Overview
You sell Toast's cloud-based POS and restaurant management platform to independent and small chain restaurants. This is full-cycle: you're making cold calls to restaurant owners, booking your own demos, walking them through the platform, negotiating contract terms, and getting them to switch from their current system. You work remotely in MT or PST time zones.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Full-cycle AE (prospecting through close) |
| Sales Motion | Outbound-heavy (100% self-sourced) |
| Deal Complexity | Consultative transactional |
| Sales Cycle | 3-8 weeks |
| Deal Size | $10-30K ACV (hardware + software + payments) |
| Quota (est.) | $40-60K MRR/month |
Company Context
Stage: Public (IPO 2021, ~$4B revenue)
Size: 7,500+ employees
Growth: Mature growth stage, established market leader but competitive hiring continues
Market Position: Category leader in restaurant POS, competing against Square, Clover, Lightspeed, legacy systems like Aloha/Micros
GTM Reality
Pipeline Sources:
- 100% Outbound - You're building lists of restaurants, cold calling owners/GMs, sending email sequences, doing LinkedIn outreach
- No inbound support mentioned for this role
- Some existing customer referrals possible but not your primary source
SDR/AE Structure: No SDR support - fully self-sourced pipeline
SE Support: Likely shared SE pool for complex technical questions or multi-location deals, but you run most demos yourself
Competitive Landscape
Main Competitors: Square for Restaurants, Clover, Lightspeed, TouchBistro, legacy systems (Aloha, Micros)
How They Differentiate: All-in-one platform (POS + online ordering + payments + payroll + loyalty), purpose-built for restaurants vs generic retail POS
Common Objections: "We just signed a contract with our current provider," switching costs/downtime concerns, "Square is cheaper," "We've used [legacy system] for 15 years"
Win Themes: Integration depth, restaurant-specific features, growth from single location to multi-unit, payments processing bundled
What You'll Actually Do
Time Breakdown
Prospecting (40%) | Active Deals (35%) | Admin/Internal (25%)
Key Activities
- Cold outreach: You're calling 50-70 restaurants per day, mostly reaching voicemail or hosts who say the owner isn't available. You're trying to book 8-12 discovery calls per week. You're pulling lists by geography, cuisine type, restaurant size.
- Discovery calls and demos: You're walking restaurant owners through the platform on Zoom, showing them how table management works, how online ordering integrates, how reporting differs from their current system. Most demos are 30-45 minutes. You're trying to understand their pain points with their current POS.
- Follow-up and objection handling: You're chasing busy restaurant owners who are hard to reach during service hours. You're sending proposal documents, answering questions about hardware costs, explaining why the switching process won't shut them down during dinner service, coordinating site surveys.
- Closing and implementation handoff: You're negotiating final terms, getting contracts signed, coordinating with implementation team on install dates. You stay involved through go-live to ensure smooth handoff.
The Honest Reality
What's Hard
- Restaurant owners are extremely busy and hard to reach - you're calling during off-hours (10am-3pm window) or they're in service. Lots of gatekeeping from hosts/managers.
- High objection rate around switching costs - restaurants are sticky, many just renewed contracts, fear downtime during the switch
- You're competing on price against Square in the lower end - some deals come down to monthly fees and processing rates
- Long tail of small deals means volume matters - you need consistent pipeline because individual deals aren't huge
- Restaurants are cyclical and cash-sensitive - deals can stall based on their current revenue situation
What Success Looks Like
- Booking 8-12 qualified discovery calls per week from your outbound efforts
- Converting 25-35% of demos to proposals
- Closing 6-10 new restaurant locations per month
- Hitting monthly MRR quota consistently ($40-60K range typical)
Who You're Selling To
Primary Buyers:
- Restaurant owners (independent, 1-3 locations)
- General Managers with purchasing authority
- Multi-unit operators (small chains, 4-10 locations)
What They Care About:
- Uptime and reliability - they can't afford POS going down during service
- Ease of staff training - high turnover means simple systems win
- Reporting and food cost management - margins are thin, they need data
- Online ordering integration - post-COVID essential
- Total cost of ownership - hardware, software, processing fees all matter
Requirements
- 1-3 years SaaS sales experience (full-cycle preferred)
- Track record of closing deals and managing objections
- Comfortable with 100% self-sourced pipeline (high outbound activity)
- Located in MT or PST time zones
- Experience selling to SMB buyers who are hands-on operators (not IT buyers)
- Ability to handle transactional volume while maintaining consultative approach