Senior Director Enterprise Sales - Workforce Solutions
Job Description
Overview
Our client is shaping the evolution of work with a holistic platform for the modern workforce—combining data, software, intelligence, and services to help many of the world’s most recognized brands manage contingent labor with speed, scale, transparency, and expertise.
As VP of Enterprise Sales, you’ll be a pivotal workforce solutions growth driver —selling across offerings like MSP, VMS, EOR, SOW, Direct Sourcing, and AI technology that integrates with VMS platforms. This is a high-impact, high-visibility individual contributor role, focused primarily on the TMT (Telecom, Media & Technology) vertical (vertical experience is welcomed, not required). You’ll own complex enterprise pursuits end-to-end, engage senior decision makers, and close strategic, multi-stakeholder deals with support from a strong internal sales infrastructure.
Required Skills
- Enterprise sales expertise selling HR Technology, MSP, VMS, or technology-enabled workforce services.
- Full-cycle, complex sales capability—from prospecting and discovery through proposal, negotiation, and close.
- Proven ability to engage and influence senior executives (C-level, SVP/EVP) and lead high-level meetings.
- Strong command of the RFx process (RFI/RFP/RFQ), including crafting winning responses and delivering executive-ready presentations.
- Consultative selling mindset: diagnosing client challenges and building tailored, value-driven solutions.
- Demonstrated strength in qualifying opportunities, driving next steps, and closing business.
- Ability to operate with autonomy, resilience, and strategic discipline in a quota-driven environment.
- Strong collaboration skills—partnering across internal teams to deliver a seamless client experience.
Nice to Have Skills
- Experience selling proprietary workforce technology and services.
- Experience positioning AI-enabled solutions, especially those that integrate with VMS platforms.
Preferred Education and Experience
- 5+ years of full-cycle sales experience within contingent workforce solutions, MSP, or VMS.
- Track record of success in high-stakes, multi-threaded enterprise sales cycles and complex contract negotiations.
Other Requirements
- Location: Open to candidates anywhere in the U.S. (all time zones).
- Travel: Approximately 30–40%, depending on client proximity.
- Comfortable representing the company at industry events, conferences, and thought leadership forums.
- Ability to thrive in a supportive, high-accountability culture where performance is primarily quota-driven.
Job Number 8111
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Additional Information
MeeDerby is an executive search firm uniquely dedicated to serving the staffing industry. For nearly three decades, we've helped thousands of executives, managers, senior sales and senior recruiters who have worked in staffing find their place in this robust industry. You spend your days helping people find the perfect job. Don’t you deserve a partner who can do the same for you? Leverage our hard-won connections to take the next step in your staffing career.
Meet Your Recruiter
Kamille Chilcutt
Executive Recruiter
Kamille has over a decade of experience in the staffing industry. She comes to MeeDerby having spent most of her career working in temporary staffing and most recently as an Area Manager with LSI Staffing in the Kansas City market. Kamille has experience recruiting across multiple verticals including industrial, accounting and finance, and office/administrative. She focuses on staffing Commercial Branch Managers, Business Development Managers and Recruiters in the Staffing Industry. Kamille is a graduate of Northwest Missouri State University – Go Bearcats!
Kamille is a mother and wife, residing in Liberty, Missouri. In addition to helping Staffing Industry Professionals find their next career role, she enjoys spending time with family and friends, knitting, playing with her dogs – Sunny and River, and catching a KC Chiefs game or KC Current match!
