Director of Sales Enablement

Overview

You're the Director of Sales Enablement at RainFocus, building the enablement function for a sales team selling event marketing platform software to Fortune 1000 companies. You work directly with the EVP of Global Sales and sales leadership to diagnose why deals stall, create content that addresses real objections, and reduce the time it takes new AEs to become productive. This is a hands-on role - you're not managing a team of enablement people, you're doing the work yourself.

Role Snapshot

Company Context

Stage: Later-stage (432 employees, selling to Fortune 1000)

Size: 432 employees

Growth: Hiring a Director of Enablement signals they're scaling the sales org and need to professionalize their processes

Market Position: Established player in event marketing software - competing for "outsized share" means they're growing in a defined category with competition

GTM Reality

Pipeline Sources:

• Likely 30-40% Inbound - Event marketing is a known category, so some hand-raisers from search/content
• 50-60% Outbound - Enterprise sales to Fortune 1000 requires direct prospecting into marketing/events teams
• 10-20% Referrals/Existing customer expansion

SDR/AE Structure: Likely dedicated SDRs given company size, but AEs probably also self-source into strategic accounts

SE Support: Definitely have SEs - event platform demos are highly technical and customized

Competitive Landscape

Main Competitors: Cvent (dominant player), Bizzabo, Aventri, Swoogo, and others in event management

How They Differentiate: RainFocus positions as more flexible/customizable for enterprise - not clear from limited info what their specific angle is

Common Objections: "We already use Cvent", "Too expensive vs simpler tools", "Our events team likes their current solution", "ROI is hard to prove"

Win Themes: Likely flexibility, integrations, enterprise-grade features that cheaper tools lack

What You'll Actually Do

Time Breakdown

Deal Support (30%) | Content Creation (25%) | Onboarding/Training (25%) | Strategy/Analysis (20%)

Key Activities

• Riding Along on Deals: You join AE calls to hear objections firsthand, then create battle cards, competitive guides, or demo scripts to address what's actually stalling deals. You're not just building generic training - you're solving specific problems that are costing revenue.
• Onboarding New AEs: You build and run the ramp program for new enterprise AEs. This means creating a 60-90 day curriculum that covers product knowledge, competitive positioning, event marketing buyer personas, and deal execution. You measure time-to-first-deal and time-to-quota.
• Creating Sales Content: You're building presentations, one-pagers, ROI calculators, case studies, and demo scripts. A lot of this is translating technical product capabilities into business outcomes that event marketers care about. You're constantly updating based on what's actually working in deals.
• Analyzing What's Working: You dig into Salesforce/Gong data to find patterns - which AEs close fastest, what messaging resonates in discovery calls, where deals get stuck, what objections kill opportunities. Then you operationalize the winners and fix the losers.

The Honest Reality

What's Hard

• You're Building from Scratch: A Director hire means this function is new or underdeveloped. You'll spend months figuring out what enablement actually needs to be here before you see results. Lots of experimentation.
• Sales Reps Will Ignore Your Content: You'll create materials that AEs don't use because they prefer their own approach or don't see the value. You have to sell enablement internally, which means proving ROI and getting leadership to enforce adoption.
• Event Marketing is Niche: You need to become an expert in a specific software category. This isn't general SaaS sales training - you need to understand event marketing buyer priorities, how events teams operate, and the competitive landscape deeply. The learning curve is real.
• You're Measured on Sales Outcomes You Don't Control: Leadership will judge you on whether AEs ramp faster and close more deals, but you're not the one prospecting or pitching. You need executive buy-in and cooperation from sales leadership to actually implement your programs.

What Success Looks Like

• New AEs hit their first deal in 90 days instead of 120+ days
• Win rate increases by 5-10% after implementing new competitive content
• AEs actually use the materials you create (tracked in Gong/Highspot/whatever CMS they use)
• Sales leadership credits enablement for specific closed deals or accelerated cycles

Who You're Selling To (Internally)

Primary Stakeholders:

• EVP of Sales (your boss) - cares about quota attainment, sales efficiency, faster ramp
• VP/Directors of Sales - care about their teams hitting number, not wasting time on training that doesn't help
• Individual AEs - care about making quota with less effort, want content that actually helps them close

What They Care About:

• Does this actually help me close deals or hit my number?
• Is this worth my reps' time or is it just more mandatory training?
• Can you prove this is working with data?

Requirements

• 5-7+ years in sales enablement at B2B SaaS companies, ideally with enterprise sales experience
• You've built enablement programs before (not just delivered someone else's training)
• Deep understanding of enterprise sales - you can ride along on a deal and immediately spot what's broken
• Content creation skills - you can build a compelling deck or battle card, not just outsource it
• Experience with enablement tools (Gong, Highspot, LMS platforms) and Salesforce analytics
• Ability to work directly with executives - the EVP is hiring you, so you need executive presence
• Event marketing software experience is NOT required but you need to learn it fast