Matt Syp

Founder

Glendale, Arizona, United States25 yrs 1 mo experience

Key Highlights

  • 25 years of experience in software and engineering leadership.
  • Expert in scaling engineering teams and systems for growth-stage companies.
  • Focused on execution, leadership, and architecture under pressure.
Stackforce AI infers this person is a seasoned leader in Engineering Management and Software Development across Healthcare and Fintech industries.

Contact

Skills

Core Skills

Leadership DevelopmentEngineering LeadershipAgile Project ManagementEngineering ManagementSoftware Project Management

Other Skills

Project DeliveryCross-functional Team LeadershipPerformance MetricsPeople ManagementSoftware Architectural DesignSoftware DevelopmentAgile MethodologiesSoftware EngineeringC#.NETKanbanLeadershipAgile Application DevelopmentDatabase DesignWeb Applications

About

I help product and engineering organizations scale when execution starts to feel harder than it should. I have spent 25 years building software and leading engineering teams, including leadership roles at Carvana, Hinge Health, Dutchie and Synapse Health where I worked on scaling engineering teams and systems as companies grew. I work primarily with growth-stage and pre-IPO companies where execution, leadership or architecture start to strain under scale. My work focuses on two areas. Execution and scale I help companies improve how work actually gets done. This includes delivery and reporting systems, process design, technical direction and defining team or domain boundaries that support sustainable growth. Leadership mentorship and coaching I support Engineering Managers, senior ICs and technical leaders with structured mentorship and ongoing coaching focused on decision-making, clarity and execution under pressure. The leadership work exists because I did not receive much support when I transitioned from IC to manager. Everything I offer today is grounded in what I learned through years of trial, refinement and mentoring other leaders across multiple organizations. If your teams are capable but execution feels harder than it should, you are probably seeing patterns like: • Delivery slowing down as more teams get involved • Ownership becoming unclear across systems or domains • Managers spending more time coordinating than leading • Architecture decisions creating friction between teams • Work feeling busy but progress becoming harder to predict These are the kinds of problems I spend most of my time helping organizations solve. You can connect with me here or learn more at mattsyp.com

Experience

25 yrs 1 mo
Total Experience
3 yrs 5 mos
Average Tenure
7 mos
Current Experience

Matt syp consulting

Founder & Principal Advisor

Oct 2025Present · 7 mos · Glendale, Arizona, United States

  • I partner with Series B to Pre-IPO, operations-heavy tech companies to reduce delivery risk and strengthen engineering leadership as they scale.
  • My work focuses on two areas:
  • Organizational Enablement
  • I help leadership clarify ownership, strengthen execution systems and align architecture with team structure. This includes delivery frameworks, reporting models, technical roadmaps and domain boundaries that reduce friction and restore predictable delivery.
  • Leadership Development
  • I provide structured Engineering Manager mentorship and leadership coaching for technical leaders. The focus is durable operating habits, clear decision-making, strong 1:1s and effective performance management that reduce executive escalation.
  • My approach is practical, bounded and focused on making execution predictable rather than heroic.
Leadership DevelopmentProject DeliveryCross-functional Team LeadershipPerformance MetricsEngineering LeadershipPeople Management+4

Synapse health

Sr. Engineering Manager

Nov 2024Oct 2025 · 11 mos · Remote

  • Led engineering for delivery and fulfillment systems supporting Synapse’s healthcare logistics platform.
  • Established engineering quality and observability standards including dashboards, alerts, and improved testing practices
  • Developed a multi-year technical roadmap aligned with company goals for 2025 and 2026
  • Redesigned the order synchronization architecture, improving system resilience and increasing processing throughput by ~10x
  • Developed engineering leaders including a Senior Engineering Manager and multiple engineering managers transitioning into leadership roles
  • Strengthened team ownership and technical decision making through structured coaching and leadership development
  • Reallocated specialized engineering talent to higher priority teams when skill surpluses were identified, improving cross-team delivery without increasing headcount
Engineering LeadershipAgile Project ManagementSoftware EngineeringPeople ManagementC#

Dutchie

Sr. Engineering Manager

Oct 2023Nov 2024 · 1 yr 1 mo · Remote

  • Led engineering for fintech systems supporting Dutchie’s point-of-sale and payment platforms in a rapidly evolving regulatory environment.
  • Led the engineering team responsible for in-store systems including POS hardware, payments, and SaaS register platforms
  • Consolidated multiple teams into a cross-functional group to improve domain coverage and operational resilience
  • Partnered with product and engineering leadership to redesign development processes and ownership models
  • Introduced testing standards, project ownership practices, and database design guidelines later adopted across the organization
  • Restructured Jira workflows across teams to improve visibility and collaboration
  • Led engineering efforts focused on adaptability and operational continuity during third-party payment processing disruptions
C#.NETEngineering ManagementEngineering LeadershipPeople Management

