Chris DiPesa
Experienced Technology Leader | Cloud Strategy | Digital Transformation | DevOps Excellence | Engineering Leadership | Certified AI Transformational Leader (CAITL)
Danvers,MA
Summary
Accomplished technology executive with over 20 years of leadership in DevOps, Site Reliability Engineering (SRE), Platform Engineering, and Cloud Technology. Proven leadership and expertise in driving digital transformation, optimizing cloud-based products, and building high-performing teams. Proficiently aligning technology strategies with business goals to deliver scalable, secure, and highly available platforms. Focused on transformational leadership in a senior executive role, such as VP or Director of DevOps, SRE, or Cloud Engineering, to unify operational excellence with strategic business objectives and innovation.
Overview
19
19
years of professional experience
7
7
years of post-secondary education
8
8
Certificates
Education
MBA - High Tech Management & Innovation Entrepreneurship
Northeastern University
Boston, MA 10.2014 - 12.2016
Bachelor of Arts - MIS & Marketing
Northeastern University
Boston, MA 09.1998 - 06.2003
Work History
Director of Site Reliability Engineering & Data
Stord
12.2023 - Current
- Increased system reliability by 25% through implementation of SRE best practices, including automation, SLIs, and SLOs, resulting in significant uptime improvement.
- Enhanced data pipeline performance by 30% by leading cross-functional collaboration between SRE and Data teams, reducing incident frequency and impact.
- Cut cloud and software licensing costs by 50% through FinOps optimization and strategic resource allocation.
- Spearheaded digital transformation by integrating AI technologies into SDLC, boosting efficiency and reducing manual effort by 35%.
- Improved speed to market by 20% through strategic planning and leadership in platform engineering modernization, delivering robust, scalable CI/CD pipelines.
- Orchestrated comprehensive, rapid migration of acquisition platform and IT technologies, leading all cross-functional team efforts to successfully complete project within 60 day deadline.
Vice President of Infrastructure
Priority Technology Holdings
08.2023 - 11.2023
- Directed global team of 70+ engineers, optimizing operational efficiency across US and India.
- Accountable for annual budgets of up to $25M and for developing multi-year long-range financial and resource plans.
- Managed $12M cloud budget and financial forecasting that ensured fiscal responsibility and maximized return on investments to support strategic goals.
- Led the Cloud Center of Excellence (CCoE) transformation, fostering a value- driven, customer-obsessed culture that significantly enhanced organizational agility, innovation, and cloud adoption strategies.
- Successfully led PCI-compliant implementation of AWS Network Firewall, enhancing cybersecurity and compliance.
- Executed product delivery modernization leveraging Kubernetes, ArgoCD, and GitOps, resulting in increased productivity, faster feedback, and improved experimentation.
Director of Engineering DevOps & SRE
Plastiq
05.2022 - 08.2023
- Achieved 25% improvement in developer productivity by implementing advanced toolchains, workflows, and self-service capabilities.
- Reduced AWS expenses by 20% through strategic cloud cost optimization and favorable Enterprise Discount Program (EDP) negotiations.
- Directed cross-functional, large-scale datacenter migration, effectively closing 2 datacenters in 6 months.
- Engineered SOC 2 and PCI-DSS compliance programs, ensuring all AWS environments and systems adhered to rigorous standards.
Sr Engineering Manager Infrastructure & DevOps
Plastiq
03.2019 - 05.2022
- Accelerated time to market by optimizing CI/CD pipelines, improving product team velocity and throughput by effectively reducing build and lead times by 25%.
- Reduced AWS costs by 44% through comprehensive cost optimization strategies, driving financial efficiency.
- Directed cross-functional teams in delivering high-quality software products, ensuring rapid and reliable deployment.
- Architected strategic and tactical BCP/DR plans and runbooks for hybrid cloud environments.
Manager Cloud DevOps
Homesite Insurance
12.2018 - 03.2019
- Managed cloud-based applications and infrastructure, ensuring 99.99% uptime and performance reliability.
- Led cloud migration and digital transformation initiatives, enhancing operational efficiency by 35% through automation and process optimization.
- Strategic and technical leadership focused on innovation, operational excellence, and service-oriented support for all cloud-based applications and resources.
Cloud Engineering Manager
Enel X
10.2017 - 11.2018
- Improved system reliability by 30% through implementation of Infrastructure as Code (IaC) and cloud-native architectures.
- Reduced operational expenses by 20% by optimizing cloud costs through continuous monitoring and management.
- Led migration of legacy systems to cloud-native architectures, resulting in improved agility and scalability.
Principal Cloud Operations Engineer
EnerNOC, Inc.
01.2016 - 10.2017
- Championed adoption of containerization and serverless architectures, increasing operational efficiency by 40%.
- Accelerated development cycles by 50% through introduction of automated testing and infrastructure as code (IaC).
- Designed and implemented robust disaster recovery plan, reducing RTO (Recovery Time Objective) and RPO (Recovery Point Objective) to under 1 hour.
