Outwitly Inc. is seeking an experienced “A-Player” Head of Talent, Recruiting and Client Success to play a strategic leadership role in scaling our staffing business to 100+ clients. You will elevate our talent operations, implement an ATS system, and streamline our recruitment processes while fostering strong relationships with both clients and candidates. Your expertise will shape the future of how we deliver high-impact design teams at scale!
This person will collaborate closely with the CEO/Founder and other department heads to optimize operational efficiencies and processes across two critical areas of our business:
- Talent Acquisition & Delivery – Ensuring we attract, vet, and place world-class UX and service design professionals.
- Client Success & Account Management – Strengthening client relationships to drive long-term partnerships and business expansion.
Outwitly’s vision is to be the #1 strategic UX partner for upskilling and resourcing UX teams for Fortune 500 clients in North America. We are looking for someone who is excited to build and 10X the impact and growth of the business over the next several years.
This Role is for You If…
- You are an A-Player Talent Acquisition & Recruiting Leader – You don’t just fill roles; you build world-class teams. You have a track record of placing top-tier talent and leading high-performing recruitment teams.
- You excel at building client relationships – You know how to nurture and grow client partnerships, increase retention, and drive business expansion through strategic relationship and account management.
- You have an entrepreneurial mindset – Resilience, resourcefulness, and problem-solving come naturally to you. You see roadblocks as challenges to overcome, not reasons to slow down.
- You work hard and smart—it’s in your DNA – You’re laser-focused on results, always looking for ways to optimize and innovate.
- You understand this is not just a 9-5 job – This is an opportunity to own and scale a talent function within a fast-growing company. We want someone who is a true partner in Outwitly’s mission to transform UX staffing.
About Outwitly
Outwitly Inc. is a premier talent and training solutions agency in UX and Service Design for large private and public sector clients across Canada and the US. Our mission is to connect top-tier talent with leading organizations, helping them build exceptional user experiences.
- Talent Solutions: We help our clients find top talent in UX design, UX research, service design, design strategy, and related disciplines on a short or long-term basis.
- Training Solutions: We are not only committed to aligning design talent with their next great opportunity – but also, creating excellence in the field of human-centered design and UX through education, upskilling, and community.
- Strategic HCD Partners: We help UX Directors and Leaders shape and grow their teams while providing executive coaching to help them get the most out of their design and research teams.
Our clients span multiple industries, including healthcare, finance, technology, and the public sector. Outwitly is a woman-owned corporation committed to diversity, equality, and inclusion. We’re very proud of living our values at work, and the incredible culture that results. Over 70% of our team are women, and 54% identify as Black, Indigenous, or People of Colour (BIPOC).
Outwitly is a 100% remote company based in Canada, with clients across all North American time zones.
Key Responsibilities:
Talent Acquisition & Recruitment:
- Oversee the end-to-end recruitment lifecycle, ensuring alignment with client needs and business goals.
- Oversee the implementation of a new ATS system and project management tool
- Develop departmental and individual team KPIs for recruitment (utilization, time to place, etc.) and ensure KPIs are tracked – use data-driven insights to evaluate/measure performance and make decisions accordingly
- Develop and implement strategic recruitment initiatives to attract and retain top UX and Service Design talent.
- Build and maintain an engaged contractor pool by creating and optimizing processes that foster long-term relationships and contractor satisfaction.
- Effectively set team priorities, optimize workflows, and execute recruitment strategies.
Client Success:
- Provide strategic oversight of client relationships, ensuring high satisfaction and long-term retention.
- Evolve and implement processes to support Account Managers/Executives in maintaining strong client relationships and identifying upsell opportunities.
- Ensure seamless collaboration between the Sales and Talent to meet client needs effectively.
- Implement performance tracking and feedback loops to optimize client satisfaction and service excellence.
Strategic Business Development:
- Identify and pursue new business opportunities within the UX and Service Design industry to expand Outwitly’s client base.
- Develop strategies to position Outwitly as a leader in UX staffing solutions through innovative talent acquisition and client success initiatives.
- Collaborate with leadership to set and achieve revenue targets, aligning sales efforts with business objectives.
Leadership & Process Optimization:
- Provide leadership and mentorship to the Talent and Sales teams, fostering a culture of high performance and continuous improvement.
- Develop and refine internal processes to improve efficiency, streamline operations, and enhance service delivery.
- Ensure alignment with company values, promoting excellence in delivery, collaboration, and client-centric approaches.
Qualifications:
- Minimum of 10 years of experience in talent acquisition, recruitment, and client success, preferably from a staffing agency
- Extensive experience in full-cycle recruitment, including sourcing, screening, interviewing, and hiring top-tier talent in IT or design roles.
- Proven leadership experience in building and leading high-performing teams.
- Strong strategic thinking capabilities with the ability to drive priorities and execution effectively.
- Experience in developing and optimizing recruitment processes to foster contractor engagement and satisfaction.
- Proven ability to build and manage relationships with hiring managers, executives, and cross-functional teams to understand hiring needs and deliver tailored recruitment solutions.
- Deep knowledge of recruitment technologies, processes, platforms, and tools, including applicant tracking systems (ATS), job boards, social media, and sourcing techniques, to optimize recruitment processes and outcomes.
- Strong analytical and problem-solving skills, with the ability to interpret data and make strategic decisions.
- Entrepreneurial mindset with a proactive and solutions-oriented approach.
- Exceptional communication and interpersonal skills to engage with internal and external stakeholders effectively.
Why Join Outwitly?
- 💡 Lead and shape the future of UX and Service Design staffing.
- 🚀 Work in a fast-paced, high-growth environment with a talented team.
- 📈 Competitive compensation & room for professional growth.
- 🌎 100% remote, flexible work culture.
If you’re a strategic leader with a passion for talent acquisition and client success, and you’re eager to drive Outwitly’s growth, we’d love to hear from you. Please note, this role will require up to 15% travel.