Head of Sales, North America

WeRoad S.r.l.; Lombardia; Remote; EUR 178,000 - 214,000; Full time

Benefits offered by this job

401(k) with employer matching

Health insurance

$1,400/year travel discount

Wedding bonus

Job summary

WeRoad is hiring a senior corporate seller to own the US B2B revenue motion. You will prospect, pitch, negotiate and close corporate deals, and then grow the accounts you land, defining the offer and packaging for corporate buyers.

Reporting to the GM, this founding role is remote in the USA, with compensation of 220K/year OTE and benefits including 401(k) matching, health insurance and travel discounts. You’ll build the playbook, collateral, and a lean US team as revenue grows.

Qualifications

• Senior seller with proven B2B sales experience and ability to prospect, pitch, negotiate and close.
• Builder who can stand up a new B2B sales motion with no existing playbook or pipeline.
• Entrepreneurial mindset; can define strategies and execute autonomously.

Responsibilities

• Own corporate revenue end to end: prospect, pitch, negotiate and close, then grow the accounts.
• Build pipeline from zero with outbound and inbound efforts.
• Define the offer: positioning, messaging, packaging and pricing for corporate buyers.

Skills

Senior seller

Builder

Entrepreneurial

Generalist

Future manager

Group travel sales

Job description

About the role

Reports to: General Manager, WeRoad US

Type: Full-time, founding role

Location: USA, Remote

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, sales process or team yet; this role builds them. 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

• Own corporate revenue end to end. Prospect, pitch, negotiate and close. Then grow the accounts you land.
• Build pipeline from zero. Run outbound to a defined target list and work inbound from the corporate page.
• Define the offer. Set positioning, messaging, packaging and pricing for corporate buyers, who buy for different reasons than our consumer travelers.
• Create the collateral. Decks, proposals, one-pagers and case studies.
• Write the playbook. Turn what works into a repeatable process, from first touch to trip handoff, that future reps can run.
• Build the team. Hire SDRs/reps as revenue supports it.

Success in the first 12 months

• About 12 corporate deals closed, roughly one a month once ramped.
• A documented playbook: target customer, messaging, pricing and sales process.
• An SDR hired and producing qualified meetings.
• Corporate travelers contributing a visible share of the 10,000-traveler 2027 goal.
• Annual revenue quota: $1M in year one.

Who you are

• A senior seller who still carries a bag. The first year is heavy on prospecting and pitching. This is not a junior role, and not a people manager from dayone role.
• A builder. You have stood up a B2B sales motion from scratch: new product, no playbook, no inherited pipeline.
• Entrepreneurial. Much of this role is undefined. You decide what to do next without being told.
• A generalist. You build your own lists, write your own collateral and run your own CRM.
• A future manager. You have hired and led sellers, or are ready to.
• Nice to have: 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 lean US team. Sales and customer experience plus digital marketing.
• Autonomy from day one.

What we can offer:

Compensation: 220K/year OTE

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
• Mock pitch and plan
• 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.