Enterprise Sales Director

Enterprise Sales Director

Opus Training is scaling its enterprise motion, and we’re looking for a second Enterprise Sales Director to grow alongside our existing team. We’ve closed our first $1M+ in enterprise revenue, built a $5M+ active pipeline across 25+ high-potential accounts, and proven the model works. Now we’re doubling down.

You’ll join an enterprise team with a peer AE, a defined playbook, and real traction across restaurants, fitness, and consumer services. The groundwork is laid. This role is about execution and expansion.

This role reports directly to the SVP of Revenue and partners with Opus co-founders. You’ll collaborate with Product, Marketing, and Customer Success to ensure seamless execution and strategic follow‑through post‑sale.

This is a high‑impact, high‑visibility role, both inside Opus and with the market. The right person thrives in strategic conversations with C‑level decision makers and knows how to navigate a multi‑threaded buying cycle while driving every detail of a complex deal across the finish line. You don’t see closed‑won as the end; you see it as the beginning. You love the thrill of opening new accounts, the complexity of driving expansion, and the reward of earning the renewal.

You’re equally skilled at building new pipelines and growing existing accounts to drive long‑term revenue.

You’ll be selling 6‑figure deals into verticals like restaurants, fitness, and home services, handling everything from sourcing your own leads to negotiating with procurement. You’ll work within a proven sales motion while bringing your own instincts and relationships to grow the pipeline further.

Success here requires someone who can:

• Guide exec‑level buyers through long, complex decision cycles
• Drive revenue with a mix of new logo wins and account expansion
• Build and manage a robust pipeline
• Balance 20+ active customers and 15+ concurrent deal cycles
• Partner cross‑functionally to ensure world‑class deal execution and handoff

• A track record of closing 6‑figure deals in complex, multi‑stakeholder enterprise environments
• Experience selling into Operations, HR and Procurement teams in traditional industries (restaurants, consumer services, etc.)
• A hunter’s instinct balanced with a long‑term relationship mindset
• Strong pipeline generation skills rooted in face‑to‑face prospecting and referrals
• Ability to prioritize deals by size, stage, and strategic value to maximize impact
• Executive presence with the ability to build trust and influence C‑level decision makers and buying committees
• Proficiency in crafting tailored proposals, ROI analyses, and business cases that win
• Hands‑on experience leading contract negotiations, navigating legal reviews, and coordinating cross‑functional deal execution
• A strategic lens for account growth, proactively monitoring account health and unlocking expansion opportunities
• Familiarity with structured sales methodologies (e.g., MEDDICC, Challenger, SPICED) is a plus. But more important is your ability to adapt to our high‑touch, consultative sales motion and shape it alongside our team.
• Experience selling into franchisors or similar distributed workforce orgs is a requirement.

• $2M+ in new revenue closed annually across 15‑20 enterprise deals (sales cycle 4‑12 months)
• 20+ enterprise customers actively managed with a focus on long‑term growth and expansion
• Collaborate with Marketing and Enterprise SDRs to drive top‑of‑funnel activity, while proactively generating pipeline through events and networking
• Deep relationships built with multiple stakeholders per account, driving trust and deal velocity
• You’ll maintain account ownership post‑sale and partner with Customer Success on onboarding and adoption. Renewals and expansions will contribute to your variable comp and overall success in the role.

Travel (30%) to be on the ground with prospects and customers and with the team in NYC when necessary, building pipeline and advancing deals in real time.

Executive Presence & Communication
- Skilled at engaging C‑level stakeholders with clarity, confidence, and empathy

Collaborative Operator
- Works cross‑functionally with product, legal, and customer success to move deals forward and deliver value post‑sale

Strategic Mindset
- Prioritizes effectively and approaches selling with business acumen and long‑game perspective

Sales Tools & Technical Fluency
- Proficient in CRM systems, sales enablement tools, and financial modeling to build business cases and track performance

Deal Mastery
- Comfortable reviewing contracts, negotiating terms, and crafting ROI‑driven proposals

Behavioral Strengths - combine grit, creativity and thoughtfulness with a drive to win.

We offer a competitive base salary and uncapped variable comp. High performers can exceed this through expansion and strategic deal execution. Equity and benefits included.