About the role
Location: US (remote)
Reports to: General Manager, US
Type: Full-time
Corporate travel is a new revenue line and a new product for WeRoad: companies book a trip as an offsite or team retreat, on any of our itineraries. Buyers are mainly remote and distributed teams, with in-office companies showing interest too, and groups are not limited to the consumer age range. There is no proven pitch, pricing model or sales process yet; you will close the first deals and write down what works. Few companies think of group adventure travel as an offsite format today, so you will be creating the category as much as selling into it.
What you'll do
Close corporate deals. Run discovery, pitch, scope the trip, negotiate and close. Then grow the accounts you land.
Own your pipeline. Work meetings booked by the business development rep, inbound from the corporate page, and your own outbound.
Shape the offer. Bring back what buyers say about pricing, packaging and messaging, and set them with the GM.
Create the collateral. Proposals, decks and case studies.
Write the playbook. Turn what works into a repeatable process, from first meeting to trip handoff, that future sellers can run.
Hand off cleanly. Brief the operations team so every trip delivers what you sold.
Success in the first 12 months
Fully ramped by the end of month 3.
A documented sales process: target customer, discovery questions, pricing guide and proposal template.
A healthy partnership with a business development rep, with a clear definition of a qualified meeting.
Referenceable first customers we can feature in case studies.
Who you are
A proven closer. Three or more years carrying a quota in B2B sales, with deals worth $50K or more.
Early-stage experienced. You have been a first or early seller at a company or product line before, with no playbook to inherit.
Consultative. Every deal is a custom trip. You can scope what a team wants and turn it into a proposal they sign.
Self-directed. There is no sales manager. You set your own priorities and hold yourself to the number.
Comfortable with ambiguity. Prices, packages and process will change as we learn.
Bonus: Experience selling group travel, offsites, events or experiences to companies.
What you're walking into
Direct support from the GM. Dan works deals alongside you: sourcing leads, joining pitches and helping close.
A dedicated business development rep booking meetings for you.
A lean US team. Sales and customer experience plus digital marketing.
Autonomy. The US business runs independently of group headquarters in Italy wherever it can.
A path up. A leadership role as the corporate team grows, if you want it.
What we can offer
Compensation:
On-target earnings are $120,000, commission is uncapped
Benefits:
401(k) with employer matching
Health insurance
$1,400/year travel discount in our WeRoad trips!
Extra benefits – $1,000 wedding bonus, one-off bonus at 5 years, and ongoing learning opportunities.
Ready to apply?
At WeRoad, cultural fit matters as much as skills. We assess both the what, what someone brings and the how, how they work and live our values. The interview process will consist of:
Introductory call with Talent Acquisition Lead
Technical interview with US General Manager
Third technical step
Culture Champions step
ABOUT WEROAD: CONNECTING PEOPLE, CULTURES, AND STORIES
WeRoad is a community-led group adventure travel company. It sells small-group trips to solo adults aged 25–49, across about 250 itineraries worldwide.
We don't act like a tour operator and we don't want to be mistaken for one. No palm trees, no stock-photo sunsets, no “book now” shouting. Our voice is friendly, a little ironic, and human, we earn attention by being culturally relevant, not by chasing people with ads. If “we attract, we don't chase” resonates with you, keep reading.
Sounds exciting? Check out our Culture Manifesto! 👥
WeRoad is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, or any other characteristic protected by applicable law.
Applicants must be authorized to work in the United States. WeRoad does not sponsor employment visas for this position.
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
