We're hiring an Investment Analyst

About The Role

Matchstick Ventures is a $75M early-stage venture capital fund investing at pre-seed and seed in exceptional founders building category-defining companies. We back ambitious software founders "between the coasts" in the US who are building to coastal standards and beyond. This is our fourth fund, and we are a small but mighty team split between Boulder, CO and Minneapolis, MN.

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We make approximately 12 investments per year, and we move with conviction. As our first investment hire, you will be the engine of our top-of-funnel, finding, attracting, and qualifying the founders we want to back before anyone else. You will also own the analytical work that helps us make great investment decisions.

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You will have direct partner access, broad ownership, and the opportunity to build something. If you are energized by cold outreach, crowded rooms, and the thrill of finding a great company no one else has noticed yet, read on.

What You'll Actually Do

Sourcing & Relationship Development (60%)

• Own top-of-funnel deal flow: build and manage a systematic pipeline of pre-seed and seed companies across our target geographies
• Conduct proactive outbound sourcing via Harmonic, LinkedIn Sales Navigator, cold email, and other channel-appropriate outreach tools, with a bias toward warm intros where possible and creative cold approaches where not
• Attend founder events, meetups, demo days, and dinners in our target markets and serve as a compelling ambassador for the firm, making founders want us on their cap table
• Build and maintain relationships with accelerators, university programs, angel networks, and other early-stage ecosystem players across our target geographies
• Calibrate deal quality to coastal standards: evaluate companies from Denver, Chicago, Austin, Salt Lake, Toronto, Minneapolis, New Mexico and similar markets against the bar set by the best deals being funded in SF and NYC
• Conduct first-look calls with founders and leave them feeling like getting our firm on their cap table is a genuine opportunity, not an interview.
• Ensure partners are meeting with the best-in-class companies in the pipeline you built.

Investment Analysis (20%)

• Own the investment memo from first draft to final version, market sizing, competitive landscape, team assessment, business model, and thesis
• Conduct market research to validate or challenge investment hypotheses; synthesize primary and secondary sources into clear, actionable insights
• Model basic financial projections and analyze deal pricing and terms relative to market comps and stage norms
• Conduct reference calls on founders and early team members
• Support partners in preparing for IC discussions with concise, well-structured analysis

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AI Experimenter and Tools User (20%)

• Develops and deploys AI-enabled workflows that measurably improve a) sourcing quality, quantity, and efficiency, b) founder response rates, c) research quality, and bonus for partner productivity.
• Track every conversation, lead, and company in our CRM (Attio) with zero gaps, own the funnel with relentless follow-through and data entry.

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Who You Are

Must-Haves

• Based in Denver/Boulder, Minneapolis, Austin, Chicago, Salt Lake City, New Mexico or Toronto: you are not on the coasts, and you understand why that matters
• A natural connector who gets energized, not drained, by walking into a room of strangers and starting conversations
• Obsessive about follow-through: you use tools, systems, and tracking to make sure nothing falls through the cracks
• Extreme self-starter, comfortable with ambiguity and self-direction; you don't need to be told what to do next. You're creative, inventive, and always looking for better ways to do things.
• Curiosity is at your core, you want to know how things work and do the research to understand it.
• Strong writer and communicator, your memos are concise, your emails get replies, your follow-ups are timely
• Data-driven by instinct: you track what works, kill what doesn't, and iterate fast
• AI fluent, knows and uses AI for sophisticated research and tasks.

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Nice-to-Haves (Will Strengthen Your Application)

• Prior experience as a founder or early employee at a startup
• Prior internship or role at a venture capital or private equity firm
• Experience in outbound sales
• Experience using deal-tracking tools (Attio, Notion, Claude and Claude Code, custom scripts, CRM workflows, and beyond)
• Existing startup network
• Experience evaluating early-stage companies at pre-seed or seed

Compensation & Structure

This is a fixed-term position, lasting up to 2 years, and is an amazing learning opportunity for the right candidate to work alongside the partners. The role can either be a full-time position for the right candidate, or can be structured as a part-time position for experienced graduate students and beyond (minimum half-time). We are looking for the right candidate over the right schedule.

• Base compensation: $50,000-$100,000 depending on hours, experience, and fit
• Location: preference for Colorado-based; however, we are remote-friendly within our target geographies; frequent travel to events and meetings required. The position is open only to those with a US work permit.
• This role is a two-year position and is not a partner track position.

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If you are interested in this role, please apply using this application link .

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