The opportunity timeline

• Overview

  Pinterest is hiring a Pilot in Chesapeake, VA.

• Role description

  Most Pilot jobs ask you to fit a mold; Pinterest in Chesapeake, VA would rather you reshape one using Empathy. Look past the title and you'll see $62,000 - $93,000, a VA base, and a mid-level role that asks you to lead, not just execute.

  Key Responsibilities

  • Build and sustain strong working relationships across departments
  • Sense when a Chesapeake relationship needs a call, not an email
  • Question the brief when the brief doesn't match reality
  • Track key metrics and report findings to your manager each week
  • Earn the trust to make detail-loving judgment calls without a committee

  What You'll Bring

  • Self-direction that survives a quiet Slack channel
  • Comfort presenting to a VA-wide audience without a script
  • Working understanding of both Emotional Intelligence and Innovation in real-world settings
  • Comfort interpreting data and translating findings into clear recommendations

  Based in Chesapeake, Pinterest has spent 4 years shaping how people work across the general space. We hire for character and maker-minded thinking, then trust the rest to follow.

  Pinterest rewards your hands-dirty work with $62,000 - $93,000, equity participation, and mentorship from accomplished general leaders.

  We bumped this posting hours ago because the role is still very much open.

  A few minutes now could reshape your next 3, so start your Pinterest application.

• Required skills

  • Innovation
  • Critical Thinking
  • Adaptability
  • Organization
  • Emotional Intelligence
  • Cultural Awareness
  • Empathy
  • Accountability
  • Leadership

• Benefits & perks

  • Disability accommodations
  • Telemedicine and virtual care access
  • Travel per diem
  • Pool Table
  • Onboarding buddy program
  • Accrued vacation time
  • Catered Lunches

• Apply before 2026-08-30

  Submit your application for this Remote general position.