Stephen Dolan
Atlanta, GA
CEO of a bootstrapped developer tools company doing millions in revenue and profit annually. Stepped up from COO during a leadership transition, returned the business to growth, and grew ARR 12% YoY with a 9-person remote team. Background spans the full stack — from writing stored procedures in Postgres to leading product, engineering, and go-to-market. Currently building AI-native internal tooling and workflows.
Tuple
Remote pair programming tool for developers who care about quality.
CEO
Took over as CEO during a leadership transition and returned the business to growth, reaching 12% YoY ARR growth to millions in revenue and profit with a 9-person remote team. Built Sherlock, an internal multi-agent system — a concierge agent in Slack routes requests to research agents (via Amp/Open Code + MCPs), ships reports to Notion, and submits PRs to improve its own skills. Migrated PR reviews to incorporate AI assistance. Automated customer intelligence pipelines: support tickets trigger enrichment with call data, usage metrics, and history via Make.com and Zapier.
Interim CEO
Stepped up from COO when the co-founders transitioned out of day-to-day operations. Maintained product velocity, team cohesion, and enterprise relationships through the transition.
Chief Operating Officer
Ran marketing, inbound sales, support, customer success, enterprise renewals, finance, and bookkeeping. Coordinated the product roadmap in Linear across engineering and customer-facing teams.
Chief of Staff
Force multiplier for Tuple's CEO — providing flawless follow-up and execution, growing the team through hiring initiatives, and managing the B2B sales process.
Head of Sales and Success
Brought order to a landscape of untended enterprise customers and leads. Organized the existing book of business and new inbound leads, handling contractual negotiations, legal redlining, and renewal negotiations.
Previous experience
Director of Account Engineeringat MerchLogix
Grew from manager to director of account engineering at a retail analytics SaaS. Led the team responsible for onboarding enterprise customers, managing technical integrations, and bridging customer needs with product development.
Account Engineer / Back End Developerat MerchLogix
Started writing Perl, PHP, and complex SQL against terabytes of PostgreSQL data. Transitioned to account engineering — gathering requirements, implementing configurations, managing integrations, and adapting the product to enterprise retail workflows.
Education
Georgia Institute of Technology — Computer Science
2013 — 2015
Clayton State University
2011 — 2012
Beyond the day job
Dad to two boys. Gardener. I do 1-on-1 productivity coaching, helping professionals build GTD systems that actually stick. Occasional podcast guest — conversations about systems, focus, and building sustainable habits.
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