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Michael

Michael Whitehead

Owner at Onepunch Technologies Inc.

Michael Whitehead is a highly skilled technical-first leader with extensive experience designing and developing complex systems across diverse industries, including digital certificates, finance, telecom and hospitality. Proven track record of driving business value by building scalable, efficient, and secure infrastructure solutions. Expertise includes hiring and building elite teams, modernizing legacy systems, automating the hard stuff, and improving system reliability. Combines technical fluency with organizational leadership, bridging the gap between vision and execution to prevent the misalignments that derail complex software projects.

Strategic
Influential
Technical

Leadership Philosophy

I believe great engineering leadership combines technical understanding with empathy, clarity, and accountability. Projects fail when leaders lose touch with the work; success comes when leadership understands the system — both human and technical — deeply enough to guide it with purpose.

I lead through principles, not ego. I believe in transparency, psychological safety, and the discipline of correctness. When leaders own mistakes publicly and communicate openly, teams learn faster and trust more — and that trust compounds into speed, quality, and innovation.

Build Elite Teams

Find exceptional talent, then create the environment where they can win. Empower engineers with autonomy, clarity, and purpose. Elite teams thrive on high standards, mutual respect, and visible success.
Technical Strategy & Architecture Vision

Define how systems evolve and ensure architectural decisions reinforce long-term business goals. Balance hands-on technical engagement with strategic oversight to maintain technical health and organizational resilience. Drive competitive differentiation through superior engineering execution.
Talent Development

Identify high-potential engineers and grow them into leaders. Coach EMs, TLs, and senior ICs to make sound technical and human decisions independently — reducing single points of failure and scaling impact across the org.
Cross-Functional Alignment

Partner closely with Product, Design, and Operations to deliver outcomes, not just outputs. Translate between executive priorities and technical reality to ensure teams build the right thing, the right way.
Execution & Process Excellence

Focus relentlessly on prioritization, delivery management, and metrics. Improve systems continuously — from agile delivery and CI/CD pipelines to incident response and QA — to balance speed, quality, and sustainability.
Conflict & Risk Management

Address disagreements directly and constructively. Anticipate technical debt, compliance risks, and capacity issues before they become problems. Create structures where difficult conversations are safe and productive.
Integrity & Authentic Leadership

Model transparency, humility, and self-awareness. Lead by example. Make hard calls with empathy and honesty. A leader’s credibility comes not from authority, but from consistency and authenticity.

Experience

1
Digital Certificates and Managed PKI

Challenge

Scaling Securely

The company needed to design and deliver a modern, highly scalable Public Key Infrastructure (PKI) platform that could meet aggressive SLAs and stringent CA/B Forum compliance requirements, while supporting enterprise growth.

Strategy and Leadership
  • Defined the technical vision and architecture strategy for a next-generation PKI platform aligned with revenue and compliance goals.
  • Bridged executive strategy with engineering execution through deep technical understanding and pragmatic tradeoff decisions.
  • Partnered with Operations and Compliance to embed auditability and security directly into development and deployment workflows.
  • Introduced architectural principles that simplified systems, reduced engineering overhead, and ensured provable correctness before production.
Impact
  • Scaled to 200M+ certificates per year while achieving full CA/B Forum compliance and ACME protocol support.
  • Automated 90% of audit and compliance overhead, freeing engineering capacity.
  • Created new enterprise product offerings, unlocking ARR growth and reducing $800K/year in infrastructure costs.
  • Established a continuous delivery pipeline with minutes-to-production deployments and end-to-end test coverage
Challenge

Sustaining Legacy Revenue Systems

The company’s legacy PKI platform—over 20 years old—remained a critical revenue driver but required modernization to support compliance and security without service disruption.

Strategy and Leadership
  • Led a cross-functional initiative to stabilize and modernize legacy systems while maintaining business continuity.
  • Guided teams to containerize 20+ services, introducing zero-downtime deployment pipelines and modern DevOps practices.
  • Architected a shared testing and QA environment to eliminate miscommunication between engineering and operations.
  • Championed secure-by-design practices across legacy codebases, improving audit readiness and reducing incident risk.
Impact
  • 10x performance improvement across legacy services.
  • 95–100% reduction in deployment-related incidents.
  • Cut time from feature completion to production from weeks to hours.
  • Fully migrated ~20 apps and repositories to modern development workflows, enabling sustainable long-term maintenance.
OptConnect

Challenge

Ensuring Reliability Across a Distributed Network

OptConnect provides managed cellular connectivity for hundreds of thousands of remote devices. Contractually bound to deliver high uptime, the company faced escalating operational costs from field service dispatches (“truck rolls”) whenever devices failed in remote regions. A new strategy was needed to improve remote administration, reliability, and observability on high-latency cellular networks.

