COOL Media - Publisher Experiences · 2 months ago
Director of Sales, COOL AI
United States
Full-time
Hybrid
Director/Executive
10+ years expCOOL Media is a company focused on enhancing user, publisher, franchisee, and advertiser experiences through innovative AI and advertising technology. The Director of Sales will build and lead the SMB sales organization from the ground up, developing strategies and processes to drive revenue and team performance.
Advertising PlatformsContent MarketingInformation TechnologyInternet of Things
Responsibilities
Build and lead the SMB sales organization from scratch to a team of 10+ sales professionals, including SDRs, AEs, and Team Leads, with full management responsibility for hiring, coaching, and performance
This will be a high energy, high throughput team setting cold call quotas, emails, linkedin outreach, with the team being in the office 5 days a week and celebrating big wins
Develop the go-to-market motion for our AI-powered product, including segmentation, ICP targeting, outreach channels, call/email scripts, demos, and conversion workflows optimized for fast sales cycles
Own pipeline development strategy with heavy emphasis on cold outbound calling to small businesses—personally lead initial cold calling efforts and build scalable processes
Drive attribution strategy and measurement across all sales activities to ensure accurate tracking of lead sources, conversion paths, and ROI on outbound efforts
Establish KPIs & productivity metrics for high-volume outbound—calls/day, email cadences, meetings booked, conversion rates, pipeline velocity, and two-click conversion optimization
Collaborate with Marketing, Product, and Customer Success to build a repeatable acquisition and retention engine focused on streamlined buyer journeys
Design and implement sales compensation plans, onboarding frameworks, playbooks, and training programs that scale with team growth
Manage weekly forecasting, pipeline inspection, and accountability systems with rigorous attribution reporting
Act as a player-coach early on—comfortable personally prospecting, cold calling SMBs, and closing initial deals as the unit scales
Track performance, optimize sales velocity, and continuously refine playbooks, messaging, and processes based on attribution data
Champion a culture of ownership, urgency, experimentation, and results, working in the office five days a week alongside your team
Qualification
Required
10+ years in B2B sales with extensive leadership experience building and scaling sales teams
Has built a successful outbound calling/outreach sales organization from scratch on at least 2 separate occasions, taking teams from scratch to revenue-generating units
Proven expertise in cold calling small businesses with deep understanding of SMB buying behavior, objection handling, and high-volume outbound prospecting
Direct experience selling AI products or technology solutions to SMBs, with ability to articulate technical value in simple terms
Strong track record in SMB acquisition with demonstrated cold calling success—comfortable making 50+ calls per day and coaching teams to do the same
Expert in attribution modeling and tracking for sales activities, pipeline sources, and conversion optimization
Deep understanding of high-volume outbound: call frameworks, email cadences, meeting conversion systems, and two-click engagement strategies
Comfortable operating in fast-moving, ambiguous environments where playbooks must be created, not followed
Systems thinker with the ability to move between strategy, execution, coaching, and process design
Excellent communicator; confident presenting to senior leadership and external partners
Values ownership, accountability, and measurable performance
Committed to being in the office 5 days per week to build culture, coach in real-time, and lead by example alongside your team
Preferred
Experience building or scaling SDR teams focused on cold outbound to SMBs
Track record of hitting aggressive revenue targets in multiple sales organisations you've built
Familiarity with CRM / Sales Automation tools (HubSpot, Salesforce, Outreach, Apollo, etc.) and attribution platforms
P&L or business unit ownership experience
Previous experience growing a sales team from 0 to 10+ members
Benefits
Competitive Salary
Health, Dental and Vision Insurance
Annual Performance Bonus
Paid Time Off
Company Holidays
Flexible work schedule
401k
Company
COOL Media - Publisher Experiences
COOL Media: Publisher Experiences believes three things – the future of social media is distributed and not siloed in the walled gardens of today; publishers deserve a one-stop shop for maximizing ad revenue; and local brick-and-mortar businesses thrive with digital media automation.
51-200 employees
Funding
Current Stage
Growth StageTotal Funding
$10.06MKey Investors
Associated Venture Management
2017-07-13Series A· $5.2M
2016-02-29Seed· $2.66M
2015-03-01Angel· $2.2M
Leadership Team
Zack Dugow
Founder & CEO
Tianyi Cong
Chief Technology Officer
Recent News
Research and Markets
2025-11-10
2024-05-08
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