Chief of Staff, Strategy & AI
10+ years
Charleston, South Carolina Metropolitan Area
Full-time
Hybrid
1 month ago
About the role
Chief of Staff, Strategy & AI
Full-Time • Hybrid (Charleston, SC) • Reports to CEO
ABOUT THE COMPANY
Family Fun & Games is a vending and amusement platform company headquartered in Charleston, SC, operating nationally across equipment sales, operator technology (SmartClaw), consumer packaged goods (American Gumball Co.), and ecommerce (CandyMachines.com, ClawMachines.com). We are in the middle of a post-acquisition transformation—scaling from $15M toward $30M+ in revenue—and building the AI-native infrastructure to get there. Our brands include Rhino Vending, SmartClaw, VendingNation, American Gumball Co., and Vendsurance.
THE ROLE
This is not a traditional Chief of Staff role. You are the CEO’s strategic right hand and the company’s intelligence layer. You sit at the intersection of business strategy, financial analytics, and applied AI—pulling together the data, building the automations, and driving the decisions that determine where this company goes next.
You will own the company’s single source of truth across all departments. You will build and operate agentic AI systems that replace manual work. You will run the weekly cadence that keeps leadership focused on what actually moves revenue, margin, and enterprise value. You are a builder and a doer—not a slide-maker who delegates to consultants.
If your instinct when you see a human doing repetitive knowledge work is to ask “Why isn’t this automated?”—this role was designed for you.
WHAT YOU OWN
1. Company KPI Dashboard — Single Source of Truth
• Revenue, gross margin, contribution margin, working capital position, SBA and debt service coverage
• Turns, aging, stockout risk, landed COGS by SKU, freight cost trends
• AOV, conversion rate, ad spend efficiency (ROAS/CAC), repeat purchase rates, customer LTV
• Pipeline velocity, quote-to-close ratio, rep-level activity, channel performance by distributor tier
• Service ticket volume, resolution time, warehouse throughput, employee productivity metrics
• True profitability after freight, support, and returns—not just gross margin
2. AI Systems & Automation
Your operating question: “Why is a human doing this?”
• Design, build, and maintain agentic AI workflows that eliminate manual knowledge work across the organization
• Deploy and integrate tools including n8n, Claude API, OpenAI APIs, vector databases, Power BI, Shopify analytics, BigQuery, Gorgias AI, RingCentral AI, Teams workflows, and custom warehouse dashboards
• Own the company’s AI roadmap: identify automation candidates, build proof-of-concept, measure ROI, and scale what works
• Partner with the CEO on AI-native product development (SmartClaw data layer, customer support, sales intelligence)
3. Executive Prioritization & Accountability
• Run a weekly strategic cadence that surfaces the biggest bottlenecks, highest-ROI initiatives, and underperforming departments
• Produce clear, prioritized action lists for leadership with owners and deadlines—not status updates, but decisions and next moves
• Track execution against the company’s 5-year growth model and 18-month cash plan
• Serve as the CEO’s force multiplier—pre-digest complexity so leadership meetings produce decisions, not discussions
4. Business Intelligence Layer
You are expected to answer questions like these on demand:
• Which SKUs are actually profitable after freight, support costs, and returns?
• Which customers convert to repeat buyers, and what’s their true LTV by acquisition channel?
• Which distributor accounts are worth the support investment vs. margin drag?
• Which ad campaigns generate high-LTV operators vs. one-time buyers?
• Which machine categories produce warranty and service headaches?
• Which vendors create hidden margin erosion through quality, lead time, or compliance failures?
• Where are the operational bottlenecks that create drag across departments?
WHO YOU ARE
• An entrepreneur trapped in an operator’s body—you think in business models, unit economics, and leverage, not just dashboards
• Fluent in modern AI tools and capable of building production workflows, not just evaluating vendor demos
• Strong in financial analysis: you can read a P&L, model a scenario, and explain what the numbers mean for the business
• A natural cross-functional leader who earns credibility through competence, not title
• Comfortable operating in ambiguity—this is a scaling company, not a Fortune 500 with established playbooks
• Relentlessly curious about where time and money are being wasted, and biased toward building the fix
QUALIFICATIONS
• 3–10 years of experience in strategy, business intelligence, operations, or a high-autonomy analytical role
• Demonstrated ability to build and ship AI/automation workflows in a business context (not just academic or experimental)
• Strong working knowledge of BI tools (Power BI, Looker, Tableau, or equivalent), SQL, and at least one scripting language
• Experience with ecommerce analytics (Shopify, Google Analytics, ad platform reporting)
• Familiarity with financial modeling, margin analysis, and KPI frameworks
• Bachelor’s degree in Business, Data Science, Finance, Engineering, or a related field; advanced degrees or relevant certifications are a plus
• Previous experience in a high-growth, founder-led, or PE-backed environment is strongly preferred
COMPENSATION & STRUCTURE
• Full-time, hybrid position based in the Charleston, SC metropolitan area with flexibility for remote work
• Competitive base salary commensurate with experience, with performance-based bonus tied to company KPIs
• Direct report to the CEO with cross-departmental authority
• Opportunity to grow as the company scales
Family Fun & Games is an equal opportunity employer.
