Head of Enablement

Monaco is building an AI-native revenue platform that replaces the fragmented GTM stack - CRM, sequencing, call recording, enrichment, pipeline management with one unified system, consolidating 6–10 disconnected tools into a single platform built for the AI era.

We launched publicly in Feb 2026, are already 65 people, and have strong early product-market fit generating millions in ARR within months of launch. You'll have the chance to both scale our core systems and build new features from 0 to 1.

We've raised $85M in our Series B from Founders Fund, Benchmark, and Human Capital, and our founders previously led Brex, Apollo, and Clari.

Come join us if you want to be part of a high autonomy, high pace team reinventing one of the biggest categories in enterprise software.

The Role

As Enablement Lead, you own GTM enablement for the entire GTM team - FDAEs (new business and post-sales), launch operations, and client operations. You're accountable for how fast new hires ramp, improving close rates, and how well both reps and customers know the product as we ship. Our reps are forward-deployed - they consult with customers on their outbound engines, not just sell - so the bar is higher than a typical sales org: every rep has to know the product, the Monaco Method, and modern outbound strategy cold. This is a 0-to-1 build. You'll create the function yourself, prove what works, and scale it as the GTM org grows.

What You'll Do

• Own the enablement strategy end to end and define what GTM readiness means at Monaco, set the program, and be accountable for ramp time, certification rates, and rep productivity
• Build and run the crawl/walk/run onboarding program that takes new FDAEs (new business and post-sales) from day one to fully productive, with product training, pitch certification, mock kickoffs and demos, shadowing plans, and clear pass/fail milestones at each stage
• Turn our weekly ship velocity into rep readiness - talk tracks, demo flows, updated objection handling, and internal launch briefs for every meaningful feature, delivered before it hits customer calls
• Capture what our best reps do in kickoffs, discovery, demos, onboarding, and outbound strategy consults, and codify it into playbooks, annotated call libraries, and certifications the whole team trains against
• Keep the team sharp through weekly call reviews, live role-plays, quarterly re-certifications on pitch and demo, and targeted coaching sprints when a specific skill gap shows up in deal or customer data
• Build the customer-facing side of product enablement - the onboarding curriculum, live training sessions, and self-serve academy content that get customer teams live on Monaco and running their outbound motion
• Partner with sales, CX, and product leadership to spot skill and knowledge gaps from real signals - call recordings, lost-deal reasons, kickoff quality scores, customer adoption data - and close them fast
• As the GTM org grows, build the team, systems, and tooling that keep enablement ahead of headcount

Who We're Looking For

Must-Haves

• 4+ years proven experience building and leading sales or GTM enablement at a high-growth B2B SaaS startup - ideally as the first or early enablement hire who took the function from 0 to 1
• 2-4+ years in a selling role; you've been an SDR, AE, or account manager and understand outbound selling firsthand, so you enable from credibility rather than theory
• Track record designing onboarding/ramp programs that measurably shortened time-to-productivity
• AI-native mentality with an enablement playbook relevant for an AI-native company
• Strong content and program-building chops: playbooks, certifications, call libraries, repositories - leveraging AI to build a knowledge context wiki - you ship fast and iterate
• Comfortable in a high-velocity, constantly-shipping environment where the product changes weekly and enablement can never be static

Strong Pluses

• Experience at a company selling CRM, sequencing, or GTM tooling - you know this buyer and this stack
• Personal experience running or coaching modern outbound (sequencing, signals, ICP/TAM strategy)
• Experience building customer education or academy programs, not just internal enablement
• Experience hiring and managing enablement teams as a function scaled
• Familiarity with tools like HubSpot, Salesforce, Outreach, Apollo, Salesloft, or Gong - and strong opinions on what an AI-native replacement should feel like
• Experience enabling forward-deployed, consultative, or services-adjacent sales teams

Our GTM Motion

You'll be enabling reps who sell and consult inside this motion, so you need to internalize it quickly.

• We sell to VC-backed B2B startups (pre-seed through Series B) with a sales-led GTM motion
• Buyers are Founders/CEOs, CROs, VPs of Sales, and Heads of GTM — reps need executive-level fluency
• High-velocity, full-cycle deals with short (2–4 week) sales cycles — ramp speed matters enormously
• Every rep is forward-deployed: they close the deal, then run onboarding, ICP alignment, and outbound strategy with the customer
• We sell against entrenched tools (HubSpot, Salesforce, Gong, Outreach, Apollo) — reps must handle pricing, commitment, and product-gap objections with confidence