Head of Sales

Role Overview

• 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. First-Year Expectations
• First 90 days : Build relationships across the team, establish operating cadence, identify quick wins, and make talent decisions where needed.
• Within 6 months: Strengthen pipeline quality, tighten stage discipline, improve forecast reliability, and show stronger early-stage opportunity creation consistent with a long sales cycle.
• Within 12 months: Improve bookings trajectory, advance state-level and enterprise-style selling, and build an organization capable of sustaining larger quota targets.

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.
• Direct experience in human services, child welfare, or adjacent public-sector domains is helpful but not required.
• Must be authorized to work in the U.S.

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