Demo

Account Executive - Outbound

Dripos
Portland, OR Full Time
POSTED ON 12/16/2025
AVAILABLE BEFORE 6/13/2026

About Dripos

Dripos is transforming the coffee shop industry with an all-in-one software solution that replaces fragmented tools like Square, Toast, 7shifts, QuickBooks and ADP. From mobile ordering and team scheduling to payroll and accounting, Dripos powers the front of house & back office of modern cafés. We're venture-backed by Base10 Partners and Cota Capital, and supported by industry leaders like Michael Seibel (Y Combinator), Shyam Rao (Punchh), and Ian Crosby (Bench).


Recent Press:

  • TechCrunch: Dripos raises $11M Series A to replace Square, Toast, and more
  • Stripe: With Dripos, it's no tall order running a coffee shop
  • Bosstab: Dripos and Bosstab



Why We're Hiring

We’re building a world-class outbound sales team and looking for an Account Executive (AE) in the Pacific Northwest to help drive the next chapter of growth at Dripos. In this role, you’ll be on the front lines, connecting with coffee shop owners and operators across the country, many of whom are running multi-million dollar businesses.


This is a remote role where you’ll collaborate closely with BDRs, AEs, and Sales Leadership. As we scale across the SMB and mid-market coffee segments, you’ll play a critical role in shaping our outbound motion and representing Dripos to some of the most exciting growing coffee brands in the U.S.



What You’ll Do

  • Own the sales process for BDR-generated pipeline.
  • Run deep, consultative discovery to understand operational pain points for coffee shop owners.
  • Deliver tailored demos that showcase how Dripos replaces 5–7 tools and streamlines FOH & BOH workflows.
  • Travel 20% for in-market sales blitzes.
  • Multi-thread conversations with owners, operators, regional managers, and directors of operations.
  • Forecast accurately and maintain meticulous deal hygiene in HubSpot.
  • Collaborate tightly with your BDR partner, providing feedback that strengthens lead quality and targeting.
  • Partner cross-functionally with Implementation to ensure a smooth handoff and smooth onboarding experience.
  • Participate in coaching sessions, call reviews, and team training to continuously refine the outbound motion.



What We're Looking For

  • 2–5 years of closing experience in SMB or mid-market SaaS.
  • Experience with outbound in-person selling.
  • Strong proficiency in discovery, objection handling, solution selling, and negotiation.
  • Excellent communication skills with the ability to simplify complex software.
  • Coachability and willingness to iterate quickly.
  • Bonus points for experience in restaurant tech, POS, retail SaaS, or hospitality.



What Success Looks Like

  • You consistently hit or exceed your ACV quota on fully BDR-sourced pipeline.
  • You run predictable, well-structured sales cycles with clean next steps and multi-threaded relationships.
  • You maintain high conversion rates from Set → Held → Demo → Closed Won.
  • You build strong relationships with BDR partners and help shape outbound messaging.
  • Your customers experience smooth onboarding with minimal friction.



Benefits

  • 💰 $150,000 OTE ($90,000 base uncapped commissions)
  • 🧘 Full healthcare (medical, dental, vision), 401(k), health & wellness stipend
  • ✈️ Unlimited PTO
  • 💡 Direct access to experienced SaaS sales leaders and startup founders

Salary.com Estimation for Account Executive - Outbound in Portland, OR
$82,636 to $113,914
If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Account Executive - Outbound?

Sign up to receive alerts about other jobs on the Account Executive - Outbound career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$103,275 - $152,386
Income Estimation: 
$133,333 - $194,768
Income Estimation: 
$55,240 - $79,001
Income Estimation: 
$104,545 - $161,038
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Not the job you're looking for? Here are some other Account Executive - Outbound jobs in the Portland, OR area that may be a better fit.

  • Redhill Search, LLC Oswego, OR
  • WHAT YOU’LL DO: Our Client provides a full suite of ethics and compliance software products. We’re an industry leader with exciting plans to continue growi... more
  • 1 Month Ago

  • Augusta Portland, OR
  • About Augusta Augusta is a fast-growing software company helping home care agencies rethink caregiver recruiting from the ground up. Our platform uses auto... more
  • 14 Days Ago

AI Assistant is available now!

Feel free to start your new journey!