Oregon Field Pilot Lead (12-Week Contract)
Location: Willamette Valley + Portland Metro
Contract: Full-time, 12 weeksStart: Summer/Fall 2026
Get in on the ground floor! Droppah is launching an exciting market validation pilot in Oregon, and we’re looking for a friendly, tech-confident, sales & field operator to lead it the pilot.
This role blends field sales, customer onboarding, light support, and market research. You’ll be visting wineries, tasting rooms, restaurants, bars, and cafés every day, showing teams how Droppah works, helping them get set up, and feeding real insights back to our product and leadership teams.
If you love talking to people, enjoy being out in the field, and want to help shape a US market entry from the ground up, this is for you.
What You’ll Do
Field Sales & Venue Engagement (60%)
- Visit 15–20 venues per day across Willamette Valley + Portland.
- Have real conversations about how they schedule staff and where the pain is.
- Run quick, simple demos on iPad/mobile device.
- Help teams start a trial on the spot.
- Capture key data.
- Represent Droppah with a warm, down-to-earth Oregon tone.
Onboarding & Light Support (20%)
- Help new trials complete the “first 10 minutes” setup.
- Track common onboarding blockers and share weekly patterns.
Pilot Operations & Reporting (20%)
- Log all activity in HubSpot (training provided).
- Share weekly insights on messaging, objections, product gaps, and customer behavior with Droppah Leadership
- Join weekly review calls with Droppah leadership.
What You Bring
Must-Have
- Field sales experience, ideally hospitality, beverage, POS.
- Strong comfort with apps, mobile tools.
- HubSpot (or similar CRM) familiarity.
- Warm, plainspoken communicator who builds trust quickly.
- Self-starter who thrives working independently across Oregon.
- Valid driver’s license + reliable transportation.
Nice-to-Have
- Experience selling to wineries, tasting rooms, restaurants, or bars.
- Hospitality management experience (shift lead, FOH manager, tasting room lead).
- Experience in early-stage startups or pilot environments.
What Success Looks Like
You’re winning when you deliver:
- 400+ venue conversations & 100+ live demos
- 30+ trials (20+ winery, 10+ restaurant)
- High-quality data on scheduling workflows
- Clear weekly insights that shape Droppah’s US playbook
- Customers who feel supported
This pilot is about learning, not closing deals. Your insights will directly influence whether Droppah expands into the US in 2027. And if you're successful, there's an opportunity to turn this into a longer trial or even a full time role.
Who You Are
- You enjoy being out in the field, talking to people, and figuring things out on the fly.
- You’re friendly, practical, and Oregon-local in tone, no corporate jargon.
- You’re curious and empathetic about how small hospitality teams work.
- You’re disciplined with tracking, logging, and follow-up.
- You’re excited by the idea of shaping a market entry from the ground up.
Pay: $32.00 per hour
Benefits:
Work Location: In person
