Vetted Vice Presidents in the Chicago Metro

“Operations leader/advisor focused on rapid, data-driven optimization and scalable org/process design. Has rebuilt internal structures, automated and streamlined customer-journey workflows, and delivered measurable cycle-time improvements (cut onboarding from 90–120 days to under 30). Previously built a new operations team that scaled to over $4M in revenue and frequently mentors non-operations executives using tailored, practical coaching.”

John Ward

Screened

Executive Applications Development & Analytics Leader specializing in enterprise transformation

Chicago, IL30y exp

“Candidate has prior startup experience building systems and has firsthand experience with a venture that lost angel funding. They show thoughtful reflection on why the startup failed—emphasizing unclear success criteria, weak funding planning, and lack of team consensus—and would seek experienced advisors earlier in future ventures.”

“Executive sales leader with 20+ years of experience spanning Director to COO/CSO/founder roles, known for building and rebuilding large sales organizations. Particularly notable for transforming a 357-person GoHealth region into the company's top performer and for creating Rewards Network's first inside sales function after 30 years of field-only selling, producing outsized early results. Brings a rare mix of public sector exposure, national-scale sales leadership, and hands-on operational design across CRM, forecasting, compliance, and manager development.”

“Serverless-focused engineer (5+ years) who has built and deployed AWS Lambda/API Gateway backends with CloudFormation-based IaC and Jenkins-driven CI/CD across dev/staging/prod. Has experience with AWS Glue/OpenSearch data pipelines and emphasizes data correctness via Golden Data automated tests; also modernized a regulated .NET account-confirmation workflow by eliminating an unreliable SMTP email dependency. Based in San Jose, seeking primarily remote work with quarterly travel to Bethesda, MD and targeting $200k base.”

Luke McConnell

Screened ReferencesModerate rec.

Executive product leader specializing in digital products and FinTech

Naperville, IL11y exp

“Product leader with deep experience building and modernizing complex systems in regulated industries, especially banking and logistics. They led a major core banking platform rebuild, introduced AI-driven operational features, and drove a mobile UX change that increased app usage by roughly 200%. Also brings people leadership experience from building a product team from scratch and a personal connection to education through ESL program work and a family background in special education.”