Sales Development Representative

Description:

Outwitly Inc. is seeking a motivated and driven Sales Development Representative (SDR) to join our team and help scale our UX & Service Design staffing business. This role focuses on identifying, nurturing, and converting new business opportunities within the North American market. The SDR will work closely with the CEO, Head of Talent, and Client Success teams to support the early stages of the sales funnel, focusing on reviving inactive leads and conducting cold outreach to potential clients. You’ll be key in supporting business growth through your prospecting efforts, primarily targeting enterprise and public sector clients.

Key Responsibilities:

• Pipeline Generation & Lead Qualification:

  • Research and identify sister companies or subsidiaries of current MSA clients to prospect additional business units.

  • Conduct cold outreach via LinkedIn, phone, and email to prospective clients.

  • Focus on Fortune 500 companies, targeting UX Directors, HR Directors, CTOs, VPs, and other staffing decision-makers.

  • Qualify leads through discovery calls, email sequences, and LinkedIn messaging.

  • Track and manage prospects through CRM/ATS systems (Copper + Bullhorn).

• Prospecting Strategy & Market Research:

  • Conduct research to identify target companies and decision-makers in UX, HR, and related departments.

  • Develop and maintain an active prospect list, categorized by priority, industry, and pipeline stage.

  • Engage with government contacts within the Vendor of Record (VOR) list to increase staffing opportunities.

  • Collaborate with marketing to align outreach with campaigns and leverage content.

• Events & Networking:

  • Attend relevant UX and design conferences (virtual and in-person) to network and generate leads.

  • Follow up with new contacts and nurture them into qualified opportunities.

• Business Development Collaboration:

  • Collaborate with the Head of Talent, Recruitment, and Client Success to align outreach with talent availability.

  • Provide insights to improve outreach messaging and lead quality.

  • Share strategies to refine the outbound sales process and build scalable systems.

Qualifications:

• Must-Have Skills & Experience:

  • 3–5 years of experience in sales development or business development in a B2B or agency setting.

  • Proven experience in cold outreach and lead generation via LinkedIn and email.

  • Familiarity with CRM systems and sales workflows.

  • Excellent written and verbal communication skills.

  • Strong research and organizational skills.

  • Self-starter with a proactive attitude and growth mindset.

  • Excited by AI-enhanced workflows and open to using tools that improve prospecting efficiency.

• Nice-to-Have Experience:

  • Experience in the recruiting/talent/staffing industry.

  • Knowledge of UX and service design.

  • Experience working with enterprise or public sector clients.

  • Experience attending or prospecting at industry conferences or virtual events.

  • Familiarity with Vendor of Record (VOR) processes or government procurement.

Why Join Outwitly?

• Work with a company defining the future of UX & Service Design staffing.

• Join a high-growth, remote-first company with strong leadership and a clear vision.

• Be part of a collaborative and ambitious team that values results and relationships.

• Flexible remote work with competitive compensation and performance-based bonuses.