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Entrepreneur in Residence; CEO​/Founder - Customer Success AI

Job in Dawson City, Yukon Territory, Canada
Listing for: FutureSight
Full Time position
Listed on 2026-06-22
Job specializations:
  • Business
    Business Management, Operations Manager, Business Analyst, Business Continuity
Job Description & How to Apply Below
Position: Entrepreneur in Residence (Future CEO / Founder) - Customer Success AI
Location: Dawson City

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 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

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 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 Rev Ops communities

Benefits

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.

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