Remote Chief Financial Officer Jobs in Springfield, MA

Job Description
WHO WE ARE
Finalsite is the most valued partner for K-12 schools to build trust, strengthen community, and grow enrollment. Ranked among the best EdTech Companies in America, Finalsite supports more than 7,000 schools and districts worldwide with an integrated platform for websites, communications, mobile apps, enrollment, and marketing services.
Headquartered in Glastonbury, Connecticut, Finalsite is a global company with employees working remotely across nearly every U.S. state, as well as throughout Europe, South America, and Asia.
We believe people do their best work when they feel supported, connected, and empowered to grow. That's why we invest in our employees through competitive benefits, professional development opportunities, and a collaborative culture built on partnership and purpose. Whether you're looking to expand your skills, take on new challenges, or make a meaningful impact in education, Finalsite offers the opportunity to grow your career while helping schools thrive.
At Finalsite, every interaction matters - with our clients, with each other, and with the schools and families we serve. Join us and help shape stronger school communities around the world
SUMMARY
The Senior Director of Sales is a hands-on, front-line sales leader responsible for building, coaching, and scaling a team of individual-contributor Education Sales Consultants focused on Finalsite's Tier 1, Tier 2, and Tier 3 public school district segments. This leader owns full-lifecycle selling across the segment - from outbound prospecting and new-logo acquisition through cross-selling and expanding relationships with existing clients - and is accountable for new-business growth and account expansion. Reporting to the Chief Sales Officer, the Senior Director operates as both a strategic leader and a deeply involved coach, engaged directly in deal strategy, pipeline generation, and team development, and partners closely with Marketing, Business Development, and Customer Success leaders to drive pipeline, win new districts, and grow the existing client base so the segment consistently exceeds its growth targets.
LOCATION
100% Remote - Anywhere within the US
RESPONSIBILITIES

• Lead, coach, and develop a team of individual-contributor Education Sales Consultants selling Finalsite's full product portfolio into Tier 1, Tier 2, and Tier 3 public school districts.
• Own the segment's full sales lifecycle - from outbound prospecting and new-logo acquisition through cross-sell, upsell, and expansion within the existing client base.
• Carry and deliver against the team's new-business and expansion (cross-sell and upsell) targets, driving consistent quarter-over-quarter performance.
• Provide hands-on, front-line coaching - including live call coaching, deal strategy sessions, and pipeline reviews - to elevate individual and team performance across the entire selling motion.
• Recruit, hire, onboard, and ramp Education Sales Consultants, building team capacity ahead of growth targets.
• Partner closely with Marketing and Business Development to build, qualify, and convert pipeline, ensuring tight alignment between demand generation, outbound prospecting, and field selling.
• Partner closely with Customer Success to surface and win cross-sell and expansion opportunities in the existing client base, coordinating on account health and a seamless client experience, with Customer Success owning renewals.
• Develop and continuously refine sales playbooks, methodologies, and qualification frameworks tailored to the public school district buying and budgeting process.
• Forecast pipeline and revenue with precision, reporting regularly on KPIs, conversion rates, expansion, and team performance to the Chief Sales Officer and broader leadership.
• Lead and facilitate weekly, monthly, and quarterly business reviews to align the team on goals, blockers, and strategy.
• Ensure Finalsite's product vision, value, competitive differentiation, and pricing are clearly and consistently articulated across every stage of the new-business and expansion cycle.
• Build a culture of accountability, urgency, and high performance, where the team is continually pushing to exceed individual and collective goals.
• Maintain rigorous sales process discipline - qualification criteria, CRM hygiene, activity logging, and deal documentation - to protect forecast accuracy and pipeline integrity.
• Represent the voice of the public school district market in cross-functional strategic planning, surfacing market trends, competitive intelligence, and customer feedback to leadership.
• Travel as needed to support team development, customer engagements, and market presence.

QUALIFICATIONS AND SKILLS

• Bachelor's degree or equivalent professional experience.
• 10+ years of SaaS or technology sales experience, including a minimum of 5 years in a front-line sales leadership role.
• Proven track record of leading teams across the full sales lifecycle - from outbound prospecting and new-logo acquisition through cross-sell and expansion.
• Experience selling into K-12, public school districts, or the broader education technology market strongly preferred.
• Demonstrated success partnering with Marketing, Business Development, and Customer Success to drive new-business growth and account expansion.
• Deep fluency in modern sales methodologies and demonstrated ability to coach a team on them.
• Strong command of Salesforce or equivalent CRM, plus sales engagement and forecasting tools.
• Demonstrated success recruiting, developing, and retaining top sales talent in a competitive hiring market.
• Sharp analytical skills, with the ability to translate pipeline and performance data into actionable strategy.
• Excellent negotiation and executive communication skills, with the ability to operate credibly with senior stakeholders internally and externally.
• Willingness and flexibility to travel as required to support team and market needs.

RESIDENCY REQUIREMENT
Finalsite offers 100% fully remote employment opportunities, however, these opportunities are limited to permanent residents of the United States. Current residency, as well as continued residency, within the United States is required to obtain (and retain) employment with Finalsite.
DISCLOSURES
Finalsite is proud to be an equal opportunity workplace and is an affirmative action employer. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. EEO is the Law. If you have a disability or special need that requires accommodation, please contact Finalsite's People Operations Team. Finalsite is committed to the full inclusion of all qualified individuals. As part of this commitment, Finalsite will ensure that persons with disabilities or special needs are provided a reasonable accommodation. Ensure your Finalsite job offer is legitimate and don't fall victim to fraud. Ask your recruiter for a phone call or other type of verbal communication and ensure all email correspondence is from a finalsite.com email address. For added security, where possible, apply through our company website at finalsite.com/jobs.