Benjamin Pessin
Creative Systems Director, Waterside Group
AI adoption & enablement across 25+ businesses
Boston, MA · ben.pessin@gmail.com · LinkedIn
I'm the Creative Systems Director at Waterside Group, a holdings company with 25+ businesses across marine, hospitality, real estate, construction, and recreation. The role has grown into leading AI adoption for the whole portfolio.
I sit with our sales, accounting, construction, marketing, and HR teams and build the tools they use every day: LLM assistants, AI agents, knowledge bases, and internal platforms. I prototype hands-on in agentic coding and AI work environments (Claude Code, Claude API), then scale what works through the 12-engineer team I manage, with the permissions, safeguards, and cost visibility to ship generative AI responsibly to non-engineering teams.
Creative Systems Director · Waterside Group
Oct 2025 - Present · Boston, MA- Lead AI rollout across the portfolio: sit with each department, earn their trust, map how work actually gets done, ship AI where it earns its keep, then train the teams who use it.
- Manage a 12-engineer team building across the portfolio, and run onboarding & mentorship for Northeastern co-op software engineers, growing internal AI capability, not just internal tools.
- Shipped 3 production LLM assistants used daily by non-engineering staff: a dealership ops assistant (Q&A over live inventory & financials, AI listing backfill), a company-wide RAG assistant over group knowledge, and a semantic-search sales chat.
- Built an AI-agent CRM (Agentic Portal): configurable agents, automation engine, DOCX/PDF/CSV knowledge-base ingestion, and run-history observability for cost and behavior tracking on every agent execution.
- Set the portfolio's rules for AI use (role-based permissions, Postgres row-level security, human-in-the-loop review on financial workflows) and advise leadership on tool evaluation, cost, and risk.
- Replaced legacy spreadsheet pipelines with governed, purpose-built software; for example, migrating field sales apps off Excel/SharePoint onto a typed, permissioned Supabase backend.
Lead Graphic Designer · Waterside Group
May 2024 - Oct 2025 · Falmouth, MA- Shaped visual identity and marketing strategy across the group's real estate, lifestyle, and entertainment brands while beginning the internal-tools buildout: shipped the first dealership operations platform and its native SwiftUI iOS companion, introducing AI-assisted workflows to a non-technical sales team.
Marketing Associate · Waterside Group
May 2023 - May 2024 · Falmouth, MA- Drove marketing execution and content across the portfolio; firsthand exposure to the manual workflows I later replaced with software.
Marketing Intern · Waterside Group (Longfellow Design Build)
May 2022 - May 2023 · Falmouth, MA- Joined as the group began acquiring businesses: created logos, brand graphics, and launch creative for incoming companies, plus social and campaign content.
Earlier: Media Production Intern, PBS, Boston (2019)