Entrepreneur in Residence (Future CEO / Founder)
- Customer Success AI

2 weeks ago Be among the first 25 applicants Get AI-powered advice on this job and more exclusive features. About FutureSight FutureSight is a venture studio that co-creates and funds world-class B2B AI software companies from Day 1. Our team of repeat founders, operators, product leaders, and investors collaborates closely with entrepreneurs, providing proven playbooks, hands-on expertise, and capital to support startups from inception through growth. The Venture: Automating Customer Success Management FutureSight aims to revolutionize Customer Success Management by proactively engaging customers to retain, expand, and delight. Our platform monitors usage signals, suggests next-best actions, and generates personalized outreach, leading to higher retention, expansion, and strategic insights. What We Bring To The Table Validated problem & early market interest with pilot engagements Embedded team of designers, engineers, marketers, and fundraisers Initial funding to build MVP and hire early team members

What You'll Do
Own the thesis & roadmap: deepen customer discovery, refine target market, and develop GTM strategy Build the product & team: collaborate with product/engineering teams to ship V1 and then hire core team members Run early pilots: secure lighthouse customers, iterate on pricing and positioning,



demonstrate retention and expansion impact Raise external capital: lead next funding round with data-backed growth stories Operate as CEO: set company culture, manage P&L;, report to the Board, and scale the venture Requirements You Bring Founder-level drive: experience building or being early at a venture-backed SaaS company GTM expertise: success in customer success, revenue operations, or enterprise SaaS sales AI & data curiosity: ability to turn product usage and CRM data into value Fundraising

skills:
craft investor narratives and close funding People leadership: attract top talent, coach, and foster company culture Nice-to-Haves Experience with CS tools (Gainsight, Totango, Catalyst, etc.) Knowledge of LLMs, agents, or predictive analytics Network in B2B SaaS (Series A-C) customer success or RevOps communities Advantages What You Can Expect Significant equity (founder-level ownership) plus stipend Hands-on support in product, design, growth, talent, finance, and fundraising Ready to Build? If automating proactive customer success excites you and you want a world-class co-founder team, apply with your résumé + LinkedIn and tell us why you're the right founder. FutureSight values diversity, equity, and inclusion and welcomes applicants from all backgrounds.

📌 Entrepreneur in Residence (Winnipeg)
🏢 FutureSight
📍 Winnipeg