Long Journey Ventures
Job Title: Gardener (no, not that kind — but kind of)
Hours: Full Time
Reports to: GP, Arielle Zuckerberg
Salary: TBD | Exempt
Location: Bay Area
Travel: 5%
Long Journey
About Us
At Long Journey, we are the second believers in the magically weird. We are a nimble team of seasoned operators investing in early-stage startups. We are not by-the-book, buttoned-up investors. In fact, we can be a little weird, sometimes even a lot weird, and maybe even occasionally funny or embarrassing too. We take our work seriously, but not ourselves, too seriously. We believe that technology can create a brighter future, and we are constantly on the lookout for the most innovative and bold ideas. We’ve been there, done that, and still love the whole long, entrepreneurial ride and are tirelessly dedicated to being our founders’ second believers in their life’s work.
About the Role
We know — “Gardener” isn’t a job title you typically see at a venture capital firm. But hear us out.
At Long Journey, we write a lot of small, early checks — through our Wayfinder program, scout network, and personal angel investments. These are seeds. Some sprout fast. Some need time. And some grow into the kind of trees you name parks after — generational companies that change everything. But if no one’s paying attention, even the best ones can wither.
That’s where you come in. We’re looking for a Gardener — someone who notices. Who tracks what’s growing. Who helps us stay close to our weird, wonderful, early-stage portfolio and makes sure we never miss the chance to double down on something magical.
This is an investment role, but the focus isn’t on sourcing new deals. Instead, you’ll be the connective tissue across our earliest-stage bets — spotting traction, surfacing follow-on opportunities, and making sure our best seedlings get the sunlight (and capital) they need.
You’ll work closely with the investment and operations teams to keep our tracking systems sharp, our breakout radar tuned, and our GPs focused on what matters most.
In short: you’ll help us grow what we’ve already planted — and make sure nothing exceptional dies from neglect. Watering can optional. Overalls encouraged.
Responsibilities
- Monitor and analyze Wayfinder, scout, and angel portfolio companies to identify breakout signals
- Responsible for building internal systems to track performance, founder updates, and follow-on readiness
- Work with the investment team to flag potential follow-on investments early and propose next steps
- Build financial models and perform analysis to support follow-on investment decisions
- Partner with the Head of Platform and Head of Operations to provide hospitality to the portfolio and manage internal fund tracking tools
- Support early-stage diligence and prepare investment memos and related write-ups
- Attend industry events and network with entrepreneurs, investors, and other key stakeholders in the startup ecosystem
- Optionally: support in one or more “bonus” areas based on your skill set — content generation, coding/data tools, or sourcing
A Day in the Life
You start your day by reviewing the latest Wayfinder company updates we’ve received over the last week. You add any relevant data from the updates to the tracker you’ve built, and in reading the updates, you read that a founder just closed a big partnership deal — you flag it as a potential breakout in the tracker and drop a note to the venture partner who wrote the original $100K check to get their take.
Mid-morning, you join the weekly Deal Flow Sync with the investment team. The team is debating investing in an early-stage round, and you share a piece of research you read a few days ago, and how that may impact the company’s market. The team is also deep in diligence on a potential follow-on investment, and you provide a status update on the diligence process, which you’ve been helping quarterback. You also share what’s bubbling up across the early-stage portfolio. You highlight a company that is growing quickly — they hit $750K in ARR last month and may be ready to consider for a core check. The partners ask you to pull together a one-pager summarizing its progress, cap table status, and what a core check could look like by the end of the week.
You hop into a 1:1 with our other investment associate, during which you trade notes on what you’re seeing both within and outside of our portfolio. You get a download of updates on the deals that he led. He also asks you if we have any recent information on a scout check that we wrote a few months ago that piqued his interest.
In the afternoon, you join a diligence call with one of the partners on a potential non-core investment. The company is pre-revenue but gaining traction fast — you listen closely, take notes, and after the call, start compiling early market comps in a short summary.
Your final meeting of the day is with our Head of Operations, as the two of you prepare for our quarterly portfolio grading process. The two of you work through the portfolios’ smaller investments and update the grading for companies that seem to be starting to ramp and should be getting special attention from us.
At the end of the day, you attend a Long Journey Founder Supper Club. You’ve invited 4 of the 12 operators who are attending the dinner (a few are on your shortlist of companies that you’re particularly interested in), and after a hot pot dinner experience, you debrief with the Platform team on approaches to help unblock something for 2 of the founders.
No two days look exactly the same, but the through-line is constant: you’re paying attention. You’re the first to notice when a company is quietly breaking out — and you help the team move faster, smarter, and more confidently as a result.
About You
You’re a kind, can-do, type-A team player who is curious and loves to learn. You’re thoughtful, analytical, and love playing the long game. You care about structure and signal, but you also trust your gut. You like watching early-stage companies grow — not just betting on them, but noticing when things start to click.
You’re self-directed but collaborative, organized but adaptable. You can take a large amount of information and condense it down, building an internal tracker that you continue to improve, while also preparing internal memos and getting the team up to speed on prospective investments. You have the ability to independently nurture and leverage partnerships across the early-stage investment community. You’re highly self-motivated and dependable.
Qualifications
- 2–4 years of experience in venture capital, early-stage startups, consulting, data analysis, or another adjacent field
- Excellent communication and interpersonal skills; team-first orientation
- Ability to handle multiple, complex, and competing priorities
- Positive attitude, good instincts, and self-motivation
- A passion for technology and weird, unconventional ideas, and a desire to help build a more magical future
- Strong organizational skills and the ability to track dozens of early-stage companies without dropping the ball
- Interest in investment decision-making and a willingness to engage with portfolio data
- Bachelor’s degree in a relevant field (such as finance, business, or engineering) is preferred but not required
- Bonus points if you bring additional value in media/content, technical skills (e.g., coding), or sourcing deals
Interested? Apply here
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