Sales Development Representative

Outwitly Inc.; Windsor; On-site; CAD 70,000 - 90,000; Full time

Job summary

Outwitly Inc. seeks a motivated Sales Development Representative to scale our UX & Service Design staffing business. The role focuses on identifying and nurturing new business opportunities, conducting outreach, and collaborating closely with leadership to support business growth.

Qualifications

• 3–5 years of experience in sales development or client outreach.
• Proven experience with high value client outreach and lead generation.
• Strong research and organizational skills.

Responsibilities

• Conduct cold outreach via LinkedIn, phone, and email.
• Research and identify potential business units within existing clients.
• Track and manage prospects through CRM.

Skills

Sales development

Lead generation

Relationship building

Cold outreach

Organizational skills

Research skills

Education

3–5 years in sales development or business development

Tools

CRM systems

Job description

Salary Range : Base pay (70,000) + Commission

Outwitly Inc. is seeking a highly motivated and driven Sales Development Representative (SDR) to help scale our UX & Service Design staffing business by identifying, nurturing, and converting new business opportunities. This is a hands-on business development role focused on pipeline growth for staffing contracts with enterprise and public sector clients across North America.

You’ll work closely with our CEO and Head of Talent, Recruitment, and Client Success to support the early stages of the sales funnel, focusing on reviving inactive leads, conducting cold outreach, and identifying strategic new clients in line with Outwitly’s growth goals.

This Role is for You If…

You are a natural prospector and relationship builder – You love the challenge of connecting with people, opening doors, and identifying pain points you can solve.

You’re organized and persistent – You follow up, follow through, and don’t give up until you get a response.

You are confident in outreach and discovery – You know how to ask the right questions to qualify leads and open sales conversations.

You have a growth mindset – You’re constantly looking to improve, learn, and take initiative.

You are passionate about UX, service design, and the impact of great design on business success.

You have a growth mindset and are excited about leveraging new tools (like AI) to work more efficiently

Key Responsibilities

• 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 prospecting efforts on Fortune 500 companies, targeting UX Directors, HR Directors, CTOs, VPs, and other key staffing decision-makers.
• Qualify leads through discovery calls, email sequences, and LinkedIn messaging.
• Track and manage prospects through our CRM / ATS (Copper + Bullhorn) and support the transition as we migrate to a new platform.
• Conduct market and account research to identify target companies and decision-makers (hiring managers, UX directors, HR leaders).
• Develop and maintain an active prospect list, categorized by priority, industry, and stage in the pipeline.
• Strategically identify and engage government contacts within our Vendor of Record (VOR) list, proactively reaching out to increase inbound staffing opportunities, while being mindful of contractual requirements with these organizations.
• Collaborate with the marketing team to align outreach with ongoing campaigns and leverage content to support engagement.

Events & Networking

• Identify and 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 from the field to improve outreach messaging, personas, and lead quality.
• Share ideas and strategies to refine the outbound sales process and help build scalable outreach systems.

Qualifications

Must-Have Skills & Experience

• 3–5 years of experience in sales development, business development, or client outreach, ideally in a B2B or agency setting.
• Proven experience with high value clients cold outreach and lead generation on LinkedIn and via email.
• Familiarity with CRM systems and comfort working within structured sales workflows.
• Excellent written and verbal communication skills.
• Strong research and organizational skills.
• Self-starter with a proactive attitude and desire to grow into a sales or account management role.
• Excited by tech and AI-enhanced workflows : You're open to testing AI tools and systems that help you prospect faster, smarter, and better.

Nice-to-Have Experience

• Experience working in the recruiting / talent / staffing industry.
• Understanding and appreciation of UX and service design.
• Experience working with or selling to 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 at a company that’s defining the future of UX & Service Design staffing.

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