Director of Sales, COOL AI

About the COOL company

At the COOL company, we believe in creating a win-win environment where everyone benefits. We are committed to ensuring users, publishers, franchisees, and advertisers all have a better experience and achieve more than they ever thought possible through our innovation, advanced AI, groundbreaking advertising technology, and teams of inspired experts. Our every move, expansion, acquisition, and upgrade is done to provide that better experience for an ever-growing list of satisfied clients and users all over the world.  

COOL Media products under the COOL company include DCO & Creative Automation, a data-driven, creative ad server capable of personalizing, automating, measuring, and optimizing digital ads and placements for advertisers; Franchise & Multi-Location, a complete advertising management platform for franchise and network businesses; Media & Attribution, a managed service solution for agencies and brands to reach and measure audiences; Publisher Experiences, a premier SSP and engagement platform for publishers; and Supply-Side Platform, delivering website and app publishers everything they need to maximize their ad revenue.

Coming soon in 2026, COOL AI is a next-generation advertising platform that builds, buys, and optimizes digital ad campaigns faster and smarter using AI. It automates every step of the media journey—from generating ad creatives to launching campaigns and optimizing performance across channels like Google and Facebook. With no agency fees or waiting, COOL AI helps brands maximize ROI through data-driven strategy, automated creative generation, and real-time performance measurement.

Collectively, the COOL company reaches over 350 million consumers monthly across their network of premium publishers and advertisers, including Disney, Hyundai, Air France, Kohler, Suzuki, Acer, Pearle Vision, Trek, Brita, Viking Cruises, MLB, Playmaker, Blitz, Evolve Media, and more.  Under the former umbrella of Insticator, the COOL company is a proud 7x recipient of the Inc 5000 list of America's fastest-growing private companies, a 2x recipient of Deloitte's Fast 500, recognized on Crain's New York Fast 50 list, recognized by Digiday's Digiday Media Awards as a company working to modernize digital media, and awarded as one of AdWeek's Top 10 Fastest Growing Solution Providers globally.

Our Core Values

At the COOL company, we believe in being C.O.O.L.:

• Creative - we look to find solutions that others can’t and new ways of doing things that are smarter, faster, better and more efficient.
  
• Open-minded - we’re always evolving and keep an open mind as to new ways of doing things, new solutions and new processes that can help us.
  
• Optimistic - The glass is always half full :) as a growing tech startup we’re always faced with new challenges, we overcome them because we see them as opportunities.
  
• Leaders - We look for drivers, people who like to set the pace of the organization, who don’t simply go with the flow, you’re setting a fast impact pace and holding others to it.  We look for speed, impact, and setting the industry benchmark.

We creatively integrate new elements in innovative combinations, fueled by our optimism to drive success. Our open-mindedness allows us to embrace new ideas and approaches, empowering us to lead our industry through bold initiatives. That’s the attitude we bring to work with us every day, and it’s what we expect from everyone who works here.

That’s just part of the values that drive us to greatness. We also believe in this trio of truths that inform every decision we make and everything we do:

• • Sleeves Up: At the COOL company, we provide you with the autonomy and creativity needed to own your role. We encourage iteration where necessary so that you can drive massive impact.
  • 100% Viewability: The COOL company is passionate about open feedback at all levels of the company. This allows us to fail fast, create in real-time, and build an open company culture
  • Be Defiantly Great:
    We're defiant, and that's in our blood. Challenging the status quo is a central part of who we are. We're capable of much more than what others deem impossible.

About the Role

We are building a new business unit focused on expanding our SMB go-to-market engine. This role is responsible for building the entire SMB sales function from the ground up—including hiring, team structure, playbooks, outbound strategy, quota design, enablement, and revenue accountability. You will be a founding leader in a high-growth division with visibility across the executive team and direct influence over company strategy and outcomes.

What You'll Do

• 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.

What Success Looks Like (First 12 Months)

• Successful hiring and onboarding of 10 core team members (SDRs, AEs).
• Clear, documented sales playbook and cold outbound motion tailored to SMB buyers.
• Fully operational SDR to  AE pipeline handoff process with complete attribution tracking.
• Consistent weekly qualified meeting production from high-volume cold calling efforts.
• Revenue trajectory aligned to quarterly goals with clear attribution to sales activities.
• Strong morale, high accountability, high velocity culture with a team working together in-office.

Who You Are

• 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.
  

Nice to Have

• 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.

Why This Role

• You will architect a new growth engine within a company that is scaling rapidly.
• High visibility role with direct influence on revenue, hiring, and go-to-market strategy.
• Strong compensation upside + meaningful equity.
• Your work directly shapes the next stage of company growth.
  

Cultural Competencies

• Must work in the office 5 days per week (Monday–Friday, 9:30 AM - 6:30 PM ET) alongside your team
• Must have a player/coach mentality, willing to both execute (including cold calling) and lead
• Ability to juggle multiple projects concurrently and set and meet deadlines
• Skilled at receiving and providing direct feedback
• Collaborative mindset and great teamwork skills
• Entrepreneurial & adaptable; great learning skills
• Curious, research-minded, data-informed (attribution-focused)
• Able to search for possible solutions and apply them
• Creative confidence
• Proactive communicator
• A sense of humor and a love of online culture
• Thrives in a start-up culture

Benefits

• Competitive Salary
• Health, Dental and Vision Insurance
• Annual Performance Bonus
• Paid Time Off
• Company Holidays
• Flexible work schedule
• 401k