Account Executive - Hotel Partnerships

Overview

You're selling B2B software to hotels across the US and Europe. You own the full sales cycle—prospecting hotel operators, running demos, negotiating, and closing. The product is likely operations/management software for hotels (based on the ERP/enterprise software positioning), but specifics will depend on the actual client CloudTask is hiring for.

Role Snapshot

Company Context

Stage: Unclear (CloudTask is the hiring marketplace, actual employer unknown)

Size: Working through CloudTask's 115-person marketplace platform

Growth: Fast-track hiring suggests urgent need or expansion

Market Position: Unknown without knowing the actual software company

GTM Reality

Pipeline Sources:

• 80-90% Outbound - You're building lists of hotels, cold calling front desk/management, sending LinkedIn messages to hotel GMs and operations directors
• 10-20% Referrals - Hotels talk to each other; if you close one property in a chain, you might get warm intros
• Minimal Inbound - Hotel software isn't typically high-intent search traffic

SDR/AE Structure: Self-sourcing. CloudTask marketplace roles rarely include dedicated SDR teams. You're doing your own prospecting.

SE Support: Unlikely to have dedicated SE support. You'll run your own demos and handle technical questions.

Competitive Landscape

Main Competitors: Unknown specifics, but likely competing against legacy hotel management systems (Opera PMS, Cloudbeds, etc.) or point solutions depending on product category

How They Differentiate: If it's an ERP play, differentiation is probably around integration and unified platform vs. multiple point solutions

Common Objections:

• "We already have a system that works"
• "Implementation will disrupt operations"
• "Our staff is too busy to learn new software"
• Budget concerns (hotels operate on thin margins)

Win Themes: ROI through operational efficiency, staff time savings, better guest experience leading to reviews/bookings

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (35%) | Admin/Internal (25%)

Key Activities

• Cold Outreach: Making 40-50 calls per day to hotel front desks trying to get transferred to the GM or operations manager. Most calls go to voicemail or you get blocked by front desk staff. You're sending LinkedIn messages and emails in parallel.
• Discovery & Demos: Running 5-8 demos per week with hotel managers. Demos are screen-shares showing how the software handles reservations, housekeeping, maintenance, reporting—whatever the core features are. You're adapting your pitch to hotel size (boutique vs. chain property).
• Proposal & Negotiation: Building custom proposals, dealing with procurement processes (larger chains), negotiating price and implementation timelines. Hotels are price-sensitive, so expect pushback on cost.
• Pipeline Management: Updating CRM, forecasting, chasing deals that go dark (common in hospitality—managers are busy and deal with emergencies daily), coordinating with implementation teams on close dates.

The Honest Reality

What's Hard

• Hotels are notoriously difficult to reach. You'll call properties multiple times and get "they're with a guest" or "they're dealing with an issue" constantly. Decision-makers are on the floor, not sitting at desks.
• Long sales cycles despite the consultative timeframe. Hotels delay decisions, especially if they're mid-season or dealing with staffing issues. Deals that should close in 6 weeks stretch to 3 months.
• Budget constraints. Hotels operate on tight margins. Even when they see value, getting budget approved—especially for independent properties—is hard.
• Time zone complexity selling US and Europe. You'll have early morning or late evening calls to catch European properties.
• Implementation anxiety. Hotels worry about disruption to operations. You'll spend time hand-holding through those concerns.

What Success Looks Like

• Closing 2-3 deals per month consistently
• Building a pipeline of 20-30 active opportunities
• Getting referrals from happy customers to other properties or sister hotels
• Shortening your sales cycle by getting better at qualifying out bad-fit properties early

Who You're Selling To

Primary Buyers:

• General Managers (independent hotels, small chains)
• Directors of Operations (larger hotel groups)
• Hotel Owners (boutique properties)

What They Care About:

• Operational efficiency: reducing manual work for front desk, housekeeping coordination, maintenance tracking
• Guest satisfaction: systems that make check-in smoother, reduce errors, improve service quality
• Revenue optimization: reporting and analytics that help them make better pricing/occupancy decisions
• Staff retention: tools that make employees' jobs easier (hospitality has high turnover)
• Implementation risk: minimal disruption, training support, data migration guarantees

Requirements

• 2-4 years full-cycle B2B sales experience (hospitality experience is a plus but not required)
• Comfortable with high-volume outbound prospecting—this isn't an inbound role
• Experience selling software in the $15K-50K ACV range to small/mid-market businesses
• Ability to work across US and European time zones (early/late calls required)
• Strong demo skills—you'll be running these solo without SE support
• Resilient—hotels are hard to reach and deals move slowly; you can't get discouraged by delays
• CRM discipline for pipeline management and forecasting
• Comfortable working remotely through a marketplace platform (CloudTask) rather than being a direct employee