Enterprise Sales Executive, Digital Transformation

We’re O3 — a design and technology consulting firm that helps companies use data and AI to work smarter and grow faster. We partner with marketing and technology leaders to solve real problems, improve operations, and create better digital experiences. With support from our dedicated AI practice, O3XO, we turn ideas into practical solutions that deliver results for your team and your customers.

O3 is also the team behind the 1682 Conference, an AI and innovation conference that serves as an anchor for our thought leadership work.

O3 is seeking an Enterprise Sales Executive to drive new business growth by opening and developing enterprise accounts across financial services, insurance, and other industries. You'll be responsible for the full sales cycle, from initial prospecting through contract signature, selling our digital experience design and technology solutions (DX) to mid-market and enterprise clients.

The Role

As our Enterprise Sales Executive, you'll hunt new accounts and build relationships with enterprise decision-makers who need digital transformation solutions. Working with average deal sizes of $500K+ and sales cycles of 2-4 months, you'll identify prospects, develop opportunities, and navigate complex enterprise buying processes to close new business for O3's core digital experience and technology services.

Key Responsibilities

New Business Development

• Prospect and develop new enterprise accounts through cold outreach, networking, and relationship building
• Identify and engage key decision-makers, including CMOs, CPOs, and C-level executives
• Build and maintain a robust pipeline of qualified opportunities
• Conduct discovery calls to understand client challenges and digital transformation needs

Account Management & Sales Execution

• Own the complete sales cycle from initial contact through contract signature
• Develop compelling value propositions that align O3's capabilities with prospect needs
• Orchestrate complex, multi-stakeholder sales processes across technical and business buyers
• Collaborate with internal SMEs to develop technical solutions and proposals
• Present proposals to senior stakeholder groups
• Negotiate contract terms and close deals (with the support of internal leadership)

• Focus on financial services and insurance verticals while remaining open to other enterprise markets
• Build industry knowledge and maintain awareness of sector-specific challenges and trends
• Attend industry events and conferences to generate leads and build market presence
• Develop territory plans and account strategies for target prospects

Revenue Generation

• Achieve annual sales quota of $1M+ in new business revenue
• Maintain accurate forecasting and pipeline reporting in CRM (Hubspot)
• Collaborate with delivery teams to ensure smooth handoffs and client satisfaction

What We're Looking For

• 5-8 years of enterprise B2B sales experience with a proven track record of quota achievement
• Experience selling professional services, digital solutions, or enterprise software
• Track record managing 6-figure deal sizes and multi-month sales cycles
• Strong prospecting skills and ability to develop new business through cold outreach
• Experience navigating complex enterprise sales processes with multiple stakeholders
• Excellent presentation and communication skills with C-level executives
• Self-directed and comfortable working independently with minimal supervision

Preferred Experience:

• Background selling to marketing, product, or digital transformation buyers
• Experience with consultative selling and technical solution discussions
• Familiarity with digital experience, CMS platforms, UX/UI design, technology, or conversion optimization services
• Experience with Amplemarket and Hubspot are a plus