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Pioneer Square Labs

Startup studio and early-stage venture investor

Founder / CEO - Metergraph, PSL Studio Spinout

Full-Time
No salary listed
Expert
Seattle, WA, USA
RemoteMust be based in or regularly present in Seattle.
Business & Strategy

About the job

Requirements
  • 7+ years in commercial leadership at infrastructure, developer tools, or software-as-a-service companies selling to technical buyers.
  • A track record of personally closing deals rather than only managing a team that closed them.
  • Founder-led sales experience or experience as the first commercial hire building a commercial function from nothing.
  • Ability to hold technical conversations about models, evaluations, and inference economics with engineers.
  • Fluency or rapidly developing fluency in the large language model ecosystem, including providers, pricing, evaluations, and deployment constraints.
  • Based in or willing to be regularly present in Seattle.
Responsibilities
  • Own founder-led sales end to end by prospecting, pitching, closing, and expanding the first cohort of paying customers among chief technology officers and engineering leaders at AI-native companies.
  • Convert live design partnerships into referenceable, paying accounts and feed deal learnings back into the product with the technical cofounder.
  • Build the go-to-market machine, including pricing and packaging, a self-serve motion, and content and demand generation aimed at technical buyers.
  • Raise the seed round through company storytelling and demonstrated traction.
  • Recruit and lead the early team, setting the culture, pace, and performance bar.
  • Own the commercial engine and the company.
  • Sharpen positioning in a market changing at model-release speed.
  • Decide what the company will not do each quarter with imperfect information.
Desired Qualifications
  • Experience selling infrastructure, developer tools, observability, or cost-optimization products to technical buyers.
  • Prior experience founding a company or serious interest in founding one.
  • Comfort with ambiguity, risk, and the emotional range of building from zero to one.
  • A low-ego partnership style and willingness to work with a strong technical cofounder.
  • Belief that doing more for less is a capability story rather than a discount story.

About the company

PSL operates as a hybrid startup studio and early-stage venture capital fund in Seattle. It co-creates and funds tech startups, offering capital and hands-on operational support. The startup studio builds companies from the ground up while the VC fund backs promising early-stage ventures with funding and strategic guidance. Revenue comes from equity stakes in portfolio companies, aligning PSL’s success with the startups' growth, with the goal of turning bold ideas into scalable, world-changing businesses.

Company Size

11-50

Company Stage

N/A

Total Funding

$165.1M

Headquarters

Seattle, Washington

Founded

2015

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Simplify Jobs

Simplify's Take

What believers are saying

  • PSL's feed showed Tin Can raised $12 million in August 2026.
  • PSL launched Lev, an AI co-founder, in 2026, tightening its creation loop.
  • Outgo exited on May 15, 2025, while Kevala and Dropzone raised follow-on capital.

What critics are saying

  • PSL's model depends on studio winners; 33 spinouts since 2015 mask concentrated hits.
  • If Lev standardizes company creation, competitors copy PSL's core advantage by 2027.
  • Any weak 2026 exit market strands studio equity, compressing returns across funds.

What makes Pioneer Square Labs unique

  • PSL's 2023 Studio III raised $20 million, backing company creation from scratch.
  • PSL Ventures manages $180 million, combining studio control with traditional seed investing.
  • Seattle hub at 240 2nd Ave S co-locates founders, operators, and capital.

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Benefits

  • Company Equity

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