Enterprise Sales Director

Opus Training Inc.•New York, NY

4d•Hybrid

About The Position

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. The Challenge 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 What You Bring 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. Our ideal customers are multi-location operators in the services industry with 75-1,000 locations, centralized operations, and a need to train and enable large deskless teams. Experience selling into franchisors or similar distributed workforce orgs is a requirement. What Success Looks Like $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 Strategic Competencies 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. You embrace and embody our company Values: Our company values "Clear a path" We strive to 'Clear a path' by reducing friction and creating space for every frontline employee to succeed in their role. Accessibility is key in ensuring that we are creating space for our users to be their whole selves at work. We commit to understanding the needs of those we serve, ensuring that our environment allows individuals to be their authentic selves while acknowledging that to be human is to be flawed. We focus on removing barriers and providing the necessary tools for success, empowering our team and customers to succeed in ways that are most meaningful to them. "It doesn't have to be that way" A mantra we've embraced since our inception. Opus exists because we believe the tools frontline workers have aren't built for them, and hold them back. Fueled by creativity and curiosity, we challenge conventional wisdom. Our approach requires thinking outside the box and discovering novel solutions to achieve our mission: “Create a world where every deskless worker has a good job.” "1% better each day" We didn’t push boundaries in one go. We built Opus by fostering a culture of iteration – improving ourselves, our product, and our culture every single day. Adaptability for us combines speed, flexibility, resilience, and a constant openness to learning and growth. And through continuous learning and microtraining, how we approach growth is how we help our customers and their teams grow as well. "Be an owner" For us to build together in a world that’s always changing, we need to operate with a high degree of accountability, integrity, and trust for ourselves and one another. We’re each a steward of our work, so that to the best of our abilities there are ‘no surprises’. We pitch in if there’s a gap to fill. We call for help if we need it. We treat everyone responsibly and professionally. This builds trust even when things go sideways. "Make it nice" 'Make it nice' isn't just about meeting expectations; it's about exceeding them, delivering superior quality, and creating memorable experiences. Amidst a backdrop of outdated technology, we aim to bring joy to our customers. Make It Nice is about attending to the finer details and consistently going the extra mile —whether through our service or our product—so that our customers trust we’re there for them. This fosters a culture of excellence where each team member takes pride in their work and is committed to achieving outstanding results. Compensation 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.

Requirements

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
Experience selling into franchisors or similar distributed workforce orgs is a requirement
Skilled at engaging C-level stakeholders with clarity, confidence, and empathy
Works cross-functionally with product, legal, and customer success to move deals forward and deliver value post-sale
Prioritizes effectively and approaches selling with business acumen and long-game perspective
Proficient in CRM systems, sales enablement tools, and financial modeling to build business cases and track performance
Comfortable reviewing contracts, negotiating terms, and crafting ROI-driven proposals
Combine grit, creativity and thoughtfulness with a drive to win

Nice To Haves

Familiarity with structured sales methodologies (e.g., MEDDICC, Challenger, SPICED)

Responsibilities

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
Maintain account ownership post-sale and partner with Customer Success on onboarding and adoption
Collaborate with Marketing and Enterprise SDRs to drive top-of-funnel activity, while proactively generating pipeline through events and networking
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