The Challenge
Toast is building an AI Marketing Agent that puts a world-class marketing manager in every restaurant's pocket. You'll lead this nascent product from foundation to scale, driving incremental revenue for thousands of merchants while transforming how local businesses approach growth.
Your Mission
Map merchant marketing pain points across 5+ customer segments; conduct 20+ user interviews to validate core agent capabilities
Define and lock product strategy: which marketing channels (email, SMS, social, offers, SEO) the agent tackles first and sequencing for merchant ROI
Ship 2-3 initial agent 'skills' (e.g., email campaign creation, offer optimization) with measurable impact on merchant engagement or revenue
Establish baseline metrics and instrumentation for agent performance (time saved, revenue lift, adoption rate)
Launch full Marketing Agent MVP with 4+ core skills; achieve 15%+ adoption among target merchant segment within first 90 days of release
Demonstrate $X incremental ARR impact per merchant; quantify efficiency gains for Toast's human marketing services team
Integrate 2+ new monetization models (premium skills, usage-based pricing) and validate willingness to pay
Build cross-functional playbook for agent skill development; define processes for Engineering, Design, Data Science collaboration
KPIs You'll Own
Merchant Activation & Adoption
% of eligible merchants using at least one Marketing Agent skill within 30 days of release.
Incremental Revenue Per Merchant
Measured lift in GMV or recurring revenue attributed to agent-driven marketing campaigns.
Time Saved / Effort Reduction
Estimated or measured hours saved per merchant monthly; target: 5-10 hours of marketing work automated.
Feature Engagement & Skill Utilization
Usage rate, frequency, and depth of each agent skill; identifies highest-impact features for scaling.
Customer Satisfaction & NPS
Agent feature NPS and qualitative feedback; guides product iteration and skill prioritization.
Cost Per Merchant Served
Infrastructure and operational cost to deliver agent capabilities; targets efficiency gains vs. human services.
Tools & Stack
Your Team
Your Manager
Head of AI Marketing or VP Product (not specified in posting)
Current Team
Cross-functional: Engineering, Design, Data Science, Marketing, Customer Success, Sales liaisons
New role; building out nascent product line
The Package
Salary
$165K-$210K base
Variable
Performance bonus (10-20% estimated for manager-level PM at Toast)
Equity
Stock options (standard for Toast, likely 0.05-0.15% depending on stage)
Remote
On-site preferred; Boston/New York area. East Coast, USA required.
Benefits & Perks
Company Intelligence
Toast is an all-in-one SaaS platform helping restaurants and local businesses operate, sell, and grow in a digital world. The company combines POS, loyalty, marketing, and staffing tools to serve thousands of merchants. Toast operates with a startup mentality within its AI initiatives, prioritizing speed, customer obsession, and measurable impact.
Customers
5,000+ restaurants and local businesses (estimated)
Culture
Entrepreneurial, fast-paced, data-driven, customer-obsessed, relentlessly focused on ROI and merchant outcomes.
Is This Role For You?
- You've shipped 2+ products in marketing automation, demand generation, or AI-powered tools and can tie each to revenue or engagement metrics
- You obsess over merchant/SMB pain points and live in Slack with customers weekly during early product phases
- You thrive in ambiguity: product strategy isn't handed to you, and you're comfortable pivoting based on data and customer feedback
- You can code-switch between technical depth (LLMs, data quality, integration patterns) and business acumen (GTM, unit economics, pricing models)
- You want meaningful equity upside and are excited by early-stage product leadership at a well-funded, growth-stage company
- You need a fully remote setup; Toast is heavily on-site for this PM role in Boston/New York area
- You're uncomfortable with AI/LLM-driven products or prefer building features with deterministic outcomes
- You expect a fully staffed, mature team; this is a nascent product line where you'll wear multiple hats and iterate fast
- You're risk-averse or prefer established playbooks; this role demands experimentation, some failed experiments, and a willingness to pivot
Interview Process
Recruiter Screen
30 min; validate PM background, AI/marketing product experience, on-site willingness.
PM Case Study
Async or live case: define strategy for a new AI-powered feature in marketing automation; focus on merchant ROI and go-to-market.
Cross-Functional Panel
4-5 interviews (1 hr each) with Engineering, Design, Data Science, Product Leadership, and a merchant-facing lead (Customer Success or Sales).
Executive Round
Conversation with Head of Product or Chief Product Officer on vision, strategy, and fit for Toast's AI roadmap.
Merchant Interview
Optional deep-dive: speak directly with a restaurant customer to demonstrate customer empathy and problem-solving mindset.
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