The Challenge
Toast is building the future of restaurant tech—now they're reimagining their entire GTM engine through AI. You'll architect how thousands of sales reps, marketers, and ops teams work with AI to drive revenue and efficiency.
Your Mission
Map Toast's GTM pain points and identify 3-5 high-ROI AI use cases (territory management, lead qualification, follow-up automation)
Build and ship 2 working prototypes using Claude/V0 that demonstrate measurable lift in rep productivity or win rate
Establish cross-functional alignment between Sales Leadership, Marketing, and Engineering on AI roadmap priorities
Define technical requirements and data infrastructure needs for first wave of AI solutions
Launch first production AI agent for sales rep workflows with adoption target of 60%+ of team
Measure and report on KPIs: rep productivity lift, time-to-close impact, win rate improvement
Expand AI solutions to 2-3 additional GTM workflows (marketing automation, forecasting, customer success)
Build repeatable process for identifying, prototyping, and scaling AI solutions across GTM organization
KPIs You'll Own
Sales Rep AI Adoption Rate
% of GTM team actively using AI solutions in daily workflow; target 60%+ by month 6.
Time-to-Close Reduction
Days saved per deal cycle after AI implementation; baseline against historical data.
Win Rate Lift
Percentage point increase in win rates for reps using AI-assisted qualification vs. control group.
Prototype-to-Production Velocity
Time from concept to shipped production feature; target sub-8 week cycle.
Rep Productivity (Activity-Based)
Calls, emails, or meetings per rep per week; measure before/after AI enablement.
Tools & Stack
Your Team
Your Manager
Not specified; likely GTM or Sales leadership
Current Team
You'll orchestrate across GTM Strat Ops, Sales Leadership, Marketing, Business Technology, and Engineering
New role creating a new GTM AI function
The Package
Salary
$165K-$210K base
Remote
On-site (location unspecified; Toast headquarters context required)
Benefits & Perks
Company Intelligence
Toast is a B2B SaaS platform serving restaurants and local businesses with point-of-sale, operations, and customer engagement tools. The company empowers thousands of business owners to succeed in digital commerce.
Customers
Restaurants and local businesses (SMB focus)
Culture
Builder-focused, mission-driven, cross-functional collaboration valued
Is This Role For You?
- You've shipped AI products in a GTM context and can speak credibly to LLM limitations and real-world constraints
- You're comfortable getting hands-on with prompts, Claude, and low-code tools—not delegating prototyping to others
- You genuinely understand B2B sales cycles and can translate rep 'gut feelings' into structured data requirements
- You thrive in high-ambiguity environments and excel at orchestrating alignment across Engineering, Sales, and Ops without formal authority
- Restaurant or restaurant-adjacent industry experience is a genuine bonus (you understand the pain)
- You're a pure strategist who doesn't want to code/prototype—this role requires hands-on AI building
- You lack sales leadership credibility or have never worked closely with enterprise sales teams
- You prefer deep specialization over T-shaped work; this is about bridging product, GTM, and engineering
- You need a fully remote setup; this is on-site only
Interview Process
Recruiter Screen
Background on AI/GTM experience, remote preference confirmation, compensation alignment
Hiring Manager (VP/Chief GTM Officer)
Deep dive on GTM AI vision, approach to cross-functional leadership, and how you'd prioritize early wins
Technical Assessment
Build a live prototype or design doc: given a sales problem, map out the AI solution, data requirements, and hand-off to Eng
Sales Leadership Round
Conversation with 1-2 VP Sales or Sales Ops leaders to validate your understanding of Toast's sales motion
Executive Panel
Final round with CPO/Chief GTM Officer + Engineering leadership to confirm alignment on roadmap and execution
Interested in this role?
Apply now and hear back within days, not weeks.
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About Growth Marketing Roles
Growth marketers drive user acquisition, activation, and retention through data-driven experimentation. They sit at the intersection of product, data, and marketing — running A/B tests, building funnels, and scaling what works.