Head of Sales Enablement

Popmenu is hiring its first dedicated Head of Sales Enablement to own the full ramp and readiness motion for our growing GTM team. This isn't a maintenance role — it's a build role. You'll design the system from the ground up: onboarding programs, playbooks, coaching frameworks, AI-powered enablement tools, and the feedback loops that connect rep performance back to content and training.

You'll work directly with Sales Leadership and report to the COO. You'll be the connective tissue between what our best reps do and what every rep can learn to do.

If you're someone who genuinely cares about why a new hire succeeds or struggles, and you feel personally invested in getting that right — this role was built for you.

WHAT YOU'LL OWN

Onboarding & Ramp

• Design and execute a structured 30/60/90-day onboarding program for all GTM hires (AEs, RSLs, Growth/Strategic AEs)
• Build role-specific certification tracks that get reps selling fast and selling well
• Measure ramp velocity and time-to-productivity; iterate based on results
• Ensure new hires have a strong first 90 days — not just completion certificates, but real quota contribution

Playbooks & Content

• Build and maintain the full sales playbook: talk tracks, discovery frameworks, objection handling, competitive positioning, demo guidance
• Partner with Marketing and Product to keep content current as the product and market evolve
• Create and manage a single source of truth for all sales collateral in Salesforce and Salesloft

AI-First Enablement

• Develop and deploy an AI-powered enablement motion — this is a core requirement, not a nice-to-have
• Identify, pilot, and roll out AI tools that accelerate onboarding, coaching, and rep performance
• Train the GTM team on how to use AI in their daily workflow (prospecting, research, outreach, objection handling)

Coaching & Continuous Learning

• Build a structured coaching program in partnership with Sales Managers
• Use call data and rep performance metrics to identify skill gaps and address them systematically
• Develop an "everboarding" program so tenured reps continue developing

GTM Rollouts

• Own the enablement layer for all major GTM initiatives: new product launches, pricing changes, market expansions, seasonal campaigns
• Coordinate cross-functionally with Sales, Marketing, Product, and RevOps to ensure reps are ready before anything goes live

Measurement

• Define and track enablement KPIs: ramp time, quota attainment at 90/180 days, win rates by segment, content usage, rep skill scores
• Report to COO on enablement impact quarterly

Requirements

Non-Negotiables

• 2–3 years in Sales Enablement — you've owned real programs with measurable outcomes, not just supported them
• 1–2 years in a quota-carrying sales role in SaaS — you understand the motion you'll be enabling because you've lived it
• Familiarity with SMB sales cycles (sub-60 days) and high-velocity, consultative selling
• Hands-on Salesforce and Salesloft proficiency — you're in the tools, not just familiar with them
• Demonstrated AI fluency — you've used AI tools in your enablement work and can show it
• You've contributed to or owned an onboarding program and can speak to the results
• Strong collaborator with Sales Leaders — you earn trust through follow-through and push back when something won't work

Strong Preference

• Background in restaurant tech, hospitality SaaS, or vertical SaaS
• Experience in a high-growth, startup or scale-up environment (you've built without a big team)
• Ability to evaluate and recommend tools that drive AE performance — you know what good looks like and can make a case for it
• Experience rolling out GTM initiatives at the rep and manager level

Who You Are

• A builder, not a maintainer — you're energized by blank whiteboards, not frustrated by them
• Obsessed with rep success — you measure yourself by how quickly new hires ramp and how long they stay
• Data-driven — you use metrics to prioritize, not just to report
• Direct and collaborative — you'll challenge Sales Leaders, and they'll respect you for it

Benefits

Who We Are

Popmenu is a fast-growing, venture-backed SaaS company transforming the restaurant industry. We started with our patented dynamic menu technology, unleashing the power of a restaurant's most important marketing tool, the menu. Since then, we have continued innovating to solve existing and