Head of Enablement

Reco•Wilmington, DE

About The Position

Reco is hiring its first enablement leader to build and own enablement across the full customer lifecycle, from discovery and technical validation through adoption, renewal, and expansion. The role supports Sales and Customer Success as a coordinated go-to-market function and begins as a hands-on individual contributor before building a team. The leader will develop the programs, technical readiness, sales and go-to-market playbooks, onboarding and coaching, and enablement systems needed to help AEs, SEs, CSMs, TAMs, Support, and BDRs become effective. The role includes translating expertise from company leaders and subject-matter experts into maintained, searchable content; ensuring field readiness alongside product releases; and tying enablement to deal progression and customer outcomes.

Requirements

At least 8 years of experience in go-to-market or revenue enablement.
Experience building an enablement function from zero at a high-growth B2B SaaS company.
Experience enabling AEs, SEs, BDRs, and CSMs.
Technical fluency sufficient to participate in a POV without a translator, including SaaS and identity architecture, cloud security, and AI or agentic risk.
Experience turning expertise held by a small number of people into a maintained body of content, including interviewing technical experts and translating their knowledge into usable value propositions.
Experience making MEDDPICC, Command of the Message, or Challenger materially change representative behavior.
Comfort owning pricing, business case, discounting, and negotiation enablement.
Metrics-driven program management skills, including establishing baselines, assigning owners, setting timelines, and ensuring follow-through.
Builder orientation and focus on measuring impact through deals progressed.

Nice To Haves

Security background is strongly preferred.

Responsibilities

Extract undocumented expertise from founders and subject-matter experts across Product, Research, and the Office of the CTO.
Run win/loss debriefs, deal teardowns, call-library curation, ride-alongs, and SME interviews.
Create structured, versioned, findable content with named owners and refresh cadences.
Build product and technical depth in the field, covering how Reco works, its architecture, and the competitive significance of rapid app coverage.
Own demo certification and hands-on labs, requiring representatives to pass a live demo bar before demonstrating independently.
Enable representatives on SaaS and identity architecture, OAuth and integration risk, AI agent and MCP exposure, and compliance frameworks.
Deliver field readiness with every product release.
Build sales playbooks for persona-based discovery, qualification, multi-threading, objection handling, and closing.
Establish MEDDPICC as a qualification and forecasting discipline and coach managers to apply it.
Own the POV playbook, including entry criteria, agreed success criteria, milestones, exit criteria, and handoff to close; stop unsuitable POVs from starting.
Own commercial enablement covering pricing and packaging, business cases, deal structure, margin, discounting discipline with Finance and RevOps, and negotiation.
Own competitive enablement for SSPM and AI security, keeping battlecards current after market changes.
Create role-based onboarding with 30/60/90 certification gates, including recorded pitches, live discovery simulations, demo passes, and customer value reviews.
Develop post-sale plays for time-to-value, adoption milestones, EBRs, renewal defense, and expansion tied to new app coverage and AI agent security.
Train CSMs to conduct commercial conversations.
Coach using real calls and equip frontline managers for weekly one-on-ones, pipeline reviews, and deal inspections.
Own the enablement stack, instrument the function, and use AI-first approaches to personalize learning paths and scale coaching.