Head of Sales

Northwoods • Dublin, OH

5d • Onsite

About The Position

The Head of Sales is a senior leadership role responsible for scaling and strengthening Northwoods’ sales organization. Reporting directly to the CEO and serving on the core leadership team, this person will raise performance standards, improve forecast accuracy, strengthen pipeline generation, and lead a more enterprise-oriented go-to-market motion across public-sector accounts. Success in this role will come through disciplined execution, strong talent development, and the ability to build a commercial engine capable of supporting the company’s next stage of growth.
This leader will establish greater accountability, urgency, and pipeline discipline across the sales organization while advancing more consistent enterprise-style selling. The Head of Sales will assess team capability, develop and strengthen talent, and develop a high-performing organization positioned to win beyond legacy selling patterns and more complex state-level opportunities. This role also partners closely with Product, Marketing, Delivery, Finance, and executive leadership to align market strategy, commercial execution, and revenue predictability.

Requirements

• Proven success leading and growing sales teams in B2B SaaS, public sector technology, or other complex enterprise environments.
• Demonstrated ability to build accountability, coach performance, strengthen pipeline creation, and increase forecast rigor in long-cycle sales motions.
• Experience leading teams that sell into complex buying environments with multiple stakeholders, formal evaluation processes, or regulated-market dynamics.
• Strong executive presence, sound commercial judgment, and the ability to partner effectively across functions and at the leadership-team level.
• Experience recruiting and developing high-performing sellers and building teams aligned to ambitious growth goals.
• Working knowledge of CRM-driven sales management and pipeline inspection; experience with HubSpot or similar platforms is helpful.
• Must be authorized to work in the U.S.

Nice To Haves

• Direct experience in human services, child welfare, or adjacent public-sector domains is helpful but not required.

Responsibilities

• Build and Lead a High-Performing Sales Team (45%)
• Recruit, coach, and develop a high-performing sales team aligned to Northwoods' public-sector strategy across current and target geographies.
• Set clear expectations for activity, pipeline creation, stage discipline, forecast quality, and quota attainment, and hold the team accountable through a rigorous operating cadence.
• Conduct regular 1:1s, pipeline reviews, and account reviews to strengthen rep performance, sharpen execution, and accelerate momentum.
• Build a culture of accountability, ownership, and execution where high performance is recognized and rewarded, and where gaps are addressed directly and constructively.
• Develop the team's capabilities in state-level and enterprise-style selling, navigating multiple stakeholders, longer buying cycles, and formal procurement requirements, while preserving productive customer relationships and market credibility.
• Evaluate team structure and make talent decisions as needed to ensure the organization is positioned to meet the company's growth targets.
• Build Pipeline, Improve Forecasting, and Win Complex Deals (40%)
• Drive consistent pipeline creation across the sales team, ensuring opportunity development aligns with the company's 12- to 18-month sales cycle and revenue targets, while actively looking for ways to compress timelines and accelerate when possible.
• Improve forecast quality by refining stage definitions, strengthening inspection rigor, enforcing qualification standards, and driving evidence-based deal management.
• Partner directly on select strategic opportunities where executive engagement, deal strategy, or cross-functional coordination can materially improve win probability.
• Use data and operating discipline to identify opportunities early, strengthen conversion across the pipeline, and improve overall bookings performance.
• Serve as a Core Leadership Team Member (15%)
• Contribute to company strategy as a core leadership team member by bringing market insight, sales signal, and commercial judgment into executive decisions.
• Partner with Product, Marketing, Delivery, Finance, and executive leadership to improve go-to-market execution, messaging, pricing alignment, and customer feedback loops.
• Help shape growth strategy by identifying market opportunities, capability gaps, and the commercial priorities required to scale.

Benefits

• Medical (includes H.S.A. option with employer contribution), dental, and vision insurance
• Short- and long-term disability
• Company paid basic life insurance
• 401(k) with 4% company match and immediate vesting
• Wellness program that helps you earn lower premiums
• Robust EAP program that includes free therapy sessions, lifestyle coaching, legal/ID theft services, and more
• 12 weeks fully paid parental leave
• Up to $5,000 adoption fee reimbursement
• $500 wellness reimbursement after 60 days of employment
• Generous PTO policy and 10 company paid holidays
• Company paid cell phone plan

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed