Peter Chestna — CEO
TL;DR: I help organizations turn complex engineering and application security challenges into clear priorities, durable platforms, and measurable outcomes. I’m an executive product, engineering, and application security leader with 20+ years of experience operating at the intersection of how software is built, how risk is managed, and how technology creates real-world business outcomes. My career spans hands-on engineering, engineering leadership, enterprise application security, and customer-facing executive roles. I’ve worked on both sides of the market—as an enterprise buyer and as a security product leader—which gives me a grounded perspective on what actually works in practice versus what sounds good in theory. I’m most effective in complex, high-friction environments where clarity, prioritization, and trust are essential. I specialize in translating technical complexity and risk into clear, defensible, outcome-driven priorities that teams can execute against—whether shaping product and platform direction, stabilizing organizations under stress, or guiding customers through difficult inflection points. Highlights from my work include: Leading a company-defining platform transformation that halted all other development, resulted in a patented innovation, and permanently shifted market positioning Turning around a large enterprise application security organization securing ~2,000 critical applications in a highly regulated environment Serving as Field CTO / Field CISO and senior advisor to enterprise customers, supporting adoption, retention, and growth Driving engineering and delivery transformations (Waterfall → Agile → DevOps → Kanban) that dramatically improved speed, predictability, and customer satisfaction I’m particularly interested in roles where product judgment, engineering execution, and customer reality must align—including VP Engineering, VP Cybersecurity, and CPO-adjacent leadership roles in application security, developer tooling, and infrastructure platforms. If you’re building, scaling, or rethinking a product or organization in this space, I’m always open to thoughtful conversations.
Stackforce AI infers this person is a SaaS and Application Security expert with extensive leadership experience.
Location: Boston, MA, USA
Experience: 34 yrs 11 mos
Skills
- Advisory & Consulting
- Devsecops
- Application Security
- Product Adoption And Retention
- Executive Leadership
- Customer Experience
- Product Strategy
- Software Engineering
Career Highlights
- Led a company-defining platform transformation.
- Transformed a large enterprise application security organization.
- Served as senior advisor to enterprise customers.
Work Experience
Checkmarx
CISO of North America/AppSec Practitioner in Residence (4 yrs 7 mos)
BMO Financial Group
Enterprise Head of Application Security (2 yrs 4 mos)
Multiple Organizations
Advisory Board Member | Investor | Contributing Editor (8 yrs 8 mos)
Veracode
Field CTO/Director of Developer Engagement (3 yrs)
Director, Platform Engineering (4 yrs 7 mos)
Principal Software Engineer (5 yrs)
Ab Initio
Consulting Engineer (2 yrs 1 mo)
HighGround Systems
Consulting Engineer (8 yrs 5 mos)
FlashPoint
Sr. Software Engineer (2 yrs)
Sytron
Software Engineer (2 yrs 8 mos)
Education
B.S. at Worcester Polytechnic Institute