To apply, send your resume and a brief note on what you’d automate first to [email protected]
Full-Time • Hybrid (Charleston, SC) • Reports to CEO
ABOUT THE COMPANY
Family Fun & Games is a vending and amusement platform company headquartered in Charleston, SC, operating nationally across equipment sales, operator technology (SmartClaw), consumer packaged goods (American Gumball Co.), and ecommerce (CandyMachines.com, ClawMachines.com). We are in the middle of a post-acquisition transformation—scaling from $15M toward $30M+ in revenue—and building the AI-native infrastructure to get there. Our brands include Rhino Vending, SmartClaw, VendingNation, American Gumball Co., and Vendsurance.
THE ROLE
This is not a traditional Chief of Staff role. You are the CEO’s strategic right hand and the company’s intelligence layer. You sit at the intersection of business strategy, financial analytics, and applied AI—pulling together the data, building the automations, and driving the decisions that determine where this company goes next.
You will own the company’s single source of truth across all departments. You will build and operate agentic AI systems that replace manual work. You will run the weekly cadence that keeps leadership focused on what actually moves revenue, margin, and enterprise value. You are a builder and a doer—not a slide-maker who delegates to consultants.
If your instinct when you see a human doing repetitive knowledge work is to ask “Why isn’t this automated?”—this role was designed for you.
WHAT YOU OWN
1. Company KPI Dashboard — Single Source of Truth
• Revenue, gross margin, contribution margin, working capital position, SBA and debt service coverage
• Turns, aging, stockout risk, landed COGS by SKU, freight cost trends
• AOV, conversion rate, ad spend efficiency (ROAS/CAC), repeat purchase rates, customer LTV
• Pipeline velocity, quote-to-close ratio, rep-level activity, channel performance by distributor tier
• Service ticket volume, resolution time, warehouse throughput, employee productivity metrics
• True profitability after freight, support, and returns—not just gross margin
2. AI Systems & Automation
Your operating question: “Why is a human doing this?”
• Design, build, and maintain agentic AI workflows that eliminate manual knowledge work across the organization
• Deploy and integrate tools including n8n, Claude API, OpenAI APIs, vector databases, Power BI, Shopify analytics, BigQuery, Gorgias AI, RingCentral AI, Teams workflows, and custom warehouse dashboards
• Own the company’s AI roadmap: identify automation candidates, build proof-of-concept, measure ROI, and scale what works
• Partner with the CEO on AI-native product development (SmartClaw data layer, customer support, sales intelligence)
3. Executive Prioritization & Accountability
• Run a weekly strategic cadence that surfaces the biggest bottlenecks, highest-ROI initiatives, and underperforming departments
• Produce clear, prioritized action lists for leadership with owners and deadlines—not status updates, but decisions and next moves
• Track execution against the company’s 5-year growth model and 18-month cash plan
• Serve as the CEO’s force multiplier—pre-digest complexity so leadership meetings produce decisions, not discussions
4. Business Intelligence Layer
You are expected to answer questions like these on demand:
• Which SKUs are actually profitable after freight, support costs, and returns?
• Which customers convert to repeat buyers, and what’s their true LTV by acquisition channel?
• Which distributor accounts are worth the support investment vs. margin drag?
• Which ad campaigns generate high-LTV operators vs. one-time buyers?
• Which machine categories produce warranty and service headaches?
• Which vendors create hidden margin erosion through quality, lead time, or compliance failures?
• Where are the operational bottlenecks that create drag across departments?
WHO YOU ARE
• An entrepreneur trapped in an operator’s body—you think in business models, unit economics, and leverage, not just dashboards
• Fluent in modern AI tools and capable of building production workflows, not just evaluating vendor demos
• Strong in financial analysis: you can read a P&L, model a scenario, and explain what the numbers mean for the business
• A natural cross-functional leader who earns credibility through competence, not title
• Comfortable operating in ambiguity—this is a scaling company, not a Fortune 500 with established playbooks
• Relentlessly curious about where time and money are being wasted, and biased toward building the fix
QUALIFICATIONS
• 3–10 years of experience in strategy, business intelligence, operations, or a high-autonomy analytical role
• Demonstrated ability to build and ship AI/automation workflows in a business context (not just academic or experimental)
• Strong working knowledge of BI tools (Power BI, Looker, Tableau, or equivalent), SQL, and at least one scripting language
• Experience with ecommerce analytics (Shopify, Google Analytics, ad platform reporting)
• Familiarity with financial modeling, margin analysis, and KPI frameworks
• Bachelor’s degree in Business, Data Science, Finance, Engineering, or a related field; advanced degrees or relevant certifications are a plus
• Previous experience in a high-growth, founder-led, or PE-backed environment is strongly preferred
COMPENSATION & STRUCTURE
• Full-time, hybrid position based in the Charleston, SC metropolitan area with flexibility for remote work
• Competitive base salary commensurate with experience, with performance-based bonus tied to company KPIs
• Direct report to the CEO with cross-departmental authority
• Opportunity to grow as the company scales
Family Fun & Games is an equal opportunity employer.
To apply, send your resume and a brief note on what you’d automate first to [email protected]
Skills
AdministrativeOnline and Mail Order Retail