Entrepreneur in Residence (Future CEO / Founder) - Customer Success AI 2 weeks ago Be among the first 25 applicants
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About Future Sight
Future Sight is a venture studio that co-creates and funds world-class B2 B 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
Future Sight 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 Saa S company
GTM expertise: success in customer success, revenue operations, or enterprise Saa S 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 B2 B Saa S (Series A-C) customer success or Rev Ops 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 + Linked In and tell us why you're the right founder.
Future Sight values diversity, equity, and inclusion and welcomes applicants from all backgrounds.

📌 Entrepreneur in residence (Winnipeg)
🏢 FutureSight
📍 Winnipeg