Product and Technology Leader | Product Direction · Architecture · Delivery

I work out what should be built, make the technical decisions, and stay involved until it works in production.

I work between customers, product, and engineering, turning unclear problems into a practical direction and helping teams move from idea to working software.

I have done this at Apple and in several startups, combining product judgment with enough technical depth to shape the architecture and build when needed. INSEAD MBA.

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8 → 1systems consolidated

50M+records in production

0downtime on cutover

$7K/mohosting costs cut

Selected outcomes

Outcome 01

Consolidated 8 legacy systems onto one multi-tenant platform

Proactively identified 8 costly legacy systems that remained in place because dependent applications relied on outdated API formats, then designed a compatibility layer that enabled consolidation without breaking them.

Business problemEight overlapping systems were being maintained separately, consuming infrastructure and support resources. Several had not been upgraded because changes to the core API would have broken the applications and integrations that still depended on the legacy response formats.

What I didInventoried the systems and evaluated their performance, infrastructure cost, dependencies, migration risk, and implementation effort. Designed a compatibility layer that allowed the current platform to produce its standard API output while translating responses back into the legacy formats required by older applications. Made the case for consolidation and led delivery of the shared platform, including a Laravel backend, React and TypeScript frontend, load-balanced AWS infrastructure, and CI/CD, working with the internal team and contractors on parts of the implementation.

Result
Consolidated 8 systems onto one multi-tenant platform, retired 3 servers, reduced redundant maintenance and infrastructure cost, and completed the migration with zero downtime. The platform supports more than 50 million product records and thousands of daily requests.

LaravelReactTypeScriptMantineREST APIsJWTOAuthAWSCloudFrontCI/CDGitHub Actions

Outcome 02

Built a self-service product from zero to one

Turned recurring support requests into a product opportunity, defining and launching a self-service portal that gave clients direct control over campaign management and reporting.

Business problemClients relied on support staff for routine campaign changes and could not directly access performance data. This created delays for customers, repetitive operational work, and a support model that would become more expensive as the client base grew.

What I didUsed client calls, site visits, and support patterns to understand the needs of client users, account teams, and support staff. Reframed the issue from a support-capacity problem into a self-service product opportunity, then defined the product vision, business case, MVP, roadmap, user workflows, and initial success criteria. Prioritized campaign management and reporting as the core release, secured CEO and executive approval, and led delivery with one other developer from requirements and architecture through testing and rollout. Stayed hands-on where needed and extended the mobile apps to support the new customer experience.

Result
Launched the portal and additional capabilities in about 6 months, replacing recurring support-dependent workflows with direct client self-service. Improved customer access to campaign controls and performance data while creating a more scalable operating model. The related AWS migration also reduced infrastructure costs by more than $7,000 per month.

Product DiscoveryCustomer ResearchProblem DefinitionBusiness CaseMVP DefinitionRoadmappingRequirementsAWSREST APIsiOSAndroid

Outcome 03

Reduced a day-long reporting process to about 10 minutes

Turned a client request for report automation into a scalable reporting product used by at least 50 product managers, then extended it to identify underserved vehicle segments.

Business problemAt least 50 product managers spent nearly a full day preparing recurring reports, followed by additional work from the content team. The existing process was slow, manual, and difficult to scale as more data and historical reports accumulated.

What I didWorked with the client to understand the reporting workflow, required outputs, users, and performance constraints. Defined the product scope, specification, success criteria, delivery plan, and technical approach, then secured approval and led a small team through implementation. Designed the system to ingest and standardize incoming data, generate large reports without overwhelming the application, and retain historical imports and reports without slowing current operations. After delivering the original automation, identified an opportunity to use the same data to compare product coverage with vehicle population and show where the client was underserved.

Result
Reduced report generation from nearly a full day to about 10 minutes for at least 50 product managers, reduced follow-on manual work for the content team, and created a new coverage analysis capability beyond the original request.

Product DiscoveryRequirementsRoadmappingETLMySQLAWS AthenaAmazon S3ParquetAPIsReact

How I work

From customer problem to shipped system

Start with the customer

Who's the customer, how will they actually use it, and why does this need to exist at all, before any spec gets written.

Make the tradeoffs explicit

Choose an approach that fits the team, budget, and risk tolerance, and lay out what you're trading off, not just what you're building.

Get people on board

Turn the plan into something leadership and stakeholders can say yes to, whether that's a CEO and investors or an engineering team.

Build it, in whatever form the problem needs

Solo when that's the fastest path, with a small team when it needs more hands, or handed off entirely when that's the right call, and technical enough to know the difference.

Experience

Independent Product & Technology Consultant2025-Present

Builds AI prototypes, modernizes client applications, and advises on product and architecture decisions. Recent work includes Bedrock-based AI tools, ETL automation, multi-tenant Laravel architecture, and React platform modernization.

Senior Software Engineer, Harbor Compliance2024-2025

Solved platform-level data, integration, migration, and security problems for a government compliance SaaS product, including a database fix that avoided a $3,000 monthly Azure upgrade and reduced recurring support issues.

Technical Product Manager, dPivot2018-2024

Owned product and technical direction for a data and media SaaS platform, from consolidating 8 systems into one multi-tenant platform to delivering custom client products, automated reporting, and scalable infrastructure.

Head of Technology, Trust Payments / Mobilize Systems2014-2018

Led product and technology initiatives for a loyalty SaaS platform, including securing executive backing for a self-service client portal, delivering it with a small team in about 6 months, and migrating the platform from a legacy datacenter to AWS.

Earlier Experience: Apple, BigMachines, and Startups

Worked across enterprise systems, product delivery, client engagements, data integration, reporting, and education technology, combining technical implementation with stakeholder and executive communication.

The roles where I do my best work

I do my best work when there is a real problem, no obvious answer, and someone needs to understand both the customer and the system well enough to decide what should happen next.

I fit best between product, architecture, and delivery. That means working out what should be built, making the technical decisions, and staying involved until it works in production.

Get in touchrobert@entwistle.tv