Enterprise Sales Director – Remote Talent & AI-Augmented Staffing

This role is only for US-based professionals.

We’re seeking a top-tier Enterprise Sales Director with a proven track record in staffing, outsourcing, or workforce solutions; someone who can hit the ground running and bring an existing book of business. This isn’t a cold-calling SDR role; it’s for a seasoned closer who knows how to navigate complex, high-value deals, understands the ins and outs of talent augmentation, and already speaks the language of decision-makers. You’ll lead our efforts in forging long-term partnerships with companies seeking exceptional outsourced teams across engineering, ad operations, project management, design, and AI-enabled support roles.

What You’ll Do:

Own and close new business deals with mid-market and enterprise clients.

Leverage your existing network to generate warm leads and quick wins

Pitch, demo, and close deals across SiiRA’s platform, services, and pricing structures

Partner with our CEO and delivery team to craft scalable solutions

Represent SiiRA at industry events and help establish category leadership

Share insights with product and marketing teams to continually refine our go-to-market strategy

What We’re Looking For

5 -10+ years of experience in enterprise sales, ideally within:

-Staffing / outsourcing / offshore team models

-EOR (Employer of Record) / talent marketplaces

-HR tech / workforce platforms

A consistent track record of achieving $1M+ in annual quota.

Strong consultative selling skills with the ability to tailor solutions to client needs

Existing relationships with HR, procurement, and business unit decision-makers

Deep understanding of sales cycles involving complex, multi-stakeholder deals

Excellent communication, negotiation, and presentation skills

Self-starter mindset with the ability to work independently and drive results

Comfortable with CRM tools and sales reporting; highly organized and data-driven

Ability to thrive in a fast-paced, startup environment and adapt to changing priorities