Senior Director, Sales

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

📋 Description

• Lead, mentor, and cultivate a team of individual-contributor Education Sales Consultants responsible for selling Finalsite’s comprehensive product portfolio to Tier 1, Tier 2, and Tier 3 public school districts.

• Manage the entire sales lifecycle for the segment — from outbound prospecting and acquiring new logos to cross-selling, upselling, and expanding within the current client base.

• Meet and exceed the team’s targets for new business and expansion (cross-sell and upsell), ensuring consistent performance from quarter to quarter.

• Provide direct, hands-on coaching — including live call coaching, deal strategy sessions, and pipeline evaluations — to enhance both individual and team performance throughout the sales process.

• Recruit, hire, onboard, and develop Education Sales Consultants, enhancing team capacity in line with growth objectives.

• Collaborate closely with Marketing and Business Development to build, qualify, and convert sales pipeline, ensuring strong alignment between demand generation, outbound prospecting, and field selling.

• Work in partnership with Customer Success to identify and secure cross-sell and expansion opportunities within the existing client base, coordinating on account health and ensuring a seamless client experience, with Customer Success managing renewals.

• Create and continuously improve sales playbooks, methodologies, and qualification frameworks that are tailored to the purchasing and budgeting processes of public school districts.

• Accurately forecast pipeline and revenue, providing regular reports on KPIs, conversion rates, expansion efforts, and team performance to the Chief Sales Officer and broader leadership team.

• Organize and lead weekly, monthly, and quarterly business reviews to align the team on objectives, challenges, and strategies.

• Ensure that Finalsite’s product vision, value proposition, competitive advantages, and pricing are clearly and consistently communicated at every stage of the new business and expansion process.

• Foster a culture of accountability, urgency, and high performance, motivating the team to consistently exceed both individual and collective goals.

• Uphold strict sales process discipline — including qualification criteria, CRM accuracy, activity logging, and deal documentation — to maintain forecast accuracy and pipeline integrity.

• Act as the voice of the public school district market in cross-functional strategic planning, identifying market trends, competitive insights, and customer feedback for leadership consideration.

• Travel as necessary to support team development, customer interactions, and to enhance market presence.

⛳️ Requirements

• Bachelor’s degree or equivalent professional experience.

• Over 10 years of experience in SaaS or technology sales, including at least 5 years in a frontline sales leadership position.

• Proven ability to lead teams throughout the entire sales lifecycle — from outbound prospecting and acquiring new logos to cross-sell and expansion efforts.

• Experience in selling to K-12 public school districts or within the broader education technology sector is highly preferred.

• Successful history of collaborating with Marketing, Business Development, and Customer Success to drive new business growth and account expansion.

• Strong understanding of modern sales methodologies and demonstrated capacity to coach teams in applying them.

• Proficient in Salesforce or a similar CRM platform, along with sales engagement and forecasting tools.

• Proven success in recruiting, developing, and retaining top sales talent in a competitive job market.

• Strong analytical skills, capable of translating pipeline and performance data into actionable strategies.

• Excellent negotiation and executive communication skills, able to engage credibly with senior stakeholders both internally and externally.

• Willingness and flexibility to travel as needed to support team and market demands.

🏝️ Benefits

• Competitive benefits package.

• Opportunities for professional development.

• A collaborative culture centered on partnership and purpose.