benjamin livingstone
@benjaminlivingstone
I build and sell AI automation solutions that solve operational and legal workflow problems.
Dominican RepublicWhat I'm looking for
At WorkLess, I build and deploy WhatsApp-based AI assistants for clinics, spas, restaurants, and retail clients. R2 answers inquiries, books appointments, and escalates conversations to people when needed.
I also built R2 Legal, a RAG-based legal assistant over Dominican statutes, including curating and structuring its document base. I work hands-on with Python, APIs, prompt engineering, OCR, and process automation.
I own the commercial cycle from prospecting and demos through closing, onboarding, and post-sale support. I’ve also designed a B2B referral program and negotiated SaaS subscription contracts under Dominican e-commerce and data-protection law.
My legal training, B2B sales experience, and bilingual customer-facing background help me connect business problems to practical AI solutions that clients will adopt and pay for.
Experience
Work history, roles, and key accomplishments
Co-Founder
WorkLess
Jan 2024 - Present (2 years 8 months)
Built R2, an AI assistant for WhatsApp handling inquiries, bookings, and escalations for service businesses. Built R2 Legal, a RAG-based legal assistant over Dominican statutes, and owned the full commercial cycle including drafting and negotiating SaaS contracts.
Logistics Coordinator
IDARD — Environmental Law District
Dec 2024 - Jan 2026 (1 year 1 month)
Coordinated logistics and organization for the district's activities and events.
Legal Assistant
Pioneer Growth
Jun 2023 - Apr 2024 (10 months)
Supported the review and drafting of contracts and legal documentation across several areas of law.
Customer Service Representative
Outplex — The New York Times account
Jun 2021 - Jan 2023 (1 year 7 months)
Handled subscriber support in English and Spanish for a high-volume international account.
Sales Representative
Caribbean Vacation Club
May 2020 - Apr 2021 (11 months)
Direct consumer sales, including objection handling and cold closing.
Education
Degrees, certifications, and relevant coursework
Pontificia Universidad Católica Madre y Maestra (PUCMM)
Bachelor of Laws, Law
2020 -
Pursuing a Bachelor of Laws (Licenciatura en Derecho), currently in the ninth semester, with an expected graduation in 2027.
Colegio Los Pininos
High School Diploma, General Studies
Completed high school education at Colegio Los Pininos in Santo Domingo, Dominican Republic.
Tech stack
Software and tools used professionally
Availability
Location
Dominican RepublicAuthorized to work in
Job categories
Skills
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