DinerDaddy: 18 Months of Daily Hands-On POS & SaaS Tech Support
4,000+ hours · Daily engagement · 100+ merchant accounts · L2/L3 Support · SQA · Payments · POS Operations
The Project
DinerDaddy operated a live POS and SaaS ecosystem supporting restaurant merchants, where technical issues could directly affect orders, payments, printers, terminals, inventory, software releases, and daily operations.
Supporting the environment required more than resolving individual tickets. Issues could originate across Android POS applications, payment hardware, peripherals, networking, cloud systems, configuration, transaction workflows, software releases, and third-party integrations.
Over the course of the engagement, I became the go-to technical resource and ultimately took ownership of end-to-end support operations, including complex issues, escalations, operational decisions, and day-to-day technical support.
Scope
For 18 months, I provided daily hands-on technical support and operations, completing 4,000+ hours across 100+ live merchant accounts. The engagement was continuous, with only 2 days off, and included 24/7 weekend coverage toward the latter part of the engagement.
My work covered:
- L2/L3 POS & SaaS support
- Android POS, hardware, printers & peripherals
- ID TECH payment hardware & transaction support
- Network, connectivity & transaction troubleshooting
- POS menu programming & configuration
- Merchant onboarding & deployment
- Pre- and post-release SQA
- DEMO/PROD validation & regression testing
- Production auditing
- Engineering & vendor escalation
- Knowledge Base & technical documentation
- Merchant & employee training
- Team building & technical leadership
- Support workflows & operations
- POS website & product improvements
- Promotional POS & social media content
- 100+ 4K technical tutorials
I tested 61 POS release cycles, identifying 68 issues across DEMO and PROD, with 32 formally reported or escalated to Development.
I also completed 3,000+ production audits, reviewing transactions, payments, taxes, tips, discounts, voids, settlements, and terminal closures.
Toward the latter part of the engagement, I handled approximately 75 hours per week, serving as the primary resource for complex technical issues, escalations, support decisions, and day-to-day operations.
Where I Made the Difference
I connected merchants, frontline support, Engineering, vendors, and the product team, allowing issues to be investigated and resolved beyond the initial ticket.
Rather than treating support as isolated incidents, I worked across the people, processes, product, and technology behind the operation.
This included team building, technical leadership, training, workflow improvements, escalations, documentation, release validation, production investigations, and feeding recurring technical findings back into the product.
I also contributed to POS website and product improvements, using real-world merchant issues to identify technical problems and improvement opportunities.
Beyond technical operations, I produced hundreds of social media and promotional content pieces, including promotional POS content.
I also worked with my team to produce 100+ 4K technical tutorials, including a video that became the opening video on the DinerDaddy website homepage.
The engagement evolved into broader ownership across support operations, QA, POS, payments, production, documentation, team leadership, product improvement, and content.
Impact
Over 18 months and 4,000+ hours, I became a trusted technical resource for a live POS/SaaS ecosystem supporting 100+ merchant accounts.
Key outcomes included:
- 61 POS release cycles tested
- 68 SQA issues identified
- 32 issues formally reported/escalated to Development
- 3,000+ production audits completed
- 150+ Knowledge Base articles created
- 100+ 4K technical tutorials produced with the team
- Hundreds of social media & promotional content pieces created
- ~75 hours/week toward the latter part of the engagement
- End-to-end support operations ownership
- Team building & technical leadership
- POS website & product improvements
- DinerDaddy homepage opening video produced
The engagement evolved from hands-on technical support into end-to-end ownership across support operations, QA, POS, payments, production, documentation, team leadership, product improvement, and content.