Head of Enablement

Reco•Wilmington, DE

About The Position

We have the category, the product, and a GTM team hiring fast. What we lack is the thing that makes every new AE, SE, CSM, and BDR as effective as our best one inside their first quarter instead of their third. You'll be Reco's first enablement leader, owning the full lifecycle from the first discovery call through technical validation, adoption, renewal, and expansion. Sales and CS sit together deliberately: in a land-and-expand security business, the story a rep tells in the deal and the value a CSM proves in month six have to match. You'll build it hands-on before you build a team.

Requirements

8+ years in GTM or revenue enablement, with experience building a function from scratch at a high-growth B2B SaaS company.
Experience enabling AEs, SEs, BDRs, and CSMs.
Technical proficiency to participate in POVs without a translator, including fluency in SaaS and identity architecture, cloud security, and AI/agentic risk.
Proven ability to extract expertise from individuals and create a maintained body of content.
Experience making methodologies like MEDDPICC, Command of the Message, or Challenger change rep behavior.
Comfort with owning enablement for pricing, business case, discounting, and negotiation.
Metrics-driven with strong program management skills, including establishing baselines, defining owners, setting realistic timelines, and ensuring follow-through.
A builder mentality, focused on driving deals forward rather than administrative tasks.

Nice To Haves

Security background strongly preferred.

Responsibilities

Extract knowledge that isn't written down, such as founders' category framing, SEs' conversion instincts, and CSMs' expansion insights.
Run program mechanics including win/loss debriefs, deal teardowns, call library curation, ride-alongs, and SME interviews across Product, Research, and the Office of the CTO.
Transform raw input into structured, versioned, and findable content with clear ownership and refresh cadences.
Deepen technical understanding of the product, including its architecture, competitive advantages, and implications for CISOs.
Own demo certification and hands-on labs, ensuring no one demos solo without passing a live bar.
Enable surrounding landscape reps to speak to SaaS and identity architecture, OAuth and integration risk, AI agent and MCP exposure, and compliance frameworks.
Ship field readiness with every product release.
Build the core sales and go-to-market playbook, covering persona-based discovery, qualification, multi-threading, objection handling, and closing.
Implement MEDDPICC as a discipline for rep qualification and forecast building, coaching managers on its application.
Own the POV playbook end-to-end, including entry criteria, success criteria, milestones, exit criteria, and handoff to close, and eliminate unsuccessful POVs.
Lead commercial enablement, covering pricing and packaging, business case development, deal structuring, margin analysis, discounting discipline with Finance and RevOps, and negotiation.
Provide competitive enablement for SSPM and AI security, ensuring battlecards are updated rapidly.
Develop role-based onboarding with meaningful 30/60/90 certification gates, including recorded pitches, live discovery simulations, demo passes, and customer value reviews.
Create post-sale plays for time-to-value, adoption milestones, EBRs, renewal defense, and expansion tied to new app coverage and AI agent security, training CSMs for commercial conversations.
Coach based on real calls, not just course completions, and equip frontline managers for effective 1:1s, pipeline reviews, and deal inspections.
Manage the enablement stack, instrument the function, and leverage AI to personalize learning paths and scale coaching.