Engine Yard, a platform-as-a-service provider with approximately 10,000 customers, was planning to lay off their 23-person remote support team and outsource support to a third-party vendor. The support organization was viewed as a cost center, customer satisfaction scores sat at 73%, and Standard Support was sold as a separate paid add-on ($30-50/month) rather than being bundled with the product.
A next-generation platform with new architecture and a redesigned experience was already in development. The existing production platform (OG) needed to remain healthy and retain customers through that transition — against a backdrop of poor data collection infrastructure that made it difficult to measure anything.
My manager departed six weeks after I joined, leaving me to lead the transformation.
Team Investment & Retention: Conducted a world tour over three months, meeting all 23 remote team members in person. Discovered career stagnation was the core issue. Immediately addressed overdue promotions and raises, and created pathways for two team members to transition into engineering roles
Engineering Partnership: Created a “Firemen” daily rotation pairing one product engineer with one support engineer. This arrangement surfaced long-standing product bugs directly to engineering and dramatically reduced time-to-resolution for persistent customer issues
Metrics Implementation: Introduced weekly customer satisfaction tracking to establish accountability and measure improvement. Metrics collection across the product more broadly was added to the roadmap — the data infrastructure had been neglected and needed rebuilding
Business Model Innovation: Proposed bundling Standard Support into the core product offering rather than selling it as an add-on. This counterintuitive move meant 100% of customers now had support (vs. a fraction who paid extra), but the support cost was built into product pricing. This reframed support as a product differentiator rather than an optional expense
Product Leadership: Following the support transformation, took on leadership of the product organization, managing 3 PMs. Developed a dual-track roadmap strategy for the OG-to-NG transition: prioritized tech debt in OG that was simultaneously required by the NG architecture, using the resulting OG improvements to maintain customer confidence during the transition. Directed designers to make incremental visual changes in OG toward the NG look and feel, so that when NG launched, customers experienced familiarity rather than disruption
Key Insight: A product transition is a customer experience problem as much as an engineering one. By making OG visibly better during the NG build — not just keeping the lights on — we gave customers a reason to stay patient. The tech debt work paid off twice: once in OG stability, once in NG readiness. That’s the job of portfolio strategy.