Strategy and Leadership
  • Established and led a Site Reliability Engineering (SRE) organization, defining its charter, structure, and key reliability metrics.
  • Aligned infrastructure modernization with uptime SLAs and customer satisfaction goals, partnering directly with executive and operations leadership.
  • Empowered EMs and TLs with frameworks emphasizing correctness, simplicity, and long-term maintainability.
  • Instituted architectural reviews and early technical validation to reduce project failure risk and improve delivery predictability.
  • Guided teams through Kubernetes adoption, zero-downtime deployments, and shared observability practices to standardize reliability across services.
Impact
  • Increased uptime of core services to 99.99%, drastically reducing costly field visits.
  • Improved remote firmware update success rate by 90%, lowering churn and operational overhead.
  • Elevated reliability culture across product and operations teams, improving trust and accountability organization-wide.
Challenge

Accelerating Fulfillment Through Firmware Innovation

Rapid sales growth exposed limitations in the firmware flashing process. Devices shipped with outdated firmware from manufacturing partners overseas, and attempts to flash multiple devices concurrently caused instability. A redesign was needed to scale throughput and eliminate errors.

Strategy and Leadership
  • Defined and executed the firmware delivery modernization strategy, leading cross-functional engineering and network teams.
  • Architected and engineered a new firmware flashing system, enabling parallel, reliable updates over both wired and wireless connections—previously believed impossible.
  • Guided the rewrite of firmware to reduce size, improve reliability, and simplify maintenance.
Impact
  • Fulfillment throughput improved by 1000%, enabling operations to scale with revenue growth.
  • Firmware size reduced by 85%, and startup times accelerated 12x.
  • Achieved 100% elimination of failed flashes, ensuring devices shipped ready for customers and commissions were recognized on time.
2
3
Omnivore

Acquired by Olo

Challenge

Breaking Vendor Lock-In

Restaurant chains were trapped in proprietary point-of-sale (POS) ecosystems, making menu updates across locations time-consuming and costly. Each vendor had unique, incompatible APIs, leading to fragmented data and operational inefficiency.

Strategy and Leadership
  • Defined the technical vision for a universal POS integration layer that would decouple restaurants from vendor lock-in.
  • Architected a bi-directional menu synchronization system, designed to handle conflicting data and schema differences across vendors.
  • Led teams in building resilient APIs and reconciliation mechanisms that automated conflict resolution and maintained data consistency.
  • Advocated for simplicity and correctness as design principles, enabling teams to build flexible systems that scaled across diverse POS technologies.
Impact
  • Empowered restaurants to manage menus centrally across multiple vendors and brands.
  • Saved millions annually in menu management and configuration costs.
  • Eliminated dependency on individual POS providers, expanding addressable market and accelerating customer onboarding.
Challenge

Expanding Restaurant Reach

Most POS systems lacked integration with modern delivery platforms like UberEats, DoorDash, and Grubhub—forcing restaurants to manage orders manually via phones and tablets, creating operational chaos and missed revenue opportunities.

Strategy and Leadership
  • Designed and led the development of a unified delivery integration framework connecting multiple third-party platforms through a single API.
  • Architected service interfaces that normalized disparate delivery workflows and ensured data integrity across providers.
Impact
  • Enabled restaurants to retire dozens of ad-hoc devices and unify all delivery orders directly into their POS systems.
  • Improved order accuracy and delivery turnaround, enhancing customer satisfaction.
  • Directly contributed to Omnivore’s acquisition by Olo, whose platform expanded nationwide using this integration technology.
BigSquid

Acquired by Qlik

Challenge

Making Enterprise Data Useful

Enterprises had massive datasets but lacked the expertise and infrastructure to transform them into actionable insights. Training predictive models was slow, costly, and computationally intensive—often requiring dedicated data science teams and prohibitive compute resources.

Strategy and Leadership
Automate a data scientist
  • Defined and executed the technical vision to “automate a data scientist” — delivering predictive analytics to non-technical business users.
  • Instrumental in securing venture funding by articulating the market opportunity, competitive differentiation, and architectural feasibility to investors; directly influenced pitch materials and technical due diligence.
  • Architected a scalable data pipeline supporting diverse sources such as BI tools, databases, and spreadsheets, enabling self-service analytics.
  • Engineered data storage and compute layers optimized for both high-speed querying and low-cost scalability.
  • Encoded data science expertise into an automated model training engine capable of tuning hyperparameters, validating models, and detecting data quality issues.
Impact
  • Delivered real-time predictive insights as customer data evolved.
  • Achieved linear infrastructure scaling relative to customer growth, reducing operational cost per client.
  • Maintained constant compute costs per customer, even for large datasets.
  • Enabled non-technical users to generate and deploy predictive models autonomously, accelerating decision-making across industries.
  • Vision and prototype were key catalysts in securing venture funding, establishing the company’s market credibility and fueling growth leading to acquisition by Qlik.
4
5
Investment Bank

Challenge

Functional Programming Workshop for Financial Systems

A quantitative engineering team struggled with the reliability and maintainability of complex C/C++ libraries and services used for financial analytics. Leadership sought to explore safer, more expressive languages — inspired by peers in other institutions adopting Rust and Haskell — but lacked the internal expertise to evaluate or apply them effectively.

