Entrepreneur in Residence (EIR) in Winnipeg

We are a venture studio. We research and validate ideas in-house, then bring in an Entrepreneur in Residence to turn the strongest of them into real companies. Each venture starts with a clear thesis, a budget and a small team already in place. As EIR, you lead one venture from early build to a standalone business. You work with a small cross-functional team across product, growth, sales and engineering, test quickly with real customers, form the company, and hand it to a long-term CEO once it is ready to raise. You are the single accountable owner from start to handover. This is a hands-on operating role, not an advisory one. You push forward when the evidence supports the venture and recommend stopping early when it doesn't.

KEY RESPONSIBILITIES

• Build: Take a validated concept and start executing from week one.
• Lead the product build with a small cross-functional team.
• Use AI and no-code tools to ship product, research and assets quickly.
• Set clear owners, deadlines and weekly milestones for every workstream.
• Validate: Launch an MVP and measure real behaviour: usage, conversion, payment and retention.
• Run short test-and-learn cycles and drop what the data doesn't support.
• Build the evidence case for continued investment.
• Recommend stopping the venture early if traction isn't there.
• External Relationships: Lead conversations with partners, early customers, suppliers and service providers.
• Drive early business development and first commercial deals.
• Manage contractors and specialists who don't report to you directly.
• Keep leadership and investors informed with regular, concise updates.
• Company Formation: Set up the legal entity, payments and core operating systems.
• Put basic finance, legal and reporting processes in place.
• Recruit the venture's first hires.
• Document decisions, systems and metrics so the business can run without you.
• Transition: Help recruit the venture's long-term CEO.
• Hand over the business cleanly and on schedule.
• Flag risks early to studio leadership before they cost time or money.
• Share lessons learned to improve how the studio builds future ventures.

SUCCESS METRICS

• MVP live with paying or active users within the first 90 days.
• Clear traction evidence that supports further investment, or an early, well-reasoned stop recommendation.
• Consistent weekly delivery across all work streams.
• Entity, payments and first hires in place on schedule.
• Long-term CEO hired and handover completed within the agreed timeline.

MUST-HAVE EXPERIENCE

• Built or led a venture from zero as a founder, early operator or EIR.
• A track record of fast, disciplined execution against a plan.
• Daily, practical use of AI tools to build, research and ship.
• Led small cross-functional teams, including contractors and external partners.
• Made the call to stop or pivot a product when the data required it.

CORE COMPETENCIES

• Execution Speed with structure.
• End-to-end ownership of outcomes.
• Judgement: Decides on data, not opinion.
• Comfortable making hard calls early.
• Leadership & Communication: Leads without formal authority.
• Clear, proactive written communication.
• 6+ years of experience in startup operations, venture building, general management, or a comparable operating role, ideally spanning more than one company.
• Direct, hands-on experience taking at least one company from zero to launch, not just supporting someone else's launch, but owning it.
• Strong working knowledge of AI tools and agentic workflows, with a track record of using them to replace team-based work, not just accelerate individual productivity.
• Experience designing or operating a structured process for de-risking new initiatives—stage gates, funnel management, or comparable venture-building systems.
• Hands-on experience managing execution across multiple work streams, products, or business lines simultaneously without relying on a large team.
• Excellent communication skills, with the ability to provide concise, honest assessments of portfolio or business health.
• Comfortable operating as an independent contractor, with compensation aligned to scope and impact rather than a traditional salary ladder.

WHAT GREAT LOOKS LIKE

• Starts shipping in the first week.
• Brings evidence, not opinions.
• Every work stream has an owner and a deadline.
• Surfaces problems before they grow.
• Stops a venture early when the data says so.
• Hands over a business that runs without them.

CANDIDATE SNAPSHOT

• A former founder or early operator who has taken a product from zero to paying customers.
• Builds with AI tools every day and ships before polishing.
• Comfortable leading people they don't directly employ.
• Wants to build multiple companies, not just one.
• Motivated by results, not titles.
• Fully remote. No office, no commute, just you, the operating system, and wherever you do your best work.
• This isn't about inheriting an established company. It's about building and continuously evolving the operating system that future ventures will run on.
• Core collaboration hours: 9:00 AM–12:00 PM PST, ensuring consistent overlap with the founding team.
• Contractor engagement, paid in USD. Full compensation details will be shared directly with shortlisted candidates.