Director, Sales Operations & Enablement

OLIVER Agency - North America•New York, NY

11h•$165,750 - $185,250

About The Position

You'll be the strategic architect behind OLIVER's sales operations excellence, ensuring our revenue engine operates with precision and insight. Working at the intersection of data, process, and sales performance, you'll translate pipeline analytics into actionable deal strategies that accelerate our growth in integrated creative and technology services. We're looking for someone who combines operational rigor with sales intuition, finding systematic approaches that support individual deal success. Success means building a sales organization that consistently delivers predictable revenue growth through optimized processes and empowered sellers

Requirements

5+ years combined sales and operations experience with at least 3 years in direct selling roles (preferably consultative B2B sales)
Deep Salesforce expertise including configuration, reporting, automation, and data governance for complex sales processes
Revenue forecasting experience with track record of maintaining forecast accuracy within 5% variance
Sales methodology proficiency (MEDDIC, Challenger, Solution Selling) applied to complex, multi-stakeholder deals
Proven ability to assess deal health and provide strategic guidance that moves opportunities through pipeline stages
Experience supporting sellers with tactical advice, content, and coaching based on deep understanding of buyer behavior
Complex sales cycle expertise including deals with 6-12 month cycles, multiple decision-makers, and seven-figure values
Understanding of professional services sales preferably in creative services, consulting, technology, or marketing services
Data analysis skills that translate pipeline metrics into actionable insights for sales teams and leadership
Process improvement experience designing and implementing sales workflows, playbooks, and enablement programs
CRM administration expertise with ability to optimize data structure, reporting, and user experience
Sales content development including battle cards, case studies, ROI calculators, and competitive positioning materials
Partnership skills with sales leadership, marketing, finance, and delivery teams to align on revenue goals and processes
Training and enablement experience developing and delivering sales training programs for diverse audiences
Stakeholder management across multiple business units, especially in matrix organizations with creative and technology teams
Communication skills that translate complex data into clear insights and recommendations for senior leadership
Marketing services industry knowledge with understanding of creative agency, consulting, or professional services business models
Technology experience preferably in martech, SaaS, or platforms serving marketing organizations
Interest in technology convergence and how creative + technology solutions address complex marketing transformation challenges

Responsibilities

Ensure forecasting accuracy through disciplined Salesforce data management, proper deal weighting, and aligned commercial forecasting processes
Partner with sales leadership to assess deal health, surface risks early, and provide strategic guidance on complex brandtech opportunities
Drive pipeline optimization by identifying deals stuck at specific stages and providing targeted content, strategies, and coaching to accelerate progression
Build and refine sales playbooks for both new business acquisition and organic growth, tailored to our creative + technology value proposition
Enable deal success through hands-on support with individual sellers, offering tactical advice based on deep understanding of buyer psychology and sales methodology
Create sales content and tools that address common objections, competitive positioning, and value demonstration for integrated creative-technology solutions
Analyze pipeline trends to identify patterns, bottlenecks, and opportunities for process improvement across the entire sales cycle
Optimize CRM configuration and data flows to provide actionable insights while minimizing administrative burden on sales teams
Lead sales training initiatives covering methodology, tools, and The Brandtech Group positioning for complex consultative sales
Deliver predictable revenue outcomes through systematic pipeline management, accurate forecasting, and consistent deal velocity improvement