SMB Sales Leader, North America

Overview

You manage a team of sales executives selling Mews' cloud property management system to SMB hotels (boutique hotels, hostels, serviced apartments). You're coaching reps through deals with hotel owners and GMs who are often switching from legacy on-premise systems or outdated cloud platforms. You spend your time in forecast calls, deal reviews, riding along on demos, and removing blockers when deals stall on implementation fears or budget concerns.

Role Snapshot

Company Context

Stage: Growth stage (1,515 employees, likely Series C/D based on size)

Size: 1,515 employees globally

Growth: Actively hiring across sales org, expanding North America SMB coverage

Market Position: Challenger in hospitality PMS space - competing against legacy players (Opera, Cloudbeds) and newer cloud platforms

GTM Reality

Pipeline Sources:

• 40-50% Inbound - hotels researching cloud PMS alternatives, demo requests from website, content downloads, referrals from existing customers
• 40-50% Outbound - reps prospecting boutique hotels, hostels, serviced apartments via LinkedIn, cold calling front desk/ownership
• 10-20% Partners - property management companies, hospitality consultants, integration partners

SDR/AE Structure: Likely dedicated AEs (full-cycle) - SMB motion typically doesn't justify SDR layer

SE Support: Shared solutions engineer pool for complex technical questions or integrations

Competitive Landscape

Main Competitors: Oracle Opera (legacy), Cloudbeds, Guesty, RMS Cloud, Little Hotelier, eZee Absolute

How They Differentiate: Modern cloud platform with mobile-first design, extensive integration marketplace (1,000+ integrations), built-in payment processing and revenue management

Common Objections: "Our current system works fine," switching costs and implementation disruption, training staff on new system, cost vs. legacy pricing, "We're too small/unique for a one-size platform"

Win Themes: Automation reduces manual front desk work, mobile operations, revenue optimization tools, seamless payments, modern guest experience

What You'll Actually Do

Time Breakdown

Coaching/1-on-1s (30%) | Pipeline/Forecast Reviews (25%) | Deal Support (25%) | Hiring/Admin (20%)

Key Activities

• Weekly 1-on-1s with each rep: Review their deals, coach through objections ("why leave our current PMS?"), strategize on stalled opportunities, discuss activity metrics (calls, demos, proposals)
• Pipeline forensics: Dig into why deals are stuck - is it budget, technical integration concerns, decision-maker access, implementation timing, or just the hotel dragging their feet?
• Riding along on calls: Join demos with skeptical hotel owners, help reps navigate technical questions about integrations (channel managers, booking engines, POS systems), handle pricing negotiations
• Forecast accuracy: Reconcile what reps say will close vs. what actually closes - SMB deals slip constantly due to "waiting until after high season" or ownership indecision
• Cross-functional battles: Push product for features SMB hotels need, fight with marketing over lead quality, coordinate with implementation team on new customer onboarding capacity
• Recruiting and ramping: Interview candidates, onboard new reps, build training on hospitality industry basics and competitive positioning

The Honest Reality

What's Hard

• Managing forecast accuracy: SMB hotel owners are notoriously unpredictable - deals that seem locked slip because "we're going into busy season" or "the owner is traveling" or they just ghost for weeks
• Coaching reps through rejection and long sales cycles: Hospitality is relationship-driven and change-averse - reps burn out cold calling hotels that hang up or dealing with hotel managers who won't switch systems mid-season
• You're often in the weeds: When a big deal is stuck on a technical integration question or a pricing exception, you're jumping in directly vs. delegating
• Segment challenges: SMB hotels have budget constraints, seasonal revenue fluctuations, and often need more hand-holding than enterprise accounts but generate smaller deal sizes
• Balancing team growth with performance: You're hiring to expand while managing underperformers - tough conversations about PIPs while also selling candidates on joining

What Success Looks Like

• Team consistently hits 90%+ of quarterly quota
• New reps ramp to productivity within 90 days (first deal closed, pipeline building)
• Pipeline coverage stays at 3-4x quota with healthy stage distribution
• Churn stays low - reps aren't burning out and leaving after 12 months
• You're not fighting fires daily - team operates semi-independently

Who You're Selling To (Your Reps Sell To)

Primary Buyers:

• Hotel Owners (boutique properties, small chains)
• General Managers (have P&L authority at independent hotels)
• Operations Directors (at small hotel groups)

What They Care About:

• Reducing manual front desk work (night audit, reconciliation, check-in/out)
• Revenue optimization (dynamic pricing, upsells, channel management)
• Guest experience improvements (mobile check-in, contactless payments)
• Implementation disruption (can't go dark during busy season)
• Total cost of ownership (switching from legacy contracts)
• Staff training burden (high turnover in hospitality)

Requirements

• 3+ years managing B2B SaaS sales teams, ideally in SMB segment
• Experience coaching reps through consultative sales (not just transactional/velocity)
• Comfortable with forecast management and pipeline metrics
• Ability to jump into deals and close directly when needed
• Understanding of hospitality industry helpful but not required (can learn)
• Willingness to travel occasionally for team meetings, customer events, QBRs
• Track record of hiring and developing sales talent