Hinge health

Engineering Manager

Oct 2022Sep 2023 · 11 mos · Remote

  • Led engineering teams within the Care Team Products organization responsible for systems used by coaches and physical therapists delivering care to members.
  • Managed the Member Records engineering team while contributing to broader platform initiatives
  • Partnered with product and design leadership to define the 2023 roadmap
  • Established and led a Design Systems team that created shared UI libraries and development patterns
  • Introduced development processes and technical standards that reduced feature cycle time by ~20%
  • Provided mentorship and leadership coaching to engineering managers across the organization
Agile Project ManagementEngineering ManagementEngineering LeadershipPerformance MetricsKanbanPeople Management

Carvana

3 roles

Senior Engineering Manager

Promoted

Jul 2020May 2022 · 1 yr 10 mos

  • Led the Wholesale Engineering organization responsible for systems supporting Carvana’s wholesale vehicle marketplace.
  • Built a multi-phase headcount roadmap that scaled the organization from one engineer to thirteen
  • Led multiple engineering teams and engineering managers responsible for the wholesale marketplace platform
  • Mentored and coached engineering managers responsible for delivery planning and team performance
  • Partnered with product leadership to define long-term technical vision and execution plans using roadmaps and OKRs
  • Directed architecture and platform design for automation and wholesale marketplace systems
  • Improved engineering execution through planning frameworks and cross-team coordination
  • Led development of marketplace systems that accelerated vehicle processing speed and reduced inventory holding time
Software Project ManagementEngineering ManagementEngineering LeadershipPerformance MetricsLeadershipKanban+2

Engineering Manager

Promoted

Aug 2018Jul 2020 · 1 yr 11 mos

  • Led engineering teams responsible for customer care platform integrations.
  • Established architectural patterns and technical standards across the Customer Care engineering cluster
  • Partnered with product and engineering leadership to define technical roadmaps
  • Mentored engineers through structured coaching and career development
Software Project ManagementEngineering ManagementEngineering LeadershipPerformance MetricsLeadershipKanban+2

Senior Engineer

Jan 2018Aug 2018 · 7 mos

  • Developed internal platforms supporting customer care operations, including a document management service used to support migration away from legacy systems.
Performance Metrics

Foreiq

Lead Developer

Jan 2015Dec 2018 · 3 yrs 11 mos · Phoenix, Arizona Area · On-site

  • Architected and built ForeIQ, a SaaS platform designed to help IT consulting firms improve profitability and resource forecasting.
  • Led all technical decisions for the platform including architecture, technology stack, and cloud infrastructure
  • Designed and built the application from concept through MVP and early production use
  • Established development practices, deployment processes, and system architecture for the platform
  • Partnered with product stakeholders to define features and translate business requirements into technical systems
Software Project ManagementEngineering ManagementPerformance MetricsLeadership

Fuller solutions

Lead Developer

Dec 2014Jan 2018 · 3 yrs 1 mo · Phoenix, Arizona Area

  • Delivered custom software solutions for enterprise clients as a technical lead within a consulting environment.
  • Led architecture and development for multiple client platforms across finance, logistics, and professional services
  • Worked with project managers and stakeholders to translate business requirements into scalable software systems
  • Provided technical leadership for development teams and ensured delivery aligned with project timelines
Software Project ManagementEngineering ManagementLeadership

Rightcare solutions

Senior Software Engineer

Dec 2013Sep 2014 · 9 mos · Horsham, PA

  • Work on an application that is used to reduce 30 day readmission rates in hospitals using C#, MVC, jQuery, Javascript, AngularJS, SQL Server 2012 and Twitter Bootstrap.

Anexinet

Senior Developer

Mar 2013Feb 2014 · 11 mos · Blue Bell, PA

  • Worked as a consultant delivering enterprise software solutions for large client organizations.
  • Architected and developed an enterprise application used to manage and distribute advertising content across a cable provider’s systems
  • Designed system architecture and user interfaces to replace multiple legacy tools with a unified platform
  • Contributed to data integration and reporting systems supporting operational workflows

Indepenent consultant

Senior Software Developer

Aug 2012Mar 2013 · 7 mos · Warrington, PA

  • Delivered custom software solutions for small businesses including CRM systems and third-party integrations.

Active data exchange

Web Application Developer

Dec 2008Aug 2012 · 3 yrs 8 mos · Bethlehem, PA · On-site

  • Developed web-based event management systems used by education and government organizations. Contributed to system architecture and core platform development.

Sypweb designs

Consultant

Jun 2001Dec 2014 · 13 yrs 6 mos

  • A small web design company that I ran to help individuals and small businesses create a web presence with a tight budget.

Sungard public sector

Programmer Analyst

Oct 2000Dec 2008 · 8 yrs 2 mos · Bethlehem, PA · On-site

  • Developed enterprise financial and administrative software used by government agencies and school districts. Designed web applications and integrations supporting accounting, HR, and budgeting systems.

Education

Hatboro Horsham High School

Jan 1992Jan 1996

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