Head of Enablement

Reco • Wilmington, DE

2d

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, including building a function from zero at a high-growth B2B SaaS company.
• You've enabled both sides — AEs, SEs, BDRs, and CSMs.
• Technical enough to sit in a POV without a translator.
• Fluency in SaaS and identity architecture, cloud security, and AI/agentic risk.
• Security background strongly preferred.
• You've walked into an org where the expertise sat in a few heads and left behind a maintained body of content.
• You can interview a principal engineer and come out with a value prop a rep can use that afternoon.
• You've made MEDDPICC (or Command of the Message, Challenger) actually change rep behavior.
• Comfortable owning pricing, business case, discounting, and negotiation enablement.
• Metrics-driven and a strong program manager: baselines, named owners, real timelines, follow-through.
• A builder, not an administrator.
• You measure your work in deals progressed.

Responsibilities

• Programmatic — get knowledge out of people's heads: Extract what isn't written down: our founders' framing of the category, the SE's instinct for which POV will convert, the CSM who knows why a customer expanded. Run the mechanics: win/loss debriefs, deal teardowns, call library curation, ride-alongs, SME interviews across Product, Research, and the Office of the CTO. Turn raw input into structured, versioned, findable content with named owners and refresh cadences, so nothing quietly goes stale.
• Technical — product depth: Take the field past feature lists: how Reco works, why the architecture matters to a CISO, and what shipping new app coverage in days means competitively. Own demo certification and hands-on labs. Nobody demos solo until they pass a live bar. Enabling the surrounding landscape reps must speak to: SaaS and identity architecture, OAuth and integration risk, AI agent and MCP exposure, compliance frameworks. Ship field readiness with every release.
• Sales and go-to-market: Build the core playbook: persona-based discovery for CISOs, security architects, and IT owners; qualification; multi-threading; objection handling; close. Make MEDDPICC the discipline behind how reps qualify and how the forecast gets built, not a CRM field. Coach managers to it. Own the POV playbook end to end — entry criteria, agreed success criteria, milestones, exit criteria, handoff to close. Kill the POVs that shouldn't have started. Own commercial enablement: pricing and packaging, business case, deal structure, margin, discounting discipline with Finance and RevOps, and negotiation. Own competitive enablement for SSPM and AI security. Battlecards current within days of a market move.
• Onboarding, CS, and coaching: Role-based onboarding with 30/60/90 certification gates that mean something: recorded pitch, live discovery sim, demo pass, customer value review. Post-sale plays: time-to-value, adoption milestones, EBRs, renewal defense, and expansion tied to new app coverage and AI agent security. Train CSMs to have commercial conversations. Coach from real calls, not course completions. Equip frontline managers for weekly 1:1s, pipeline reviews, and deal inspections. Own the enablement stack, instrument the function, and work AI-first to personalize paths and scale coaching.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed