Account Executive - Restaurant Technology

Overview

You sell Toast's all-in-one restaurant POS system to independent restaurants and small chains in North Oklahoma City. You own the full sales cycle from cold outreach to signed contract, covering 3-6 in-person demos per day at restaurants. You're selling hardware (tablets, terminals, kitchen display systems) plus software subscriptions and payment processing, competing against Square, Clover, and legacy systems like Aloha.

Role Snapshot

Company Context

Stage: Public (IPO 2021, ~$4B revenue)

Size: 7,500+ employees

Growth: Scaled rapidly 2018-2022, now optimizing for profitability. Still hiring but more selective than hyper-growth phase.

Market Position: Category leader in restaurant tech with ~30% market share in full-service restaurants. Competing against Square (quick-service focus) and legacy providers.

GTM Reality

Pipeline Sources:

• 80% Outbound - cold calling restaurant owners, driving past locations, referrals from existing customers
• 15% Inbound - restaurants that submit web forms (often tire-kickers comparing multiple vendors)
• 5% Partner referrals - accountants, restaurant consultants

SDR/AE Structure: No SDR support. You source your own pipeline entirely. Marketing provides some inbound leads but volume is inconsistent.

SE Support: No dedicated SEs. You do your own demos, implementation planning, and technical Q&A. Support team helps with complex integrations post-sale.

Competitive Landscape

Main Competitors:

• Square (stronger with QSR/fast-casual, price-sensitive buyers)
• Clover (Fiserv-backed, bank partnerships)
• SpotOn (similar full-service focus)
• Legacy systems (Aloha, Micros - entrenched but outdated)

How They Differentiate: All-in-one platform (POS + payroll + online ordering + loyalty), purpose-built for restaurants vs generic retail POS. Strong integration ecosystem.

Common Objections:

• "Too expensive vs Square" (true - you're 30-40% more)
• "We just signed a 3-year processing contract" (contract buyout objections)
• "Our current system works fine" (change resistance)
• "I need to talk to my partner/accountant" (multi-stakeholder delays)

Win Themes:

• Labor management and scheduling features (reduces manager hours)
• Kitchen display system integration (improves ticket times)
• Reporting and P&L visibility (owners love the data)
• Online ordering commission savings vs DoorDash/Uber

What You'll Actually Do

Time Breakdown

Prospecting (30%) | Demos/Meetings (40%) | Closing/Admin (20%) | Internal (10%)

Key Activities

• Cold calling and door-knocking: You drive around your territory calling restaurants, stopping by during slow hours (2-4pm). Most owners don't answer or say "email me something." Goal is 40-60 touches per day to book 4-6 demos for the week.

• On-site demos: You bring an iPad to the restaurant and walk through the POS for 30-45 minutes. You're demonstrating how to ring in orders, modify items, run reports. Owners often interrupt to handle staff issues or take customer calls.

• Proposal building and follow-up: You configure hardware packages in Toast's quoting tool, send proposals, and chase for decisions. Lots of "let me think about it" or "can you call me next week." You're managing 20-30 active opportunities at various stages.

• Contract signing and onboarding handoff: Once they commit, you coordinate equipment shipping, schedule training with the implementation team, and occasionally help with menu setup. Some hand-holding required even post-close.

The Honest Reality

What's Hard

• Rejection volume: Most cold calls and drop-bys lead nowhere. Restaurant owners are busy during service and tired during off-hours. You hear "not interested" 50+ times per day.

• Long decision cycles for small deals: A $25K deal shouldn't take 6 weeks, but owners delay, ghost, or need to "run numbers with their accountant." You'll have deals slip month after month.

• Price objections: Toast is premium-priced. You lose deals to Square regularly because they're half the cost. You need to sell value, not price.

• Implementation issues affect your reputation: If onboarding goes poorly (equipment arrives late, training is rushed), the owner blames you. You're accountable for their first 90 days even though you don't control it.

• Quota pressure: 8-12 closes per month is aggressive. You need 40-50 active opps to hit it consistently. If you have a slow month, you're in the red and pressure builds fast.

What Success Looks Like

• Hit 10+ new locations per month consistently (top 20% of reps)
• Build a referral engine where existing customers introduce you to other owners
• Keep pipeline at 50+ active opps so you're not scrambling when deals fall through
• Average deal size above $30K (upselling payroll, online ordering, loyalty)

Who You're Selling To

Primary Buyers:

• Restaurant owners (often immigrant entrepreneurs, 45-65 years old)
• Operating partners for small chains (2-5 locations)

What They Care About:

• Cost: Monthly fees, processing rates, upfront hardware cost. They're watching every dollar.
• Reliability: Can't afford system downtime during dinner rush. They've been burned before.
• Ease of use: Staff turnover is high. System needs to be intuitive for new servers/bartenders.
• Speed: Faster ticket times = more table turns. Kitchen display integration is a big deal.
• Data: Owners want to see food cost %, labor %, sales trends without hiring a bookkeeper.

Requirements

• 2+ years in B2B sales (field sales experience preferred)
• Comfortable with high rejection and self-sourced pipeline
• Valid driver's license and reliable vehicle (you'll drive 100+ miles per day)
• Ability to demo software on the fly without heavy technical support
• Restaurant or hospitality experience helpful but not required
• Comfortable working evenings/weekends occasionally (restaurants operate 7 days)
• Resilience to handle quota pressure and commission swings