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Head of Product

Thoughtful Automation

Thoughtful Automation

San Francisco, CA, USA · New York, NY, USA · Austin, TX, USA
Posted on Friday, May 12, 2023


Thoughtful is actively seeking a confident, experienced, and resourceful product leader to join our mission. The ideal candidate will have a proven track record of successfully leading product efforts that deliver exceptional results for B2B customers. Our clients are healthcare companies with complex, fragmented software systems; your role will be to create sophisticated product experiences that effectively address their most critical business challenges. As the first PM hired by Thoughtful (previously founder-led), you will be responsible for building a product and design team as the company achieves growth milestones.

In this role, you will:

  • Possess a diverse range of skills to be an exceptional product manager, including a strong UX sense, as well as a fundamental understanding of modern software development.
  • Become the expert in our customer’s problems and be able to articulate the product bets we as a company should make to address these problems and differentiate in the market.
  • Collaborate with company leadership to establish a long-term product strategy for our products and platforms.
  • Take responsibility for developing and delivering a compelling product roadmap that is based on customer needs, resources, and strategic opportunities.
  • Make product design and prioritization decisions for the product roadmap in collaboration with engineering counterparts.
  • Spearhead the product research strategy.
  • Ensure that we are utilizing the appropriate metrics to inform our product roadmap and evaluate our success.
  • Design the product function at Thoughtful, including its responsibilities, how it interacts with other teams, and how it will evolve over time.
  • Build and manage a highly skilled Product Management and Design team that consistently exceeds expectations as the company scales.

We are looking for someone who has:

  • Extensive experience in building and leading product initiatives, with over 8 years of experience in a product management or leadership role.
  • 4+ years building B2B software for non-SMB customers.
  • A bias towards action and takes pride in their ability to make progress quickly.
  • Demonstrates a strong track record of successfully shipping customer-facing products that users love.
  • Desire to roll up their sleeves and serve as an effective individual contributor until we start to scale the product team.
  • A passion for building teams, developing people, and creating a strong identity and culture.
  • Experience approaching product management from a user’s perspective and is motivated by the opportunity to improve the lives of customers.
  • Experience managing technical software products from kick-off to ship.
  • Strong written and verbal communication skills, with a talent for precisely articulating customer challenges.

Bonus Points:

  • Have experience working with AI-powered products
  • Have knowledge of Healthcare RCM
  • You’ve been a scrappy trailblazing product manager at a hyper-growth startup that has matured into a high-velocity product organization

Thoughtful Automation Benefits

  • Employee stock options
  • Remote work some days
  • Medical, dental, and vision insurance
  • Flex vacation, we encourage you to unwind and disconnect for at least 3 weeks per year while still getting paid