$80K - 130K a year
Drive outbound sales growth by identifying and engaging new enterprise clients, managing complex sales cycles, and partnering internally to ensure client success.
5+ years of successful outbound sales experience selling leadership development or related services to large enterprise clients, strong diagnostic and communication skills, and a bachelor's degree.
Are you a "hunter"? Are you a consultative salesperson who has sold performance improvement solutions - specifically either leadership development OR sales training OR coaching OR human capital consultancy to enterprise clients before? If you you have said "yes" to the above, please read on! We are recruiting on behalf of our client. A client who is an award winning Leadership Development business which helps large organizations navigate complexity and achieve outperformance through leadership. About the Role As part of their continuing growth strategy, they have an immediate requirement to add a Client Strategist (pure sales role) who will focus on driving outbound sales growth and securing new enterprise client partnerships. This is a “hunter” type of role involving sales pipeline development, cold outreach, consultative and complex sales skills through to closing. This role is critical for the business and the ideal candidate will be someone who thrives on the challenge of building new relationships, diagnosing complex needs, and strategically closing deals that make a real impact on the clients' leadership potential. This is a key role in that you will be responsible for driving business growth in Chicago and the Midwest. Responsibilities Outbound Growth & New Business Acquisition: • Pipeline Generation: Proactively identify and engage new prospective clients within target large enterprise accounts (e.g., Healthcare, Financial Services, Technology, etc.) through targeted research, cold outreach (calls, email, social), networking, and strategic prospecting. • Discovery & Diagnosis: Conduct deep, diagnostic discovery calls with senior leaders (e.g., CLOs, CHROs, Business Unit Heads) to uncover their strategic talent challenges, pain points related to HIPO development, talent mobility, and leadership effectiveness. • Solution Selling: Articulate the unique value proposition by aligning the solutions suite of executive coaching, leadership development, and team effectiveness solutions directly to identified client needs and desired business outcomes. • Deal Management: Lead complex sales cycles from initial contact to close, managing all aspects including proposal development, presentations, negotiations, and contract execution. • Strategic Planning: Develop and execute account plans for new target clients, outlining strategies for engagement, qualification, and acceleration through the sales funnel. Client Strategist & Partnering: • Market Insights: Continuously learn and adapt to understand evolving market trends, competitive landscapes, and client challenges, particularly in the talent management and organizational development space. • Internal Collaboration: Partner closely with Client Success, Client Lead, Solutions and Coach/ Facilitator teams to ensure a seamless client experience from sales to delivery, and to share market intelligence for product/service refinement. • Value Articulation: Clearly demonstrate the ROI and impact of the services to executive-level stakeholders. Professional Excellence & Discipline: • Self-Management: Exhibit strong self-discipline and work ethic to manage a demanding outbound pipeline, prioritize activities, and consistently hit activity and revenue targets. • Performance Accountability: Proactively track, manage, and report on sales activities and pipeline health against individual KPIs and revenue goals. • Continuous Learning: Actively seek feedback, participate in ongoing professional development, and quickly integrate new learning into the day-to-day role. • Culture Championship: Embody and promote the firm’s core behaviors and values both internally and in every client interaction. Qualifications • 5+ years of demonstrable success in an outbound, hunter-based sales role selling complex B2B services to large enterprise clients, preferably in leadership development, HR consulting, executive education, talent management, or professional services. • Proven ability to independently generate new pipeline and close significant deals from scratch. • Exceptional diagnostic questioning skills and a track record of uncovering nuanced client pain points. • Highly resourceful and adaptable, with a strong desire to learn and quickly master new concepts, industries, and sales methodologies. • Outstanding communication, presentation, and negotiation skills. • Demonstrated strong work ethic, self-discipline, and resilience in managing a demanding sales pipeline. • Comfortable operating in a dynamic, smaller organizational environment where proactive initiative is highly valued. • Bachelor's degree required; advanced degree is a plus.
This job posting was last updated on 10/23/2025