Strategy and Leadership
  • Designed and led a multi-day Haskell workshop for quantitative and software engineers, focused on bridging functional programming theory with practical finance applications.
  • Translated advanced engineering tradeoffs into clear business terms, helping senior technologists and managers understand where Haskell could reduce defects and operational risk.
  • Guided participants through hands-on API and service development, including secure authentication to financial data sources and end-to-end analysis pipelines — all implemented in Haskell.
  • Taught key design abstractions (Monoids, Functors, Monads) and demonstrated how they eliminate entire categories of bugs while accelerating development.
  • Mentored team on how to integrate Haskell with existing C/C++ and Rust systems via foreign function interfaces.
Impact
  • Equipped the team to make informed, data-driven decisions about functional programming adoption.
  • Improved the team’s ability to evaluate language and architecture tradeoffs aligned with business needs.
  • Sparked organizational momentum toward safer, more maintainable systems, with measurable reduction in defect rates on subsequent projects.
O.C. Tanner

Challenge

Accelerating Customer Onboarding

O.C. Tanner’s recognition platform was highly customized for each enterprise client. Implementing a new customer required months of engineering effort and manual configuration, delaying revenue recognition and creating friction between sales and delivery teams.

Strategy and Leadership
  • Defined and led the technical vision for a configuration engine that automated customer setup while preserving full branding flexibility.
  • Applied advanced type theory and functional programming principles to guarantee correctness and prevent configuration errors at compile-time.
  • Guided engineering teams through adoption of extreme-programming and advanced language design practices to raise code quality and maintainability.
  • Partnered with platform teams to decouple the product from legacy Oracle dependencies, paving the way for a modern cloud-native architecture.
Impact
  • Reduced customer implementation time from months to days.
  • Eliminated configuration-related defects, improving reliability and customer satisfaction.
  • Freed engineering capacity to focus on feature innovation instead of manual setup.
  • Advanced the company’s long-term vision toward a modular, database-independent SaaS platform.
6
7
SoFi

Challenge

Automating Regulated Financial Workflows

SoFi’s student-loan division needed to integrate with multiple government and banking data sources under strict compliance requirements. Manual data exchange slowed approvals and limited scalability.

Strategy and Leadership
  • Architected secure, automated integrations with external financial systems and government APIs to streamline loan processing.
  • Implemented advanced type-safety and property-based testing frameworks to ensure correctness and regulatory compliance.
  • Partnered with compliance and product teams to translate regulatory constraints into verifiable technical rules.
  • Advocated for “correct-by-construction” design, embedding reliability into every stage of the development lifecycle.
Impact
  • Enabled new lending products and faster go-to-market for regulated financial offerings.
  • Reduced compliance overhead and audit risk through provably correct integrations.
  • Accelerated loan approvals, cutting manual review time and improving customer experience.
Mediaforge

Acquired by Rakuten

Challenge

Delivering Immediate Marketing Intelligence

Mediaforge needed an internal analytics platform to help clients measure and improve ad-spend effectiveness in real time. Existing tools lacked performance, consistency, and accessibility for sales and marketing teams.

Strategy and Leadership
  • Architected and engineered an internal analytics and visualization platform unifying sales, marketing, and ad-creation data.
  • Integrated disparate data sources into a centralized warehouse and designed a purpose-built query engine optimized for ad-spend analysis.
  • Led cross-functional collaboration with marketing leadership to define actionable metrics and intuitive UI workflows.
  • Introduced modern engineering practices and documentation standards, reducing maintenance risk and onboarding time.
Impact
  • Improved query performance for ad-spend analytics by 200%, enabling near-real-time insight.
  • Enhanced sales and marketing productivity through unified, self-service dashboards.
  • Lowered long-term maintenance costs and increased engineering velocity via standardized, documented systems.
  • Contributed to Rakuten’s acquisition of Mediaforge, expanding its global advertising analytics portfolio.
8

Tech Stack Philosophy

My goal is to select technologies that balance correctness, scalability, and simplicity — tools that make it easier to prove software does what it’s supposed to do and to maintain that correctness over time.