Head of Mid Market Sales

Accountabilities: Sales Leadership and Team Development: Lead, recruit, coach, and develop the Mid Market sales organization across the Americas, initially overseeing three sales managers, with the team expected to grow to four. Build a high-performing organization by developing managers and account executives, strengthening leadership capabilities, and making timely performance management decisions. Revenue Ownership and Execution: Take full responsibility for regional revenue targets and overall sales performance. Translate strategic business objectives into actionable sales plans, establish clear priorities, and ensure consistent execution across all market segments. Sales Strategy Development: Design and implement scalable sales strategies and programs that improve productivity, strengthen execution, and support ambitious year-over-year growth targets. Pipeline Generation: Develop modern pipeline generation strategies that ensure sustainable pipeline coverage. Establish effective programs to improve lead generation, conversion rates, sales productivity, and forecasting accuracy. Market Expansion: Identify opportunities to expand the serviceable addressable market by targeting new industries, customer segments, and product opportunities. Contribute to the broader growth strategy, supporting the ambition of reaching more than $200 million in annual recurring revenue by 2027. Multi-Product Sales Strategy: Develop effective strategies for selling a growing multi-product platform, increasing cross-selling and expansion opportunities, and positioning solutions against established competitors in competitive replacement and consolidation sales cycles. Cross-Functional Collaboration: Partner with Revenue Operations, Marketing, Product, and other senior stakeholders to align go-to-market initiatives, improve operational efficiency, and identify new opportunities for sustainable business growth. Business Performance Analysis: Evaluate regional performance, identify operational challenges, and use data-driven insights to determine the most impactful areas for improvement. Go beyond forecasting and reporting by actively implementing initiatives that accelerate business performance. Sales Excellence and Customer Experience: Promote a collaborative, customer-focused sales culture built around deep product knowledge, industry expertise, and a strong understanding of talent acquisition challenges. Organizational Development: Establish a culture of accountability, continuous learning, clear communication, and high-quality execution while supporting career progression and leadership development throughout the sales organization. Requirements Extensive experience as a second-line sales leader within a high-growth B2B SaaS organization, ideally with a business generating at least $100 million in annual recurring revenue. Proven experience managing sales managers and leading multi-layered sales organizations, rather than exclusively managing individual contributors. Demonstrated success recruiting, developing, and retaining high-performing sales managers and account executives, with the ability to make effective performance management decisions when necessary. Strong experience leading a sales-led Mid Market go-to-market strategy, ideally targeting businesses with approximately 100 to 1,000 employees. A successful track record of achieving ambitious revenue targets and driving sustainable year-over-year growth in competitive SaaS markets. In-depth understanding of modern pipeline generation strategies, including pipeline coverage, demand generation programs, sales productivity, and forecasting practices. Experience developing sales strategies for multi-product platforms, including competitive replacement opportunities, product expansion, and complex sales cycles. Strong commercial and strategic thinking, with the ability to assess business performance, identify growth opportunities, and translate insights into practical initiatives. Excellent leadership and coaching skills, with the ability to empower managers, build accountability, and develop a culture of high performance. Outstanding collaboration and relationship-building abilities, particularly when working with senior stakeholders and cross-functional teams. Strong communication and change management skills, with the ability to influence stakeholders, implement operational improvements, and drive organizational alignment. A proactive, ownership-oriented mindset, with a focus on creating measurable business impact rather than simply monitoring forecasts and reporting results. A customer-centric approach and genuine interest in developing deep expertise in SaaS products and the talent acquisition technology industry. Benefits Competitive Compensation: Annual on-target earnings ranging from $340,000 to $407,500 USD for candidates based in Tier 1 locations (San Francisco and New York metropolitan areas), and $320,000 to $380,000 USD for Tier 2 locations. Base Salary and Commission: A 50/50 compensation structure combining base salary and performance-based commission, offering significant earning potential. Equity Participation: Opportunity to receive company equity and participate in long-term business growth. Unlimited Paid Time Off: Flexible vacation policy, with four weeks of annual time off recommended and actively encouraged. Paid Family Leave: Twelve weeks of fully paid family leave for eligible employees based in the United States. Remote-First Environment: Flexibility to work remotely while collaborating with a distributed, high-performing team. Equipment and Workspace Budget: Generous budget for professional equipment, software, and office furniture to create a comfortable and productive working environment. Learning and Development: Monthly education allowance of $100, with additional support for higher-cost learning opportunities, such as conferences, subject to manager approval. Long-Term Equity Flexibility: Ten-year exercise window for stock options, providing greater flexibility when making decisions about equity after leaving the organization. Career Development: Opportunities for professional growth and advancement, supported by a strong culture of coaching, leadership development, and internal mobility. Collaborative Culture: An environment that values ownership, thoughtful communication, teamwork, continuous learning, and high-quality work. Meaningful Impact: The opportunity to shape a growing sales organization, influence go-to-market strategy, and contribute directly to ambitious business expansion plans.