Head of Sales

SkillsWave is on a mission to drive people and businesses forward—building tomorrow’s most valued skills, today. By providing quality learning opportunities that align with organizational needs, we’re helping organizations transform their workforce into a competitive advantage. Our upskilling platform and strategic education partnerships not only propel career and company growth, but also deliver measurable and meaningful ROI for learning. To learn more, visit SkillsWave.com.

Job Summary:

The Head of Sales for SkillsWave is responsible for growing new corporate clients by leading a team of sales executives. This individual will establish and implement plans to exceed pipeline generation goals, closing enterprise deals in the learning upskilling space.

This leader will have their own sales quota and will also manage a team of Account Executives by identifying and establishing key relationships with high level decision makers, initiating the discovery process and maintaining a pipeline of qualified, prospective customers that ultimately leads to new business growth. This is a unique opportunity to grow clients and lead a team to high performance by refining processes, and driving the team to a sophisticated, consultative approach leading to effective outcomes.

This leader is knowledgeable about the field of education-as-a-benefit and corporate training, and maintains a high level of currency in the field.

How Will I Make an Impact?

• Partner closely with Marketing, Product, and Ed Partnerships to align messaging with activities, and ensuring cross-functional transparency to drive growth.
• Supervise staff where needed and provide constructive feedback to support continual growth and development.
• Develop strong relationships with new and existing clients to ensure high adoption of the SkillsWave platform and the accompanying training and education.
• Responsible for continually increasing the usage of the SkillsWave platform with existing clients and new clients.
• Interface with internal and key partners in the field of corporate learning.
• Foster a culture of customer empathy, partnership, and continuous value creation.
• Responsible for supporting vision, planning, and defining team objectives, and leading execution of objectives.
• Work with your peers and leaders to drive productivity, efficiency, and hold the team accountable for high-quality outcomes.
• Produce and actively participate in knowledge sharing as well as professional development initiatives.
• Develop sound risk management and mitigation framework and reporting that highlights strong leading indicators and predictive methodology to prevent churn and increase net revenue retention.
• Recruit, develop and coach team members to be domain-level experts in consultative sales, with intermediate to advanced knowledge of the field of learning and development upskilling where those roles consist of prospecting, opportunity identification and pipeline generation.
• Create and implement strategies to increase lead conversion rates.
• Maintain accurate and timely forecast data and be able to identify opportunities for continuous improvement.
• Move fast and close the loop on leads from multiple sources, including leads from SkillsWave leadership.
• Expertise in the competitive landscape & customer needs across the corporate and learning and development markets so your organization can effectively position SkillsWave's value proposition to prospective clients.
• Provide support in the partnership, planning and execution of marketing events.
• Exceed monthly, quarterly, annual activity and pipeline targets, across all markets.
• Define, monitor, and deliver on performance goals.
• Implement and improve sales processes focused on messaging, data, and continual improvement.
• Work closely with the Integrated Marketing teams on joint initiatives such as campaigns, account based marketing and social media strategies to increase awareness.
• Understand and optimize the tech stack and advocate for the effective use of tools and technology that are essential to the sales team’s ability to exceed targets and scale efficiently.

What you'll bring to the role:

• Ability to effectively communicate to stakeholders at all levels of the organization – with excellent written, oral, and presentation skills.
• Model high energy level, demonstrated drive to succeed, with a sense of urgency in a fast paced and rapidly growing organization.
• Experience in the field of corporate learning and development in the US.
• Ability to formulate and communicate a clear, long term business development strategy aligned with the organization's overall goals and market dynamics.
• Strong interpersonal skills to establish and maintain relationships with key industry players, potential clients, and strategic partners.
• Understanding of financial models, cost structures, and revenue streams to assess the financial viability of potential opportunities and partnerships.
• Ability to lead and inspire a high-performing sales team, fostering a collaborative and results-driven culture.
• Experience within a growth-oriented software and services company is ideal.
• Strong analytical and problem-solving skills.
• Thorough understanding of business management, forecasting strategy and techniques.
• Experience working in education technology or knowledge of business drivers for adult learning is a plus.

Suggested Qualifications/Experience:

• Experience managing clients and/or partnerships for revenue generation in corporate learning and development.
• Experience leading teams.
• Experience with interpreting data and analytics.
• Experience implementing either educational technology initiatives, online learning programs, or partnership programs.
• Experience managing clients within the field of education – external and internal – and of varying sizes.

Business Development & Sales:

• 10+ years of Sales or equivalent experience with 5+ years of progressive leadership roles in enterprise-level sales in the corporate learning space.
• Direct evidence of closing large enterprise-wide deals in short timeframes.
• CRM experience a must, Outreach or equivalent platform experience a plus.
• Knowledge of competition in the space of upskilling platforms for example: Guild, InStride, EdAssist, 360Learning or similar, along with strategies of competitors.
• Past software sales experience is preferred.

This role is a remote position. The Head of Sales must be comfortable conducting initial meetings with prospects, vendors and clients in-person and/or using MS Teams from their home residence. The individual must be able to travel to prospect locations in Canada or the U.S. as well as visit the SkillsWave office located within the Kitchener-Waterloo region. The current office location for SkillsWave is a co-working space at Catalyst Commons (137 Glasgow Street, Kitchener) but this location may change at any time based on company growth.

Compensation:

The maximum annual compensation for this position is in the range of $220,000 to $260,000 (50/50 split between base salary and commissions). The candidate must meet the minimum level of work experience and qualifications as listed above. This position requires a minimum of 40 hours of work per week. More senior candidates may apply but note that the salary and commissions for the position has been set at the range listed.

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To all recruitment agencies: SkillsWave does not accept agency resumes. Please do not forward resumes to our HR alias e-mail address, to any SkillsWave employee, or to other SkillsWave e-mail addresses. SkillsWave will not pay any fees related to unsolicited resumes.