IT service provider securing all Microsoft 365 services and data across many customers.

Problem

The legacy product was too broad

Built around a PowerShell-centric feature set, the product assumed a power user with technical proficiency and domain knowledge — and had built deep features to match. Usage metrics showed stagnant adoption across several of them. We scoped deliberately to reporting and left the rest behind.

Navigator reporting moved forward. Manager's command-and-workflow feature set didn't.

Approach

Invest in the platform

I pushed beyond a rebuild — fixing onboarding friction and UX debt that had accumulated across multiple releases, without adding scope. Before any security feature could ship, partners needed their Microsoft 365 tenants connected. I designed the Microsoft integration and made the case to build it as shared platform infrastructure — a live, syncing data source with value beyond our product scope. I worked across platform and product teams to build agreement on the approach. Another team had it on their roadmap before we finished shipping.

A code-based prototype — interactions and edge cases validated before development started.

Solution

We didn't rebuild everything — we rebuilt the right things

Moving into ConnectWise meant a broader, less technical partner base. Each capability was scoped to deliver clear value fast — a manageable journey for partners, a simple story for sales. The product needed to drive its own adoption.

Engagement cards

I brought in a pattern I'd proven at SkyKick — engagement cards on the overview page, each reflecting how far a partner has gotten with a key feature — starting empty, prompting the next step. ConnectWise had no equivalent; partners depended on the service team to get set up and discover features. I defined the components in the design system so other teams could build on the approach.

Engagement cards in active state — live metrics across connections, reporting, configuration, and monitoring.

Automated reporting

For an IT service provider, getting a multi-customer security report delivered to your inbox Monday morning was dreamy. A scheduled task got them there — every run logged, past reports accessible for client reviews.

Scheduled tasks setup wizard for automated reporting with options to deliver via email.

Security posture

IT service providers are accountable for their clients’ security posture. I designed it so users could assign a custom baseline or use any framework-based standard (e.g., Microsoft, CIS, HIPAA). At the individual control level, users can review historical activity — seeing what changed, remediating issues, and demonstrating ongoing stewardship to clients.

Activity log of a security baseline control, allowing a user to track drift and remediate.

Outcomes

Beyond scope

Our team demoed SaaS Security internally, and before launch leadership promoted it above the legacy security products in the platform navigation. We shipped the Microsoft integration first, SaaS Security close behind — on time, with all-new UX. The work reached past our own product: the Microsoft tenant data from the integration became the foundation for a new Microsoft Defender product — and the team building it brought me in to guide its UX and technical direction.

“Now our ops team is able to validate and report on all our client's security posture in a single pane … allows us to manage more clients with the same resources.”
— Cloud Solutions Architect

With more time

There was no shared vision for the security suite. The product owner and I set out to build one — I started mapping the partner journey. A partner-first experience across the Security org: multiple products, one journey from activation to full adoption. That's the work I'd have pushed for.