Overview
You sell Toast's all-in-one restaurant POS and management platform to independent restaurants, chains, and hospitality groups. This means convincing restaurant owners to rip out their existing system and trust Toast with their entire front-of-house, kitchen, and back-office operations. You're competing in a mature, crowded market where every POS provider claims to understand restaurants.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Full-cycle AE (likely) - prospecting through close |
| Sales Motion | Outbound-heavy with some inbound |
| Deal Complexity | Consultative - multi-stakeholder, requires on-site demos |
| Sales Cycle | 1-3 months for SMB, 3-6 months for multi-unit |
| Deal Size | $3-15K ACV (single location), $50K+ (multi-unit) |
| Quota (est.) | $400K-600K/year depending on territory |
Company Context
Stage: Public (NYSE: TOST, IPO'd in 2021)
Size: 7,538 employees
Growth: Mature growth stage - moved from hyper-growth startup to optimizing efficiency post-IPO
Market Position: Category leader in restaurant POS, competing with Square, Clover, Aloha, Micros
GTM Reality
Pipeline Sources:
- 30% Inbound - restaurants researching new POS systems, trade show leads, referrals from existing customers
- 60% Outbound - cold calling restaurants in your territory, door-knocking, networking at industry events
- 10% Partner/Channel - introductions from restaurant consultants, franchise development groups
SDR/AE Structure: Varies by segment - Enterprise has SDRs, SMB is self-sourced
SE Support: Solutions Engineers available for complex multi-location deals
Competitive Landscape
Main Competitors: Square (price-sensitive buyers), Clover (bank relationships), Aloha/NCR (legacy enterprise), TouchBistro (Canada-strong)
How They Differentiate: "Built for restaurants" positioning, integrated payments processing, kitchen display systems, online ordering, deep reporting
Common Objections:
- "Too expensive vs Square" (SMB)
- "Switching costs/training disruption"
- "Already locked into X-year contract"
- "My current system works fine"
Win Themes: All-in-one platform eliminates multiple vendors, better reporting than legacy systems, commission-free online ordering during pandemic created goodwill
What You'll Actually Do
Time Breakdown
Prospecting (35%) | Active Deals (40%) | Internal/Admin (25%)
Key Activities
- Cold Outreach: Calling restaurants from a territory list, dropping by during slow hours (2-4pm), asking to speak with the owner/GM. Most don't have time to talk. You're trying to book on-site demos.
- On-Site Demos: Driving to restaurants to show the POS system in action. You bring an iPad and card reader, walk through a mock transaction, show kitchen screens. These happen during pre-service hours or right after lunch rush.
- Multi-Call Follow-Up: Restaurant owners are terrible at responding. You'll call/text/email 8-12 times before getting a "yes" or "no." Many deals stall because they get busy with service.
- Proposal/Pricing Negotiation: Building custom hardware bundles (terminals, printers, KDS screens). Fighting over monthly subscription costs vs. upfront hardware fees. Navigating payment processing rates.
- Implementation Coordination: Once sold, you hand off to onboarding team but stay involved through install day. If the install goes badly (system crashes during dinner service), you'll hear about it.
The Honest Reality
What's Hard
- Restaurant owners work when you work - demos happen early morning, mid-afternoon, or late evening. Your schedule bends to theirs.
- High rejection rate - most are "happy" with current system or can't afford downtime to switch mid-season
- Implementation anxiety - restaurants are terrified of system failures during busy service, so they drag their feet
- Economic sensitivity - restaurant margins are thin (3-5%), so economic downturns or labor cost increases kill deals
- Long payment processing evaluation - they need to compare Toast's rates vs. their current processor, which adds weeks
- Churn/customer quality issues reflect on you - if the restaurant you sold goes out of business, it impacts your comp structure
What Success Looks Like
- 8-12 new location installs per quarter (SMB territory)
- 2-3 multi-unit deals per year (5+ locations)
- 85%+ retention in your book of business
- Winning referrals from existing customers (restaurants talk to each other)
- Building a territory where you're known at industry meetups and restaurant association events
Who You're Selling To
Primary Buyers:
- Independent restaurant owners (50-65 years old, technophobic, skeptical of salespeople)
- Restaurant GMs/Operating Partners (younger, more tech-savvy, but need owner approval)
- Multi-unit franchisees (buying for 5-20 locations, more sophisticated)
- Hospitality groups (VP of Ops, CFO - enterprise deal)
What They Care About:
- System reliability during service - cannot go down Friday night
- Ease of staff training - high turnover means simple interface is critical
- Reporting/theft prevention - want to see what's really happening when they're not there
- Payment processing costs - obsessed with basis points and monthly fees
- Switching cost/disruption - when can we install without killing business?
Requirements
- 2-4 years sales experience (B2B preferred, not required)
- Comfortable with field sales - driving around a territory, popping into businesses unannounced
- Restaurant/hospitality experience helpful but not required (they teach the product)
- Thick skin for rejection and ghosting - restaurant owners are tough audiences
- Flexible schedule - demos happen when restaurants are slow, not 9-5
- Valid driver's license and reliable transportation
- CRM hygiene discipline (Salesforce) - Toast tracks activity metrics closely