We’re a fast-growing, VC-backed startup that partners with top executives and global companies to deliver high-value human capital solutions. Backed by investors from UC Berkeley and trusted by thousands of clients worldwide, we’re scaling rapidly — and now we’re looking for a founding outbound enteprise sales rep to own enterprise outreach and pipeline creation.
This Role Is For You If:
- You know how to identify, reach, and engage C-suite executives with precision and confidence.
- You have a process-driven approach to enterprise sales that goes beyond cold outreach — you build systems that surface intent, target pain points, and create urgency.
- You’ve sold and closed $10k–$100k+ deals in the past, especially in services or SaaS.
- You’re someone who likes to aim high: 20-FTE deals are your sweet spot, but you know how to close the 1s, 2s, and 3s too.
- You understand how to navigate the enterprise buying journey, set timelines, and secure internal champions.
- You’re comfortable pitching at the top (C-level) and working your way down. Executive buy-in is your entry point — not your endgame.
What You’ll Be Doing:
- Own outbound: Develop, test, and scale outbound lead generation strategies targeting enterprise clients
- Develop and own a targeted account list and develop a territory plan for winning business with companies between 201-1,000 employees
- Manage the customer buying journey from start to finish, providing subject matter expertise and guidance to prospective customers
- Meet or exceed monthly and yearly revenue targets
- Continually develop a robust sales pipeline through individual outreach, collaborating with your sales development representative, and managing inbound prospects
- Keep CRM system up to date with customer information, forecasts, and pipeline data so we can learn more about our business and our sales process
- Build and optimize prospecting systems (think: enrichment, sequencing, data intelligence)
Book qualified meetings directly with C-suite, VP, and Director-level prospects
- Work closely with our sales leadership to define ICPs, messaging, and target verticals
- Use your consultative selling chops to identify gaps, surface pain points, and push urgency
- Contribute to strategy, not just execution — this is a foundational hire
Who You Are:
- 3–7+ years of experience in enterprise B2B outbound sales
- Proven track record of engaging and booking meetings with C-level decision makers
- Comfortable with consultative and value-based sales
- Obsessed with creating pipeline and hitting targets
- You’ve sold to companies like Dell, Microsoft, Virgin, Apple — or want to
- A natural relationship-builder who can hold conversations at every level
- Systems thinker who knows how to scale what works
Bonus Points For:
- Background in staffing, SaaS, outsourcing, or professional services
- Familiarity with CRMs (Pipedrive, HubSpot, Salesforce), Apollo, Salesloft/Outreach, Linkedin Navigator
- Experience with enterprise sales in early-stage or high-growth companies
Perks & Compensation:
- Competitive base salary + performance-based commission
- Equity options
- Fully remote team with a hybrid set up
- Fast-paced, collaborative team culture
- Direct access to leadership and the chance to shape the outbound engine from the ground up
Top Skills
What We Do
Wing provides SMBs, startups, and executives with top-tier remote talent to take over recurring work such as Social Media Management, Executive Assistance, Data Entry, Sales Calling, etc. Wing is your super affordable team member to whom you can delegate excess work while you do the important things to grow your business.
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