Maveron Portfolio Companies You'll Love To Work For...

CTO- Picco (AI Automation)

Pioneer Square Labs

Pioneer Square Labs

Software Engineering, Data Science
Seattle, WA, USA
Posted on Friday, April 19, 2024

Location: Seattle, WA


Picco, the software agent, is powering AI operations for all knowledge work, starting with Go-to-Market (GTM) operations. Picco builds everyday skills (and learns on top of those skills) to execute repetitive tasks that take up 50% of knowledge workers' time. We are solving both the redundant task and workflow challenges as well as the copy-paste challenges between the many SaaS tools it takes to run an organization. Picco executes tasks you describe in English – no drag and drop workflows. We're seeking a CTO to lead Picco's journey and shape its future.

For more on the underlying technology, check out Picco, a Voyager Inspired Software Agent. and AI First Software Architecture.


  • Serve as a thought leader and strategy driver for the company in tandem with the CEO
  • Work with customers, business, development, design, and fulfillment teams to understand and influence product vision and requirements
  • Develop and own all technical aspects of Picco’s strategy
  • Translate our strategy into an achievable roadmap and action plan
  • Help assess the specific skills and qualities needed for a world-class engineering team and the task at hand
  • Lead by example by being hands-on and actively involved in the development process, including the ability and willingness to write and review production-level code as needed
  • Budget for, hire and manage a team of developers
  • Act as a champion for our inclusive values and as a source of mentorship and growth
  • Provide management and execution against project plans and delivery commitments
  • Cultivate a sense of customer empathy to continue building an exceptional product


  • Bachelor's degree in Computer Science, Computer Engineering or related technical discipline
  • 5+ years of relevant software engineering experience (including LLM prompting, production SAAS products, distributed cloud services, and exposure to machine learning).
  • Experience in the following is a plus:
    • AI prompt engineering
    • Generative AI product development experience
    • Retrieval-augmented generation (RAG)
    • Familiarity with the current AI foundation model landscape
  • 5+ years of team management experience
  • Problem-solving aptitude
  • Ability and experience scaling a company

About Pioneer Square Labs

Pioneer Square Labs (PSL) is a premier startup studio and early-stage venture capital fund focused on fostering the next generation of technology companies. PSL Studio collaborates with exceptional entrepreneurs to develop ideas from scratch, validate them, and build venture-scale companies. The AI Engineer will work directly with the PSL engineering team during the onboarding and ramp up period.

Over the past eight years, PSL has successfully spun out over 35 businesses. We are continuously seeking extraordinary individuals to build with us.