Head of Sales

This is a fully remote position, open to applicants in Ohio.

📋 Description

• Build and Lead a High-Performing Sales Team (45%)

• Recruit, coach, and develop a top-tier sales team that aligns with Northwoods' public-sector strategy across existing and target regions.

• Establish clear expectations for activities, pipeline generation, stage discipline, forecast quality, and quota achievement, while holding the team accountable through a stringent operating cadence.

• Conduct regular one-on-ones, pipeline evaluations, and account assessments to enhance representative performance, refine execution, and boost momentum.

• Foster a culture of accountability, ownership, and execution where high performance is acknowledged and rewarded, and where gaps are directly and constructively addressed.

• Enhance the team's skills in state-level and enterprise-style selling, managing multiple stakeholders, navigating longer buying cycles, and adhering to formal procurement processes, while maintaining productive customer relationships and market credibility.

• Assess team structure and make talent decisions as necessary to ensure the organization is well-positioned to achieve the company's growth objectives.

• Build Pipeline, Improve Forecasting, and Win Complex Deals (40%)

• Drive consistent pipeline generation across the sales team, ensuring opportunity development aligns with the company's 12- to 18-month sales cycle and revenue goals, while actively seeking ways to shorten timelines and accelerate progress when feasible.

• Enhance forecast accuracy by refining stage definitions, increasing inspection rigor, enforcing qualification standards, and promoting evidence-based deal management.

• Collaborate directly on select strategic opportunities where executive involvement, deal strategy, or cross-functional coordination can significantly enhance win probability.

• Utilize data and operational discipline to identify early opportunities, strengthen conversion throughout the pipeline, and enhance overall bookings performance.

• Serve as a Core Leadership Team Member (15%)

• Contribute to company strategy as a core leadership team member by providing market insights, sales signals, and commercial judgment to executive decisions.

• Collaborate with Product, Marketing, Delivery, Finance, and executive leadership to enhance go-to-market execution, messaging, pricing alignment, and customer feedback mechanisms.

• Assist in shaping growth strategy by identifying market opportunities, capability gaps, and commercial priorities needed for scaling.

• First-Year Expectations

• First 90 days: Establish relationships within the team, set an operating cadence, identify quick wins, and make necessary talent decisions.

• Within 6 months: Improve pipeline quality, tighten stage discipline, enhance forecast reliability, and demonstrate stronger early-stage opportunity development consistent with a lengthy sales cycle.

• Within 12 months: Boost bookings trajectory, advance state-level and enterprise-style selling, and develop an organization capable of sustaining larger quota targets.

⛳️ Requirements

• Proven track record in leading and expanding sales teams in B2B SaaS, public sector technology, or other complex enterprise environments.

• Demonstrated capability in fostering accountability, coaching performance, enhancing pipeline creation, and increasing forecast rigor in lengthy sales cycles.

• Experience managing teams that engage in complex buying contexts with multiple stakeholders, formal evaluation procedures, or regulated-market dynamics.

• Strong executive presence, sound commercial judgment, and the ability to collaborate effectively across functions and at the leadership-team level.

• Experience in recruiting and developing high-performing sales professionals and building teams aligned with ambitious growth objectives.

• Familiarity with CRM-driven sales management and pipeline evaluation; experience with HubSpot or similar platforms is advantageous.

• Direct experience in human services, child welfare, or related public-sector areas is beneficial but not mandatory.

• 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 of 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