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Tim Gunter

Tim Gunter

Chief Technology Officer

Summary

Technology leader and systems-thinking CTO with a deep background in software architecture and operations. I've led engineering organizations of approximately 300 people, delivered multi-team eight-figure engagements, and scaled a SaaS business from $0 to $10M ARR that culminated in acquisition.

I stay hands-on technically while leading at scale--building automation, observability, and resilient multi-cloud infrastructure that cuts operational cost and human toil without sacrificing delivery speed.

I am a force of nature when surrounded by other leaders with a shared vision and focused on a goal I believe in.

Skills

Strategy
Culture
Operational Innovation
Customer Experience
Executive Leadership
Communication
Software Engineering
Solution Architecture
  • Strategy
  • Culture
  • Operational Innovation
  • Customer Experience
  • Executive Leadership
  • Communication
  • Software Engineering
  • Solution Architecture

Experience

Vice President of Engineering

.Monks, Remote

Jul 2024 - Present

Monks (formerly TheoremOne and Formula.Monks) tackles ambitious, convoluted, and scary software engineering challenges on behalf of large organizations that aren't nimble enough to go it alone.

Stepped into global leadership of a 300-person engineering org distributed across North America, Latin America, and EMEA during extreme organizational volatility following a predecessor's exit. Tasked with stabilizing 30+ concurrent projects while pivoting toward an AI-native service model. Reduced turnover through radical transparency and data-driven resource management.

  • Resource Arbitrage & Product Innovation: Architected and delivered LiveVision, an AI-powered real-time video processing platform, by putting "bench" engineering resources to work and securing non-traditional Capex funding. Validated the architecture via a live CES 2026 Foundry demo and an invited session at NVIDIA GTC 2026.
  • Fiscal Discipline & Staffing Automation: Engineered a data-driven staffing and margin calculator to replace "spreadsheets and whispers." Automated the generation of finance-ready "justification snippets," forcing architectural and budgetary alignment between Sales and Delivery.
  • Organizational Stabilization: Assumed leadership of a globally distributed 300-person engineering org spanning NA, LATAM, and EMEA during extreme corporate volatility. Maintained 90%+ retention of critical SMEs through radical transparency and the deployment of a searchable "Skillbased" talent database.
  • Revenue-Focused SME Program: Stood up a pre-sales Subject Matter Expert (SME) program, giving the sales team direct access to deep technical authority to compress sales cycles and secure high-complexity Enterprise deals.

Director of Engineering

.Monks, Remote

Feb 2022 - Jul 2024

Exercised senior technical authority over a major account group, overseeing the engineering execution of high-complexity, multi-team engagements.

  • High-Stakes Delivery: Led the successful execution of multiple 8-figure, multi-team projects. Managed end-to-end delivery including technical staffing, performance management, and strict budgetary control.
  • Trust-Based Pre-Sales: Established immediate client confidence in high-pressure pre-sales environments, translating Monks' technical capabilities into defensible delivery roadmaps for Enterprise prospects.
  • Engagement Orchestration: Structured and staffed high-performing delivery teams across multiple time zones and cultures for ongoing client projects, maintaining technical continuity and keeping delivery aligned with business goals.
  • Operational Tooling: Iterated on internal engagement management tools to increase reporting accuracy and improve project sightlines, so teams could catch risks earlier.

Global Platform Leader

Higher Logic, Remote

May 2021 - Jan 2022

Joined Higher Logic via their acquisition of Vanilla Forums.

Post-acquisition platform lead responsible for the integration of Vanilla Forums into the Higher Logic ecosystem. Audited legacy infrastructure and enforced modern DevOps standards across five global platforms to reduce operational risk and optimize COGS.

  • Modernization of Legacy Debt: Led the transition of a legacy Windows/.NET stack from "artisanal" manual deployments to a versioned, automated blue/green pipeline. Massively increased deployment frequency while reducing human toil and COGS.
  • Architecture De-risking: Initiated the refactoring of a vertically-scaled, 768GB single-point-of-failure database architecture into a horizontally scalable model, regaining technical sovereignty and reducing cloud provider lock-in (AWS).
  • Cultural Export: Served as the technical bridge during the Vanilla acquisition, training legacy staff on modern IaC, observability, and automated deployment paradigms to standardize high-performance engineering across five global platforms.

Chief Operating Officer

Vanilla Forums, Montreal

Sep 2017 - May 2021

Vanilla delivers customized online community software targeted at customer support and brand engagement sectors.

Scaling and Operations lead on the journey from $0 to $10M ARR. Architected the cross-functional organizational infrastructure (HR, InfoSec, CX, and Engineering) required to sustain high growth, eventually leading the organization through a successful, profitable acquisition by Higher Logic.

  • Organizational Scaling ($0 to $10M ARR): Designed and executed the "Human Stack" required for a profitable acquisition, scaling the engineering, CX, and Infosec teams from inception through successful exit.
  • Security as a Sales Lever: Built the Infosec organization from scratch and achieved SOC2 compliance, moving security from a "cost center" to a competitive advantage that unlocked the Fortune 500 market.
  • Infrastructure Sovereignty: Scaled the global footprint from one to four data centers (including EU expansion). Used a private-cloud-first strategy to maintain higher total utilization and lower overhead than industry standard public cloud alternatives.

Vice President of Operations

Vanilla Forums, Montreal

Nov 2013 - Sep 2017

Designed and built the foundational multi-tenant SaaS architecture from the ground up. Executed a strategic move from public to private cloud to reclaim performance margins and reliability, establishing the technical sovereignty that defined Vanilla's market competitiveness.

  • SaaS Foundation Engineering: Conceived, designed, and implemented the multi-tenant SaaS hosting architecture that powered Vanilla's core offering.
  • IaC & Observability: Developed a proprietary agent-based provisioning and monitoring system, establishing a "single pane of glass" observability culture that enabled high-availability across multi-provider and multi-region deployments.

Director of Operations

Vanilla Forums, Montreal

Jul 2012 - Nov 2013

Tasked with transitioning the core open-source product into a multi-tenant SaaS platform while overcoming the performance and reliability limitations of public cloud infrastructure.

  • Cloud Repatriation: Executed the strategic migration from public to private cloud infrastructure to reclaim performance margins and reliability.
  • SaaS Engineering: Engineered the custom production code and tooling required to transform a single-instance open-source codebase into a high-scale, multi-tenant SaaS platform.
  • Support Org Foundation: Established the initial Customer Support team; defined service level objectives (SLOs), hiring criteria, and cultural standards to align technical support with business growth.

Languages

English (Native speaker)Engineer (Native speaker)French (A2)

Certifications

Certified Scrum Master (CSM) - Scrum Alliance Sep 2019
Certified Scrum Product Owner (CSPO) - Scrum Alliance Dec 2019