- Automated routine cloud operations tasks using scripting (Python, Bash) and infrastructure as code, reducing manual intervention by 25%.
Senior Cloud Operations Engineer
EnerNOC, Inc.
08.2014 - 01.2016
- Spearheaded design and implementation of scalable and resilient cloud architectures on AWS, ensuring high availability and performance.
- Introduced and optimized CI/CD pipelines significantly reducing deployment times and increasing release frequency by 50%.
- Collaborated with senior leadership to define cloud strategy and roadmap, aligning technology initiatives with business goals to drive digital transformation.
Senior Linux Engineer
EnerNOC, Inc.
01.2013 - 08.2014
Linux Administrator II
EnerNOC, Inc.
09.2011 - 01.2013
Server Analyst
Osram Sylvania
04.2011 - 09.2011
Systems Administrator
Flipkey
06.2009 - 04.2011
Network Engineer
Euro RSCG Edge
02.2008 - 06.2009
Systems Analyst II
MA Department of Revenue
04.2005 - 02.2008
Certification
AWS Certified Solutions Architect – Associate
Skills
Cloud Strategy
DevOps Leadership
CI/CD & Automation
Kubernetes
Platform Engineering
FinOps
DevSecOps
Cloud Cost Optimization
Containerization
SRE Leadership
Digital Transformation
Information Security
AI
Machine Learning
Incident Response
Disaster Recovery
Business Continuity Planning
Vendor Management
Stakeholder Management
Governance, Risk & Compliance
Work Availability
monday
tuesday
wednesday
thursday
friday
saturday
sunday
morning
afternoon
evening
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Projects
Fractional CTO / Advisor, Giv
- Developed and executing on 2-year platform and functionality scaling plan, expanding team from 4 to 15 employees.
- Co-led developing growth and innovation plan for leading SaaS product launch (Q1 2024) to $500k ARR in 2024.
- Spearheaded data driven analysis for product market pivot and complete overhaul of flagship SaaS product.
- Actively involved in VC and angel investor pitch meetings.
- Developed coherent and evolved application architectures that promote speed to market and drive development efficiencies.
- Set technological vision and long-term company strategy that translates into achievable road map.
- Roadmap and technical R&D for product integrations with Hubspot, Salesloft and Outreach.
Work Preference
Work Type
Full TimeLocation Preference
RemoteHybridImportant To Me
Work-life balanceFlexible work hoursQuote
“When you arise in the morning, think of what a precious privilege it is to be alive - to breathe, to think, to enjoy, to love.”
Marcus Aurelius, Meditations
Accomplishments
- Orchestrated comprehensive, rapid migration of acquisition platform and IT technologies, leading all cross-functional team efforts to successfully complete project within 60 day deadline.
- Spearheaded digital transformation by integrating AI technologies into SDLC, boosting efficiency and reducing manual effort by 35%.
- Directed cross-functional, large-scale datacenter migration, effectively closing 2 datacenters in 6 months.
- Engineered SOC 2 and PCI-DSS compliance programs, ensuring all AWS environments and systems adhered to rigorous standards.
Timeline
CERTIFIED AI TRANSFORMATION LEADER (CAITL™)
06-2024
CERTIFIED AI TRANSFORMATION LEADER (CAITLTM)
06-2024
AWS Certified Advanced Networking - Specialty
04-2024
Director of Site Reliability Engineering & Data
Stord
12.2023 - Current
Vice President of Infrastructure
Priority Technology Holdings
08.2023 - 11.2023
AWS Certified SysOps Administrator - Associate
07-2023
AWS Certified DevOps Engineer - Professional
07-2023
Director of Engineering DevOps & SRE
Plastiq
05.2022 - 08.2023
AWS Certified Security – Specialty
03-2021
AWS Certified Solutions Architect – Associate
07-2020
AWS Certified Solutions Architect – Professional
07-2020
Sr Engineering Manager Infrastructure & DevOps
Plastiq
03.2019 - 05.2022
Manager Cloud DevOps
Homesite Insurance
12.2018 - 03.2019
Cloud Engineering Manager
Enel X
10.2017 - 11.2018
Principal Cloud Operations Engineer
EnerNOC, Inc.
01.2016 - 10.2017
MBA - High Tech Management & Innovation Entrepreneurship
Northeastern University
10.2014 - 12.2016
Senior Cloud Operations Engineer
EnerNOC, Inc.
08.2014 - 01.2016
Senior Linux Engineer
EnerNOC, Inc.
01.2013 - 08.2014
Linux Administrator II
EnerNOC, Inc.
09.2011 - 01.2013
Server Analyst
Osram Sylvania
04.2011 - 09.2011
Systems Administrator
Flipkey
06.2009 - 04.2011
Network Engineer
Euro RSCG Edge
02.2008 - 06.2009
Systems Analyst II
MA Department of Revenue
04.2005 - 02.2008
Bachelor of Arts - MIS & Marketing
Northeastern University
09.1998 - 06.2003