Midmarket Sales Director
About Us
Job Description
This is a remote role.
As we expand our reach in the small and mid-sized business market, we’re hiring a strategic Midmarket Sales Director to drive new client acquisition in the high-growth sector of venture capital backed technology companies.
The Midmarket Sales Director is a new business hunter responsible for driving growth in the SMB and lower mid-market segments (50–1,500 employees). You will lead outbound and inbound sales efforts, manage full-cycle deals, and help prospective customers navigate the complexities of international growth—from hiring abroad, to establishing legal entities, to ensuring that in-country operations are operating in compliance with local requirements.
This is a quota-carrying role focused on new logo acquisition and expansion, with support from marketing, solutions, and partnerships.
Responsibilities:
- Identify and close new business opportunities with SMB and midmarket technology companies exploring or executing international expansion.
- Sell HSP’s global services—including HR, payroll, Employer of Record (EoR), compliance, direct and indirect taxes, and entity setup—into key stakeholders (HR, Finance, Payroll, Tax, Ops, Legal).
- Conduct discovery to uncover needs, pain points, and business goals, and align HSP’s services to address them.
- Own the full sales cycle: from prospecting and discovery through proposal, negotiation, and close.
- Build and manage a healthy pipeline using Salesforce, LinkedIn, referrals, and outbound tactics.
- Partner with marketing and SDRs to run targeted campaigns and follow up on inbound interest.
- Collaborate cross-functionally with Solution Architects and Delivery teams to ensure strong handoffs and client satisfaction.
- Provide accurate sales forecasts, maintain CRM hygiene, and contribute to quarterly planning.
Qualifications and Requirements:
- 5–8 years of B2B sales experience, including at least 2+ years selling into technology companies in the VC-backed midmarket or SMB segments
- Proven track record of meeting or exceeding quota in a new business (hunter) sales role.
- Experience selling complex services or SaaS platforms to HR, Finance, or Operations buyers.
- Familiarity with global operations, such as EOR, payroll, entity setup, or international compliance (a strong plus).
- Proficiency with CRM tools (Salesforce preferred) and modern prospecting techniques (LinkedIn, Outreach, etc.).
- Excellent communication, discovery, and solution selling skills.
You’ll be part of a purpose-driven company that empowers global businesses to grow responsibly and compliantly. You’ll gain the tools, support, and flexibility to succeed while making a direct impact on our growth in the underserved SMB market. If you would like to be part of a fast-paced, client first environment; where we focus on solutions rather than challenges, come and join our #HSPGlobalSolutionTeam!
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