Jack Tripp
£1M+ in cold email revenue | 3x founder | Prosperra.ai | Getpylot.io
I’m the Co-founder & Technical Director at Prospero AI - where we’re building the next evolution of outbound sales: fully AI-driven, hyper-personalised outreach that doesn’t sound like it came from a robot.
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We help: - Founders get pipeline without hiring SDRs - SDRs hit quota with smarter messaging in less time - Sales managers scale personalisation without burning out their teams - Agencies and consultants deliver high-performance outbound without bloating headcount At Prospero, I lead product strategy, R&D, and our AI systems - including the brains behind our Research & Generative engine ("R&G"), which combines deep prospect research with natural, human-sounding email copy in seconds. Whether you’re a solo operator or leading a team, I believe outbound should feel like it was written just for your prospect - without the hours of research and rewriting.
GTM Index
- PYLOTJOB
- Co-Founder8M
Co-Founder
Pylot
Pylot is an AI-powered lead generation platform that helps businesses find, reach, and engage the right prospects without relying on agencies or complicated tools. Simply describe your ideal customer, and Pylot handles the research, targeting, messaging, outreach, and follow-up behind the scenes. Built for founders, agencies, and sales teams who need more conversations, more opportunities, and a simpler way to generate pipeline.
- PROSPERRAJOB
- Founder/CEO & GTM Specialist2Y 3M
Founder/CEO & GTM Specialist
Prosperra
- ESMIJOB
- Dir9Y 11M
Director
ESMI
We make personal insurance clear, simple, and hassle-free. Quote and buy affordable life, critical illness, and sickness & accident cover online in minutes all with no medical exams or medical questions. Why not protect yourself today with cover starting from less than £5 a month?
- BD Mgr/Sales Dir4Y 3M
Business Development Manager/Sales Director
ESMI
- VESTDJOB
- Equity Consultant2Y 4M
Equity Consultant
Vestd
"Our mission is to create a world in which everybody has a stake, because anyone who contributes to a company's success deserves: 🥧 A slice of the pie ⚽ Skin in the game We believe (as research shows) that company share schemes improve loyalty, productivity and performance. And that builds stronger businesses - driven by motivated teams. As the UK's first and most advanced share scheme platform for startups, scaleups and SMEs, we know a thing or two about share schemes! To quote one of our customers, "What Vestd doesn't know about share schemes isn't worth knowing". We make it simple for company leaders to give their teams shares or options. And not just to employees, but advisors, co…
- PARADISE GARDENS HYDRO & URBAN LIFESTYLE SHOWJOB
- Co-Founder - Sales, Mktg &…1Y 10M
Co-Founder - Sales, Marketing & Partner Relations
Paradise Gardens Hydro & Urban Lifestyle Show
- Job: Pylot — Co-Founder · 2025-12 – present — Pylot is an AI-powered lead generation platform that helps businesses find, reach, and engage the right prospects without relying on agencies or complicated tools. Simply describe your ideal customer, and Pylot handles the research, targeting, messaging, outreach, and follow-up behind the scenes. Built for founders, agencies, and sales teams who need more conversations, more opportunities, and a simpler way to generate pipeline.
- Job: Prosperra — Founder/CEO & GTM Specialist · 2024-05 – present
- Job: ESMI — Director · 2016-09 – present — We make personal insurance clear, simple, and hassle-free. Quote and buy affordable life, critical illness, and sickness & accident cover online in minutes all with no medical exams or medical questions. Why not protect yourself today with cover starting from less than £5 a month?
- Job: ESMI — Business Development Manager/Sales Director · 2016-09 – 2020-12
- Job: Vestd — Equity Consultant · 2022-10 – 2025-02 — "Our mission is to create a world in which everybody has a stake, because anyone who contributes to a company's success deserves: 🥧 A slice of the pie ⚽ Skin in the game We believe (as research shows) that company share schemes improve loyalty, productivity and performance. And that builds stronger businesses - driven by motivated teams. As the UK's first and most advanced share scheme platform for startups, scaleups and SMEs, we know a thing or two about share schemes! To quote one of our customers, "What Vestd doesn't know about share schemes isn't worth knowing". We make it simple for company leaders to give their teams shares or options. And not just to employees, but advisors, co…
- Job: Paradise Gardens Hydro & Urban Lifestyle Show — Co-Founder - Sales, Marketing & Partner Relations · 2020-12 – 2022-10
- School: Uppingham School — Business Studies, History, Philosophy
- School: Maidwell Hall
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